Name: 71310-21-9|11-Mercaptoundecanoic acid|98%
Brand: Ambeed
SKU: A426627
Rating: 91 (30 reviews)

1
[ 6974-31-8 ]
[ 71310-21-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With sodium tetrahydroborate In ethanol at 20℃; for 4h; chemoselective reaction;
	With potassium hydroxide
	With aq. base

With hydroxide

Reference： [1]Location in patent: experimental part Sereda, Grigoriy; Pothula, Swetha; Dreessen, James [Synthetic Communications, 2010, vol. 40, # 9, p. 1312 - 1321]
[2]Koenig et al. [Journal of Organic Chemistry, 1958, vol. 23, p. 1525,1529]
[3]Burghard, M.; Schmelzer, M.; Roth, S.; Goepel, W. [Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 1994, vol. 252, p. 39 - 48]
[4]Finklea, Harry O.; Liu, Luna; Ravenscroft Melissa S.; Punturi, Sesto [Journal of Physical Chemistry, 1996, vol. 100, # 28, p. 18852 - 18858]

2
[ 2834-05-1 ]
[ 17356-08-0 ]
[ 71310-21-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol Verseifen mit wss.-alkoh.NaOH;

Reference： [1]Snyder et al. [Journal of the American Chemical Society, 1946, vol. 68, p. 1426] Rapoport; Smith; Newman [Journal of the American Chemical Society, 1947, vol. 69, p. 693,694]

3
[ 71310-21-9 ]
[ 74-88-4 ]
[ 80683-81-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide

Reference： [1]Rapoport; Smith; Newman [Journal of the American Chemical Society, 1947, vol. 69, p. 693,694]

4
[ 18542-39-7 ]
[ 71310-21-9 ]
[ 87050-15-5 ]

Yield	Reaction Conditions	Operation in experiment
80%	With triethylamine In chloroform for 24h; Ambient temperature;
80%	In chloroform

Reference： [1]Samuel, N. K. P.; Singh, Maninder; Yamaguchi, Kazuo; Regen, Steven L. [Journal of the American Chemical Society, 1985, vol. 107, # 1, p. 42 - 47]
[2]Regen, Steven L.; Yamaguchi, Kazuo; Samuel, N.K.P.; Singh, Maninder [Journal of the American Chemical Society, 1983, vol. 105, # 20, p. 6354 - 6355]
[3]Niwa, Masazo; Mori, Toshiaki; Nishio, Emi; Nishimura, Hirokazu; Higashi, Nobuyuki [Journal of the Chemical Society. Chemical communications, 1992, # 7, p. 547 - 549]

5
[ 2834-05-1 ]
[ 71310-21-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydroxide; sulfuric acid; thiourea In water	Preparation of 11-mercaptoundecanoic acid Preparation of 11-mercaptoundecanoic acid 4 g (15.09 mmol) 11-bromoundecanoic acid is added along with 1.505 g thiourea (19.82 mmol) and 15 ml water to a round botton flask, and the mixture is refluxed for 3 hours. 10.2 ml 3M sodium hydroxide (30.6 mmol) was then added and the mixture was refluxed for one additional hour. The reaction mixture was cooled in an ice bath, and dilute sulfuric acid was added dropwise until the solution had a pH of about 2. The cloudy solution was then extracted with ether (2*25 ml), dried over anhydrous MgSO4, and concentrated under reduced pressure to give a white solid (3.1 g, 94%). 1 H-NMR (300 MHz, CDCl3) 1.28, m, 10 H; 1.60, m, 7 H; 2.35, t, 2 H, J=7.3 Hz; 2.50, q, 2 H, J =7.5 Hz.
92%	Stage #1: 11-bromoundecanoic acid With thiourea In ethanol for 20h; Reflux; Schlenk technique; Stage #2: With sodium hydroxide In water at 90℃; for 20h; Inert atmosphere; Schlenk technique; Stage #3: With sulfuric acid In water Cooling with ice; Inert atmosphere; Schlenk technique;
90%	Stage #1: 11-bromoundecanoic acid With thiourea In water for 2.5h; Heating; Stage #2: With sodium hydroxide for 2h; Heating;

	With sodium hydroxide; thiourea 1.) EtOH, 2.) EtOH; Yield given. Multistep reaction;
	With sodium; tiolacetic acid
	Stage #1: 11-bromoundecanoic acid With trisodium thiophosphate In water; N,N-dimethyl-formamide for 5h; Stage #2: With hydrogenchloride In N,N-dimethyl-formamide
	Multi-step reaction with 2 steps 2: OH^(1-)
	Multi-step reaction with 2 steps 1: aqueous NaHCO₃; Na₂S₂ 2: zinc; glacial acetic acid; HCl
	Multi-step reaction with 2 steps 1: natrium carbonate 2: aqueous alcoholic NH₃
	With hydrogenchloride; sodium hydroxide; Hg; thiourea In ethanol; water	5 Preparation of 11-mercaptoundecanoic acid (a precursor) EXAMPLE 5 Preparation of 11-mercaptoundecanoic acid (a precursor) A mixture of 200 g of 11-bromoundecanoic acid, 60 g of thiourea and 600 mL of absolute ethanol was stirred and heated at reflux for two hours. After heating was stopped a solution of 80 g of sodium hydroxide in 250 mL of water was then added dropwise. The mixture was held overnight and then heated at reflux for three hours. After cooling to room temperature a solid precipitated from solution. The reaction mixture was poured into a mixture of ice and 200 g of concentrated hydrochloric acid. The solids were filtered from solution then slurried with ice water, isolated by filtration and washed twice. The off-white solid was stored in a crystallizing dish for one week, then dried under vacuum (~1 mm of Hg) at about 45° C. The product was distilled under vacuum (~1 mm of Hg at ~160° C.). NMR analysis indicated the desired product was obtained.
	Stage #1: 11-bromoundecanoic acid With thiourea Reflux; Stage #2: With sodium hydroxide for 1h;	1 Example 1 Borate Moiety-Contained Linker MB1 [0032] In thiol substitution reaction (as shown in Scheme 1), 11-bromoundecanoic acid (1) and thiourea perform substitution reaction, and thus thiol group (-SH) substitutes bromine group (-Br) to form 11-mercaptoundecanoic acid (2).

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF NOTRE DAME DU LAC - US5587475, 1996, A
[2]Rühling, Andreas; Schaepe, Kira; Rakers, Lena; Vonhören, Benjamin; Tegeder, Patricia; Ravoo, Bart Jan; Glorius, Frank [Angewandte Chemie - International Edition, 2016, vol. 55, # 19, p. 5856 - 5860][Angew. Chem., 2016, vol. 128, # 19, p. 5950 - 5955,6]
[3]Su, Chia-Hao; Wu, Pei-Lin; Yeh, Chen-Sheng [Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 1, p. 189 - 193]
[4]Guo, Bo Zhang; Tripathi, Sadhana; Taylor, D. Martin; Stirling, Charles J. M. [Journal of the Chemical Society. Chemical communications, 1991, # 7, p. 479 - 481]
[5]Bercegol, Herve; Boerio, F. James [Journal of Physical Chemistry, 1995, vol. 99, # 21, p. 8763 - 8767]
[6]Naud; Calas; Blancou; Commeyras [Journal of Fluorine Chemistry, 2000, vol. 104, # 2, p. 173 - 183]
[7]Cavalleri; Natale; Stroppolo; Relini; Cosulich; Thea; Novi; Gliozzi [Physical Chemistry Chemical Physics, 2000, vol. 2, # 20, p. 4630 - 4635]
[8]Finklea, Harry O.; Liu, Luna; Ravenscroft Melissa S.; Punturi, Sesto [Journal of Physical Chemistry, 1996, vol. 100, # 28, p. 18852 - 18858]
[9]Cohen [Journal of the Chemical Society, 1932, p. 593,598]
[10]Bauer; Stockhausen [Journal fur praktische Chemie (Leipzig 1954), 1931, vol. <2>130, p. 40] Cohen [Journal of the Chemical Society, 1932, p. 593,598]
[11]Current Patent Assignee: Monsanto (in: Bayer); BAYER AG - US5004558, 1991, A
[12]Current Patent Assignee: NATIONAL YANG MING CHIAO TUNG UNIVERSITY - US2014/5398, 2014, A1 Location in patent: Paragraph 0032

6
[ 71310-21-9 ]
[ 54654-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride In gaseous matrix for 0.166667h;

Reference： [1]Duevel, Robert V.; Corn, Robert M. [Analytical Chemistry, 1992, vol. 64, # 4, p. 337 - 342]

7
[ 71310-21-9 ]
[ 100-46-9 ]
[ 138153-91-0 ]

Yield	Reaction Conditions	Operation in experiment
	In gaseous matrix

Reference： [1]Duevel, Robert V.; Corn, Robert M. [Analytical Chemistry, 1992, vol. 64, # 4, p. 337 - 342]

8
[ 71310-21-9 ]
[ 625-51-4 ]
11-(Acetylamino-methylsulfanyl)-undecanoic acid [ No CAS ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 3725 - 3734

