Name: 1191-08-8|1,4-Butanedithiol|99+%
Brand: Ambeed
SKU: A698021
Rating: 98 (29 reviews)

1
[ 110-52-1 ]
[ 1191-08-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogensulfide; ethylene glycol unter Einleiten von Schwefelwasserstoff;
77 % Chromat.	With hexamethyldisilathiane; tetrabutyl ammonium fluoride In tetrahydrofuran at -10 - 20℃;

Reference： [1]Fukui et al. [Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, 1956, vol. 59, p. 482,484][Chem.Abstr., 1958, p. 3661]
[2]Hu, Jun; Fox, Marye Anne [Journal of Organic Chemistry, 1999, vol. 64, # 13, p. 4959 - 4961]

2
[ 1191-08-8 ]
[ 505-20-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	Stage #1: 1,4-Butanedithiol With 10-molybdo-2-vanadophosphoric acid In ethanol; water monomer at 70℃; for 0.25h; Stage #2: With potassium permanganate In ethanol; water monomer at 80℃; for 8h;
98%	With benzyltriphenylphosphonium peroxodisulfate In acetonitrile for 1.2h; Heating;
98%	With 1-butyl-4-aza-1-azoniabicyclo[2.2.2]octane dichromate In acetonitrile for 1.2h; Heating;

98%	With iodine; triethylamine In dichloromethane	S.2 Synthesis Example 2 Triethylamine (42.5g, 400mmol) is dissolved in dichloromethane (400ml) and cooled to 0°C in an ice bath. 1,4-Butanedithiol (25g, 200mmol) and iodine (51.9g, 400mmol) are added simultaneously so that the solution turns slightly yellow and the reaction temperature is below 5°C. After the end of the addition the reaction mixture is washed with dilute sodium thiosulphate solution (10%, 50ml) and water (2 x 50ml). The organic layer is separated and dried over magnesium sulphate overnight. The solid is filtered off and the solvent is evaporated (18mbar, 50°C). The reaction gives 1,2-dithiane (24.6g, 98% crude yield). The oil is dissolved in hexane (250ml) and recrystallized (at -78°C) as a yellow solid (15.40g, 63% isolated yield).
97%	With potassium permanganate; copper(II) sulphate In dichloromethane for 1.33333h; Ambient temperature;
97%	With oxygen In dichloromethane at 0℃; for 0.166667h;
96%	With water monomer; bromine; mesoporous silica In dichloromethane
96%	With tetramethylammonium chlorochromate In acetonitrile for 2h; Heating;
95%	With iodine; triethylamine In chloroform at 20℃; for 5h; Inert atmosphere; Schlenk technique;
94%	With Re(O)Cl₃(PPh₃)2 In dichloromethane; dimethyl sulfoxide at 25℃;
88%	With 2',3',4',5'-tetra-O-acetylriboflavin; iodine In <i>tert</i>-butyl alcohol at 26℃; for 24h; Darkness; Green chemistry;	Dioctyl Disulfide (3a): Typical Procedure General procedure: A mixture of octane-1-thiol (2a; 73.1 mg, 0.50 mmol), flavin 1a(13.6 mg, 0.025 mmol), I2 (6.35 mg, 0.025 mmol), and t-BuOH(1.0 mL) was stirred at 26 °C (water bath) for 8 h under air (1atm, balloon) in the dark. The solvent was then evaporated andthe residue was purified by column chromatography (silica gel,CHCl3) to give a colorless oil: yield: 70.7 mg (97%).
85%	With bromine; mesoporous silica In dichloromethane; water monomer
83%	With bromine In dichloromethane; water monomer for 0.0833333h; Molecular sieve;
83%	With bromine; mesoporous silica In water monomer; 4-(dicyanomethylene)-2-methyl-6-(4-dimethylaminostyryl)-4H-pyran at 20℃; for 0.0833333h;	Synthesis of 1,2-dithiane Preparation of 1,2-dithiane was adapted from a known literature procedure. Silica gel (40-60 μπι particle size, 60 A pore size, 41 g) was added to a round bottom flask and distilled water (102 mL) was added slowly with rigorous stirring until a uniform suspension had formed. Dichloromethane (200 mL) and 1,4-butanedithiol (2.00 g, 16.4 mmol, 1 equiv) were added to the suspension while stirring. A solution of Br2 (2.88 g, 18 mmol, 1.10 equiv) in dichloromethane (16 mL) was added dropwise to the off-white suspension while stirring vigorously. The reaction mixture was stirred for 5 minutes, and reaction completion was confirmed by TLC analysis. The reaction mixture was filtered over celite into a flask containing a stirred solution of 1.25 M NaOH (12 mL). The colorless organic phase was removed, washed with distilled water (3 x 50 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure and the crude product crystallized from hexanes at -20 °C to yield 1,2-dithiane as a white crystalline solid (1.63 g, 83%). Rf= 0.80 (5: 1 hexanes:EtOAc); MR (400 MHz, CDCl3, δ): 1.97 (bs, 4H), 2.85 (bs, 4H); 13C NMR (100 MHz, CDCl3, δ): 27.9, 33.5. mp 29 - 32 °C (lit. 28-30 °C).
82%	With KO₂ In benzene for 6h; Ambient temperature;
80%	With dimethyl sulfoxide at 80 - 90℃;
79%	Multistep reaction;
69%	With di(p-methoxyphenyl) telluride; 5,10,15,20-tetraphenyl-21H,23H-porphine In benzene at 0℃; for 1h; Irradiation;
65%	With N-(tert-butyl)-N-chloro-cyanamide; sodium bromide In acetone at 20℃;
50%	With sulphur In ammonia for 2h; Ambient temperature;
40%	With di-isopropyl azodicarboxylate; triphenylphosphine In benzene for 1h; Ambient temperature;
17%	With potassium permanganate; copper(II) sulphate In dichloromethane for 1.5h;
	With methanol; tert.-butylhydroperoxide; iron(III) chloride
	With Carbon tetrachloride; bromine
1.5 g	With hydrogenchloride In dimethyl sulfoxide for 36h; Ambient temperature;
	With tributyltin chloride; iodine; triethylamine 1.) CCl₄, 3 h, 2.) CH₂Cl₂, 0 deg C, 10 min; Yield given. Multistep reaction;
85 % Spectr.	With di-isopropyl azodicarboxylate; triphenylphosphine In hexadeuterobenzene at 10℃; other α,ω-dithiols and monothiols, other solvents, other concenteration of reagents, var. temperatures;
	With oxidized dithiodiketopiperazine In chloroform-d1 at 30℃; for 120h;
	With phosphate buffer; lipoamide dehydrogenase; oxidized lipoamide; NAD; egg albumin In methanol; water monomer at 30℃; E'₀ (-0.328) is related to the half-cell potential for the NAD+/NADH couple;
	With 3,7,8,10-tetramethylisoalloxazine; p-toluenesulfonic acid sodium salt In ethanol; water monomer at 30℃; further reagents, and reagent concentrations; anaerob;
	With DTT^0x In d⁽⁴⁾-methanol; water-d2 at 25℃; phosphate buffer(0.5 mM, pH 7.0);
96 %Spectr.	With [IrCl(cis,cis-1,5-cyclooctadiene)(1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene)]; Cs₂CO₃ In d⁽⁴⁾-methanol at 45℃; for 3h; Sealed tube;

Reference： [1]Location in patent: experimental part Harutyunyan; Rezvani; Heravi, Majid M. [Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2011, vol. 41, # 1, p. 94 - 99]
[2]Hajipour, Abdol R.; Ruoho, Arnold E. [Phosphorus, Sulfur and Silicon and the Related Elements, 2003, vol. 178, # 6, p. 1277 - 1281]
[3]Hajipoura; Bagheri, Hamid; Ruoho, Arnold E. [Journal of Chemical Research, 2004, # 4, p. 286 - 287]
[4]Current Patent Assignee: SWANSEA UNIVERSITY - EP866049, 1998, A2
[5]Noureldin, Nazih A.; Caldwell, Marguerite; Hendry, Jennifer; Lee, Donald G. [Synthesis, 1998, # 11, p. 1587 - 1589]
[6]Sathe, Manisha; Ghorpade, Ramarao; Kaushik, Mahabir Parshad [Chemistry Letters, 2006, vol. 35, # 9, p. 1048 - 1049]
[7]Ali, Mohammed Hashmat; McDermott, Mario [Tetrahedron Letters, 2002, vol. 43, # 35, p. 6271 - 6273]
[8]Hajipour, Abdol R.; Ruoho, Arnold E. [Journal of Chemical Research - Part S, 2002, # 11, p. 547 - 549]
[9]Abul-Futouh, Hassan; Almazahreh, Laith R.; Harb, Mohammad Kamal; Görls, Helmar; El-Khateeb, Mohammad; Weigand, Wolfgang [Inorganic Chemistry, 2017, vol. 56, # 17, p. 10437 - 10451]
[10]Arterburn; Perry; Nelson; Dible; Holguin [Journal of the American Chemical Society, 1997, vol. 119, # 39, p. 9309 - 9310]
[11]Iida, Hiroki; Kozako, Ryo; Oka, Marina [Synlett, 2021, vol. 32, # 12, p. 1227 - 1230]
[12]Location in patent: experimental part Ananikov, Valentine P.; Gayduk, Konstantin A.; Beletskaya, Irina P.; Khrustalev, Victor N.; Antipin, Mikhail Yu. [European Journal of Inorganic Chemistry, 2009, # 9, p. 1149 - 1161]
[13]Donnelly, Daniel P.; Dowgiallo, Matthew G.; Salisbury, Joseph P.; Aluri, Krishna C.; Iyengar, Suhasini; Chaudhari, Meenal; Mathew, Merlit; Miele, Isabella; Auclair, Jared R.; Lopez, Steven A.; Manetsch, Roman; Agar, Jeffrey N. [Journal of the American Chemical Society, 2018, vol. 140, # 24, p. 7377 - 7380]
[14]Current Patent Assignee: NORTHEASTERN UNIVERSITY IN SHENYANG, CHINA - WO2019/14311, 2019, A1 Location in patent: Paragraph 00178; 00179
[15]Crank, George; Makin, Mohammad I. H. [Australian Journal of Chemistry, 1984, vol. 37, # 11, p. 2331 - 2337]
[16]Boldyrev, B. G.; Luzhetskaya, O. V. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, # 3, p. 608 - 609][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 3, p. 669 - 670]
[17]Zoller; Ducep; Tahtaoui; Hibert [Tetrahedron Letters, 2000, vol. 41, # 51, p. 9989 - 9992]
[18]Location in patent: experimental part Oba, Makoto; Tanaka, Kazuhito; Nishiyama, Kozaburo; Ando, Wataru [Journal of Organic Chemistry, 2011, vol. 76, # 10, p. 4173 - 4177]
[19]Location in patent: experimental part Kumar, Vinod; Kaushik, Mahabir Parshad [Bulletin of the Chemical Society of Japan, 2008, vol. 81, # 1, p. 160 - 162]
[20]Sato, Ryu; Saito, Satoru; Chiba, Hiroshi; Goto, Takehiko; Saito, Minoru [Bulletin of the Chemical Society of Japan, 1988, vol. 61, # 5, p. 1647 - 1652]
[21]Camp, David; Jenkins, Ian D. [Australian Journal of Chemistry, 1990, vol. 43, # 1, p. 161 - 168]
[22]Brock, Nelson L.; Menke, Markus; Klapschinski, Tim A.; Dickschat, Jeroen S. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 25, p. 4318 - 4323]
[23]Schoeberl; Graefje [Justus Liebigs Annalen der Chemie, 1958, vol. 614, p. 66,79]
[24]Jacini et al. [Gazzetta Chimica Italiana, 1952, vol. 82, p. 297,301]
[25]Singh, Rajeeva; Whitesides, George M. [Journal of the American Chemical Society, 1990, vol. 112, # 17, p. 6304 - 6309]
[26]Harpp, David N.; Bodzay, Steve J.; Aida, T.; Chan, T. H. [Tetrahedron Letters, 1986, vol. 27, # 4, p. 441 - 444]
[27]Camp, David; Jenkins, Ian D. [Australian Journal of Chemistry, 1990, vol. 43, # 1, p. 161 - 168]
[28]Szajewski, Richard P.; Whitesides, George M. [Journal of the American Chemical Society, 1980, vol. 102, # 6, p. 2011 - 2026]
[29]Szajewski, Richard P.; Whitesides, George M. [Journal of the American Chemical Society, 1980, vol. 102, # 6, p. 2011 - 2026]
[30]Shinkai, Seiji; Inuzuka, Kenichi; Miyazaki, Osamu; Manabe, Osamu [Journal of the American Chemical Society, 1985, vol. 107, # 13, p. 3950 - 3955]
[31]Houk,J.; Whitesides,G.M. [Journal of the American Chemical Society, 1987, vol. 109, p. 6825]
[32]Iali, Wissam; Suleiman, Rami K.; El Ali, Bassam [Applied Organometallic Chemistry, 2022, vol. 36, # 4]

3
[ 1191-08-8 ]
[ 20576-45-8 ]
[ 73816-28-1 ]

Yield	Reaction Conditions	Operation in experiment
77%	With triethylamine In acetone at 0℃; for 2h;

Reference： [1]Simons, Stoney S.; Pons, Michel; Johnson, David F. [Journal of Organic Chemistry, 1980, vol. 45, # 15, p. 3084 - 3088]

4
[ 1191-08-8 ]
[ 31236-94-9 ]
[ 98051-58-2 ]

Yield	Reaction Conditions	Operation in experiment
18%	With phosphorus pentoxide In toluene at 120℃; for 8h;

Reference： [1]Nickon, Alex; Rodriguez, Abimael D.; Shirhatti, Vilas; Ganguly, Rathindra [Journal of Organic Chemistry, 1985, vol. 50, # 22, p. 4218 - 4226]

5
[ 1191-08-8 ]
[ 67660-38-2 ]
[ 122172-12-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium hydroxide In tetrahydrofuran; ethanol; benzene for 14h; Heating;

Reference： [1]Shultz, David A.; Fox, Marye Anne [Journal of the American Chemical Society, 1989, vol. 111, # 16, p. 6311 - 6320]

6
[ 1191-08-8 ]
[ 81644-55-5 ]
C₈₈H₁₄₆O₆₈S₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,1994,vol. 35,p. 4275 - 4278

7
[ 1191-08-8 ]
[ 105456-45-9 ]
[ 105456-47-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	With triethylamine In dichloromethane at 0℃; for 0.5h;

Reference： [1]Harmon, J. Patrick; Field, Lamar [Journal of Organic Chemistry, 1986, vol. 51, # 26, p. 5235 - 5240]

8
[ 1191-08-8 ]
[ 115321-58-9 ]
[ 115321-68-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	With N-ethyl-N,N-diisopropylamine; hydroquinone In methanol at -40℃;

Reference： [1]Brocchini, Stephen J.; Eberle, Martin; Lawton, Richard G. [Journal of the American Chemical Society, 1988, vol. 110, # 15, p. 5211 - 5212]

9
[ 1191-08-8 ]
[ 110-01-0 ]

Yield	Reaction Conditions	Operation in experiment
66 % Chromat.	at 175℃; for 1h;
	With hydrogen at 350℃; for 1h; Flow reactor;	1.2. Catalytic Measurements General procedure: The reactions were performed in a conventional continuous flow microreactor operated at atmospheric pressure.23 In a typical experiment, a weighed sample (10.0 mg) of 1 or supported 1 on silica gel (1/SiO2) was packed into a borosilicate glass tube (3 mm id), which was placed in the center of an electric furnace. The catalyst sample was initially heated to 350 °C for 1 h in a helium stream (600 mL h-1) for activation, and then reactant was introduced at 350 °C into the stream usinga syringe pump (0.50 mmol h-1). The reaction was monitored by sampling the reaction gas (1 ml) every 30 min using a six-way valve and analyzing the collected gas using an on-line gas-liquid chromatography (GLC). The products were identified by GLC, nuclear magnetic resonance spectrometry, and mass spectrometry by comparison with authentic samples. Conversion =products/(products + recovered reactant) 100%; selectivity = product/(total amount of products) 100%. For the measurement of a typical reaction profile (Figure S1), effect of temperature (Figure 1), and reactivities of various halide cluster catalysts (Table S1), the amount of 1,4-butanediol was increased (1.50 mmol h-1) to reduce the conversion. Reactants were diluted with water (for alcohols) or tetrahydrofuran (for non-alcohols) to almost-saturated solutions or low-viscosity liquids at ambient temperature for introduction where necessary.

Reference： [1]Kotkar, Dilip; Mahajan, Satish W.; Mandal, Arun K.; Ghosh, Pushpito K. [Journal of the Chemical Society. Perkin transactions I, 1988, p. 1749 - 1752]
[2]Nagashima, Sayoko; Sasaki, Tomoaki; Kamiguchi, Satoshi; Chihara, Teiji [Chemistry Letters, 2015, vol. 44, # 6, p. 764 - 766]

10
[ 1191-08-8 ]
[ 505-20-4 ]
[ 51272-05-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With Diethyl 2-bromomalonate In dichloromethane at -16℃; for 1.16667h;
	With Diethyl 2-bromomalonate In dichloromethane at -16℃; for 1.16667h;

Reference： [1]Kato, Eishin; Oya, Masayuki; Iso, Tadashi; Iwao, Jun-ichi [Chemical and pharmaceutical bulletin, 1986, vol. 34, # 2, p. 486 - 495]
[2]Kato, Eishin; Oya, Masayuki; Iso, Tadashi; Iwao, Jun-ichi [Chemical and pharmaceutical bulletin, 1986, vol. 34, # 2, p. 486 - 495]

11
[ 1191-08-8 ]
[ 3079-82-1 ]

Yield	Reaction Conditions	Operation in experiment
67%	With chlorine In water; acetic acid at 30℃; for 0.25h;

Reference： [1]Lee, Chew; Field, Lamar [Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 45, p. 35 - 46]

12
[ 1191-08-8 ]
[ 104-12-1 ]
Tetramethylen-1,4-bis(N-4-chlorphenyl-thiolurethan) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

13
[ 1191-08-8 ]
[ 4083-64-1 ]
Tetramethylen-1,4-bis(N-4-tolyl-sulfonyl-thiolurethan) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

14
[ 1191-08-8 ]
[ 103-71-9 ]
Tetramethylen-1,4-bis(N-phenyl-thiolurethan) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

15
[ 1191-08-8 ]
[ 622-58-2 ]
Tetramethylen-1,4-bis(N-4-tolyl-thiolurethan) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

16
[ 1191-08-8 ]
[ 1195-45-5 ]
Tetramethylen-1,4-bis(N-4-fluorphenyl-thiolurethan) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

17
[ 1191-08-8 ]
[ 3173-53-3 ]
[ 102732-86-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

18
[ 1191-08-8 ]
[ 830-13-7 ]
[ 98051-54-8 ]

Yield	Reaction Conditions	Operation in experiment
76%	With aluminium trichloride In dichloromethane for 0.25h;

Reference： [1]Nickon, Alex; Rodriguez, Abimael D.; Shirhatti, Vilas; Ganguly, Rathindra [Journal of Organic Chemistry, 1985, vol. 50, # 22, p. 4218 - 4226]

19
[ 1191-08-8 ]
[ 329-01-1 ]
Tetramethylen-1,4-bis(N-3-trifluoromethyl-phenyl-thiolurethan) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

20
[ 1191-08-8 ]
[ 111-36-4 ]
Tetramethylen-1,4-bis(N-butyl-thiolurethan) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

21
[ 1191-08-8 ]
[ 38464-20-9 ]
S,S'-bis(3-nitro-2H-1-benzopyran-2-on-4-yl)-1,4-butanedithiol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine In benzene at 20℃; for 1h;

Reference： [1]Drozd, V. N.; Nam, N. L.; Knyazev, V. N.; Yufit, D. S.; Struchkov, Yu. T.; Savel'ev, V. L. [Journal of Organic Chemistry USSR (English Translation), 1992, vol. 28, # 7, p. 1184 - 1193][Zhurnal Organicheskoi Khimii, 1992, vol. 28, # 7, p. 1496 - 1507]

22
[ 1191-08-8 ]
[ 1795-48-8 ]
[ 102732-84-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	In diethyl ether at 20℃; for 1h;

Reference： [1]Hanefeld; Schulze-Weisschu [Archiv der Pharmazie, 1986, vol. 319, # 2, p. 167 - 176]

23
[ 75-15-0 ]
[ 1191-08-8 ]
[ 100-39-0 ]
benzyl 4-(benzylthio)butyl trithiocarbonate [ No CAS ]
1,4-butanediyl bis(benzyl trithiocarbonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 84% 2: 14%	With sodium hydroxide In water at 20℃; for 5h;

Reference： [1]Sugawara, Akira; Hasegawa, Ken; Suzuki, Ken-ichi; Takahashi, Yukio; Sato, Ryu [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 1, p. 435 - 437]

24
[ 75-15-0 ]
[ 1191-08-8 ]
[ 75-03-6 ]
ethyl 4-(ethylthio)butyl trithiocarbonate [ No CAS ]
1,4-butanediyl bis(ethyl trithiocarbonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 87% 2: 12%	With sodium hydroxide In water at 20℃; for 5h;

Reference： [1]Sugawara, Akira; Hasegawa, Ken; Suzuki, Ken-ichi; Takahashi, Yukio; Sato, Ryu [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 1, p. 435 - 437]

25
[ 75-15-0 ]
[ 1191-08-8 ]
[ 107-08-4 ]
propyl 4-(propylthio)butyl trithiocarbonate [ No CAS ]
1,4-butanediyl bis(propyl trithiocarbonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 10%	With sodium hydroxide In water at 20℃; for 5h;

Reference： [1]Sugawara, Akira; Hasegawa, Ken; Suzuki, Ken-ichi; Takahashi, Yukio; Sato, Ryu [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 1, p. 435 - 437]

26
[ 75-15-0 ]
[ 1191-08-8 ]
[ 96-32-2 ]
methoxycarbonylmethyl 4-(methoxycarbonylmethylthio)butyl trithiocarbonate [ No CAS ]
1,4-butanediyl bis(methoxycarbonylmethyl trithiocarbonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 90% 2: 6%	With sodium hydroxide In water at 20℃; for 5h;
1: 8% 2: 90%	With sodium hydroxide In water at 20℃; for 5h;

Reference： [1]Sugawara, Akira; Hasegawa, Ken; Suzuki, Ken-ichi; Takahashi, Yukio; Sato, Ryu [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 1, p. 435 - 437]
[2]Sugawara, Akira; Hasegawa, Ken; Suzuki, Ken-ichi; Takahashi, Yukio; Sato, Ryu [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 1, p. 435 - 437]

27
[ 75-15-0 ]
[ 1191-08-8 ]
[ 74-88-4 ]
methyl 4-(methylthio)butyl trithiocarbonate [ No CAS ]
1,4-butanediyl bis(methyl trithiocarbonate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 86% 2: 12%	With sodium hydroxide In water at 20℃; for 5h;

Reference： [1]Sugawara, Akira; Hasegawa, Ken; Suzuki, Ken-ichi; Takahashi, Yukio; Sato, Ryu [Bulletin of the Chemical Society of Japan, 1987, vol. 60, # 1, p. 435 - 437]

28
[ 1191-08-8 ]
[ 63279-58-3 ]
[ 111220-27-0 ]
C₂₈H₂₈S₄ [ No CAS ]

Reference： [1]Tetrahedron Letters,1996,vol. 37,p. 1603 - 1604

29
[ 1191-08-8 ]
[ 468-44-0 ]
17-mercapto-3α,10-dihydroxy-20-norgibberella-7,19-dioic acid 19,10-lactone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 2,2'-azobis(isobutyronitrile); bis(tri-n-butyltin)oxide In 1,4-dioxane Yield given;

Reference： [1]Pulici, Maurizio; Asami, Tadao; Robertson, Masumi; Seto, Hideharu; Yoshida, Shigeo [Bioorganic and Medicinal Chemistry Letters, 1996, vol. 6, # 21, p. 2549 - 2552]

31
[ 1191-08-8 ]
[ 380305-91-9 ]
[ 380305-97-5 ]

Yield	Reaction Conditions	Operation in experiment
66%	In chloroform-d1 at 20℃;

Reference： [1]Goto, Kei; Nagahama, Michiko; Mizushima, Tadashi; Shimada, Keiichi; Kawashima, Takayuki; Okazaki, Renji [Organic Letters, 2001, vol. 3, # 22, p. 3569 - 3572]

32
[ 1191-08-8 ]
[ 101020-89-7 ]
C₃₄H₅₀O₁₀S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	Stage #1: 1,4-Butanedithiol With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.75h; Stage #2: (3R,5aS,6R,8aS,12S,12aR)-3,6-dimethyl-9-methyleneoctahydro-12H-3,12-epoxy[1,2]dioxepino[4,3-i]isochromen-10(3H)-one In tetrahydrofuran at -78℃; for 5h; Further stages.;

Reference： [1]Ekthawatchai; Kamchonwongpaisan; Kongsaeree; Tarnchompoo; Thebtaranonth; Yuthavong [Journal of Medicinal Chemistry, 2001, vol. 44, # 26, p. 4688 - 4695]

33
[ 100-69-6 ]
[ 1191-08-8 ]
1,10-bis(2'-pyridyl)-3,8-dithiadecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	In ethanol for 48h; Heating;
5.3 g	In isopropyl alcohol at 20℃; Reflux;	1.1.22 Example 1.22: 1,10-Bis(2-pyridyl)-3,8-dithiadecane To a solution of 2,33 ml 1 ,4-butanedithiol in 25 ml iso-propanol were added 4,44 ml 2- vinylpyridine. After stirring 7 hours at reflux the reaction mixture was cooled to room temperature and stirred overnight. After concentration in vacuo the residue was purified by chromatography on silica gel with dichloromethane/methanol as the eluents (eluation with a gradient) to yield 5.3 g of 1 ,10-Bis(2-pyridyl)-3,8-dithiadecane as a yellowish oil. (assay by C- NMR >95%).

Reference： [1]Gilbert, Jayakumar G.; Addison, Anthony W.; Palaniandavar, Mallayan; Butcher, Raymond J. [Journal of Heterocyclic Chemistry, 2002, vol. 39, # 2, p. 399 - 404]
[2]Current Patent Assignee: BASF SE - WO2019/185468, 2019, A1 Location in patent: Page/Page column 38

34
[ 69983-02-4 ]
[ 1191-08-8 ]
[ 108-24-7 ]
[ 571169-78-3 ]
C₅₄H₇₈O₃₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 79% 2: 11%	Stage #1: methyl O-(2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside; 1,4-Butanedithiol With potassium hexamethylsilazane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene at -78 - 20℃; Stage #2: acetic anhydride With pyridine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene for 12h;

Reference： [1]Hinou, Hiroshi; Sun, Xue-Long; Ito, Yukishige [Journal of Organic Chemistry, 2003, vol. 68, # 14, p. 5602 - 5613]

35
[ 1191-08-8 ]
[ 108-24-7 ]
[ 152501-23-0 ]
[ 571169-74-9 ]
C₅₄H₈₀N₂O₃₀S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 70% 2: 14%	Stage #1: 1,4-Butanedithiol; methyl O-(2,3,4-tri-O-acetyl-6-O-p-toluenesulfonyl-β-D-galactopyranosyl)-(1<*>4)-3,6-di-O-acetyl-2-acetamido-2-deoxy-β-D-glucopyranoside With potassium hexamethylsilazane In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene at -78 - 20℃; Stage #2: acetic anhydride With pyridine In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; toluene for 12h;

Reference： [1]Hinou, Hiroshi; Sun, Xue-Long; Ito, Yukishige [Journal of Organic Chemistry, 2003, vol. 68, # 14, p. 5602 - 5613]

36
[ 1191-08-8 ]
1,3-(dimethylmethylenedioxy)-2-methyl-2-(methylene-p-toluenesulfonyl)propane [ No CAS ]
[ 688310-83-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium In ethanol

Reference： [1]Sharrad, Clint A.; Cavigliasso, German E.; Stranger, Robert; Gahan, Lawrence R. [Dalton Transactions, 2004, # 5, p. 767 - 777]

37
[ 1191-08-8 ]
[ 610314-61-9 ]
(2S,3R,4R,5R)-N-(2,2-diethoxycarbonylvinyl)-5-hydroxy-3,4-(isopropylidenedioxy)-2-(4-mercaptobutylthio)piperidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With 4 A molecular sieve; toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 0.25h;

Reference： [1]Fuentes, Jose; Illangua, Jose M.; Sayago, Francisco J.; Angulo, Manuel; Gasch, Consolacion; Pradera, M. Angeles [Tetrahedron Asymmetry, 2004, vol. 15, # 23, p. 3783 - 3789]

38
[ 574-98-1 ]
[ 1191-08-8 ]
1,10-diphthalimido-3,8-dithiodecane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 1,4-Butanedithiol With n-butyllithium In hexane; toluene at -30℃; for 0.5h; Stage #2: 2-(2-bromoethyl)isoindoline-1,3-dione In hexane; toluene at 20℃;

Reference： [1]Koschabek, Rene; Gleiter, Rolf; Rominger, Frank [European Journal of Inorganic Chemistry, 2006, # 3, p. 609 - 620]

39
[ 591-50-4 ]
[ 1191-08-8 ]
[ 5330-89-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide; copper(II) oxide In dimethyl sulfoxide at 80℃; for 5h;

Reference： [1]Rout, Laxmidhar; Sen, Tamal K.; Punniyamurthy, Tharmalingam [Angewandte Chemie - International Edition, 2007, vol. 46, # 29, p. 5583 - 5586]

40
[ 634607-40-2 ]
[ 1191-08-8 ]
C₅₃H₅₄N₆O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78.8%	With triethylamine for 1h;	3 Preparation of Compound 6 Compound 6 was prepared according to the preparation procedure above for Compound 2 except that 1,2-ethanedithiol was replaced by 1.42 g (11.63 mmol) of 1,4-butanedithiol (commercially obtained from Aldrich, Milwaukee, Wis.). The reaction time was 1 h. The yield of Compound 6 was 8.8 g (78.8%). The infrared absorption spectrum resulted in the identification of the following peaks: IR (KBr) (frequency, cm-1): 3620-3140 (OH); 3080, 3030 (CHaromatic.); 2940, 2910, 2860 (CHaliphatic.); 830, 755, 700 (CHCH of mono, p-disubstituted benzene). A 1H-NMR spectrum of Compound 6 was obtained in CDCl3 with a 250 MHz NMR. The peaks were found at (ppm) δ=7.58 (s, 2H, CHN); δ=7.50-6.86 (m, 38H, Ar); δ=4.08 (m, 2H, CH); δ=3.94 (m, 4H, NCH2); δ=2.89 (m, 2H, OH); δ=2.78-2.45 (m, 8H, CH2SCH2); δ=1.62 (m, 4H, SCH2CH2CH2CH2S). An elemental analysis found the following weight percents of the elements: C, 74.81; H, 6.09; N, 8.51, which compares with the following calculated elemental weight percent for a compound with a formula C60H60N6O2S2: C, 74.97; H, 6.29; N, 8.74

Reference： [1]Current Patent Assignee: HP INC. - US2003/232261, 2003, A1 Location in patent: Page 13

41
C₄H₅O₃Pol [ No CAS ]
[ 1191-08-8 ]
C₈H₁₅O₃PolS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In methanol	8.a (a) Thiol-Modified Polymethacrylate Beads 10 g of poly(glycidylmethacrylate-co-ethylene dimethacrylate)polymer beads (Suprema 1000u) were suspended in 100 ml of methanol and ultra-sonicated for 10 minutes in order to break up all aggregates and obtain a homogeneous suspension. The suspension was transferred to a flask equipped with a mechanical stirrer. 80 mmol (=9.4 ml) of 1,4-butanedithiol and 80 mmol (=4.48 g) of potassium hydroxide dissolved in 30 ml of methanol were added. The reaction mixture was stirred for 72 hours at room temperature under a nitrogen atmosphere. Thereupon, the polymer particles were filtered, thoroughly washed with methanol, THF, chloroform and diethyl ether (twice in each case) and dried. An elemental analysis yielded 8.0% (% by weight) S, which is equal to an occupancy of 1.25 mmol thiol/g polymer.