9
[ 71310-21-9 ]
[ 221002-03-5 ]
11-mercapto-undecanoic acid 2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.0^12,17]dotriaconta-1⁽²⁸⁾,12⁽¹⁷⁾,13,15,29,31-hexaen-14-ylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3.08333h;

Reference： [1]Fitzmaurice, Donald; Rao, S. Nagaraja; Preece, Jon A.; Stoddart, J. Fraser; Wenger, Sabine; Zaccheroni, Nelsi [Angewandte Chemie - International Edition, 1999, vol. 38, # 8, p. 1147 - 1150]

10
[ 76-84-6 ]
[ 71310-21-9 ]
[ 122-97-4 ]
3-phenyl-1-propyl 11-triphenylmethylthioundecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With dodecylbenzene-sulphonic acid In water for 48h;

Reference： [1]Manabe, Kei; Iimura, Shinya; Sun, Xiang-Min; Kobayashi, Shu [Journal of the American Chemical Society, 2002, vol. 124, # 40, p. 11971 - 11978]

11
[ 71310-21-9 ]
3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-propionic acid [ No CAS ]
9H-fluoren-9-ylmethyl N-(4-aminobutyl)carbamate hydrochloride [ No CAS ]
11-mercapto-undecanoic acid [4-(3-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-propionylamino)-butyl]-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Multistep reaction;
	Multistep reaction;

Reference： [1]Cheung, Chin Li; Camarero, Julio A.; Woods, Bruce W.; Lin, Tianwei; Johnson, John E.; De Yoreo, Jim J. [Journal of the American Chemical Society, 2003, vol. 125, # 23, p. 6848 - 6849]
[2]Cheung, Chin Li; Chung, Sung-Wook; Chatterji, Anju; Lin, Tianwei; Johnson, John E.; Hok, Saphon; Perkins, Julie; De Yoreo, James J. [Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10801 - 10807]

12
[ 71310-21-9 ]
3-[2-[2-[2-[2-(9H-fluoren-9-ylmethoxycarbonylamino)ethoxy]ethoxy]ethoxy]ethoxy]propanoic acid [ No CAS ]
9H-fluoren-9-ylmethyl N-(4-aminobutyl)carbamate hydrochloride [ No CAS ]
11-mercapto-undecanoic acid {4-[3-(2-{2-[2-(2-amino-ethoxy)-ethoxy]-ethoxy}-ethoxy)-propionylamino]-butyl}-amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	Multistep reaction;

Reference： [1]Cheung, Chin Li; Camarero, Julio A.; Woods, Bruce W.; Lin, Tianwei; Johnson, John E.; De Yoreo, Jim J. [Journal of the American Chemical Society, 2003, vol. 125, # 23, p. 6848 - 6849]

13
[ 71310-21-9 ]
[ 10419-77-9 ]
[ 634158-90-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With caesium carbonate In N,N-dimethyl-formamide at 20℃;

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

14
[ 71310-21-9 ]
[ 75-36-5 ]
[ 6974-31-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With acetic acid; zinc In dichloromethane at 0 - 20℃; for 1h;

Reference： [1]Kleinert, Mike; Roeckendorf, Niels; Lindhorst, Thisbe K. [European Journal of Organic Chemistry, 2004, # 18, p. 3931 - 3940]

15
[ 110-81-6 ]
[ 71310-21-9 ]
[ 87050-15-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine at 70℃; for 24h;

Reference： [1]Su, Chia-Hao; Wu, Pei-Lin; Yeh, Chen-Sheng [Bulletin of the Chemical Society of Japan, 2004, vol. 77, # 1, p. 189 - 193]

16
[ 6066-82-6 ]
[ 71310-21-9 ]
[ 240125-70-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
60%	With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 24h;
38%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;

	Stage #1: 11-mercaptounadecanoic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride Stage #2: 1-hydroxy-pyrrolidine-2,5-dione Further stages.;
	Stage #1: 1-hydroxy-pyrrolidine-2,5-dione; 11-mercaptounadecanoic acid In tetrahydrofuran at -5℃; for 0.25h; Stage #2: With dicyclohexyl-carbodiimide In tetrahydrofuran for 24.75h;

Reference： [1]Tavernaro, Isabella; Hartmann, Sebastian; Sommer, Laura; Hausmann, Heike; Rohner, Christian; Ruehl, Martin; Hoffmann-Roeder, Anja; Schlecht, Sabine [Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 81 - 97]
[2]Charvet, Nicolas; Reiss, Peter; Roget, Andre; Dapuis, Alain; Gruenwald, Didier; Carayon, Sophie; Chandezon, Frederic; Livache, Thierry [Journal of Materials Chemistry, 2004, vol. 14, # 17, p. 2638 - 2642]
[3]Camodeca, Caterina; Nuti, Elisa; Tosetti, Francesca; Poggi, Alessandro; D'Arrigo, Cristina; Zocchi, Maria Raffaella; Rossello, Armando [ChemMedChem, 2018, vol. 13, # 19, p. 2119 - 2131]
[4]Kaminska, Agnieszka; Inya-Agha, Obianuju; Forster, Robert J.; Keyes, Tia E. [Physical Chemistry Chemical Physics, 2008, vol. 10, # 28, p. 4172 - 4180]
[5]Antuch, Manuel; Abradelo, Dario G.; Cao, Roberto [New Journal of Chemistry, 2014, vol. 38, # 1, p. 386 - 390]

17
[ 71310-21-9 ]
bacterial poly(3-hydroxyalkanoate-co-3-hydroxyalkenoate), produced by Pseudomonas putida Gpo₁ (ATTC 29347) fed with octanoic (75 percent) and 10-undecenoic (25 percent) acids, 25 percent terminal side-chain double bonds, M_n 107500, M_w/M_n 2.3 [ No CAS ]
poly[3-hydroxyalkanoate-co-hydroxyalkenoate], produced by Pseudomonas putida fed with octanoic (75 percent) and 10-undecenoic (25 percent) acids, radical addition of 11-mercaptodecanoic acid to terminal side-chain double bonds, M_n 111500, M_w/M_n 2.6, DP 567 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With 2,2'-azobis(isobutyronitrile) In toluene at 75℃;

Reference： [1]Hany, Roland; Boehlen, Christine; Geiger, Thomas; Hartmann, Rene; Kawada, Jumpei; Schmid, Manfred; Zinn, Manfred; Marchessault, Robert H. [Macromolecules, 2004, vol. 37, # 2, p. 385 - 389]

18
[ 100-02-7 ]
[ 71310-21-9 ]
4-nitrophenyl 11-mercaptoundecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With pyridine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 23℃; for 6h;

Reference： [1]Belser, Thomas; Stoehr, Meike; Pfaltz, Andreas [Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8720 - 8731]

19
(3R,4R)-3,4-bis(diphenylphosphorothioyl)pyrrolidine [ No CAS ]
[ 71310-21-9 ]
1-[(3R,4R)-3,4-Bis-(diphenyl-phosphinothioyl)-pyrrolidin-1-yl]-11-mercapto-undecan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 23℃; for 6h;

Reference： [1]Belser, Thomas; Stoehr, Meike; Pfaltz, Andreas [Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8720 - 8731]

20
[ 71310-21-9 ]
[ 99135-90-7 ]
1-((3R,4R)-3,4-Bis-diphenylphosphanyl-pyrrolidin-1-yl)-11-mercapto-undecan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 23℃; for 6h;

Reference： [1]Belser, Thomas; Stoehr, Meike; Pfaltz, Andreas [Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8720 - 8731]

21
[ 71310-21-9 ]
[ 23483-56-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With sulfuryl dichloride In dichloromethane at 0℃; for 0.5h; Inert atmosphere;
91%	With iodine In tetrahydrofuran; dimethyl sulfoxide at 45℃;
87%	With dihydrogen peroxide; sodium hydroxide In water at 20℃; for 1.5h;	4.1.1 4.1.1. 11,11'-Dithiobis(undecanoic acid) (2).^30,37 To a suspension of 11-mercaptoundecanoic acid (1.15 g, 5.00 mmol) in H2O (540 mL) was added sodium hydroxide (2.80 g, 67.9 mmol) and hydrogen peroxide solution (30 wt %, 11 mL) was filled to a well-stirred clear solution. After being stirred for 90 min, concentrated HCl (37 wt %, 11 mL) was added and the mixture was extracted with EtOAc (3150 mL). The organic solution was washed with distilled water (250 mL), saturated aqueous NaCl (50 mL) and dried over Na2SO4. After removing the solvent, disulfide 2 was obtained as a white solid (945 mg, 87%). Mp 90.8-92.2 °C; 1H NMR (300 MHz, DMSO-d6) δ 1.18-1.34 (m, 24H), 1.43-1.52 (m, 4H), 1.54-1.66 (m, 4H), 2.18 (t, J=7.3 Hz, 4H), 2.69 (t, J=7.2 Hz, 4H); 13C NMR (75 MHz, DMSO-d6) δ 24.5, 27.8, 28.6, 28.6, 28.8, 28.9, 29.9, 33.7, 38.0, 174.6.