Reference： [1]Current Patent Assignee: DAICEL CORPORATION - US7064234, 2006, B2 Location in patent: Page/Page column 32

42
[ 88324-57-6 ]
[ 1191-08-8 ]
1-[4-(4-Mercaptobutylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In ISOPROPYLAMIDE	14 1-[4-(4-Mercaptobutylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one EXAMPLE 14 1-[4-(4-Mercaptobutylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one 40 g (0.15 mol) of 1-(4-chlorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one and 109 g (0.89 mol) of 1,4-butanedithiol are dissolved in 300 ml of dimethylacetamide, and the solution is stirred at around 100° C. together with 41 g of potassium carbonate for 5 h. Then the solution is cooled to room temperature and poured into water. The crude product is extracted with ethyl acetate, washed with saturated sodium chloride solution, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with ethyl acetate -hexane (20:80) as an eluent. Melting point 98 ° C. The structure is confirmed by the 1 H-NMR spectrum (CDCl3): δ [ppm] 1.31 (s, 6H), 1.36 (t, 1H), 1.76-1.90 (m, 4H), 2.53-2.62 (m, 6H), 2.98-3.04 (m, 2H), 3.69 (t, 4H), 7.25 (d, 2H), 8.50 (d, 2H).

Reference： [1]Current Patent Assignee: BASF SE - US6022906, 2000, A

43
[ 1191-08-8 ]
[ 52-86-8 ]
(1,4-butanethioacetal)-4-[4-(p-chlorophenyl)-4-hydroxypiperidinyl]-4'-fluorobutyrophenone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With trifluoroborane diethyl ether; In methanol; hexane; dichloromethane;	EXAMPLE 20 For the synthesis of (1,4-butanethioacetal)-4-[4-(p-chlorophenyl)-4-hydroxypiperidinyl]-4'-fluorobutyrophenone (UCSF23), 1 mL of boron trifluoride etherate was added dropwise to a stirred suspension of <strong>[52-86-8]haloperidol</strong> (300 mg) and 1,4-butanedithiol (175 mul) in 10 mL of methanol. The clear solution was stirred at room temperature in a sealed flask for 5 days. The solution was poured into 30 mL of saturated aqueous NaHCO3 and the mixture was extracted with 60 mL of diethyl ether, The ether was washed with 30 mL of saturated NaCl solution and was dried over anhydrous sodium sulfate. Removal of the solvent on a rotary evaporator gave a white solid that, dissolved in a minimum of CH2 Cl2, was purified by flash chromatography on 9.8 g of silica gel. The column was eluted with 25% to 50% ethyl acetate in hexane. The thioketal was obtained as an oil and was resubmitted to silica gel chromatography. This gave 50 mg (13% yield) of an oil with a slight olefin contamination; Rf =0.49 in 100% ethyl acetate. The identity of the product was confirmed as that of (1,4-butanethioacetal)-4-[4-(p-chlorophenyl)-4-hydroxypipefidinyl]-4'-fiuorobutyrophenone by IR, proton NMR, LSIMS, and MS molecular weight determination.

Reference： [1]Patent: US5583000,1996,A

44
[ 18321-15-8 ]
[ 1191-08-8 ]
Disodium (1,4-Butylenedithio)bis(4-butanesulfinate) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium In methanol; water	5 Disodium (1,4-Butylenedithio)bis(4-butanesulfinate) (E) EXAMPLE 5 Disodium (1,4-Butylenedithio)bis(4-butanesulfinate) (E) Sodium (230 mg, 10 mg atoms) dissolved in methanol (15 mL) was added dropwise to a mixture of 1,2-dithiane 1,1-dioxide (1.52 g, 10 mmol) and 1,4-butanedithiol (0.61 g, 5.0 mmol) in methanol. Isolation by precipitation and reprecipitation as usual afforded 2.0 g (74% based on the tetrahydrate of the titled salt E.) Thin layer chromatography (TLC) showed one spot (Rf 0.54: 1:1 methanol-acetone). Additional TLC spots appeared in 5 min. or less after dissolution of the disulfide sulfinate E in H2 O, the solution became turbid, and the 1H NMR spectrum (D2 O) changed. IR (KBr) 3400, 2950, 1660, 1440, 1220, 1000 (br), 980, 800, 720 cm-1; NMR (D2 O δ 3.40-2.64 (m, 8H), 2.60-2.20 (m, 4H), 2.04-1.40 (m, 12H). Anal. Calcd for C12 H24 Na2 O4 S6.4H2 O: C, 26.55; H, 5.94; S, 35.44. Found: C, 26.06; H, 5.15; S, 34.80.

Reference： [1]Current Patent Assignee: VANDERBILT UNIVERSITY - US4883890, 1989, A

45
η6-m-chlorotoluene-η5-cyclopentadienyliron hexafluorophosphate [ No CAS ]
[ 1191-08-8 ]
((C₆H₄CH₃)Fe(C₅H₅))2S(CH₂)4S⁽²⁺⁾*2PF₆^(1-)=[((C₆H₄(CH₃))Fe(C₅H₅))2S(CH₂)4S](PF₆)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide stirring under N2 atmosphere for 16 h at room temperature; filtn. through a sintered glass crucible into a HCl soln., evapn. (reduced pressure), addn. of aq. NH4PF6, filtn., drying (vac.), washing (ether), drying;

Reference： [1]Abd-El-Aziz, Alaa S.; Epp, Karen M.; De Denus, Christine R.; Fisher-Smith, Grant [Organometallics, 1994, vol. 13, # 6, p. 2299 - 2308]

46
(η6-chlorobenzene)(η5-cyclopentadienyl)iron(II) hexafluorophosphate [ No CAS ]
[ 1191-08-8 ]
((C₆H₅)Fe(C₅H₅))2S(CH₂)4S⁽²⁺⁾*2PF₆^(1-)=[((C₆H₅)Fe(C₅H₅))2S(CH₂)4S](PF₆)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide stirring under N2 atmosphere for 16 h at room temperature; filtn. through a sintered glass crucible into a HCl soln., evapn. (reduced pressure), addn. of aq. NH4PF6, filtn., drying (vac.), washing (ether), drying;

Reference： [1]Abd-El-Aziz, Alaa S.; Epp, Karen M.; De Denus, Christine R.; Fisher-Smith, Grant [Organometallics, 1994, vol. 13, # 6, p. 2299 - 2308]

47
(1,3-dichloro-η6-benzene)(η5-cyclopentadienyl)iron(II) hexafluorophosphate [ No CAS ]
[ 1191-08-8 ]
((C₆H₄Cl)Fe(C₅H₅))2S(CH₂)4S⁽²⁺⁾*2PF₆^(1-)=[((C₆H₄Cl)Fe(C₅H₅))2S(CH₂)4S](PF₆)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide stirring under N2 atmosphere for 16 h at room temperature; filtn. through a sintered glass crucible into a HCl soln., evapn. (reduced pressure), addn. of aq. NH4PF6, filtn., drying (vac.), washing (ether), drying;

Reference： [1]Abd-El-Aziz, Alaa S.; Epp, Karen M.; De Denus, Christine R.; Fisher-Smith, Grant [Organometallics, 1994, vol. 13, # 6, p. 2299 - 2308]

48
2-methylchlorobenzene-eta.5-cyclopentadienyliron hexafluorophosphate [ No CAS ]
[ 1191-08-8 ]
((C₆H₄CH₃)Fe(C₅H₅))2S(CH₂)4S⁽²⁺⁾*2PF₆^(1-)=[((C₆H₄(CH₃))Fe(C₅H₅))2S(CH₂)4S](PF₆)2 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In tetrahydrofuran; N,N-dimethyl-formamide stirring under N2 atmosphere for 16 h at room temperature; filtn. through a sintered glass crucible into a HCl soln., evapn. (reduced pressure), addn. of aq. NH4PF6, filtn., drying (vac.), washing (ether), drying;

Reference： [1]Abd-El-Aziz, Alaa S.; Epp, Karen M.; De Denus, Christine R.; Fisher-Smith, Grant [Organometallics, 1994, vol. 13, # 6, p. 2299 - 2308]

49
[ 59831-02-6 ]
[ 1191-08-8 ]
[ 191341-60-3 ]

Yield	Reaction Conditions	Operation in experiment
47%	With NEt₃ In dichloromethane byproducts: Et3NHCl; N2-atmosphere; addn. of equimolar amt. of dithiol and 3-4 drops NEt3 to Pd-complex suspn.; washing (H2O), drying (MgSO4), pptn. on Et2O addn.; elem. anal.;

Reference： [1]Fornies-Camer; Aaliti; Ruiz; Masdeu-Bulto; Claver; Cardin [Journal of Organometallic Chemistry, 1997, vol. 530, # 1-2, p. 199 - 209]

50
[ 1191-08-8 ]
[ 106131-61-7 ]
[ 1206227-55-5 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 6121 - 6128

51
[ 936616-94-3 ]
[ 1191-08-8 ]
tert-butyl 2,2'-(1,1'-(12,12'-(butane-1,4-diylbis(sulfanediyl))bis(dodecane-12,1-diyl))bis(3-(2-amino-2-oxoacetyl)-2-methyl-1H-indole-4,1-diyl))bis(oxy)diacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	Stage #1: 1,4-Butanedithiol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: tert-butyl 2-(3-(2-amino-2-oxoacetyl)-1-(12-bromododecyl)-2-methyl-1H-indol-4-yloxy)acetate In N,N-dimethyl-formamide at 0 - 20℃; Stage #3: With ammonium chloride In water; N,N-dimethyl-formamide at 0℃;	11.4 EXAMPLE11.4: COMPOUND (5-25)3[00396] The t-Bu protected compound, fe/t-Butyl 2,2'-(1,1'-(12,12'-(butane-1,4- diylbis(sulfanediyl))bis(dodecane-12,1-diyl))bis(3-(2-amino-2-oxoacetyl)-2-methyl-1/Y- indole-4,1-diyl))bis(oxy)diacetate, 2 was first prepared as follows.[00397] 1 ,4-Butanedithiol (0.06 mL, 0.51 mmole) was added to 95% sodium hydride (0.028 g, 1.10 mmole) in dry DMF (4 mL), at O0C under nitrogen. After 0.5 h this mixture was added to the bromide 1 (0.602 g, 1.03 mmole) (prepared as in Example 11B) in dry DMF (6 > l e ftrf rhθ reaction was maintained at O0C for 9 h a d s y warmed to room temperature overnight. The mixture was cooled to O0C, quenched with ammonium chloride solution (5 mL), diluted with dichloromethane (50 mL) and ammonium chloride solution (40 mL). The organic phase was separated and the aqueous phase extracted with dichloromethane (5 x 40 mL). The combined organic phase was washed with brine (50 mL), dried (Na2SO4), filtered and evaporated to a red/brown syrup. Purification by chromatography over silica gel, using chloroform/ethyl acetate (2:1 to 1 :1) as the eluant, gave the product as an orange/brown semi-solid (0.224 g, 39%).
39%	Stage #1: 1,4-Butanedithiol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: tert-butyl 2-(3-(2-amino-2-oxoacetyl)-1-(12-bromododecyl)-2-methyl-1H-indol-4-yloxy)acetate In N,N-dimethyl-formamide at 0 - 20℃;	7.4 1,4-Butanedithiol (0.06 mL, 0.51 mmole) was added to 95% sodium hydride (0.028 g, 1.10 mmole) in dry DMF (4 mL), at 0° C. under nitrogen. After 0.5 h this mixture was added to the bromide 1 (0.602 g, 1.03 mmole) (prepared as in Example 11B) in dry DMF (6 mL), at 0° C. under nitrogen. The reaction was maintained at 0° C. for 9 h and slowly warmed to room temperature overnight. The mixture was cooled to 0° C., quenched with ammonium chloride solution (5 mL), diluted with dichloromethane (50 mL) and ammonium chloride solution (40 mL). The organic phase was separated and the aqueous phase extracted with dichloromethane (5×40 mL). The combined organic phase was washed with brine (50 mL), dried (Na2SO4), filtered and evaporated to a red/brown syrup. Purification by chromatography over silica gel, using chloroform/ethyl acetate (2:1 to 1:1) as the eluant, gave the product as an orange/brown semi-solid (0.224 g, 39%).

Reference： [1]Current Patent Assignee: AMGEN INC - WO2007/56279, 2007, A2 Location in patent: Page/Page column 154-155
[2]Current Patent Assignee: AMGEN INC - US2007/135385, 2007, A1 Location in patent: Page/Page column 66-67

52
[ 936616-93-2 ]
[ 1191-08-8 ]
C₅₄H₇₈N₄O₁₀S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	Stage #1: 1,4-Butanedithiol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: tert-butyl 2-(3-(2-amino-2-oxoacetyl)-1-(8-bromooctyl)-2-methyl-1H-indol-4-yloxy)acetate In N,N-dimethyl-formamide at -20 - 0℃; Stage #3: With ammonium chloride In water; N,N-dimethyl-formamide at -20℃;	11.13 [00443] 2,2'-(1,r-(8,8l-(butaϖe-1,4-diyIbis(sulfanediyI))bis(octane-8,1-diyl))bis(3-(2- amino-2-oxoacetyl)-2-methyl-1H-indoIe-4,1-diyl))bis(oxy)diacetic acid (ILY-V-23) A solution of 1 ,4-butanedithiol (280 μi_, 2.4 mmol, 290 mg) in 5 mL of anhydrous DMF was cooled in an ice bath and dry sodium hydride (125 mg, 5.23 mmol, 2.2 equiv) was added. After stirring under nitrogen for 15 min at 00C1 the mixture was transferred drop wise into a solution of N1-bromoalkyl indole 1 (2.6 g, 5.0 mmol, 2.1 equiv) in 10 mL of anhydrous DMF also cooled in an ice bath. The resulting orange mixture was stirred under nitrogen for 8 h at 00C. After an overnight refrigerating at -2O0C, the reaction mixture was quenched with 10 mL of NH4CI, and it was then allowed to warm to RT. It was diluted with 50 mL of DCM, washed with NH4CI (25 mL) and twice with brine (2 x 30 mL), dried over MgSO4 and concentrated in vacuo to afford the crude product as an orange oil. Purification by flash-chromatography (H/EA: 2/3, 3/7 and 1/4) yielded the pure dimer (1.2 g, 51%) as a yellow solid.1H NWlR (CD2CI2, 300 MHz): δ 7.14 (dd, 2H, J = 8.1 , 8.1 Hz, H-6), 7.08 (d, 2H, J = 8.1 , H-5), 6.6 (br s, 2H, NH2), 6.51 (d, 2H1 J = 8.1 Hz, H-7), 6.0 (br s, 2H, NH2), 4.59 (s, 4H, H-10), 4.09 (t, 4H, J = 7.8 Hz, H-14), 2.59 (s, 6H, H-9), 2.50 (m, 8H, S-CH2), 1.78 (m, 4H, CH2), 1.66 (m, 4H, CH2), 1.57 (m, 4H, CH2), 1.47 (s, 18H, C(CH3)3), 1.36 (m, 16H, CH2)-13C NMR (CD2CI2, 75.5 WIHz): δ 188.5 (12), 168.3 (11), 167.5 (13), 152.0 (4), 144.2 (1), 137.8 (8), 123.2 (3), 117.0 (6), 110.3 (5), 104.1 (7 + 2), 82.1 (C(CH3)3), 66.3 (10), 44.0 (14), 36.4 (CH2), 32.1 (CH2), 31.7 (CH2), 31.2 (CH2), 29.8 (CH2), 29.4 (CH2), 29.3 (CH2), 29.0 (CH2), 28.0 (C(CHs)3), 27.1 (CH2), 11.6 (9). a .
51%	Stage #1: 1,4-Butanedithiol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: tert-butyl 2-(3-(2-amino-2-oxoacetyl)-1-(8-bromooctyl)-2-methyl-1H-indol-4-yloxy)acetate In N,N-dimethyl-formamide at -20 - 0℃;	7.13 A solution of 1,4-butanedithiol (280 μL, 2.4 mmol, 290 mg) in 5 mL of anhydrous DMF was cooled in an ice bath and dry sodium hydride (125 mg, 5.23 mmol, 2.2 equiv) was added. After stirring under nitrogen for 15 min at 0° C., the mixture was transferred drop wise into a solution of N1-bromoalkyl indole 1 (2.6 g, 5.0 mmol, 2.1 equiv) in 10 mL of anhydrous DMF also cooled in an ice bath. The resulting orange mixture was stirred under nitrogen for 8 h at 0° C. After an overnight refrigerating at -20° C., the reaction mixture was quenched with 10 mL of NH4Cl, and it was then allowed to warm to RT. It was diluted with 50 mL of DCM, washed with NH4Cl (25 mL) and twice with brine (2×30 mL), dried over MgSO4 and concentrated in vacuo to afford the crude product as an orange oil. Purification by flash-chromatography (H/EA: 2/3, 3/7 and 1/4) yielded the pure dimer (1.2 g, 51%) as a yellow solid. 1H NMR (CD2Cl2, 300 MHz): δ 7.14 (dd, 2H, J=8.1, 8.1 Hz, H-6), 7.08 (d, 2H, J=8.1, H-5), 6.6 (br s, 2H, NH2), 6.51 (d, 2H, J=8.1 Hz, H-7), 6.0 (br s, 2H, NH2), 4.59 (s, 4H, H-10), 4.09 (t, 4H, J=7.8 Hz, H-14), 2.59 (s, 6H, H-9), 2.50 (m, 8H, S-CH2), 1.78 (m, 4H, CH2), 1.66 (m, 4H, CH2), 1.57 (m, 4H, CH2), 1.47 (s, 18H, C(CH3)3), 1.36 (m, 16H, CH2). 13C NMR (CD2Cl2, 75.5 MHz): δ 188.5 (12), 168.3 (11), 167.5 (13), 152.0 (4), 144.2 (1), 137.8 (8), 123.2 (3), 117.0 (6), 110.3 (5), 104.1 (7+2), 82.1 (C(CH3)3), 66.3 (10), 44.0 (14), 36.4 (CH2), 32.1 (CH2), 31.7 (CH2), 31.2 (CH2), 29.8 (CH2), 29.4 (CH2), 29.3 (CH2), 29.0 (CH2), 28.0 (C(CH3)3), 27.1 (CH2), 11.6 (9). MS (ESI, MeOH): m/z 1029.5 [M+Na]+.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2007/56279, 2007, A2 Location in patent: Page/Page column 174-175
[2]Current Patent Assignee: AMGEN INC - US2007/135385, 2007, A1 Location in patent: Page/Page column 79-80

53
[ 1191-08-8 ]
[ 51-80-9 ]
[ 1369273-08-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With samarium(III) chloride hexahydrate In chloroform at 60℃; for 1.5h; Inert atmosphere; chemoselective reaction;

Reference： [1]Location in patent: experimental part Khairullina; Akmanov; Tyumkina; Kunakova; Ibragimov [Russian Journal of Organic Chemistry, 2012, vol. 48, # 2, p. 175 - 179]

54
[ 1191-08-8 ]
cinchonidine [ No CAS ]
[ 1395063-76-9 ]

Yield	Reaction Conditions	Operation in experiment
40%	With 2,2'-azobis(isobutyronitrile) In chloroform at 70℃;

Reference： [1]Location in patent: experimental part Haraguchi, Naoki; Ahamed, Parbhej; Parvez, Masud; Itsuno, Shinichi [Molecules, 2012, vol. 17, # 6, p. 7569 - 7583]

55
[ 1191-08-8 ]
tricarbonyl[(1-5-η)-pentadienyl]manganese [ No CAS ]
Mn₃(CO)₆(μ-S(CH₂)₄S-κ²-S,S′)₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In cyclohexane at 20℃; for 6h; Inert atmosphere; Schlenk technique;	4.2 Synthesis of Mn₃(CO)₆(μ-S(CH₂)_nS-κ²-S,S′)₃ (2)-(4) General procedure: Complex (1) (1.0 mmol, 206.0 mg) was dissolved in 100 mL of dry cyclohexane in a 250 mL round bottom flask with a magnetic stirrer previously purged with nitrogen. Alkanedithiol was added (1.0 mmol). The reaction mixture was left at room temperature for 4 h (except for (4), see below). Samples were taken every 30 min for monitoring purposes. As the reaction progressed there was a change in color from light yellow to dark green. At the end of the reaction a green precipitate was formed. The mixture was filtered through a cannula. The filtrate was washed with hexane (to eliminate unreacted (1)) and dissolved in dichloromethane. Elimination of dichloromethane under reduced pressure gave complexes (2)-(4) as green solids.

Reference： [1]Salas-Martin, Karla P.; Reyes-Lezama, Marisol; Höpfl, Herbert; Zúñiga-Villarreal, Noé [Journal of Organometallic Chemistry, 2014, vol. 751, p. 356 - 360]

56
[ 50-00-0 ]
[ 1191-08-8 ]
[ 141-43-5 ]
[ 1604783-95-0 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: formaldehyd; 1,4-Butanedithiol In ethanol; water at 20℃; for 0.333333h; Stage #2: ethanolamine	11 Preparation of 1,5,3-dithiazepanes 3a-e and macroheterocycles 4a-d, 5a-f, 6a-d and 10a,b General procedure: Dithiol 2a-e or 9a,b (1 mmol) was mixed with a 37 % solution of formaldehyde (0.15 mL, 2 mmol), and ethanol (3 mL) at room temperature over a period of 20 min. A solution of 0.07 g (1 mmol) of hydroxylamine hydrochloride 1a in water (3 mL) was added to the reaction mixture and the mixture was stirred for 3-4 h at room temperature. The product obtained from hydroxylamine hydrochloride was neutralized with a 10 % solution of NaOH. White precipitate that formed was filtered off and washed with H2O (3*15 mL) then dried. The corresponding amino alcohol 1b-e (1 mmol) in CHCl3 (15 mL) was added dropwise to the reaction mixture and the mixture was stirred for 3-4 h at room temperature. The water was removed and the solution was dried with anhydrous MgSO4. Solvent was removed, and the crude product was separated by column chromatography to give a pure sample 3a-e, 5a-f and 6a-d, which was analyzed by NMR spectroscopy. The precipitate that formed from dithiol 2b-e and hydroxylamine hydrochloride 1a was filtered off, then was washed with water and dried. The product was washed with CHCl3 and dried. The details of further purification performed for the new compounds are described in Product Data. 4.2.11. 2-[12-(2-Hydroxyethyl)-1,5,1,14-tetrathia-3,12-diazacycloоctadecanyl]-1-ethanol (5b). Colourless oil, yield (0.16 g) 77%, Rf 0.65 (СH2Сl2/EtOH, 5:1). vmax (liquid film) 662 (-C-S-), 1050, 1436, 2925; δH (400 MHz, CDCl3, 25 °C) 1.67 (8Н, s, SCH2CH2), 2.66 (8Н, s, SCH2CH2), 2.85 (4Н, t, 3J 5.4, HOCH2), 3.62 (4Н, t, 3J 5.4, NCH2CH2), 4.03 (8Н, s, NCH2S); δC (100 MHz, CDCl3) 29.1 (SCH2CH2), 31.6 (SCH2CH2), 54.1 (HOCH2), 57.1 (NCH2S), 59.2 (NCH2CH2); ESI (70 eV); m/z (%): 437 (22) [M+Na]+, 208 (60) [M+2H]2+. Anal. Calcd for С16Н34N2О2S4: С, 46.34; Н, 8.26; N, 6.75; S, 30.93. Found: С, 46.40; Н, 8.60; N, 7.00; S, 30.86.
77%	Stage #1: formaldehyd; 1,4-Butanedithiol In ethanol; water at 20℃; for 0.333333h; Stage #2: ethanolamine In ethanol; chloroform; water at 20℃; for 4.3h;

Reference： [1]Khabibullina, Guzel R.; Akhmetova, Vnira R.; Abdullin, Marat F.; Tyumkina, Tatiana V.; Khalilov, Leonard M.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2014, vol. 70, # 21, p. 3502 - 3509]
[2]Akhmetova; Khabibullina; Galimzyanova; Ibragimov [Russian Journal of Applied Chemistry, 2014, vol. 87, # 3, p. 294 - 298][Zh. Prikl. Khim. (S.-Peterburg, Russ. Fed.), 2014, vol. 87, # 3, p. 328 - 332,5]

57
[ 50-00-0 ]
[ 1191-08-8 ]
[ 13325-10-5 ]
[ 1604784-09-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: formaldehyd; 1,4-Butanedithiol In ethanol; water at 20℃; for 0.333333h; Stage #2: 4-Aminobutanol In ethanol; water at 20℃;	17 Preparation of 1,5,3-dithiazepanes 3a-e and macroheterocycles 4a-d, 5a-f, 6a-d and 10a,b General procedure: Dithiol 2a-e or 9a,b (1 mmol) was mixed with a 37 % solution of formaldehyde (0.15 mL, 2 mmol), and ethanol (3 mL) at room temperature over a period of 20 min. A solution of 0.07 g (1 mmol) of hydroxylamine hydrochloride 1a in water (3 mL) was added to the reaction mixture and the mixture was stirred for 3-4 h at room temperature. The product obtained from hydroxylamine hydrochloride was neutralized with a 10 % solution of NaOH. White precipitate that formed was filtered off and washed with H2O (3*15 mL) then dried. The corresponding amino alcohol 1b-e (1 mmol) in CHCl3 (15 mL) was added dropwise to the reaction mixture and the mixture was stirred for 3-4 h at room temperature. The water was removed and the solution was dried with anhydrous MgSO4. Solvent was removed, and the crude product was separated by column chromatography to give a pure sample 3a-e, 5a-f and 6a-d, which was analyzed by NMR spectroscopy. The precipitate that formed from dithiol 2b-e and hydroxylamine hydrochloride 1a was filtered off, then was washed with water and dried. The product was washed with CHCl3 and dried. The details of further purification performed for the new compounds are described in Product Data. 4.2.17. 4-[12-(4-Hydroxybutyl)-1,5,10,14-tetrathia-3,12-diazacyclooctadecanyl]-1-butanol (6b). Colourless oil, yield (0.20 g) 86%; vmax (liquid film) 649 (C-S), 1076, 1269, 1455, 3401 cm-1; δH (400 MHz, CDCl3, 25 °C) 1.54 (8H, br s, NCH2(CH2)2CH2OH), 1.65 (8H, br s, SCH2CH2), 2.53 (8Н, br s, SCH2CH2), 2.63 (4Н, s, NCH2CH2), 3.58 (4H, s, HOCH2CH2), 3.97 (8H, s, NCH2S); δC (100 MHz, CDCl3) 24.1 (NCH2CH2), 29.2 (SCH2CH2), 30.6 (HOCH2CH2), 31.6 (SCH2CH2), 51.6 (NCH2CH2), 56.7 (NCH2S), 62.3 (CH2OH); ESI (70 eV); m/z (%): 236 (12) [M+2H]2+. Anal. Calcd for С20Н42N2О2S4: С, 51.02; Н, 8.99; N, 5.95; S, 27.24. Found: С, 50.98; Н, 8.84; N, 5.96; S, 27.34.

Reference： [1]Khabibullina, Guzel R.; Akhmetova, Vnira R.; Abdullin, Marat F.; Tyumkina, Tatiana V.; Khalilov, Leonard M.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2014, vol. 70, # 21, p. 3502 - 3509]

58
[ 50-00-0 ]
[ 1191-08-8 ]
[ 1604783-85-8 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: formaldehyd; 1,4-Butanedithiol In ethanol; water at 20℃; for 0.333333h; Stage #2: With hydroxylamine hydrochloride In ethanol; water at 20℃; Stage #3: With sodium hydroxide In ethanol; water at 20℃;	7 Preparation of 1,5,3-dithiazepanes 3a-e and macroheterocycles 4a-d, 5a-f, 6a-d and 10a,b General procedure: Dithiol 2a-e or 9a,b (1 mmol) was mixed with a 37 % solution of formaldehyde (0.15 mL, 2 mmol), and ethanol (3 mL) at room temperature over a period of 20 min. A solution of 0.07 g (1 mmol) of hydroxylamine hydrochloride 1a in water (3 mL) was added to the reaction mixture and the mixture was stirred for 3-4 h at room temperature. The product obtained from hydroxylamine hydrochloride was neutralized with a 10 % solution of NaOH. White precipitate that formed was filtered off and washed with H2O (3*15 mL) then dried. The corresponding amino alcohol 1b-e (1 mmol) in CHCl3 (15 mL) was added dropwise to the reaction mixture and the mixture was stirred for 3-4 h at room temperature. The water was removed and the solution was dried with anhydrous MgSO4. Solvent was removed, and the crude product was separated by column chromatography to give a pure sample 3a-e, 5a-f and 6a-d, which was analyzed by NMR spectroscopy. The precipitate that formed from dithiol 2b-e and hydroxylamine hydrochloride 1a was filtered off, then was washed with water and dried. The product was washed with CHCl3 and dried. The details of further purification performed for the new compounds are described in Product Data. 4.2.7. 1,5,10,14-Tetrathia-3,12-diazacyclooctadecane-3,12-diol (4b). White solid, yield (0.10 g) 67%, mp 103-104 °С. vmax (Nujol) 724 (C-S), 1110, 3326 cm-1; δH (400 MHz, DMSO-d6, 25 °C) 1.62 (8H, br s, SCH2CH2), 2.63 (8Н, br s, SCH2CH2), 4.02 (8H, s, NCH2S); δC (100 MHz, DMSO-d6) 29.0 (SCH2CH2), 31.9 (SCH2CH2), 59.8 (NCH2S). ESI (70 eV); m/z (%): 393 (71) [M+Cl]-, 359 (5) [M+H]+; 180 (20) [M+2H]2+; Мcr=354+-10.19; Anal. Calcd for С12Н26N2O2S4: С, 40.19; Н, 7.31; N, 7.81; S, 35.77. Found: С, 40.26; Н, 7.11; N, 7.85; S, 35.85.