77%	With dihydrogen peroxide; sodium iodide In water at 20℃; for 0.5h;
70.5%	With trifluoroacetic acid In dichloromethane; acetone at 20℃; for 0.808333h;	1.1 (1) Take a 100 mL round bottom flask and add 20 mL of dichloromethane, 0.74 mL (10 mmol) of acetone and two drops of trifluoroacetic acid, and stir at room temperature for 30 minutes to activate the acetone. Add 4.37g (20mmol) of 11-mercaptoundecanoic acid to the activated acetone, and stir at room temperature for 48h. Then placed in a refrigerator at -20°C, filtered after the solid precipitated, washed the solid alternately with iced n-hexane and water, and dried to obtain the product formula (3) (n=10), a white solid, with a yield of 70.5%.
63%	With sodium hydroxide; iodine; potassium iodide In methanol for 0.5h;
63%	With iodine; potassium iodide; sodium hydroxide In methanol at 20℃; for 0.5h;
55%	With sodium hydroxide; dihydrogen peroxide In water for 0.5h;
	Stage #1: 11-mercaptounadecanoic acid With potassium hydroxide; iodine In ethanol at 20℃; for 1h; Stage #2: With hydrogenchloride In ethanol; water	2 Preparative Example 2; Preparation of; A solution of KOH (2.7 g) in ethanol (30.8 g) was magnetically stirred at room temperature. 11-Mercaptoundecanoic acid (5.0 g) was added slowly to the KOH solution. After the addition was complete, a solution of iodine (2.9 g) in ethanol (62.2 g) was added and the mixture was stirred for approximately one hour longer. The mixture was then poured into 1N aqueous HCl and the precipitated solid was isolated by filtration. The solid was washed with deionized water and was dried in air to afford 5.0 g of product.
	With dihydrogen peroxide; sodium iodide In ethyl acetate	5 Example 5 Borate Moiety-Contained Linker DB3 [0051] In dimer polymerization (as shown in Scheme 12), 11-mercaptoundecanoic acid (2) and hydrogen peroxide (H2O2) perform dimer polymerization to form a second intermediate (13) containing a disulfide bond.
	With bromine In N,N-dimethyl-formamide at 0℃; for 3h;

Reference： [1]Locatelli, Erica; Ori, Guido; Fournelle, Marc; Lemor, Robert; Montorsi, Monia; Comes Franchini, Mauro [Chemistry - A European Journal, 2011, vol. 17, # 33, p. 9052 - 9056]
[2]Cho, Hong-Jun; Park, Sungjun; Kim, Jungwon; Lee, Sang-Myung; Lee, Yoon-Sik [Synlett, 2013, vol. 24, # 1, p. 20 - 23]
[3]Sóti, Péter Lajos; Yamashita, Hiroki; Sato, Kohei; Narumi, Tetsuo; Toda, Mitsuo; Watanabe, Naoharu; Marosi, György; Mase, Nobuyuki [Tetrahedron, 2016, vol. 72, # 16, p. 1984 - 1990]
[4]Sabbatella, Gianfranco; Antonaroli, Simonetta; Diociauti, Marco; Nucara, Alessandro; Carbone, Marilena [New Journal of Chemistry, 2015, vol. 39, # 4, p. 2489 - 2496]
[5]Current Patent Assignee: NINGBO UNIVERSITY - CN112341367, 2021, A Location in patent: Paragraph 0019; 0044-0045
[6]Belser, Thomas; Stoehr, Meike; Pfaltz, Andreas [Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8720 - 8731]
[7]Li, Xiuru; Martin, Sharon J. H.; Chinoy, Zoeisha S.; Liu, Lin; Rittgers, Brandon; Dluhy, Richard A.; Boons, Geert-Jan [Chemistry - A European Journal, 2016, vol. 22, # 32, p. 11180 - 11185]
[8]Naka, Kensuke; Itoh, Hideaki; Chujo, Yoshiki [Bulletin of the Chemical Society of Japan, 2005, vol. 78, # 3, p. 501 - 505]
[9]Current Patent Assignee: 3M CO - US2005/107615, 2005, A1 Location in patent: Page/Page column 16
[10]Current Patent Assignee: NATIONAL YANG MING CHIAO TUNG UNIVERSITY - US2014/5398, 2014, A1 Location in patent: Paragraph 0051
[11]Dalton, Hannah L.; Estalayo-Adrián, Sandra; Gunnlaugsson, Thorfinnur; Kelly, John M.; McManus, Gavin J.; Savyasachi, Aramballi J. [Dalton Transactions, 2020, vol. 49, # 40, p. 14158 - 14168]

22
[ 71310-21-9 ]
[ 78277-30-2 ]
[ 888616-13-5 ]

Yield	Reaction Conditions	Operation in experiment
58%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h;

Reference： [1]Denoyelle, Severine; Polidori, Ange; Brunelle, Melanie; Vuillaume, Pascal Y.; Laurent, Sylvette; ElAzhary, Yousef; Pucci, Bernard [New Journal of Chemistry, 2006, vol. 30, # 4, p. 629 - 646]

23
[ 71310-21-9 ]
tris(10-carboxydecyl) trithioarsenite [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With arsenic(III) trioxide In methanol at 20℃; for 48h;

Reference： [1]Tsivgoulis, Gerasimos M.; Fotopoulou, Theano C.; Ioannou, Panayiotis V. [Phosphorus, Sulfur and Silicon and the Related Elements, 2006, vol. 181, # 2, p. 413 - 425]

24
[ 108-30-5 ]
[ 71310-21-9 ]
[ 129179-17-5 ]
9H-fluoren-9-ylmethyl N-(4-aminobutyl)carbamate hydrochloride [ No CAS ]
[ 166108-71-0 ]
2-(bis-carboxymethyl-amino)-6-{3-[2-(2-[4-(11-mercapto-undecanoylamino)-butylcarbamoyl]-methoxy}-ethoxy)-ethylcarbamoyl]-propionylamino}-hexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multistep reaction;

Reference： [1]Cheung, Chin Li; Chung, Sung-Wook; Chatterji, Anju; Lin, Tianwei; Johnson, John E.; Hok, Saphon; Perkins, Julie; De Yoreo, James J. [Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10801 - 10807]

25
[ 934499-56-6 ]
[ 71310-21-9 ]
11-(dodec-1-yldisulfanyl)undecanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With triethylamine In dichloromethane at 20℃; for 0.25h;

Reference： [1]Antoniow, Sylwia; Witt, Dariusz [Synthesis, 2007, # 3, p. 363 - 366]

26
[ 75-15-0 ]
[ 71310-21-9 ]
[ 100-39-0 ]
[ 939984-30-2 ]

Yield	Reaction Conditions	Operation in experiment
87.51%	Stage #1: carbon disulfide; 11-mercaptounadecanoic acid With sodium hydroxide In water at 20℃; for 0.5h; Stage #2: benzyl bromide In water at 20℃; for 24h; Further stages.;

Reference： [1]Samakande, Austin; Sanderson, Ronald D.; Hartmann, Patrice C. [Synthetic Communications, 2007, vol. 37, # 21, p. 3861 - 3872]

27
[ 75-21-8 ]
[ 71310-21-9 ]
α-carboxy-ω-hydroxy poly(ethylene glycol), thiol-anionic polymerization, M_n = 9820 (GPC), M_n = 6300 (NMR), M_w/M_n = 1.19 (GPC); monomer(s): ethylene oxide; 11-mercaptoundecanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 11-mercaptounadecanoic acid With Naphthalene anion ( K⁽¹⁺⁾ is the counterion) In tetrahydrofuran at 0℃; Stage #2: oxirane In tetrahydrofuran at 40℃; for 24h; Further stages.;

Reference： [1]Zeng, Faquan; Allen, Christine [Macromolecules, 2006, vol. 39, # 19, p. 6391 - 6398]

28
[ 75-21-8 ]
[ 71310-21-9 ]
α-carboxy-ω-hydroxy poly(ethylene glycol), thiol-anionic polymerization, M_n = 13600 (GPC), M_n = 9600 (NMR), M_w/M_n = 1.20 (GPC); monomer(s): ethylene oxide; 11-mercaptoundecanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 11-mercaptounadecanoic acid With Naphthalene anion ( K⁽¹⁺⁾ is the counterion) In tetrahydrofuran at 0℃; Stage #2: oxirane In tetrahydrofuran at 40℃; for 24h; Further stages.;

Reference： [1]Zeng, Faquan; Allen, Christine [Macromolecules, 2006, vol. 39, # 19, p. 6391 - 6398]

29
[ 71310-21-9 ]
[ 858972-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 63 percent / NaOH; KI; I₂ / methanol / 0.5 h 2: oxalyl chloride / CH₂Cl₂ / 12 h / 23 °C 3: 2.91 g / pyridine / CH₂Cl₂ / 12 h / 23 °C

Reference： [1]Belser, Thomas; Stoehr, Meike; Pfaltz, Andreas [Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8720 - 8731]