Reference： [1]Khabibullina, Guzel R.; Akhmetova, Vnira R.; Abdullin, Marat F.; Tyumkina, Tatiana V.; Khalilov, Leonard M.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2014, vol. 70, # 21, p. 3502 - 3509]

59
[ 1191-08-8 ]
[ 118-75-2 ]
[ 1612192-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In chloroform for 12h;	Synthesis of Cyclic (Thio)crown Ether Compound (12) Compound 12 was synthesized by the reaction of 1 (p-chloranil (1) (0.5 g,2.034 mmol) with 1,4-butanedithiol (10) (0.250 g, 2.045 mmol) in chloroform as solvent (40mL). Triethylamine (1mL) was added to the reaction mixture slowly. Without heating, the mixture was stirred for 12 h. The color of the solution quickly changed, and the extent of the reaction was monitored by thin-layer chromatography(TLC). Chloroform (30 mL) was added to the reaction mixture. The organic layer was separated, washed with water (430 mL), and dried with Na2SO4. Afterthe solvent was evaporated, the residue was purified by column chromatographyon silica gel.

Reference： [1]Ibis, Cemil; Ayla, Sibel Sahinler; Dogan, Yagmur; Ozen, Mesut [Synthetic Communications, 2014, vol. 44, # 11, p. 1614 - 1618]

60
[ 1191-08-8 ]
[ 118-75-2 ]
[ 1612192-35-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In chloroform for 12h;	General procedure: p-Chloranil and thiol were stirred in methanol as solvent (40mL). Triethylamine (1 mL) wasa dded to reaction mixture slowly without heating, the mixture was stirred for 12 h. The colorof the solution quickly changed, and the extent of the reaction was monitored by TLC.Chloroform (30 mL) was added to the reaction mixture. The organic layer was separated,wash with water (4 x 30 mL), and dried with Na2SO4. After the solvent was evaporated, theresidue was purified by column chromatography on silica gel.

Reference： [1]Ibis, Cemil; Ayla, Sibel Sahinler; Dogan, Yagmur; Ozen, Mesut [Synthetic Communications, 2014, vol. 44, # 11, p. 1614 - 1618]

61
[ 1191-08-8 ]
[α-methylene-Sar]-3-[(γ-hydroxy)-NMeLeu]-4-cyclosporin [ No CAS ]
[(S)-(4-mercaptobutylthio)methyl-Sar]-3-[(γ-hydroxy)-N-MeLeu]-4-cyclosporin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium hydroxide In methanol at 20℃;	133 Example 133 -(4-Mercaptobutylthio)methyl-Sar]-3-[(y-hydroxy)-N-MeLeu]-4-cyclosporin Example 133 -(4-Mercaptobutylthio)methyl-Sar]-3-[(y-hydroxy)-N-MeLeu]-4-cyclosporin Molecular Weight: 1230.65 Molecular Weight: 1352.89 [a-Methylene-Sar]-3-[(y-hydroxy)-N-MeLeu]-4-cyclosporin (0.25 g, 0.20 mmol) and 1,4- butanedithiol (0.30 g, 2.27 mmol) were dissolved in methanol (15 ml), followed by adding lithium hydroxide (50 mg, 2.08 mmol). The mixture was stirred at room temperature overnight. After removal of solvent, the residue was dissolved in dichloromethane (30 ml). The dichloromethane solution was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by flash chromatography using dichloromethane/methanol as eluent to give a product [Molecular Formula: C67H121N11O13S2; Exact Mass: 1351.88; MS (m/z): 1352.39 (M+l)+; TLC Rf: 0.27 (ethyl acetate/methanol = 6/1); HPLC RT: 16.12 min. (C8 reverse phase column: 250 mm; acetonitrile/water (0.05% trifluoroacetic acid); operation temperature: 64 °C; detector: 210 nm)].

Reference： [1]Current Patent Assignee: S T GLOBAL - WO2014/145686, 2014, A2 Location in patent: Page/Page column 215

62
[ 1191-08-8 ]
[ 13657-44-8 ]
3-phenyl-1,5,3-dithiazonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: N,N-bis(methoxymethyl)-N-phenylamine In ethyl acetate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In ethyl acetate at 20℃; for 5h; Inert atmosphere;	Cycloaminomethylation of α,ω-dithiols (1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol) with N,N-bis(methoxymethyl)-N-arylamines General procedure: General procedure. N,N-Bis(methoxymethyl)-N-arylamine (1.00 mmol) obtained in situ by a reported procedure,25 the solvent (10 mL), and Sm(NO3)3/γ-Al2O3 (0.05 mmol) were stirred under argon for 30 min at room temperature, then α,ω-dithiol (1,4-butanedithiol, 1,5-pentanedithiol or 1,6-hexanedithiol) (1.00 mmol) in 1 mL of the solvent was added. The reaction mixture was stirred at ∼20 °C for 5 h and concentrated, and the residue was chromatographed on a column with SiO2 to isolate pure heterocyclic products.

Reference： [1]Makhmudiyarova, Nataliya N.; Mudarisova, Liliya V.; Meshcheryakova, Ekaterina S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2015, vol. 71, # 2, p. 259 - 265]

63
[ 1191-08-8 ]
[ 1443365-03-4 ]
3-(m-methylphenyl)-1,5,3-dithiazonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	Stage #1: N,N-bis(methoxymethyl)-N-(m-methylphenyl)amine In dichloromethane; ethyl acetate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In dichloromethane; ethyl acetate at 20℃; for 5h; Inert atmosphere;	Cycloaminomethylation of α,ω-dithiols (1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol) with N,N-bis(methoxymethyl)-N-arylamines General procedure: General procedure. N,N-Bis(methoxymethyl)-N-arylamine (1.00 mmol) obtained in situ by a reported procedure,25 the solvent (10 mL), and Sm(NO3)3/γ-Al2O3 (0.05 mmol) were stirred under argon for 30 min at room temperature, then α,ω-dithiol (1,4-butanedithiol, 1,5-pentanedithiol or 1,6-hexanedithiol) (1.00 mmol) in 1 mL of the solvent was added. The reaction mixture was stirred at ∼20 °C for 5 h and concentrated, and the residue was chromatographed on a column with SiO2 to isolate pure heterocyclic products.

Reference： [1]Makhmudiyarova, Nataliya N.; Mudarisova, Liliya V.; Meshcheryakova, Ekaterina S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2015, vol. 71, # 2, p. 259 - 265]

64
[ 1191-08-8 ]
[ 1443365-06-7 ]
3-(m-methoxyphenyl)-1,5,3-dithiazonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: N,N-bis(methoxymethyl)-N-(m-methoxyphenyl)amine In ethanol; ethyl acetate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In ethanol; ethyl acetate at 20℃; for 5h; Inert atmosphere;	Cycloaminomethylation of α,ω-dithiols (1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol) with N,N-bis(methoxymethyl)-N-arylamines General procedure: General procedure. N,N-Bis(methoxymethyl)-N-arylamine (1.00 mmol) obtained in situ by a reported procedure,25 the solvent (10 mL), and Sm(NO3)3/γ-Al2O3 (0.05 mmol) were stirred under argon for 30 min at room temperature, then α,ω-dithiol (1,4-butanedithiol, 1,5-pentanedithiol or 1,6-hexanedithiol) (1.00 mmol) in 1 mL of the solvent was added. The reaction mixture was stirred at ∼20 °C for 5 h and concentrated, and the residue was chromatographed on a column with SiO2 to isolate pure heterocyclic products.

Reference： [1]Makhmudiyarova, Nataliya N.; Mudarisova, Liliya V.; Meshcheryakova, Ekaterina S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2015, vol. 71, # 2, p. 259 - 265]

65
[ 1191-08-8 ]
[ 1451094-78-2 ]
3-(p-chlorphenyl)-1,5,3-dithiazonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: N,N-bis(methoxymethyl)-N-(p-chlorophenyl)amine In ethyl acetate at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In ethyl acetate at 20℃; for 5h; Inert atmosphere;	Cycloaminomethylation of α,ω-dithiols (1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol) with N,N-bis(methoxymethyl)-N-arylamines General procedure: General procedure. N,N-Bis(methoxymethyl)-N-arylamine (1.00 mmol) obtained in situ by a reported procedure,25 the solvent (10 mL), and Sm(NO3)3/γ-Al2O3 (0.05 mmol) were stirred under argon for 30 min at room temperature, then α,ω-dithiol (1,4-butanedithiol, 1,5-pentanedithiol or 1,6-hexanedithiol) (1.00 mmol) in 1 mL of the solvent was added. The reaction mixture was stirred at ∼20 °C for 5 h and concentrated, and the residue was chromatographed on a column with SiO2 to isolate pure heterocyclic products.

Reference： [1]Makhmudiyarova, Nataliya N.; Mudarisova, Liliya V.; Meshcheryakova, Ekaterina S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2015, vol. 71, # 2, p. 259 - 265]

66
[ 1191-08-8 ]
N,N-bis(methoxymethyl)-N-(m-bromophenyl)amine [ No CAS ]
3-(m-bromphenyl)-1,5,3-dithiazonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	Stage #1: N,N-bis(methoxymethyl)-N-(m-bromophenyl)amine In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol In dichloromethane at 20℃; for 5h; Inert atmosphere;	Cycloaminomethylation of α,ω-dithiols (1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol) with N,N-bis(methoxymethyl)-N-arylamines General procedure: General procedure. N,N-Bis(methoxymethyl)-N-arylamine (1.00 mmol) obtained in situ by a reported procedure,25 the solvent (10 mL), and Sm(NO3)3/γ-Al2O3 (0.05 mmol) were stirred under argon for 30 min at room temperature, then α,ω-dithiol (1,4-butanedithiol, 1,5-pentanedithiol or 1,6-hexanedithiol) (1.00 mmol) in 1 mL of the solvent was added. The reaction mixture was stirred at ∼20 °C for 5 h and concentrated, and the residue was chromatographed on a column with SiO2 to isolate pure heterocyclic products.

Reference： [1]Makhmudiyarova, Nataliya N.; Mudarisova, Liliya V.; Meshcheryakova, Ekaterina S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2015, vol. 71, # 2, p. 259 - 265]

67
[ 1191-08-8 ]
N,N-bis(methoxymethyl)-N-(p-bromophenyl)amine [ No CAS ]
3-(p-bromphenyl)-1,5,3-dithiazonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: N,N-bis(methoxymethyl)-N-(p-bromophenyl)amine at 20℃; for 0.5h; Inert atmosphere; Stage #2: 1,4-Butanedithiol at 20℃; for 5h; Inert atmosphere;	Cycloaminomethylation of α,ω-dithiols (1,4-butanedithiol, 1,5-pentanedithiol, 1,6-hexanedithiol) with N,N-bis(methoxymethyl)-N-arylamines General procedure: General procedure. N,N-Bis(methoxymethyl)-N-arylamine (1.00 mmol) obtained in situ by a reported procedure,25 the solvent (10 mL), and Sm(NO3)3/γ-Al2O3 (0.05 mmol) were stirred under argon for 30 min at room temperature, then α,ω-dithiol (1,4-butanedithiol, 1,5-pentanedithiol or 1,6-hexanedithiol) (1.00 mmol) in 1 mL of the solvent was added. The reaction mixture was stirred at ∼20 °C for 5 h and concentrated, and the residue was chromatographed on a column with SiO2 to isolate pure heterocyclic products.

Reference： [1]Makhmudiyarova, Nataliya N.; Mudarisova, Liliya V.; Meshcheryakova, Ekaterina S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2015, vol. 71, # 2, p. 259 - 265]

68
[ 1191-08-8 ]
[ 150304-28-2 ]
C₆₈H₁₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With titanium tetrachloride In tetrahydrofuran; 1,2-dichloro-benzene at 20℃; for 0.5h;

Reference： [1]Mikie, Tsubasa; Saeki, Akinori; Masuda, Hiroyuki; Ikuma, Naohiko; Kokubo, Ken; Seki, Shu [Journal of Materials Chemistry A, 2015, vol. 3, # 3, p. 1152 - 1157]

69
[ 1191-08-8 ]
[ 110-01-0 ]
[ 505-20-4 ]

Yield	Reaction Conditions	Operation in experiment
	at 350℃; for 1h; Inert atmosphere; Flow reactor;	1.2. Catalytic Measurements General procedure: The reactions were performed in a conventional continuous flow microreactor operated at atmospheric pressure.23 In a typical experiment, a weighed sample (10.0 mg) of 1 or supported 1 on silica gel (1/SiO2) was packed into a borosilicate glass tube (3 mm id), which was placed in the center of an electric furnace. The catalyst sample was initially heated to 350 °C for 1 h in a helium stream (600 mL h-1) for activation, and then reactant was introduced at 350 °C into the stream usinga syringe pump (0.50 mmol h-1). The reaction was monitored by sampling the reaction gas (1 ml) every 30 min using a six-way valve and analyzing the collected gas using an on-line gas-liquid chromatography (GLC). The products were identified by GLC, nuclear magnetic resonance spectrometry, and mass spectrometry by comparison with authentic samples. Conversion =products/(products + recovered reactant) 100%; selectivity = product/(total amount of products) 100%. For the measurement of a typical reaction profile (Figure S1), effect of temperature (Figure 1), and reactivities of various halide cluster catalysts (Table S1), the amount of 1,4-butanediol was increased (1.50 mmol h-1) to reduce the conversion. Reactants were diluted with water (for alcohols) or tetrahydrofuran (for non-alcohols) to almost-saturated solutions or low-viscosity liquids at ambient temperature for introduction where necessary.

Reference： [1]Nagashima, Sayoko; Sasaki, Tomoaki; Kamiguchi, Satoshi; Chihara, Teiji [Chemistry Letters, 2015, vol. 44, # 6, p. 764 - 766]

70
[ 1191-08-8 ]
Und-6CC [ No CAS ]
UndS-b6CC [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	at 20℃; UV-irradiation;	1.4.B Step 4B - Thiol-ene reaction: 6-membered cyclic biscarbonate synthesis (UndS-b6CC) Step 4B - Thiol-ene reaction: 6-membered cyclic biscarbonate synthesis (UndS-b6CC) [0113] [0114] The Und-6CC obtained following Step 3 (4 g, 17.7 mmol) and 1,4-butanedithiol (2.38 g, 19.4 mmol, 1.1 eq.) were weighed into a flask. The reaction mixture was then UV-irradiated (254 nm) at room temperature. The reaction was monitored with 1H NMR spectroscopy with the disappearance of the double bond. After completion of the reaction, UndS-b6CC was purified by recrystallization in a mixture of cyclohexane and ethyl acetate (70:30) and obtained as a white solid. Yield=37%. 1H NMR (CDCl3, 25°C, 400 MHz) δ (ppm): 4.40 (m, 4H), 4.09 (m, 4H), 2.52 (m, 8H), 2.20 (m, 2H), 1.68 (m, 4H), 1.57 (m, 4H), 1.35-1.28 (m, 28H). 13C NMR (CDCl3, 25°C, 100 MHz) δ (ppm): 148.71 (OCOO), 72.24 (CH-CH2-OCO), 32.31 and 31.90 (CH2-S-CH2), 31.42 (CH-CH2-OCO), 29.78 and 26.72 (CH2-CH2-S-CH2-CH2), 29.60-26.72 (CH2). IR (cm-1): 2922, 2850, 1750, 1727. Tm=82°C (melting temperature).
37%	at 20℃; UV-irradiation;	1.4.B Step 4B - Thiol-ene reaction: 6-membered cyclic biscarbonate synthesis (UndS- Step 4B - Thiol-ene reaction: 6-membered cyclic biscarbonate synthesis (UndS- The Und-6CC obtained following Step 3 (4 g, 17.7 mmol) and 1 ,4-butanedithiol (2.38 g, 19.4 mmol, 1 .1 eq.) were weighed into a flask. The reaction mixture was then UV- irradiated (254 nm) at room temperature. The reaction was monitored with 1 H NMR spectroscopy with the disappearance of the double bond. After completion of the reaction, UndS-b6CC was purified by recrystallization in a mixture of cyclohexane and ethyl acetate (70:30) and obtained as a white solid. Yield=37%. 1 H NMR (CDCI3, 25

Reference： [1]Current Patent Assignee: INST CORPS GRAS ETUDES ET RECH S TECH ITERG; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF BORDEAUX 1; INSTITUT POLYTECHNIQUE DE BORDEAUX - EP2883873, 2015, A1 Location in patent: Paragraph 0113-0114
[2]Current Patent Assignee: INST CORPS GRAS ETUDES ET RECH S TECH ITERG; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; UNIVERSITY OF BORDEAUX 1; INSTITUT POLYTECHNIQUE DE BORDEAUX - WO2015/91499, 2015, A1 Location in patent: Page/Page column 15-16

71
calcium carbide [ No CAS ]
[ 1191-08-8 ]
[ 36648-04-1 ]

Yield	Reaction Conditions	Operation in experiment
89%	With water; potassium hydroxide In N,N-dimethyl-formamide at 100℃; for 3h; Sealed tube;	Synthesis of vinyl sulfides General procedure: Potassium hydroxide (1.5 mmol), thiol(1 mmol) / dithiol (0.5 mmol), and water (4 mmol) were added to a reactiontube (8 ml, Duran glass) with 1 ml of DMSO (DMF in the case of dithiols;DMSO and DMF were stored under molecular sieves). Freshly powderedcalcium carbide (2 mmol) was added; the tube was sealed and placed in100 °C bath with vigorous stirring for 3 h. After heating the mixture wasdiluted with 10% aqueous solution of KOH (10 ml), extracted with diethylether (4×10 ml), organic layers were combined, washed with brine, dried overNa2SO4, and concentrated in vacuo to yield a crude product. The temperatureduring solvent evaporation should be controlled to avoid product loss due tothe volatility of some vinyl sulfides. The crude material was further purifiedby column chromatography on silica gel (hexane and diethyl ether/hexane).For further purification, if required, the products can be distilled in vacuo. Elemental analysis was carried out using a Euro EA3028-HT apparatus.HRMS were recorded on a Bruker maXis Q-TOF instrument.1,4-Bis(vinylthio)butane 1. 1H NMR (400 MHz, CDCl3) d: 1.78 (m,4 H), 2.72 (m, 4 H), 5.11 (d, 2 H, J 16.7 Hz), 5.20 (d, 2 H, J 10.3 Hz), 6.35(dd, 1H, J 16.7 Hz, J 10.3 Hz). 13C NMR (100.6 MHz, CDCl3) d: 28.2,31.0, 111.0, 132.3. MS, m/z (%): 115 (33), 86 (100), 85 (29), 73 (78),55 (36), 45 (51). Found (%): C, 54.89; H, 8.06. Calc. for C8H14S2 (%):C, 55.12; H, 8.09.

Reference： [1]Rodygin, Konstantin S.; Kostin, Anton A.; Ananikov, Valentine P. [Mendeleev Communications, 2015, vol. 25, # 6, p. 415 - 416]

72
[ 1191-08-8 ]
[ 122039-27-4 ]
2-phenyl-1,3,2-dithiaphosphepane-2-selenide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	In toluene at 130℃; for 6h; Schlenk technique; Inert atmosphere;	General Procedure for Preparation of Heterocycles 1-10. General procedure: A white or brown suspension of LR or FcLR or WR(1.0 mmol) and alkyl- or aryl-dithiol (2.0 mmol) in dry toluene (20 mL) was heated at 130 °C for 6 h. Uponcooling to room temperature and removing unreacted solid the filtrate was dried in vacuo and the residue wasdissolved in dichloromethane (ca. 2 mL) and loaded onto a silica gel column (1 : 1 hexane/dichloromethane ordichloromethane as eluent) to give compounds 1-10.

Reference： [1]Hua, Guoxiong; Cordes, David B.; Slawin, Alexandra M. Z.; Woollins, J. Derek [Arkivoc, 2016, vol. 2017, # 3, p. 9 - 20]

73
[ 1191-08-8 ]
[ 343251-03-6 ]
2-ferrocenyl-1,3,2-dithiaphosphepane 2-sulfide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	In toluene at 130℃; for 6h; Schlenk technique; Inert atmosphere;	General Procedure for Preparation of Heterocycles 1-10. General procedure: A white or brown suspension of LR or FcLR or WR(1.0 mmol) and alkyl- or aryl-dithiol (2.0 mmol) in dry toluene (20 mL) was heated at 130 °C for 6 h. Uponcooling to room temperature and removing unreacted solid the filtrate was dried in vacuo and the residue wasdissolved in dichloromethane (ca. 2 mL) and loaded onto a silica gel column (1 : 1 hexane/dichloromethane ordichloromethane as eluent) to give compounds 1-10.

Reference： [1]Hua, Guoxiong; Cordes, David B.; Slawin, Alexandra M. Z.; Woollins, J. Derek [Arkivoc, 2016, vol. 2017, # 3, p. 9 - 20]

74
[ 1191-08-8 ]
[ 229162-26-9 ]
1,3,4,6-tetrakis[3-(4-mercaptobutylsulfanyl)propyl]glycoluril [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With 2,2'-azobis(isobutyronitrile) at 70℃; for 3h; Inert atmosphere;	2 Synthesis of 1,3,4,6-tetrakis[3-(4-mercaptobutylsulfanyl)propyl]glycoluril In a 50 mL flask equipped with a thermometer, 300 mg (1.0 mmol) of 1,3,4,6-tetraallyl glycoluril, 4.89 g (40 mmol) of 1,4-butanedithiol was placed, After adding 20 mg (0.12 mmol) of azobisisobutyronitrile thereto,The reaction was carried out at 70 ° C. for 3 hours while stirring in a nitrogen atmosphere. The resulting reaction mixture was concentrated under reduced pressure at 120 ° C. and purified by column chromatography. Chloroform was used as the eluent. The obtained solution was concentrated to obtain 450 mg of 1,3,4,6-tetrakis [3- (4-mercaptobutylsulfanyl) propyl] glycoluril as a pale yellow oil. Yield 59%

Reference： [1]Current Patent Assignee: SHIKOKU CHEMICALS CORPORATION - JP2016/164134, 2016, A Location in patent: Paragraph 0141; 0142

75
[ 50-00-0 ]
[ 1191-08-8 ]
[ 56-40-6 ]
C₈H₁₅NO₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: formaldehyd; 1,4-Butanedithiol In water at 20℃; for 0.5h; Stage #2: glycine In water at 20℃; for 4h;	Thiazacycloalkanes. General method. General procedure: A mixture of 15 mmol of aliphatic α,ω-dithiol and 0.22 mL (30 mmol) of 37% aqueous solution of formaldehyde was stirred at room temperature for 30 min, then dropwise 15 mmol of amino acid dissolved in 4 mL of water and 8 mL of chloroform were added, and the reaction mixture was stirred for 4 h at room temperature. Side oxadithiacycloalkanes were extracted with chloroform, compounds 1a and 1b were isolated from the aqueous layer by evaporating water in air. Similarly from the aqueous phase compounds 2a and 2b were isolated, the precipitate was dried in air. Synthesis of compounds 3 and 3b was similarly carried out adding 5 mol % of SmCl3·6H2O to the reaction mixture as a catalyst.

Reference： [1]Khabibullina; Fedotova; Abdullin; Tyumkina; Akhmetova; Ibragimov [Russian Journal of Organic Chemistry, 2017, vol. 53, # 2, p. 277 - 281][Zh. Org. Khim., 2017, vol. 53, # 2, p. 277 - 281,5]

76
[ 109-57-9 ]
[ 1191-08-8 ]
[ 51-80-9 ]
N,N'-(2,7-dithiaoctane-1,8-diyl)bis(N'-allylthiourea) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane With caesium carbonate In chloroform at 20℃; for 0.5h; Stage #2: Allylthiourea In ethanol; chloroform at 60℃; for 6h;	Thiomethylation of substituted thioureas with N,N,N′,N′-tetramethylmethanediamine and α,ω-alkanedithiols (general procedure) General procedure: A glass reactor was charged with 10 mmol of N,N,N′,N′-tetramethyl-methanediamine and 10 mmol of the corresponding α,ω-alkanedithiol in 5 mL of chloroform, and the mixture was stirred for 30 min at room temperature. A solution of 20 mmol of N-substituted thiourea in 10 mL of ethanol and 1 mmol of cesium carbonate were then added, and the mixture was stirred for 6 h at 60 °C. Compounds 1(a-e)-5(a-e) were isolated from the reaction mixture.

Reference： [1]Khairullina; Geniyatova; Meshcheryakova; Tyumkina; Khalilov; Ibragimov; Dzhemilev [Russian Journal of Organic Chemistry, 2017, vol. 53, # 3, p. 315 - 321][Zh. Org. Khim., 2017, vol. 53, # 3, p. 319 - 325,7]

77
[ 1191-08-8 ]
[ 51-80-9 ]
[ 103-85-5 ]
N,N'-(2,7-dithiaoctane-1,8-diyl)bis(N'-phenylthiourea) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane With caesium carbonate In chloroform at 20℃; for 0.5h; Stage #2: monophenylthiourea In ethanol; chloroform at 60℃; for 6h;	Thiomethylation of substituted thioureas with N,N,N′,N′-tetramethylmethanediamine and α,ω-alkanedithiols (general procedure) General procedure: A glass reactor was charged with 10 mmol of N,N,N′,N′-tetramethyl-methanediamine and 10 mmol of the corresponding α,ω-alkanedithiol in 5 mL of chloroform, and the mixture was stirred for 30 min at room temperature. A solution of 20 mmol of N-substituted thiourea in 10 mL of ethanol and 1 mmol of cesium carbonate were then added, and the mixture was stirred for 6 h at 60 °C. Compounds 1(a-e)-5(a-e) were isolated from the reaction mixture.

Reference： [1]Khairullina; Geniyatova; Meshcheryakova; Tyumkina; Khalilov; Ibragimov; Dzhemilev [Russian Journal of Organic Chemistry, 2017, vol. 53, # 3, p. 315 - 321][Zh. Org. Khim., 2017, vol. 53, # 3, p. 319 - 325,7]

78
[ 1191-08-8 ]
[ 51-80-9 ]
[ 538-32-9 ]
N,N'-(2,7-dithiaoctane-1,8-diyl)bis(N'-benzylurea) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane With caesium carbonate In chloroform at 20℃; for 0.5h; Stage #2: benzylurea In ethanol; chloroform at 60℃; for 6h;	Thiomethylation of substituted thioureas with N,N,N′,N′-tetramethylmethanediamine and α,ω-alkanedithiols (general procedure) General procedure: A glass reactor was charged with 10 mmol of N,N,N′,N′-tetramethyl-methanediamine and 10 mmol of the corresponding α,ω-alkanedithiol in 5 mL of chloroform, and the mixture was stirred for 30 min at room temperature. A solution of 20 mmol of N-substituted thiourea in 10 mL of ethanol and 1 mmol of cesium carbonate were then added, and the mixture was stirred for 6 h at 60 °C. Compounds 1(a-e)-5(a-e) were isolated from the reaction mixture.

Reference： [1]Khairullina; Geniyatova; Meshcheryakova; Tyumkina; Khalilov; Ibragimov; Dzhemilev [Russian Journal of Organic Chemistry, 2017, vol. 53, # 3, p. 315 - 321][Zh. Org. Khim., 2017, vol. 53, # 3, p. 319 - 325,7]

79
[ 1191-08-8 ]
[ 51-80-9 ]
[ 557-11-9 ]
N,N'-(2,7-dithiaoctane-1,8-diyl)bis(N'-allylurea) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane With caesium carbonate In chloroform at 20℃; for 0.5h; Stage #2: allylurea In ethanol; chloroform at 60℃; for 6h;	Thiomethylation of substituted thioureas with N,N,N′,N′-tetramethylmethanediamine and α,ω-alkanedithiols (general procedure) General procedure: A glass reactor was charged with 10 mmol of N,N,N′,N′-tetramethyl-methanediamine and 10 mmol of the corresponding α,ω-alkanedithiol in 5 mL of chloroform, and the mixture was stirred for 30 min at room temperature. A solution of 20 mmol of N-substituted thiourea in 10 mL of ethanol and 1 mmol of cesium carbonate were then added, and the mixture was stirred for 6 h at 60 °C. Compounds 1(a-e)-5(a-e) were isolated from the reaction mixture.

Reference： [1]Khairullina; Geniyatova; Meshcheryakova; Tyumkina; Khalilov; Ibragimov; Dzhemilev [Russian Journal of Organic Chemistry, 2017, vol. 53, # 3, p. 315 - 321][Zh. Org. Khim., 2017, vol. 53, # 3, p. 319 - 325,7]

80
[ 1191-08-8 ]
[ 51-80-9 ]
[ 64-10-8 ]
N,N'-(2,7-dithiaoctane-1,8-diyl)bis(N'-phenylurea) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane With caesium carbonate In chloroform at 20℃; for 0.5h; Stage #2: phenyl carbamate In ethanol; chloroform at 60℃; for 6h;	Thiomethylation of substituted thioureas with N,N,N′,N′-tetramethylmethanediamine and α,ω-alkanedithiols (general procedure) General procedure: A glass reactor was charged with 10 mmol of N,N,N′,N′-tetramethyl-methanediamine and 10 mmol of the corresponding α,ω-alkanedithiol in 5 mL of chloroform, and the mixture was stirred for 30 min at room temperature. A solution of 20 mmol of N-substituted thiourea in 10 mL of ethanol and 1 mmol of cesium carbonate were then added, and the mixture was stirred for 6 h at 60 °C. Compounds 1(a-e)-5(a-e) were isolated from the reaction mixture.

Reference： [1]Khairullina; Geniyatova; Meshcheryakova; Tyumkina; Khalilov; Ibragimov; Dzhemilev [Russian Journal of Organic Chemistry, 2017, vol. 53, # 3, p. 315 - 321][Zh. Org. Khim., 2017, vol. 53, # 3, p. 319 - 325,7]

81
[ 1191-08-8 ]
[ 51-80-9 ]
[ 17356-08-0 ]
1,7-dithia-3,5-diazacycloundecane-4-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane In ethanol at 20℃; for 0.0833333h; Stage #2: thiourea With caesium carbonate In ethanol at 60℃; for 8h;	4.2 Cyclothiomethylation of (thio)urea with bis-(N,N-dimethylamino)methane and α,ω-alkanedithiols. Method A General procedure: In a glass reactor placed on a magnetic stirrer bis-(N,N-dimethylamino)methane (2mmol), α,ω-alkanedithiol (1mmol) and EtOH (5mL) are charged and stirred for 5minat room temperature (∼20°C), and then, (thio)urea (1mmol) and Cs2CO3 (0.1mmol) in EtOH (5mL) are added. The reaction mixture is stirred for 8hat 60°C. The separated powder of compounds 1,7-dithia-3,5-diazacycloalkan-4-ones 2- or 1,7-dithia-3,5-diazocycloalkane-4-thiones 3- are filtered off, washed with water, and dried.