30
[ 71310-21-9 ]
1-((3R,4R)-3,4-Bis-diphenylphosphanyl-pyrrolidin-1-yl)-11-[11-((3R,4R)-3,4-bis-diphenylphosphanyl-pyrrolidin-1-yl)-11-oxo-undecyldisulfanyl]-undecan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 63 percent / NaOH; KI; I₂ / methanol / 0.5 h 2: oxalyl chloride / CH₂Cl₂ / 12 h / 23 °C 3: 4.60 g / Et₃N / CH₂Cl₂ / 12 h / 23 °C

Reference： [1]Belser, Thomas; Stoehr, Meike; Pfaltz, Andreas [Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8720 - 8731]

31
[ 71310-21-9 ]
[ 851778-52-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 63 percent / NaOH; KI; I₂ / methanol / 0.5 h 2: oxalyl chloride / CH₂Cl₂ / 12 h / 23 °C
	Multi-step reaction with 2 steps 1: sodium hydroxide; dihydrogen peroxide / water / 1.5 h / 20 °C 2: oxalyl dichloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

Reference： [1]Belser, Thomas; Stoehr, Meike; Pfaltz, Andreas [Journal of the American Chemical Society, 2005, vol. 127, # 24, p. 8720 - 8731]
[2]Sóti, Péter Lajos; Yamashita, Hiroki; Sato, Kohei; Narumi, Tetsuo; Toda, Mitsuo; Watanabe, Naoharu; Marosi, György; Mase, Nobuyuki [Tetrahedron, 2016, vol. 72, # 16, p. 1984 - 1990]

32
[ 71310-21-9 ]
N-{(S)-1-[(E)-2-(10-Carbamoyl-decane-1-sulfonyl)-vinyl]-3-methyl-butyl}-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

33
[ 71310-21-9 ]
N-{(S)-1-[(E)-2-(10-Carbamoyl-decane-1-sulfonyl)-vinyl]-3-methyl-butyl}-2-methoxy-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

34
[ 71310-21-9 ]
(E)-(S)-5-(10-Carbamoyl-decane-1-sulfonyl)-3-[(pyridine-4-carbonyl)-amino]-pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

35
[ 71310-21-9 ]
N-[(E)-(S)-3-(10-Carbamoyl-decane-1-sulfonyl)-1-(2-carbamoyl-ethyl)-allyl]-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

36
[ 71310-21-9 ]
(E)-(S)-5-(10-Carbamoyl-decane-1-sulfonyl)-3-(2-methoxy-benzoylamino)-pent-4-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

37
[ 71310-21-9 ]
N-{(S)-5-Amino-1-[(E)-2-(10-carbamoyl-decane-1-sulfonyl)-vinyl]-pentyl}-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

38
[ 71310-21-9 ]
N-[(E)-(S)-3-(10-Carbamoyl-decane-1-sulfonyl)-1-(4-hydroxy-benzyl)-allyl]-isonicotinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

39
[ 71310-21-9 ]
N-[(E)-(S)-3-(10-Carbamoyl-decane-1-sulfonyl)-1-(2-carbamoyl-ethyl)-allyl]-2-methoxy-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

40
[ 71310-21-9 ]
N-{(S)-5-Amino-1-[(E)-2-(10-carbamoyl-decane-1-sulfonyl)-vinyl]-pentyl}-2-methoxy-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

41
[ 71310-21-9 ]
N-[(E)-(S)-3-(10-Carbamoyl-decane-1-sulfonyl)-1-(4-hydroxy-benzyl)-allyl]-2-methoxy-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 85 percent / Cs₂CO₃ / dimethylformamide / 20 °C

Reference： [1]Wang, Gang; Yao, Shao Q. [Organic Letters, 2003, vol. 5, # 23, p. 4437 - 4440]

42
[ 765-04-8 ]
[ 71310-21-9 ]

Reference： [1]Journal of Physical Chemistry,1996,vol. 100,p. 18852 - 18858

43
[ 71310-21-9 ]
[ 87050-11-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 80 percent / CHCl₃ 2: 91 percent / DCC 3: 95 percent / tri-n-butylphosphine / H₂O; ethanol
	Multi-step reaction with 3 steps 1: 80 percent / triethylamine / CHCl₃ / 24 h / Ambient temperature 2: 91 percent / 4-(dimethylamino)pyridine, dicyclohexylcarbodiimide / CHCl₃ / 48 h / Ambient temperature; dark 3: 95 percent / tri-n-butylphosphine / ethanol; H₂O / 11 h / Ambient temperature; dark

Reference： [1]Regen, Steven L.; Yamaguchi, Kazuo; Samuel, N.K.P.; Singh, Maninder [Journal of the American Chemical Society, 1983, vol. 105, # 20, p. 6354 - 6355]
[2]Samuel, N. K. P.; Singh, Maninder; Yamaguchi, Kazuo; Regen, Steven L. [Journal of the American Chemical Society, 1985, vol. 107, # 1, p. 42 - 47]

44
[ 71310-21-9 ]
[ 87050-14-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 80 percent / CHCl₃ 2: 91 percent / DCC
	Multi-step reaction with 2 steps 1: 80 percent / triethylamine / CHCl₃ / 24 h / Ambient temperature 2: 91 percent / 4-(dimethylamino)pyridine, dicyclohexylcarbodiimide / CHCl₃ / 48 h / Ambient temperature; dark

Reference： [1]Regen, Steven L.; Yamaguchi, Kazuo; Samuel, N.K.P.; Singh, Maninder [Journal of the American Chemical Society, 1983, vol. 105, # 20, p. 6354 - 6355]
[2]Samuel, N. K. P.; Singh, Maninder; Yamaguchi, Kazuo; Regen, Steven L. [Journal of the American Chemical Society, 1985, vol. 107, # 1, p. 42 - 47]

45
[ 71310-21-9 ]
[ 93404-45-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 80 percent / triethylamine / CHCl₃ / 24 h / Ambient temperature 2: 91 percent / 4-(dimethylamino)pyridine, dicyclohexylcarbodiimide / CHCl₃ / 48 h / Ambient temperature; dark 3: 95 percent / tri-n-butylphosphine / ethanol; H₂O / 11 h / Ambient temperature; dark 4: 25 percent / triethylamine, iodine / benzene / 5 h / Ambient temperature

Reference： [1]Samuel, N. K. P.; Singh, Maninder; Yamaguchi, Kazuo; Regen, Steven L. [Journal of the American Chemical Society, 1985, vol. 107, # 1, p. 42 - 47]

46
[ 71310-21-9 ]
[ 4230-11-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: alcoholic KOH 2: H₂O₂; glacial acetic acid / 90 - 100 °C

Reference： [1]Rapoport; Smith; Newman [Journal of the American Chemical Society, 1947, vol. 69, p. 693,694]

47
[ 112-38-9 ]
[ 71310-21-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: petroleum ether; 10.11-epoxy-undecanoic acid ⁽¹⁾; HBr / bei Anwesenheit von Luftsauerstoff 2: ethanol / Verseifen mit wss.-alkoh.NaOH

Reference： [1]Snyder et al. [Journal of the American Chemical Society, 1946, vol. 68, p. 1426]

48
C₃₁H₂₃BrN₂O₇ [ No CAS ]
[ 71310-21-9 ]
C₄₂H₄₄N₂O₉S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In DMF (N,N-dimethyl-formamide)	1 Reaction of 5-carboxyfluorescein with N-hydroxysuccinimide (NHS) and 1,3-dicyclohexylcarbodiimide (DCC) in DMF gave the corresponding NHS ester, which was then treated with ethylenediamine. The resulting amine was reacted with α-bromophenylacetic acid NHS ester to afford the desired α-bromo derivative 1 (see FIG. 6A). Treatment of 1 with 11-mercaptoundecanoic acid and ET3N in DMF provided the acid 2. Finally, conversion of 2 to its NHS ester followed by reaction with dioctadecylamine gave the target structure Pro28-amide, also referred to herein as Pro28.

Reference： [1]Current Patent Assignee: LABORATORY CORPORATION OF AMERICA HOLDINGS - US2004/22843, 2004, A1 Location in patent: Page/Page column 27; Sheet 15/17

49
[ 71310-21-9 ]
[ 185815-93-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With toluene-4-sulfonic acid In benzene	Preparation of allyl 11-mercaptoundecanoate Preparation of allyl 11-mercaptoundecanoate 1.09 g (5 mmol) 11-mercaptoundecanoic acid was placed along with 3 g (51.7 mmol) allyl alcohol, 0.57 g p-toluenesulfonic acid and 40 ml benzene in a round bottom flask and heated for 25 minutes with azeotropic removal of water using a Dean-Stark apparatus. The reaction mixture was then cooled and washed with 10% aqueous sodium bicarbonate solution (3*20 ml). The benzene layer was dried over anhydrous MgSO4, and removal of solvent yielded a colorless oil (0.997 g, 77%). 1 H-NMR (300 MHz, CDCl3) 1.27, m, 12 H; 1.60, m, 5 H; 2.33, t, 2 H, J=7.5 Hz; 2.51, q, 2 H, J=7.4 Hz; 4.59, dt, 2 H, J=5.7, 1.4 Hz; 5.20-5.39, m, 2 H; 5.85-6.00, m, 1 H; IR (film) 2560 (SH), 1730 (C=O), 1640 cm-1 (C=C); EI-MS; 258 (M+).

Reference： [1]Current Patent Assignee: THE UNIVERSITY OF NOTRE DAME DU LAC - US5587475, 1996, A

50
[ 934751-37-8 ]
[ 71310-21-9 ]
[ 1002347-32-1 ]

Yield	Reaction Conditions	Operation in experiment
94%	In dichloromethane at 20℃; Inert atmosphere;
	In dichloromethane at 20℃;
	In dichloromethane at -30 - 20℃; for 0.5h; Inert atmosphere;	General procedure for thepreparation of disulfanyl derivatives 1 General procedure: Br2 (0.96g, 6.0 mmol) was added to a solution of bis-(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinanyl)disulfane (2.76 g, 7.0 mmol) in anhydrous CH2Cl2 (50 mL)at -30 °C and under N2. After 15 min, a solution of 11-sulfanylundecan-1-ol (2.25 g, 11 mmol) in anhydrous CH2Cl2 (5 mL) was added. The mixture was stirred at r.t. for 30 min, diluted with CH2Cl2(50mL), washed with H2O (50 mL), dried (MgSO4), filtered,and evaporated under vacuum. The residue was purified by column chromatography (silica gel, CH2Cl2) to give 1b as a white solid; yield: 4.42 g (95%); mp 40-42 °C.

Reference： [1]Location in patent: experimental part Kertmen, Ahmet; Lach, Slawomir; Rachon, Janusz; Witt, Dariusz [Synthesis, 2009, # 9, p. 1459 - 1462]
[2]Szymelfejnik, Mateusz; Demkowicz, Sebastian; Rachon, Janusz; Witt, Dariusz [Synthesis, 2007, # 22, p. 3528 - 3534]
[3]Lach, Slawomir; Demkowicz, Sebastian; Witt, Dariusz [Tetrahedron Letters, 2013, vol. 54, # 51, p. 7021 - 7023]

51
decacarbonyl-1κ(4)C,2κ(3)C,3κ(3)C-μ-hydrido-2:3κ(2)H-μ-hydroxy-2:3κ(2)O-trisosmium-(3 Os-Os) [ No CAS ]
[ 71310-21-9 ]
[ 881200-21-1 ]
[ 1024617-00-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 44% 2: 4%	With HBF₄ In diethyl ether; toluene (Ar or N2); using Schlenk techniques; addn. of excess of HS(CH2)10COOH and HBF4/ether (one drop) to soln. of Os3(CO)10(μ-H)(μ-OH) in toluene; reflux for 5 h; removal of solvent in vac., chromy. using hexane/CH2Cl2 as eluent; elem.anal.;

Reference： [1]Li, Chunxiang; Leong, Weng Kee [Journal of Organometallic Chemistry, 2008, vol. 693, # 7, p. 1292 - 1300]

52
[ 33941-15-0 ]
[ 71310-21-9 ]
[ 1071764-00-5 ]

Yield	Reaction Conditions	Operation in experiment
41.9%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃;

Reference： [1]Douglass Jr., Eugene F.; Driscoll, Peter F.; Liu, Deli; Burnham, Nancy A.; Lambert, Christopher R.; McGimpsey, W. Grant [Analytical Chemistry, 2008, vol. 80, # 20, p. 7670 - 7677]

53
[ 71310-21-9 ]
[ 76-83-5 ]
[ 202462-83-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	In dichloromethane at 20℃; for 2.5h;
95.2%	In dichloromethane at 20℃; for 6h;	1 Dissolve 1g/4.58mmol mercaptoundecanoic acid in 20mL of anhydrous dichloromethane, add 2.55g/9.16mmol of triphenylchloromethane in dichloromethane dropwise while stirring, and react at room temperature for 6h. After the completion of the reaction, the reaction solution was concentrated and recrystallized twice with 200 mL of petroleum ether to obtain 2.01 g of a white solid with a yield of 95.2%.
92%	With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 5h; Inert atmosphere;

90%	With N-ethyl-N,N-diisopropylamine In toluene for 24h;	1 11 -tritylsulfenylundecanoic acid (5) To a solution of 11 -mercaptoundecanoic acid (2g, 9.09 mmol) and DIPEA (4.8mL, 27.42 mmol) in toluene (60 mL), trityl chloride (5.12 g, 18.41 mmol) wasadded and stirred for 24 hours. The solvent was evaporated and the crudewas purified by column chromatography (AcOEt : Hex, 1:9) affording 5 (3.6 g,90%) as a white solid. 1H NMR (300 MHz, 0D013) 67.48-7.34 (m, 6H), 7.31-7.21 (m, 9H), 2.38 (t, 2H, J= 8.2 Hz), 2.18 (t, 2H, J= 7.5 Hz), 1.71-1.61 (m,2H), 1.47-1.22 (m, 12H), 0.95-0.88 (m, 2H).
73%	With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 20h;	4 A solution of 11-mercaptoundecanoic acid (2.70 g, 12.4 mmol), trityl chloride (4.14 g, 14.8 mmol), and DIPEA (5.17 mmol, 28.7 mmol) in toluene (40 mL) was stirred at room temperature for 20 h. The reaction was concentrated under reduced pressure and the crude residue was dissolved in DCM (100 mL), washed with H2O (3×100 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to a crude yellow oil. Purification by column chromatography yielded 10 as a white solid (4.14 g, 73%).
56%	With sodium acetate In N,N-dimethyl-formamide for 48h;
	With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 4h;
	With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 3h;
	In dichloromethane at 20℃; for 2h;

Reference： [1]Location in patent: experimental part Weissenborn, Martin J.; Wehner, Johannes W.; Gray, Christopher J.; Sardzik, Robert; Eyers, Claire E.; Lindhorst, Thisbe K.; Flitsch, Sabine L. [Beilstein Journal of Organic Chemistry, 2012, vol. 8, p. 753 - 762]
[2]Current Patent Assignee: YANTAI UNIVERSITY - CN113072582, 2021, A Location in patent: Paragraph 0048-0052
[3]Liu, Dingbin; Xie, Yunyan; Shao, Huawu; Jiang, Xingyu [Angewandte Chemie - International Edition, 2009, vol. 48, p. 4406 - 4408][Angew. Chem., Int. Ed., 2009, vol. 121, p. 4470 - 4472]
[4]Current Patent Assignee: GOVERNMENT OF SPAIN; UNIVERSITY OF SEVILLE - WO2017/50979, 2017, A1 Location in patent: Page/Page column 44
[5]Current Patent Assignee: OHMX - US9250203, 2016, B2 Location in patent: Page/Page column 49
[6]Ali, Muhammad; Hasenöhrl, Dominik H.; Zeininger, Lukas; Müllner, Alexander R. M.; Peterlik, Herwig; Hirsch, Andreas [Helvetica Chimica Acta, 2019, vol. 102, # 4]
[7]Zhou, Yang; Wang, Shixing; Zhang, Ke; Jiang, Xingyu [Angewandte Chemie - International Edition, 2008, vol. 47, # 39, p. 7454 - 7456]
[8]Liu, Dingbin; Chen, Wenwen; Sun, Kang; Deng, Ke; Zhang, Wei; Wang, Zhuo; Jiang, Xingyu [Angewandte Chemie - International Edition, 2011, vol. 50, # 18, p. 4103 - 4107]
[9]Jung, Sascha; Fuchs, Natalie; Johe, Patrick; Wagner, Annika; Diehl, Erika; Yuliani, Tri; Zimmer, Collin; Barthels, Fabian; Zimmermann, Robert A.; Klein, Philipp; Waigel, Waldemar; Meyr, Jessica; Opatz, Till; Tenzer, Stefan; Distler, Ute; Räder, Hans-Joachim; Kersten, Christian; Engels, Bernd; Hellmich, Ute A.; Klein, Jochen; Schirmeister, Tanja [Journal of Medicinal Chemistry, 2021, vol. 64, # 16, p. 12322 - 12358]

54
[ 934751-37-8 ]
[ 71310-21-9 ]
C₁₈H₃₅O₂PS₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	In dichloromethane at -30℃;

Reference： [1]Location in patent: body text Szymelfejnik, Mateusz; Demkowicz, Sebastian; Witt, Dariusz; Rachon, Janusz [Phosphorus, Sulfur and Silicon and the Related Elements, 2008, vol. 183, # 2-3, p. 415 - 419]

55
[ 71310-21-9 ]
C₁₄₅H₁₄₀N₄O₂₅ [ No CAS ]
C₁₅₅H₁₅₈N₄O₂₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate In dichloromethane at 20℃; for 2h;

Reference： [1]Location in patent: experimental part Frein, Stephane; Boudon, Julien; Vonlanthen, Mireille; Scharf, Toralf; Barbera, Joaquin; Suess-Fink, Georg; Buergi, Thomas; Deschenaux, Robert [Helvetica Chimica Acta, 2008, vol. 91, # 12, p. 2321 - 2337]

56
[ 71310-21-9 ]
[ 866718-67-4 ]
[ 1129546-14-0 ]

Yield	Reaction Conditions	Operation in experiment
46%	With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate In dichloromethane at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Frein, Stephane; Boudon, Julien; Vonlanthen, Mireille; Scharf, Toralf; Barbera, Joaquin; Suess-Fink, Georg; Buergi, Thomas; Deschenaux, Robert [Helvetica Chimica Acta, 2008, vol. 91, # 12, p. 2321 - 2337]

57
[ 71310-21-9 ]
3,5-bis{3',4',5'-tris[p-(n-dodecan-1-yloxy)benzyloxy]benzyloxy}benzyl alcohol [ No CAS ]
[ 1129546-19-5 ]

Yield	Reaction Conditions	Operation in experiment
34%	With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; 4-(dimethylamino)pyridinium tosylate In dichloromethane at 20℃; for 24h;

Reference： [1]Location in patent: experimental part Frein, Stephane; Boudon, Julien; Vonlanthen, Mireille; Scharf, Toralf; Barbera, Joaquin; Suess-Fink, Georg; Buergi, Thomas; Deschenaux, Robert [Helvetica Chimica Acta, 2008, vol. 91, # 12, p. 2321 - 2337]

58
[ 884539-90-6 ]
[ 71310-21-9 ]
C₄₃H₆₆N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 23℃; for 6h;

Reference： [1]Location in patent: experimental part Belsera, Thomas; Jacobsena, Eric N. [Advanced Synthesis and Catalysis, 2008, vol. 350, # 7-8, p. 967 - 971]

59
[ 71310-21-9 ]
[ 1220709-84-1 ]
[ 1220709-94-3 ]

Yield	Reaction Conditions	Operation in experiment
53%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Comes Franchini, Mauro; Bonini, Bianca Flavia; Camaggi, Carlo Maurizio; Gentili, Denis; Pession, Annalisa; Rani, Monica; Strocchi, Elena [European Journal of Medicinal Chemistry, 2010, vol. 45, # 5, p. 2024 - 2033]

60
[ 71310-21-9 ]
[ 216854-39-6 ]
[ 1220709-79-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Comes Franchini, Mauro; Bonini, Bianca Flavia; Camaggi, Carlo Maurizio; Gentili, Denis; Pession, Annalisa; Rani, Monica; Strocchi, Elena [European Journal of Medicinal Chemistry, 2010, vol. 45, # 5, p. 2024 - 2033]

61
[ 71310-21-9 ]
[ 1146648-01-2 ]
[ 1146648-04-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With dmap In tetrahydrofuran at 20℃; for 16h; Inert atmosphere;

Reference： [1]Bertin, Paul A.; Ahrens, Michael J.; Bhavsar, Kinjal; Georganopoulou, Dimitra; Wunder, Markus; Blackburn, Gary F.; Meade, Thomas J. [Organic Letters, 2010, vol. 12, # 15, p. 3372 - 3375]

62
[ 98-00-0 ]
[ 71310-21-9 ]
[ 1206186-56-2 ]

Yield	Reaction Conditions	Operation in experiment
45.2%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; Inert atmosphere;

Reference： [1]Location in patent: experimental part Liu, Xiaofeng; Liu, Huibiao; Zhou, Weidong; Zheng, Haiyan; Yin, Xiaodong; Li, Yuliang; Guo, Yanbing; Zhu, Mei; Ouyang, Canbin; Zhu, Daoben; Xia, Andong [Langmuir, 2010, vol. 26, # 5, p. 3179 - 3185]

63
[ 71310-21-9 ]
[ 1228007-69-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuryl dichloride In toluene at 20℃; for 0.25h;

Reference： [1]Location in patent: scheme or table Falciani, Chiara; Brunetti, Jlenia; Pagliuca, Chiara; Menichetti, Stefano; Vitellozzi, Lucia; Lelli, Barbara; Pini, Alessandro; Bracci, Luisa [ChemMedChem, 2010, vol. 5, # 4, p. 567 - 574]

64
[ 71310-21-9 ]
[ 1262447-14-2 ]
[ 1262447-17-5 ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine In dichloromethane at 20℃; for 0.25h; air;

Reference： [1]Location in patent: experimental part Lach, Slawomir; Sliwka-Kaszynska, Magdalena; Witt, Dariusz [Synlett, 2010, # 19, p. 2857 - 2860]

65
[ 71310-21-9 ]
[ 18156-74-6 ]
[ 1333319-14-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	In dichloromethane at 60℃; for 18h; Inert atmosphere;

Reference： [1]Caldwell, Marissa A.; Albers, Aaron E.; Levy, Seth C.; Pick, Teresa E.; Cohen, Bruce E.; Helms, Brett A.; Milliron, Delia J. [Chemical Communications, 2011, vol. 47, # 1, p. 556 - 558]

66
[ 71310-21-9 ]
[ 313538-20-4 ]
[ 1242410-98-5 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 11-mercaptounadecanoic acid; hypocrellin C With triethylamine In dimethyl sulfoxide at 25℃; for 5h; Inert atmosphere; Darkness; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide

Reference： [1]Location in patent: experimental part Zhang, Yang; Song, Liming; Xie, Jie; Qiu, Haixia; Gu, Ying; Zhao, Jingquan [Photochemistry and Photobiology, 2010, vol. 86, # 3, p. 667 - 672]

67
[ 95-14-7 ]
[ 71310-21-9 ]
[ 1311269-55-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	Stage #1: 1,2,3-Benzotriazole With thionyl chloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 11-mercaptounadecanoic acid In dichloromethane for 3h;	Synthesis of MUA-Bt as ligand; 1 l-(lH-benzotriazole-l-yl)-l 1-oxoundecane-l -thiol (MUA-Bt) was prepared according to following literature method (A.R. Katritzky, Y. Zhang, S.K. Singh, Synthesis 18 (2003) 2795-2798.) Thionylchloride (S0C12) (1 eq) was added to solution of lH-Benzotriazolee (Bt-H) (3eq) in CH2CI2 ( 100 mL) under nitrogen atmosphere at room temperature. After stirring 30 min, 1 1-mercaptoundecanoic acid (MUA) was poured into the reaction mixture. Upon the addition white precipitate was formed. The reaction mixture was stirred 3 h. After this perion white solid was filtered and washed with CH2CI2. The collected filtrate was extracted with 2 M NaOH (3x50 mL) to remove excess of Bt-H. The organic layer was dried with MgS04, the solvent was removed under vacuum. The crude product was purified using ethyl acetate-hexane mixture over silicagel column to get MUA-Bt as white microcrystals in %87 yield. 1H NMR (500 MHz, CDCl3-d), δ: 8.32 (d, J= 8.27 Hz, 1H), 8.15 (d, J= 8.30 Hz, 1H), 7.68 (t, J= 7.15 Hz, 1H), 7.53 (t, J= 7.17 Hz, 1H), 3.44 (t, J= 7.50 Hz), 2.89 (t, J= 7.50 Hz, 1H), 2.70 (t, J=7.50 Hz, 1H), 1.89-1.97 (m, 2H), 1.66-1.79 (m, 2H), 1.65-1.160 (m, 1H), 1.54-1.46 (m, 2H), 1.44-1.37 (m, 4H), 1.35-1.28 (m, 6H) ppm.13C NMR (125 MHz, CDCl3-d), δ: 24.5, 28.5, 28.8, 29.1 , 29.2, 29.4, 29.4, 35.5, 38.9, 39.2, 1 14.5, 120.1 , 126.1, 130.3, 131.14, 146.2, 172.7 ppm.

Reference： [1]Current Patent Assignee: SAY - WO2011/70402, 2011, A1 Location in patent: Page/Page column 14

68
[ 71310-21-9 ]
[ 38565-53-6 ]
C₂₂H₂₆F₁₇O₃S^(1-)*K⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 11-mercaptounadecanoic acid With potassium hydroxide In water; isopropyl alcohol Stage #2: (2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluorononyl)oxirane In water; isopropyl alcohol at 60℃; for 7.5h; Inert atmosphere;	4 Example 4; The following product is synthesized: [Show Image] The following are loaded into the same apparatus as Example 1: a) 21.84 g (0.1 mol) of 11-mercaptoundecanoic acid b) 5.61 g (0.1 mol) of potassium hydroxide c) 109.8 g of 2-propanol d) 10 g of water Under agitation and after complete solubilization, the pH of the solution is adjusted so as to obtain a value equal to 7-7.5. The solution is brought to 60°C and the following is introduced by means of a dripping funnel and in a nitrogen atmosphere: e) 47.6 g of epoxide (IV) (0.1 mol). The reaction is monitored by gas chromatographic analysis, extracting the epoxide with a non-polar solvent such as chloroform. The reaction ends after 7.5 hours. The product is solubilized with 63.21 g of water and another 36.62 g of 2-propanol. The solution thus obtained has 25% dry fraction, 25% water and 50% 2-propanol. It has a clear yellow color.

Reference： [1]Current Patent Assignee: GUARNIFLON - EP2343270, 2011, A2 Location in patent: Page/Page column 19

69
[ 54258-41-2 ]
[ 71310-21-9 ]
[ 1337529-71-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 25h;

Reference： [1]Elmes, Robert B. P.; Orange, Kim N.; Cloonan, Suzanne M.; Williams, D. Clive; Gunnlaugsson, Thorfinnur [Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 15862 - 15865]

70
[ 64-17-5 ]
[ 71310-21-9 ]
[ 1725-06-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sulfuric acid for 2h; Reflux;
80.6%	With Amberlyst-15 at 70℃; for 24h; Molecular sieve; Inert atmosphere;

Reference： [1]Brunetti, Fulvio G.; Isla, Helena; Arago, Juan; Orti, Enrique; Perez, Emilio M.; Martin, Nazario [Chemistry - A European Journal, 2013, vol. 19, # 30, p. 9843 - 9848]
[2]Location in patent: experimental part Compton, David L.; Jackson, Michael A. [Journal of the American Oil Chemists' Society, 2011, vol. 88, # 11, p. 1799 - 1805]

71
[ 71310-21-9 ]
[ 67000-89-9 ]
4-(pyren-4-yl) butyl-11-mercaptoundecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With hafnium/THF In toluene for 48h; Reflux; Molecular sieve;

Reference： [1]Location in patent: experimental part Aguilera-Sigalat, Jordi; Sanchez-Sanmartin, Jaime; Agudelo-Morales, Carlos E.; Zaballos, Elena; Galian, Raquel E.; Perez-Prieto, Julia [ChemPhysChem, 2012, vol. 13, # 3, p. 835 - 844]

72
1,6,9,12,15,18-hexachloro[C₆₀-I_h]fullerene [ No CAS ]
[ 71310-21-9 ]
C₁₁₅H₁₀₆O₁₀S₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With N-ethyl-N,N-diisopropylamine In toluene at 20℃;

Reference： [1]Location in patent: scheme or table Khakina, Ekaterina A.; Yurkova, Anastasiya A.; Peregudov, Alexander S.; Troyanov, Sergey I.; Trush, Vyacheslav V.; Vovk, Andrey I.; Mumyatov, Alexander V.; Martynenko, Vyacheslav M.; Balzarini, Jan; Troshin, Pavel A. [Chemical Communications, 2012, vol. 48, # 57, p. 7158 - 7160]

73
[ 71310-21-9 ]
[ 1443919-53-6 ]
[ 1443919-60-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 2,2-dimethoxy-2-phenylacetophenone In methanol at 90℃; UV-irradiation;

Reference： [1]Sassi, Mauro; Mascheroni, Luca; Ruffo, Riccardo; Salamone, Matteo M.; Pagani, Giorgio A.; Mari, Claudio M.; D'Oorazio, Giuseppe; La Ferla, Barbara; Beverina, Luca [Organic Letters, 2013, vol. 15, # 14, p. 3502 - 3505]

74
[ 71310-21-9 ]
[ 475290-46-1 ]
[ 1346753-25-0 ]

Yield	Reaction Conditions	Operation in experiment
76%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h; Inert atmosphere;

Reference： [1]Brunetti, Fulvio G.; Isla, Helena; Arago, Juan; Orti, Enrique; Perez, Emilio M.; Martin, Nazario [Chemistry - A European Journal, 2013, vol. 19, # 30, p. 9843 - 9848]

75
[ 697-45-0 ]
[ 71310-21-9 ]
[ 1002347-32-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5,5-dimethyl-2-thiolo-2-thiono-1,3,2-dioxaphosphorinane With bromine In dichloromethane at -30℃; for 0.25h; Inert atmosphere; Stage #2: 11-mercaptounadecanoic acid In dichloromethane at 20℃; for 0.5h;	11-[(5,5-Dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)di-sulfanyl]undecan-1-ol (1b);Typical Procedure Using Method A General procedure: Br2 (1.92 g, 12.0 mmol) was added to a solution of 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane (2.78 g, 14.0 mmol) in anhydrous CH2Cl2 (50 mL) at -30 °C and under N2. After 15 min, a solution of 11-sulfanylundecan-1-ol (2.25 g, 11 mmol) in anhydrous CH2Cl2 (5 mL) was added. The mixture was stirred at r.t. for 30 min, diluted with CH2Cl2(50mL), washed with H2O (50 mL), dried (MgSO4), filtered, and evaporated under vacuum. Theresidue was purified by column chromatography (silica gel, CH2Cl2) to give 1b
	Stage #1: 5,5-dimethyl-2-thiolo-2-thiono-1,3,2-dioxaphosphorinane With bromine Stage #2: 11-mercaptounadecanoic acid

Reference： [1]Lach, Slawomir; Witt, Dariusz [Synlett, 2013, vol. 24, # 15, p. 1927 - 1930]
[2]Lach, Slawomir; Witt, Dariusz [Heteroatom Chemistry, 2014, vol. 25, # 1, p. 10 - 14]

76
[ 71310-21-9 ]
[ 4073-59-0 ]
[ 1002347-32-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 0℃; for 0.0833333h;
	Stage #1: bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinan-2-yl)disulfide With bromine In dichloromethane at -30℃; for 0.25h; Inert atmosphere; Stage #2: 11-mercaptounadecanoic acid In dichloromethane at 20℃; for 0.5h;	11-[(5,5-Dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)disulfanyl]undecane-1-ol (1b);Typical Procedure Using Method B General procedure: Br2 (0.96 g, 6.0 mmol) was added to a solution of bis-(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinanyl) disulfane (2.76 g, 7.0 mmol) in anhydrous CH2Cl2 (50 mL) at -30 °Cand under N2. After 15 min, a solution of 11-sulfanylundecan-1-ol (2.25 g, 11 mmol) inanhydrous CH2Cl2 (5 mL) was added. The mixture was stirred at r.t. for 30 min, diluted with CH2Cl2(50 mL), washed with H2O (50 mL), dried (MgSO4), filtered, and evaporated under vacuum. The residue was purified by column chromatography (silica gel, CH2Cl2) to give 1b
	Stage #1: bis-(5,5-dimethyl-2-thiono-1,3,2-dioxaphosphorinan-2-yl)disulfide With bromine Stage #2: 11-mercaptounadecanoic acid

Reference： [1]Musiejuk, Mateusz; Klucznik, Tomasz; Rachon, Janusz; Witt, Dariusz [RSC Advances, 2015, vol. 5, # 40, p. 31347 - 31351]
[2]Lach, Slawomir; Witt, Dariusz [Synlett, 2013, vol. 24, # 15, p. 1927 - 1930]
[3]Lach, Slawomir; Witt, Dariusz [Heteroatom Chemistry, 2014, vol. 25, # 1, p. 10 - 14]

77
[ 71310-21-9 ]
5'-(1-methylethylidene)-5'-deoxy-2',3'-O-isopropylideneadenosine [ No CAS ]
C₂₅H₃₉N₅O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With pyridine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 3h;

Reference： [1]Vanegas, Julie P.; Peisino, Lucas E.; Pocovi-Martinez, Salvador; Zaragoza, Ramon J.; Zaballos-Garcia, Elena; Perez-Prieto, Julia [Chemistry - A European Journal, 2013, vol. 19, # 48, p. 16248 - 16255]

78
[ 71310-21-9 ]
[ 151013-83-1 ]
[ 1384472-02-9 ]

Yield	Reaction Conditions	Operation in experiment
650 mg	With sodium acetate In toluene at 50 - 60℃; for 1h; Inert atmosphere;	3 Example 3. The synthesis of compound 1c. Chlorfullerene C60Cl6 (500 mg, 0.5 mmol) was dissolved in argon atmosphere in 400 ml of freshly distilled toluene. To the solution there was added 3-5 g of dry sodium acetate crushed in a mortar and a large excess of 11-mercaptoundecanoic acid (1462 mg, 7 mmol). The reaction mixture was heated to 50-60°C with vigorously stirring for one hour. The reaction was accompanied by the formation of reddish orange product precipitate. After completing the reaction, the precipitate was filtered, washed with acetone and then washed off the filter with distilled water. To the resulting bright red solution there was dropwise added hydrochloric acid until complete precipitation of polycarboxylic derivative 1c. The resulting bright red precipitate was separated by centrifugation, washed three times with distilled water and then transferred to a round bottom flask with acetone of 250ml and evaporated to dryness. The yield of product was 650 mg (72% of theory). 1H NMR (600 MHz, (CD3)2CO:CS2 (1:1), δ, ppm): 1.36 (m, 50 H), 1.60 (m, 20 H), 1.84 (m, 10H), 2.26 (m, 10 H), 3.31 (m, 10H), 5.15 (s, 1H.). 13C NMR (150 MHz, (CD3)2CO:CS2 (1:1), δ, ppm): 25.19, 29.52, 29.63, 29.67, 29.77, 29.08, 30, 30.05, 30.09, 33.6, 33.71, 33.87, 53.99, 55.91, 56.59, 60.50, 143.19, 143.22, 143.28, 143.60, 144.01, 144.12, 144.17, 144.34 , 144.39, 144.43, 144.69, 145.24, 145.34, 146.77, 146.85, 147.60, 147.95, 148.12, 148.30, 148.51, 148.59, 148.71, 150.35, 151.22, 153.15, 154.34, 174.26

Reference： [1]Current Patent Assignee: RUSSIAN ACADEMY OF SCIENCES - EP2692722, 2014, A1 Location in patent: Paragraph 0032; 0033; 0034

79
[ 71310-21-9 ]
[ 76-83-5 ]
C₂₉H₃₄O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With N-ethyl-N,N-diisopropylamine In toluene at 20℃; for 20h; Inert atmosphere;

Reference： [1]Tavernaro, Isabella; Hartmann, Sebastian; Sommer, Laura; Hausmann, Heike; Rohner, Christian; Ruehl, Martin; Hoffmann-Roeder, Anja; Schlecht, Sabine [Organic and Biomolecular Chemistry, 2015, vol. 13, # 1, p. 81 - 97]

80
[ 71310-21-9 ]
[ 108-24-7 ]
[ 6974-31-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	In pyridine at 0 - 20℃;

Reference： [1]Ferreira, Miguel F.; Gonalves, Janaina; Mousavi, Bibimaryam; Prata, Maria I. M.; Rodrigues, Srgio P. J.; Calle, Daniel; Lpez-Larrubia, Pilar; Cerdan, Sebastian; Rodrigues, Tiago B.; Ferreira, Paula M.; Helm, Lothar; Martins, Jos A.; Geraldes, Carlos F. G. C. [Dalton Transactions, 2015, vol. 44, # 9, p. 4016 - 4031]

81
[ 71310-21-9 ]
C₂HF₃O₂*C₂₇H₃₄BFeN₃O₅ [ No CAS ]
C₃₈H₅₄BFeN₃O₆S*C₂HF₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;	1 Compound 1 To a solution of 11-mercaptoundecanoic acid (0.045 g, 0.206 mmol) and HATU (0.078 g, 0.206 mmol) in dichloromethane:N,N-dimethylformamide (1:1 v/v, 5 mL) was added compound 5 (0.105 g, 0.159 mmol) and diisopropylethylamine (0.083 mL, 0.477 mmol). The reaction was stirred at room temperature for 2 hours. The reaction mixture was diluted into ethyl acetate (150 mL) and washed with brine (3×50 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to crude residue that was purified by column chromatography (methanol:ethyl acetate:dichloromethane, 0.5:1.5:8) to yield the title compound as a yellow solid (0.035 g, 0.047 mmol, 30%). 1H NMR, 13C{1H} NMR, and HRMS were consistent with the title compound.

Reference： [1]Current Patent Assignee: OHMX - US9250203, 2016, B2 Location in patent: Page/Page column 38

82
[ 71310-21-9 ]
C₂₇H₃₄BFeN₃O₅ [ No CAS ]
C₃₈H₅₄BFeN₃O₆S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;	1 Compound 1 Compound 1. To a solution of 11 -mercaptoundecanoicacid (0.045 g, 0.206 mmol) and HATU (0.078 g, 0.206 mmol)in dichloromethane:N,N-dimethylformamide (1:1 v/v, 5 mL)was added compoundS (0.105 g, 0.159 mmol) and diisopropylethylamine (0.083 mL, 0.477 mmol). The reaction wasstirred at room temperature for 2 hours. The reaction mixturewas dilutedinto ethyl acetate (l5OmL) andwashedwithbrine(3x50 mL). The organic phase was dried over Na2SO4, filtered, and concentrated to crude residue that was purified bycolunm chromatography (methanol:ethyl acetate:dichloromethane, 0.5:1.5:8) to yield the title compound as a yellowsolid (0.035 g, 0.047 mmol, 30%). ‘H NMR, ‘3C{’H} NMR,and HRMS were consistent with the title compound.

Reference： [1]Current Patent Assignee: OHMX - US9250234, 2016, B2 Location in patent: Page/Page column 36

83
[ 71310-21-9 ]
3-(3-bromopropyl)-1-methyl-1H-imidazol-3-ium bromide [ No CAS ]
11-((3-(1-methyl-1H-imidazol-3-ium-3-yl)propyl)thio)undecanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate In ethanol at 20℃; for 72h; Schlenk technique;

Reference： [1]Rühling, Andreas; Schaepe, Kira; Rakers, Lena; Vonhören, Benjamin; Tegeder, Patricia; Ravoo, Bart Jan; Glorius, Frank [Angewandte Chemie - International Edition, 2016, vol. 55, # 19, p. 5856 - 5860][Angew. Chem., 2016, vol. 128, # 19, p. 5950 - 5955,6]

84
[ 71310-21-9 ]
[ 69655-76-1 ]
C₁₀₄H₂₀₀O₂₈S₈Si₈ [ No CAS ]

Reference： [1]New Journal of Chemistry,2016,vol. 40,p. 5997 - 6000

85
[ 71310-21-9 ]
[ 29265-73-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With sulfuryl dichloride In dichloromethane at 0℃; for 0.1h;

Reference： [1]Borsley, Stefan; Kay, Euan R. [Chemical Communications, 2016, vol. 52, # 58, p. 9117 - 9120]

86
[ 2645-22-9 ]
[ 71310-21-9 ]
C₁₆H₂₅NO₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With 2,4,6-trimethyl-pyridine; In N,N-dimethyl-formamide; at 20℃; for 2h;pH Ca. 7;	To a stirred solution of 11-mercapto undecanoic acid (10 mg, 4.6310-5 mol) in DMF (0.5 ml), 4,4-dithiodipyridyl(50 mg, 0.23 mmol) and 2,4,6-trimethyl pyridine (pH adjusted to -7) were added and mixed for 2 hr at room temperature.The reaction was followed by analytical HPLC. Upon water addition, the product precipitated. After washing 3 times withwater and centrifugation, 7.2 mg of undecanoic acid dithio-pyridyl were received (yield 48percent), and was then analyzed bymass spectrometry [M-H]+=326 g/mol.

Reference： [1]Patent: EP2437786,2016,B1 .Location in patent: Paragraph 0098

87
[ 71310-21-9 ]
1-(2-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl)pyrrole-2,5-dione [ No CAS ]
10-(2,5-dioxopyrrolidin-3-ylthio)decanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 11-mercaptounadecanoic acid; 1-(2-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethoxy)ethyl)pyrrole-2,5-dione In water; N,N-dimethyl-formamide for 0.116667h; Stage #2: With sodium hydrogencarbonate In water; N,N-dimethyl-formamide for 1h;	2.1 Preparation of PEG5-MAL-S-(CH2)10-COOH To a stirred solution of PEG5-MAL (50 mg in 2 ml H2O) 2.3 mg of 11-sulfanylundecanoic acid were added (0.1ml from a fresh solution of HS-(CH2)10-COOH in dimethylformamide, DMF, 23 mg/ml). After 7 min, 10 mg of solid NaHCO3were added. The reaction was carried out for 1 h, and after centrifugation the supernatant was dialyzed overnight againstH2O and lyophilized. The product thus obtained is 5,5’-bisdithio(2-nitrobenzoic acid) (DTNB; Ellman’s reagent)-negative.

Reference： [1]Current Patent Assignee: WEIZMANN INSTITUTE OF SCIENCE - EP2437786, 2016, B1 Location in patent: Paragraph 0088

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	71310-21-9	MDL No. :	MFCD00022096
Formula :	C₁₁H₂₂O₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GWOLZNVIRIHJHB-UHFFFAOYSA-N
M.W :	218.36	Pubchem ID :	543502
Synonyms :

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	3335
Hazard Statements:	H315-H319-H413-H372	Packing Group:	Ⅲ
GHS Pictogram:

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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

[ CAS No. 71310-21-9 ] {[proInfo.proName]}

Quality Control of [ 71310-21-9 ]

Related Doc. of [ 71310-21-9 ]

Product Details of [ 71310-21-9 ]

Safety of [ 71310-21-9 ]

Application In Synthesis of [ 71310-21-9 ]

[ 71310-21-9 ] Synthesis Path-Downstream 1~87

Related Functional Groups of
[ 71310-21-9 ]

Aliphatic Chain Hydrocarbons

Carboxylic Acids

Thiols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 71310-21-9 ] {[proInfo.proName]}

Quality Control of [ 71310-21-9 ]

Related Doc. of [ 71310-21-9 ]

Product Details of [ 71310-21-9 ]

Safety of [ 71310-21-9 ]

Application In Synthesis of [ 71310-21-9 ]

[ 71310-21-9 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 71310-21-9 ]

Aliphatic Chain Hydrocarbons

Carboxylic Acids

Thiols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 71310-21-9 ]