Reference： [1]Khairullina, Regina R.; Geniyatova, Alfiya R.; Tyumkina, Tatyana V.; Karamzina, Diana S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2017, vol. 73, # 50, p. 7079 - 7084]

82
[ 1191-08-8 ]
[ 51-80-9 ]
[ 57-13-6 ]
1,7-dithia-3,5-diazacycloundecan-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane In ethanol at 20℃; for 0.0833333h; Stage #2: urea With caesium carbonate In ethanol at 60℃; for 8h;	4.2 Cyclothiomethylation of (thio)urea with bis-(N,N-dimethylamino)methane and α,ω-alkanedithiols. Method A General procedure: In a glass reactor placed on a magnetic stirrer bis-(N,N-dimethylamino)methane (2mmol), α,ω-alkanedithiol (1mmol) and EtOH (5mL) are charged and stirred for 5minat room temperature (∼20°C), and then, (thio)urea (1mmol) and Cs2CO3 (0.1mmol) in EtOH (5mL) are added. The reaction mixture is stirred for 8hat 60°C. The separated powder of compounds 1,7-dithia-3,5-diazacycloalkan-4-ones 2- or 1,7-dithia-3,5-diazocycloalkane-4-thiones 3- are filtered off, washed with water, and dried.

Reference： [1]Khairullina, Regina R.; Geniyatova, Alfiya R.; Tyumkina, Tatyana V.; Karamzina, Diana S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2017, vol. 73, # 50, p. 7079 - 7084]

83
[ 1191-08-8 ]
[ 98425-53-7 ]
1,7-dithia-3,5-diazacycloundecane-4-thione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: N,N′-bis[(dimethylamino)methyl]thiourea With caesium carbonate In ethanol at 20℃; for 0.166667h; Stage #2: 1,4-Butanedithiol In ethanol at 60℃; for 6h;	4.3 Condensation of N,N′-bis[(dimethylamino)methyl](thio)urea with α,ω-alkanedithiols. Method B General procedure: In a glass reactor placed on a magnetic stirrer N,N′-bis[dimethylaminomethyl](thio)urea (1mmol) and Cs2CO3 (0.1mmol) in EtOH (5mL) are loaded and stirred for 10minat room temperature (∼20°C). Then, α,ω-alkanedithiol (1mmol) is added and the reaction mixture is stirred for 6hat 60°C. The separated powder of compounds 1,7-dithia-3,5-diazacycloalkan-4-ones 2- or 1,7-dithia-3,5-diazocycloalkane-4-thiones 3- are filtered off, washed with water, and dried.

Reference： [1]Khairullina, Regina R.; Geniyatova, Alfiya R.; Tyumkina, Tatyana V.; Karamzina, Diana S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2017, vol. 73, # 50, p. 7079 - 7084]

84
[ 1191-08-8 ]
[ 52663-01-1 ]
1,7-dithia-3,5-diazacycloundecan-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: N,N′-bis[(dimethylamino)methyl]urea With caesium carbonate In ethanol at 20℃; for 0.166667h; Stage #2: 1,4-Butanedithiol In ethanol at 60℃; for 6h;	4.3 Condensation of N,N′-bis[(dimethylamino)methyl](thio)urea with α,ω-alkanedithiols. Method B General procedure: In a glass reactor placed on a magnetic stirrer N,N′-bis[dimethylaminomethyl](thio)urea (1mmol) and Cs2CO3 (0.1mmol) in EtOH (5mL) are loaded and stirred for 10minat room temperature (∼20°C). Then, α,ω-alkanedithiol (1mmol) is added and the reaction mixture is stirred for 6hat 60°C. The separated powder of compounds 1,7-dithia-3,5-diazacycloalkan-4-ones 2- or 1,7-dithia-3,5-diazocycloalkane-4-thiones 3- are filtered off, washed with water, and dried.

Reference： [1]Khairullina, Regina R.; Geniyatova, Alfiya R.; Tyumkina, Tatyana V.; Karamzina, Diana S.; Ibragimov, Askhat G.; Dzhemilev, Usein M. [Tetrahedron, 2017, vol. 73, # 50, p. 7079 - 7084]

85
[ 1191-08-8 ]
6-methyl-2-phenyl-4H-benzo[d] [1,3]dioxin-8-carbaldehyde [ No CAS ]
8-(1,3-dithiepan-2-yl)-6-methyl-2-phenyl-4H-benzo[d] [1,3]dioxin [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
11%	With chloro-trimethyl-silane In chloroform at 20℃; for 2h;	General Procedure for the Preparation of (5, 6, 7, 8, 9, 12, 13, 14, 15, 19) General procedure: To a well-stirred solution of 10 mmol of 4 or 11 and 20 mmol of corresponding thiol (or 10 mmol dithiol) in chloroform at r. t. 12-15 mmol TMSCl was added slowly over a period of 20 min. After an hour, the reaction mixture was washed with a 5% aqueous sodium carbonate solution and chloroform phase was washed by water. The organic layer was dried by Na2SO4, filtered and the chloroform was evaporated. The residue amorphic solids were purified by HPLC or by regular silica gel chromatography.

Reference： [1]Rozentul, Naomi; Avrahami, Yosef; Shubely, Moran; Levy, Laura; Munder, Anna; Cohen, Guy; Cerasi, Erol; Sasson, Shlomo; Gruzman, Arie [Pharmaceutical Research, 2017, vol. 34, # 12, p. 2873 - 2890]

86
[ 1191-08-8 ]
[ 109209-97-4 ]
6-(1,3-dithiepan-2-yl)-2-phenylchroman [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
13%	With chloro-trimethyl-silane In chloroform at 20℃; for 2h;	General Procedure for the Preparation of (5, 6, 7, 8, 9, 12, 13, 14, 15, 19) General procedure: To a well-stirred solution of 10 mmol of 4 or 11 and 20 mmol of corresponding thiol (or 10 mmol dithiol) in chloroform at r. t. 12-15 mmol TMSCl was added slowly over a period of 20 min. After an hour, the reaction mixture was washed with a 5% aqueous sodium carbonate solution and chloroform phase was washed by water. The organic layer was dried by Na2SO4, filtered and the chloroform was evaporated. The residue amorphic solids were purified by HPLC or by regular silica gel chromatography.

Reference： [1]Rozentul, Naomi; Avrahami, Yosef; Shubely, Moran; Levy, Laura; Munder, Anna; Cohen, Guy; Cerasi, Erol; Sasson, Shlomo; Gruzman, Arie [Pharmaceutical Research, 2017, vol. 34, # 12, p. 2873 - 2890]

87
[ 50-00-0 ]
[ 1191-08-8 ]
[ 364-76-1 ]
3-(4-fluoro-3-nitrophenyl)-1,5,3-dithiazonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: formaldehyd; 1,4-Butanedithiol In water at 20℃; for 0.5h; Stage #2: 4-Fluoro-3-nitroaniline With samarium(III) chloride hexahydrate In chloroform; water at 40℃;	Cyclothiomethylation of nitroanilines 4f,g with CH₂O and aliphatic α,ω-dithiols (General method) General procedure: A mixture ofthe appropriate α,ω-dithiol (1 mmol) and 37% formalin(0.15 ml, 2 mmol) was stirred for 30 min at roomtemperature. Then a solution of nitroaniline 4f,g (1 mmol) and SmCl3·6H2O (0.02 g, 5 mol %) in 5 ml of suitable solvent (compound 4f - CHCl3, compound 4g - Me2CO) was added dropwise. The mixture was stirred for 3-4 h at 40°C, then evaporated on a rotary evaporator. The product was purified by column chromatography.

Reference： [1]Khabibullina, Guzel R.; Fedotova, Ekaterina S.; Meshcheryakova, Ekaterina S.; Buslaeva, Tatyana M.; Akhmetova, Vnira R.; Ibragimov, Askhat G. [Chemistry of Heterocyclic Compounds, 2016, vol. 52, # 10, p. 840 - 848][Khim. Geterotsikl. Soedin., 2016, vol. 52, # 10, p. 840 - 848]

88
[ 50-00-0 ]
[ 119-34-6 ]
[ 1191-08-8 ]
4-(1,5,3-dithiazonan-3-yl)-2-nitrophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		General procedure: A mixture ofthe appropriate alpha,omega-dithiol (1 mmol) and 37% formalin(0.15 ml, 2 mmol) was stirred for 30 min at roomtemperature. Then a solution of nitroaniline 4f,g (1 mmol) and SmCl3·6H2O (0.02 g, 5 mol %) in 5 ml of suitable solvent (compound 4f - CHCl3, compound 4g - Me2CO) was added dropwise. The mixture was stirred for 3-4 h at 40C, then evaporated on a rotary evaporator. The product was purified by column chromatography.

Reference： [1]Chemistry of Heterocyclic Compounds,2016,vol. 52,p. 840 - 848
Khim. Geterotsikl. Soedin.,2016,vol. 52,p. 840 - 848,9

89
[ 1191-08-8 ]
C₂₅H₃₁NO₃ [ No CAS ]
C₂₉H₃₉NO₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.15%	With hydrogen bromide; trimethyl orthoformate In toluene at 110℃; for 6h;	4.S4 S4’:ketal reaction 21.44 g of 1,4-butanedithiol, 10.53 g of trimethylorthoacetate,60 ml of toluene was separately added to the reaction flask, stirred, and 0.24 g of 5% hydrobromic acid was added.23.0 g of the above compound IV was added. Stir at 110°C for 6h. Samples are taken for TLC analysis. After the reaction is complete,Under stirring, the reaction solution was poured into 73 ml of toluene, cooled to 0° C., stirred for 1 hour, and filtered.It was dried to obtain 20.73 g of the dried compound Vb in a yield of 90.15%.

Reference： [1]Current Patent Assignee: GUANGXI WONDER PHARMACEUTICAL - CN108101950, 2018, A Location in patent: Paragraph 0089; 0091; 0099; 0100

90
[ 1191-08-8 ]
[ 1025-15-6 ]
1,3,5-tris[3-(4-mercaptobutylsulfanyl)propyl]isocyanurate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With 2,2'-azobis(isobutyronitrile); at 70℃; for 4h;	A 100 mL flask equipped with a thermometer was charged with 249 mg (1.0 mmol) of 1,3,5-<strong>[1025-15-6]triallyl isocyanurate</strong>,And 3.7 g (30 mmol) of 1,4-butanedithiol,, And 20 mg of azobisisobutyronitrile(0.12 mmol) was added thereto,The reaction was carried out at 70 C. for 4 hours while stirring.After completion of the reaction,It was concentrated at 100 C.,589 mg of 1,3,5-tris [3- (4-mercaptobutylsulfanyl) propyl] isocyanurate as a clear liquid. Yield 96%.

Reference： [1]Patent: JP6420185,2018,B2 .Location in patent: Paragraph 0103

91
[ 1191-08-8 ]
[ 57693-23-9 ]

Yield	Reaction Conditions	Operation in experiment
	With chlorine In paraffin oil at 0 - 10℃; for 2h;	3.2 Step 2: Preparation of 1,4-second sulfonyl chloride butane: Adding 0.5 mol of 1,4-didecylbutane and paraffinic base oil to the reaction kettle,Dilute 1,4-diodecyl butane to a temperature between 0 and 10 ° C.Then, 0.65 mol of chlorine gas was introduced to carry out the reaction.The temperature was maintained between 0 and 10 ° C for 2 hours.

Reference： [1]Current Patent Assignee: SHANDONG YANGGU HUATAI CHEMICAL COMPANY LIMITED - CN108689912, 2018, A Location in patent: Paragraph 0043; 0046

92
[ 50-00-0 ]
[ 1191-08-8 ]
C₂₅H₃₆N₂O₄ [ No CAS ]
C₃₁H₄₆N₂O₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: formaldehyd; 1,4-Butanedithiol In chloroform at 20℃; for 0.5h; Stage #2: C₂₅H₃₆N₂O₄ In ethanol; chloroform at 20℃; for 25h;	General procedure for heterocyclization of amino derivatives of maleopimaric acid methyl ester with formaldehyde and carbochain α,ω-dithiols. General procedure: A mixture of 0.25 mmol of α,ω-dithiol and 0.5 mmol of formalin (37% solution, 0.05 mL) in 4 mL of chloroform was stirred at room temperature (~20°C) for 30 min, then was added dropwise 0.25 mmol of hydrazide 8 or aminoimide 10 of maleopimaric acid methyl ester dissolved in a mixture of EtOH-CHCl 3 (1 : 1). The mixture was stirred for 25 h at room temperature (~20°C), then evaporated on a rotary evaporator. The residue was chromatographed. Com-pound 11 was washed with hot water.

Reference： [1]Khabibullina; Fedotova; Tretyakova; Tyumkina; Parfenova; Ibragimov [Russian Journal of General Chemistry, 2019, vol. 89, # 1, p. 25 - 31][Zh. Obshch. Khim., 2019, vol. 89, # 1, p. 31 - 38,8]

93
[ 50-00-0 ]
[ 1191-08-8 ]
[ 109-73-9 ]
3-butyl-1,5,3-dithiazonane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: formaldehyd; 1,4-Butanedithiol With samarium(III) chloride hexahydrate In chloroform at 20℃; for 0.5h; Stage #2: N-butylamine In chloroform at 0 - 20℃; for 3h;	General procedure for cyclothiomethylation of aliphatic amines with formaldehyde and α,ω-dithiols. General procedure: A mixture of 1 mmol of aliphatic α,ω-dithiol (or 0.16 mL of 3,6-dioxa-1,8-octanedithiol) and formalin (37%, 2 mmol, 0.15 mL) in 1 mL of chloroform was stirred at room temperature (~20°) for 30 min, then cooled to 0°C. After adding of 1 mmol of primary amine, the mixture was stirred for 3 h at 20°C in chloroform, then extracted with chloroform. The organic phase was dried with MgSO 4 . After removal of the solvent, the residue was chromato-graphed. Synthesis of compounds 4b-4e was carried out similarly using 5 mol% of SmCl 3 ·6H 2 O as a catalyst.

Reference： [1]Khabibullina; Fedotova; Tretyakova; Tyumkina; Parfenova; Ibragimov [Russian Journal of General Chemistry, 2019, vol. 89, # 1, p. 25 - 31][Zh. Obshch. Khim., 2019, vol. 89, # 1, p. 31 - 38,8]

94
[ 117-80-6 ]
[ 1191-08-8 ]
C₁₄H₁₂O₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With sodium carbonate In ethanol for 6h;	General Procedure 2 General procedure: Sodium carbonate (0.934 g, 8.81 mmol) was dissolved (60 mL) in ethanol. 1,4-NQ 1 and nuchleophilies were added slowly to this solution. Without heating, the mixture was stirred for 6 h. The colour of the solution quickly changed and the extent of the reaction was monitored by TLC. Chloroform (3x40 mL) was added to the reaction mixture. The organic layer was washed with water (100 mL), and dried with CaCl2. After the solvent was evaporated the residue was purified by column chromatography with solvents.

Reference： [1]Gokmen, Zeliha; Onan, Mehmet Erdi; Deniz, Nahide Gulsah; Karakas, Didem; Ulukaya, Engin [Synthetic Communications, 2019, vol. 49, # 21, p. 3008 - 3016]

95
[ 110-65-6 ]
[ 1191-08-8 ]
2,3-bis(mercaptomethyl)-1,4-dithiocane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 1,4-dihydroxybut-2-yne; 1,4-Butanedithiol With 2,2'-azobis(isobutyronitrile) In tetrahydrofuran at 70 - 80℃; for 6h; Stage #2: With hydrogenchloride; thiourea In water at 105℃; for 5h; Stage #3: With sodium hydroxide In water; toluene at 35 - 75℃;	4 Synthesis of 2,3-bis (mercaptomethyl) -1,4-dithiocane After putting a stirrer, a thermometer and a condenser in a 4-liter four-necked flask,2-butyn-1,4-diol (100.0 g, 1.16 mol)It was added to 2 L of tetrahydrohuran (THF).0.2 g of AIBN [2,2'-Azobis (2-methylpropionitrile)] was added and the reaction temperature was 70 ° C. butane-1,4-dithiol(141.8 g, 1.16 mol) was added slowly dropwise. After the dropwise addition, the reaction was carried out while maintaining the temperature at 80 ° C., and when the catalyst was exhausted on HPLC, the reaction was carried out by continuously adding the AIBN catalyst.The AIBN catalyst was added until no further reaction and further proceeded at 80 ° C. for 6 hours to complete the reaction.In the preparation, the entire reaction process was confirmed by HPLC. At the end of the reaction the volatiles were removed under reduced pressure and the reaction of step (1) was brought down to room temperature.Step (2): After adding thiourea (180.45 g, 2.32 mol) and concentrated hydrochloric acid (35 mol%, 294.43 g, 2.9 mol) to the reaction of step (1),It was refluxed at 105 ° C. for 5 hours (step 2-1).After the reflux reaction, to room temperature,Aqueous sodium hydroxide solution below 35 (15 wt%, 451.63 g, 1.69 mol) was slowly added dropwise and tolueneAfter adding (400g), the hydrolysis reaction was carried out at 75 stepThe reaction product of (2) was obtained (step 2-2).Step (3):The reaction product of step (2) was cooled to room temperature and transferred to a separatory funnel to separate layers. Specifically,The water layer was discarded and the organic layer was washed once with concentrated hydrochloric acid and washed three times with water.The reaction product obtained by drying the obtained organic layer with manganese and filtering was concentrated under reduced pressure.1-4 polythiol compounds (239.8 g, 86%) were obtained.

Reference： [1]Current Patent Assignee: SKC CO LTD - KR102045150, 2019, B1 Location in patent: Paragraph 0133-0141

96
[ 1191-08-8 ]
[ 88-26-6 ]
2,6-di-tert-butyl-4-(((4-mercaptobutyl)thio)methyl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With toluene-4-sulfonic acid at 20℃;	2.2 Synthesis of mono-substituent of BHTderivatives General procedure: Benzyl alcohol (1 mmol, 0. 2364 g) and thiol (1.1 mmol,0.1543 g) were mixed with catalyst, p-toluenesulfonic acid(PTSA) and were stirred for an appropriate time at roomtemperature. The reaction mixture was poured and dilutedwith ethyl acetate (5 mL) and the catalyst was allowed tosettle. The ethyl acetate supernatant was poured off, rinsedwith ethyl acetate (5 mL) and the mixed organic solventwas evaporated under reduced pressure to obtain crudeproduct, which was purified using column chromatography(Silica gel: 230-400 mesh, petroleum ether (40-60 C):ethyl acetate = 9:1) to obtain a pure product.

Reference： [1]Ahmad, Mohd H; Rahman, Noorsaadah Abd; Kadir, Farkaad A; Al-Ani, Lina A; Hashim, Najihah M; Yehye, Wageeh A [Journal of Chemical Sciences, 2019, vol. 131, # 10]

97
[ 1191-08-8 ]
[ 51-80-9 ]
[ 28144-70-9 ]
2-[({4-[([2-(aminocarbonyl)phenyl]amino}methyl)thio]butyl}thio)methyl]amino}benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane In ethanol; chloroform for 0.5h; Stage #2: anthranilic acid amide With samarium(III) chloride hexahydrate In ethanol; chloroform at 70℃; for 24h;	Thiomethylation of 2-aminobenzamide (1) using bis(N,N-dimethylamino)methane (4) and α,ω-dithiols 5a-d (general procedure).Method A. General procedure: A two-neck fl ask was charged with α,ω-alkanedithiol5a-d (1 mmol; 0.083 mL of 1,2-ethanedithiol (5a), 0.100 mL of 1,3-propanedithiol (5b), 0.117 mL of 1,4-butanedithiol(5c) or 0.134 mL of 1,5-pentanedithiol (5d)), bis(N,Ndimethylamino)methane (4) (0.300 mL, 2 mmol), and solvent(10 mL, a 1 : 1 mixture of EtOH-CHCl3). The resulting mixturewas stirred for 30 min, then catalyst SmCl3•6H2O (0.04 g, 0.1 mmol)and a solution of 2-aminobenzamide (1) (0.272 g, 2 mmol) inEtOH (5 mL) were added. The reaction mixture was stirred for24 h. Acyclic products 7a-d were isolated by silica gel columnchromatography (eluent hexane-ethyl acetate, 1 : 1).

Reference： [1]Ibragimov, A. G.; Khairullina, R. R.; Tyumkina, T. V. [Russian Chemical Bulletin, 2021, vol. 70, # 4, p. 757 - 762][Izv. Akad. Nauk, Ser. Khim., 2021, # 4, p. 757 - 762,6]

98
[ 1191-08-8 ]
[ 51-80-9 ]
[ 3544-24-9 ]
3-(1,5,3-dithiazonan-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane In ethanol; chloroform for 0.5h; Stage #2: 3-Aminobenzamide With samarium(III) nitrate hexahydrate In ethanol; chloroform at 70℃; for 24h;	Thiomethylation of 2-aminobenzamide (1) using bis(N,N-dimethylamino)methane (4) and α,ω-dithiols 5a-d (general procedure).Method A. General procedure: A two-neck fl ask was charged with α,ω-alkanedithiol5a-d (1 mmol; 0.083 mL of 1,2-ethanedithiol (5a), 0.100 mL of 1,3-propanedithiol (5b), 0.117 mL of 1,4-butanedithiol(5c) or 0.134 mL of 1,5-pentanedithiol (5d)), bis(N,Ndimethylamino)methane (4) (0.300 mL, 2 mmol), and solvent(10 mL, a 1 : 1 mixture of EtOH-CHCl3). The resulting mixturewas stirred for 30 min, then catalyst SmCl3•6H2O (0.04 g, 0.1 mmol)and a solution of 2-aminobenzamide (1) (0.272 g, 2 mmol) inEtOH (5 mL) were added. The reaction mixture was stirred for24 h. Acyclic products 7a-d were isolated by silica gel columnchromatography (eluent hexane-ethyl acetate, 1 : 1).

Reference： [1]Ibragimov, A. G.; Khairullina, R. R.; Tyumkina, T. V. [Russian Chemical Bulletin, 2021, vol. 70, # 4, p. 757 - 762][Izv. Akad. Nauk, Ser. Khim., 2021, # 4, p. 757 - 762,6]

99
[ 1191-08-8 ]
[ 51-80-9 ]
[ 2835-68-9 ]
4-(1,5,3-dithiazonan-3-yl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	Stage #1: 1,4-Butanedithiol; bis-(dimethylamino)methane In ethanol; chloroform for 0.5h; Stage #2: 4-aminobenzamide With samarium(III) nitrate hexahydrate In ethanol; chloroform at 70℃; for 24h;	Thiomethylation of 2-aminobenzamide (1) using bis(N,N-dimethylamino)methane (4) and α,ω-dithiols 5a-d (general procedure). Method A. General procedure: Thiomethylation of 3- and 4-aminobenzamides 2 and 3 usingbis(N,N-dimethylamino)methane (4) and α,ω-dithiols 5a-d.Method B. The reactions were carried out similarly to method Aexcept that the molar ratio aminobenzamide : 4 : dithiol :: [Sm(NO3)3•6H2O] was 1 : 2 : 1 : 0.1. 1,5,3-Dithiazacycloalkanes8a-d and 9a-d were isolated by silica gel column chromatography(eluent ethyl acetate-acetone, 1 : 1).

Reference： [1]Ibragimov, A. G.; Khairullina, R. R.; Tyumkina, T. V. [Russian Chemical Bulletin, 2021, vol. 70, # 4, p. 757 - 762][Izv. Akad. Nauk, Ser. Khim., 2021, # 4, p. 757 - 762,6]

100
[ 59-67-6 ]
[ 1191-08-8 ]
[ 1576-35-8 ]
S-(4-(tosylthio)butyl) pyridine-3-carbothioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: nicotinic acid; 1,4-Butanedithiol With dmap; diisopropyl-carbodiimide In dichloromethane at 20℃; for 12h; Stage #2: toluene-4-sulfonic acid hydrazide With tert.-butylhydroperoxide; sodium iodide In water at 20℃;

Reference： [1]Rather, Suhail A.; Bhat, Mohammad Yaqoob; Hussain, Feroze; Ahmed, Qazi Naveed [Journal of Organic Chemistry, 2021, vol. 86, # 19, p. 13644 - 13663]

101
[ 1191-08-8 ]
[ 1576-35-8 ]
[ 4010-05-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With tert.-butylhydroperoxide; sodium iodide In water; acetonitrile at 20℃;

Reference： [1]Rather, Suhail A.; Bhat, Mohammad Yaqoob; Hussain, Feroze; Ahmed, Qazi Naveed [Journal of Organic Chemistry, 2021, vol. 86, # 19, p. 13644 - 13663]

102
[ 1191-08-8 ]
[ 18321-15-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dihydrogen peroxide; glacial acetic acid In lithium hydroxide monohydrate at 80℃; for 4h;
20%	With dihydrogen peroxide; glacial acetic acid In lithium hydroxide monohydrate at 0 - 20℃; for 12h;

Reference： [1]Rather, Suhail A.; Bhat, Mohammad Yaqoob; Hussain, Feroze; Ahmed, Qazi Naveed [Journal of Organic Chemistry, 2021, vol. 86, # 19, p. 13644 - 13663]
[2]Cheng, Yangyang; Kato, Takehiro; Lim, Bumhee; Matile, Stefan; Maynard, John; Moreau, Dimitri; Pham, Anh-Tuan; Poblador-Bahamonde, Amalia I.; Sakai, Naomi [Journal of the American Chemical Society, 2022, vol. 2, # 4, p. 839 - 852]

103
[ 1191-08-8 ]
[ 103-05-9 ]
1,4-bis((2-methyl-4-phenylbutan-2-yl)thio)butane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With copper(II) bis(trifluoromethanesulfonate) In 1,2-dichloro-ethane at 70℃; for 12h; Schlenk technique;	General procedure for the reaction of tertiary alkyl alcohols with thiols General procedure: To a flame-dried Schlenk tube was charged with a tertiary alcohol (0.30 mmol, 100 mol %), Cu(OTf)2 (1.1 mg, 0.003 mmol, 1 mol %). The tube was capped with a rubber septum. Mercaptan (0.30 mmol, 100 mol %) was added followed by addition of DCE (1 mL) via syringes. The reaction mixture was allowed to stir in an oil bath for 12 h under an air atmosphere at 70oC. Then, the reaction mixture was directly loaded onto a silica column without work-up. The residue was rinsed with PE or the eluent for column chromatography, with which the product was isolated.

Reference： [1]Xu, Bing; Ye, Yang; Lin, Ying; Bai, Renren; Ye, Xiang-Yang; Xie, Tian [Tetrahedron Letters, 2022, vol. 89]

104
[ 1191-08-8 ]
[ 617-94-7 ]
C₂₂H₃₀S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(II) bis(trifluoromethanesulfonate) In dichloromethane at 25℃; for 12h;

Reference： [1]Lin, Ying; Xie, Tian; Xu, Bing; Xu, Li; Ye, Xiang-Yang; Ye, Yang [RSC Advances, 2021, vol. 12, # 2, p. 692 - 697]

105
[ 50-00-0 ]
[ 1191-08-8 ]
[ 137-07-5 ]
4,5,6,7,9,10-hexahydro-1,3,8,10-benzotrithiazacyclododecine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: paraformaldehyd; 1,4-Butanedithiol In water monomer at 20℃; for 0.5h; Stage #2: 2-amino-benzenethiol With samarium(III) nitrate hexahydrate In ethanol; water monomer at 20℃; for 2.5h;	Cyclothiomethylation of isomeric aminobenzenethiolswith formaldehyde and alkanedithiols (generalprocedure). General procedure: A mixture of 1 mmol of ethane-1,2-dithiol, propane-1,3-dithiol, or butane-1,4-dithiol and0.148 mL (2 mmol) of 37% aqueous formaldehyde wasstirred at room temperature for 30 min. A solution of0.125 g (1 mmol) of 2- or 4-aminobenzenethiol in15 mL of ethanol and 0.022 g (0.05 mmol) ofSm(NO3)3.6H2O were then added, and the mixture wasstirred at ~20°C for 2.5 h. The reactions with 3-aminobenzenethiolwere carried out in a similar way using2 mmol of the amino thiol, 4 mmol of CH2O, and2 mmol of dithiol. The mixture was evaporated, andthe residue was subjected to silica gel column chromatographyto isolate pure heterocycles 1-8.

Reference： [1]Ibragimov, A. G.; Rakhimova, E. B. [Russian Journal of Organic Chemistry, 2022, vol. 58, # 3, p. 439 - 442][Zh. Org. Khim., 2022, vol. 58, # 3, p. 326 - 330]

106
[ 50-00-0 ]
[ 1191-08-8 ]
[ 22948-02-3 ]
C₂₄H₃₄N₂S₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	Stage #1: paraformaldehyd; 1,4-Butanedithiol In water monomer at 20℃; for 0.5h; Stage #2: 3-aminothiophenol With samarium(III) nitrate hexahydrate In ethanol; water monomer at 20℃; for 2.5h;	Cyclothiomethylation of isomeric aminobenzenethiolswith formaldehyde and alkanedithiols (generalprocedure). General procedure: A mixture of 1 mmol of ethane-1,2-dithiol, propane-1,3-dithiol, or butane-1,4-dithiol and0.148 mL (2 mmol) of 37% aqueous formaldehyde wasstirred at room temperature for 30 min. A solution of0.125 g (1 mmol) of 2- or 4-aminobenzenethiol in15 mL of ethanol and 0.022 g (0.05 mmol) ofSm(NO3)3.6H2O were then added, and the mixture wasstirred at ~20°C for 2.5 h. The reactions with 3-aminobenzenethiolwere carried out in a similar way using2 mmol of the amino thiol, 4 mmol of CH2O, and2 mmol of dithiol. The mixture was evaporated, andthe residue was subjected to silica gel column chromatographyto isolate pure heterocycles 1-8.

Reference： [1]Ibragimov, A. G.; Rakhimova, E. B. [Russian Journal of Organic Chemistry, 2022, vol. 58, # 3, p. 439 - 442][Zh. Org. Khim., 2022, vol. 58, # 3, p. 326 - 330]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	1191-08-8	MDL No. :	MFCD00004906
Formula :	C₄H₁₀S₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SMTOKHQOVJRXLK-UHFFFAOYSA-N
M.W :	122.25	Pubchem ID :	79148
Synonyms :

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	3334
Hazard Statements:	H315-H319-H413-H372	Packing Group:	Ⅲ
GHS Pictogram:

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 1191-08-8 ] {[proInfo.proName]}

Quality Control of [ 1191-08-8 ]

Related Doc. of [ 1191-08-8 ]

Product Details of [ 1191-08-8 ]

Safety of [ 1191-08-8 ]

Application In Synthesis of [ 1191-08-8 ]

[ 1191-08-8 ] Synthesis Path-Downstream 1~106

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry