[ CAS No. 112-71-0 ] {[proInfo.proName]}

Name: 112-71-0|1-Bromotetradecane|98%
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Quality Control of [ 112-71-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 112-71-0 ]

CAS No. :	112-71-0	MDL No. :	MFCD00000228
Formula :	C₁₄H₂₉Br	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KOFZTCSTGIWCQG-UHFFFAOYSA-N
M.W :	277.28	Pubchem ID :	8208
Synonyms :

Calculated chemistry of [ 112-71-0 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	12
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	77.28
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-2.21 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.44
Log Po/w (XLOGP3) :	8.14
Log Po/w (WLOGP) :	6.08
Log Po/w (MLOGP) :	5.4
Log Po/w (SILICOS-IT) :	5.93
Consensus Log Po/w :	6.0

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.9
Solubility :	0.000353 mg/ml ; 0.00000127 mol/l
Class :	Moderately soluble
Log S (Ali) :	-8.0
Solubility :	0.00000279 mg/ml ; 0.00000001 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-6.38
Solubility :	0.000116 mg/ml ; 0.000000417 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.98

Safety of [ 112-71-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 112-71-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 112-71-0 ]
Downstream synthetic route of [ 112-71-0 ]

[ 112-71-0 ] Synthesis Path-Upstream 1~8

1
[ 1120-36-1 ]
[ 112-71-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With hydrogen bromide In 1,4-dioxane; hexane at 20℃; for 1 h;	To a mixture of tetradecene (393 mg, 2 mmol) in hexane (2 mL), was added 1c (17 wtpercent, 1.3 g,2.7 mmol) at room temperature. The mixture was then stirred for 1 h. The resulting mixture was quenched with water (10 mL) and extracted with diethyl ether (10 mL × 3). The combined organic extract was washed with brine (15 mL × 2) and then dried over Na2SO4 (5 g) and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (eluent: hexane) to afford bromotetradecane (543 mg, 98percent) as a colourless liquid. 1H-NMR (500 MHz, CDCl3) δ 0.89 (t, J = 6.9 Hz, 3H), 1.26 -1.31 (m, 18H), 1.84 (dd, J = 7.7 Hz, J= 6.7 Hz, 2H), 3.41 (t, J = 6.9 Hz, 2H); 13C NMR (126 MHz, CDCl3) δ 14.21, 22.85, 28.38, 28.97,29.55, 29.64, 29.74, 29.85 (4C), 32.11, 33.03, 33.59.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1190 - 1193
[2] Synlett, 2010, # 13, p. 2014 - 2018

2
[ 52756-06-6 ]
[ 112-71-0 ]
[ 6064-45-5 ]
[ 1950-69-2 ]

Reference： [1] Tetrahedron, 1983, vol. 39, # 24, p. 4097 - 4102

3
[ 1120-36-1 ]
[ 112-71-0 ]
[ 74036-95-6 ]

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 12, p. 1190 - 1193

4
[ 112-72-1 ]
[ 112-71-0 ]

Reference： [1] Journal of Organic Chemistry, 1942, vol. 7, p. 229
[2] Acta Chemica Scandinavica (1947-1973), 1948, vol. 2, p. 169[3] Acta Chemica Scandinavica (1947-1973), 1949, vol. 3, p. 939
[4] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1943, vol. 279, p. 76,83
[5] Journal of the Chemical Society, 1948, p. 642[6] Journal of the Chemical Society, 1934, p. 339
[7] Organic Syntheses, 1935, vol. 15, p. 26
[8] Journal fuer Praktische Chemie (Leipzig), 1960, vol. 10, p. 265 - 289
[9] Acta Chemica Scandinavica (1947-1973), 1964, vol. 18, p. 77 - 82
[10] Journal of Organometallic Chemistry, 1998, vol. 557, # 2, p. 157 - 161
[11] Patent: GB565452, 1944, ,

5
[ 83486-04-8 ]
[ 112-71-0 ]
[ 32294-60-3 ]

Reference： [1] Chemistry Letters, 1982, p. 1081 - 1084

6
[ 77774-34-6 ]
[ 1034-39-5 ]
[ 112-71-0 ]

Reference： [1] Journal of Organic Chemistry, 1986, vol. 51, # 25, p. 4941 - 4943

7
[ 67-56-1 ]
[ 629-73-2 ]
[ 112-71-0 ]

Reference： [1] Tetrahedron, 1989, vol. 45, # 18, p. 5971 - 5978

8
[ 112-71-0 ]
[ 75-50-3 ]
[ 1119-97-7 ]

Reference： [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2006, vol. 49, # 2, p. 147 - 151
[2] Bulletin de la Societe Chimique de France, 1955, p. 634
[3] Journal of Physical Chemistry, 1984, vol. 88, # 21, p. 5093 - 5099
[4] Bulletin of the Chemical Society of Japan, 2011, vol. 84, # 3, p. 312 - 319
[5] International Journal of Chemical Kinetics, 2013, vol. 45, # 1, p. 1 - 9

[ 112-71-0 ] Synthesis Path-Downstream 1~88

1
[ 5335-75-1 ]
[ 112-71-0 ]
4-butyl-1-tetradecyl-pyridinium; bromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 3959,3960, 3962

2
[ 1802-20-6 ]
[ 112-71-0 ]
3-pentyl-1-tetradecyl-pyridinium; bromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 3959,3960, 3962

3
[ 1129-69-7 ]
[ 112-71-0 ]
2-hexyl-1-tetradecyl-pyridinium; bromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 3959,3960, 3962

4
[ 27876-24-0 ]
[ 112-71-0 ]
4-hexyl-1-tetradecyl-pyridinium; bromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 3959,3960, 3962

5
[ 90-89-1 ]
[ 112-71-0 ]
[ 124202-99-9 ]

Reference： [1]Journal of the American Chemical Society,1957,vol. 79,p. 2211,2212

6
[ 2867-59-6 ]
[ 112-71-0 ]
[ 17952-38-4 ]

Reference： [1]Patent: US2874185,1956,

7
[ 112-71-0 ]
[ 2079-95-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ethanol; potassium hydrosulfide
	With sodium hydrogensulfide; ethanol; hydrogen sulfide
	Multi-step reaction with 2 steps 1: aqueous methanol; Na₂S₂ 2: zinc; H₂SO₄

Reference： [1]Fore; Bost [Journal of the American Chemical Society, 1937, vol. 59, p. 2557]
[2]Halpern; Glasser [Journal of the American Pharmaceutical Association (1912), vol. 38, p. 288][Chem.Abstr., 1949, p. 8610]
[3]Noller; Gordon [Journal of the American Chemical Society, 1933, vol. 55, p. 1091]

8
[ 112-71-0 ]
[ 2294-76-0 ]
2-pentyl-1-tetradecyl-pyridinium; bromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1951,vol. 73,p. 3959,3960, 3962

9
[ 112-71-0 ]
[ 109-46-6 ]
N,N'-dibutyl-S-tetradecyl-isothiourea; hydrobromide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 4271

10
[ 13093-04-4 ]
[ 112-71-0 ]
[ 71181-88-9 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1979,vol. 44,p. 773 - 780

11
[ 13093-04-4 ]
[ 112-71-0 ]
[ 71181-82-3 ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1979,vol. 44,p. 773 - 780

12
[ 112-71-0 ]
[ 19853-10-2 ]
[ 17454-98-7 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1967,vol. 36,p. 238 - 245

13
[ 112-71-0 ]
[ 603-35-0 ]
[ 25791-20-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	In acetonitrile;Reflux;	General procedure: 1-Bromotridecane or 1-bromotetradecane (30 mmol) and triphenyl phosphine (30 mmol) were refluxed in 125 mL dry CH3CN for overnight. The solvent was removed under reduced pressure and the residue was repeatedly washed with hexane or diethyl ether until the compound precipitate out. Further, it was recrystallized with benzene, ether (1:1) mixture to give white solid.
87%	at 140℃; for 8h;	PPh3 (12.4 g, 47.3 mmol)And CH3 (CH2) 12CH2Br (1-bromo tetradecane) (14.5 g, 52.3 mmol)Add into a round bottom flask,140 oil bath, the reaction under reflux 8h.Round bottom flask for the yellow viscous liquid,While it is hot (the temperature will lower it will solidify) Pour it into the beaker,Appropriate amount of ether was added, stirred vigorously, a white solid appeared, filtered, and the residue was drained dry and protected from light to give 14 as a white solid (23.67 g, 87%).Due to poor mass spectrometry, compounds were identified by NMR.
79%	In toluene; for 24h;Inert atmosphere; Reflux;	To a solution of commercial 1-bromotetradecane (5.47 g, 19.73 mmol) in dry toluene (16.5 mL) was added Ph3P (6.21 g, 23.67 mmol), and the resulting mixture was stirred and heated at reflux for 24 h. Removal of the solvent and chromatography of the residue on silica gel (CH2Cl2/MeOH, 20:1) gave 8.41 g (79%) of compound 13 25 as a white solid; mp 75-76 C (recrystallized from Et2O); lit. 25a mp not reported; lit. 25b mp 83-84 C. IR (neat) numax 2918, 2850, 1586, 1483, 1467, 1436, 1316, 1184, 1160, 1112, 1027 cm-1; 1H NMR (400 MHz, CDCl3): delta 0.87 (t, 3H, J = 6.8 Hz, CH3), 1.19-1.31 (m, 20H, 10 * CH2), 1.62-1.63 (m, 4H, 2 * CH2), 3.72-3.79 (m, 2H, CH2), 7.69-7.74 (m, 6H, Ph), 7.79-7.87 (m, 9H, Ph); 13C NMR (100 MHz, CDCl3): delta 14.0 (CH3), 22.5 (CH2), 22.6 (CH2), 22.9 (CH2), 29.1 (2 * CH2), 29.2 (CH2), 29.4 (CH2), 29.5 (CH2), 29.6 (2 * CH2), 30.3 (CH2), 30.4 (CH2), 31.8 (CH2), 117.9 (2 * Ci), 118.7 (Ci), 130.3 (3 * CHPh), 130.5 (3 * CHPh), 133.5 (3 * CHPh), 133.6 (3 * CHPh), 134.9 (3 * CHPh). Anal. Calcd for C32H44BrP: C, 71.23; H, 8.22. Found: 71.30; H, 8.16.

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 8624 - 8631
[2]Journal of the American Chemical Society,1984,vol. 106,p. 7861
[3]Journal of Chemical Ecology,1998,vol. 24,p. 867 - 889
[4]ARKIVOC,2012,vol. 2012,p. 421 - 436
[5]Patent: CN104497064,2017,B .Location in patent: Paragraph 0030; 0031
[6]Phosphorus, Sulfur and Silicon and the Related Elements,1990,vol. 53,p. 299 - 306
[7]Tetrahedron Asymmetry,2015,vol. 26,p. 1394 - 1407
[8]Pharmazie,1999,vol. 54,p. 26 - 30
[9]Organic Letters,2009,vol. 11,p. 939 - 942
[10]Recueil des Travaux Chimiques des Pays-Bas,1995,vol. 114,p. 153 - 156
[11]Chemistry and Physics of Lipids,2001,vol. 111,p. 111 - 138
[12]Journal of the Chemical Society. Perkin transactions I,1997,p. 2389 - 2393
[13]Helvetica chimica acta,1976,vol. 59,p. 2753 - 2764
[14]Journal of Organic Chemistry,1970,vol. 35,p. 3521 - 3524
[15]Agricultural and Biological Chemistry,1991,vol. 55,p. 2561 - 2570
[16]Journal of Medicinal Chemistry,1995,vol. 38,p. 2176 - 2187
[17]Journal of Chemical Ecology,2001,vol. 27,p. 1133 - 1149
[18]Beilstein Journal of Organic Chemistry,2009,vol. 5

14
[ 2150-45-0 ]
[ 112-71-0 ]
[ 130442-13-6 ]
2,6-Bis-tetradecyloxy-benzoic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662
[2]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

15
[ 112-71-0 ]
[ 56552-80-8 ]
[ 36314-50-8 ]

Yield	Reaction Conditions	Operation in experiment
79.4%	With sodium hydroxide In benzene for 20h; Heating;
79%	With sodium hydride In N,N-dimethyl-formamide at 20 - 60℃; for 16h;
75%	With sodium hydride In N,N-dimethyl-formamide at 60℃; for 10h;

Reference： [1]Ogawa, Tomoya; Beppu, Kazuo [Agricultural and Biological Chemistry, 1982, vol. 46, # 1, p. 255 - 262]
[2]Kasireddy, Krishnudu; Ali, Shoukath M.; Ahmad, Moghis U.; Choudhury, Sreeti; Chien, Pei-Yu; Sheikh, Saifuddin; Ahmad, Imran [Bioorganic Chemistry, 2005, vol. 33, # 5, p. 345 - 362]
[3]Kasireddy, Krishnudu; Ahmad, Moghis U.; Ali, Shoukath M.; Ahmad, Imran [Tetrahedron Letters, 2004, vol. 45, # 13, p. 2743 - 2746]

16
[ 112-71-0 ]
[ 494-38-2 ]
3,6-Bis-dimethylamino-10-tetradecyl-acridinium; bromide [ No CAS ]

Reference： [1]Journal of Physical Chemistry,1981,vol. 85,p. 281 - 285

17
[ 112-71-0 ]
[ 615-67-8 ]
[ 140466-86-0 ]
[ 140466-87-1 ]
2-Chloro-1,4-bis-tetradecyloxy-benzene [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 1650 - 1662

18
[ 112-71-0 ]
[ 117087-18-0 ]
[ 171191-13-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1995,vol. 43,p. 594 - 602

19
[ 2150-43-8 ]
[ 112-71-0 ]
[ 148452-93-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere;
82%	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16.5h;
69%	With 18-crown-6 ether; potassium carbonate In butanone Heating;

With potassium carbonate; potassium iodide In acetone Reflux;

Reference： [1]Location in patent: experimental part Elgueta; Parra; Barbera; Vergara; Ulloa [Supramolecular Chemistry, 2011, vol. 23, # 11, p. 721 - 730]
[2]Percec, Virgil; Rudick, Jonathan G.; Peterca, Mihai; Wagner, Martin; Obata, Makoto; Mitchell, Catherine M.; Cho, Wook-Dong; Balagurusamy, Venkatachalapathy S. K.; Heiney, Paul A. [Journal of the American Chemical Society, 2005, vol. 127, # 43, p. 15257 - 15264]
[3]Tuffin, Rachel P.; Toyne, Kenneth J.; Goodby, John W. [Journal of Materials Chemistry, 1996, vol. 6, # 8, p. 1271 - 1282]
[4]Sánchez, Ignacio; Fernández-Lodeiro, Adrián; Oliveira, Elisabete; Campo, José Antonio; Torres, M. Rosario; Cano, Mercedes; Lodeiro, Carlos [Dyes and Pigments, 2016, vol. 135, p. 184 - 200]

20
[ 112-71-0 ]
[ 6520-83-8 ]
[ 110202-81-8 ]

Reference： [1]Journal of Chemical Research, Miniprint,1997,p. 228 - 240

21
[ 57103-02-3 ]
[ 112-71-0 ]
[ 197860-64-3 ]

Reference： [1]Journal of Materials Chemistry,1999,vol. 9,p. 893 - 898
[2]Tetrahedron Letters,1997,vol. 38,p. 1785 - 1788

22
[ 112-71-0 ]
[ 5617-32-3 ]
1-(2-{2-[2-(2-{2-[2-(2-tetradecyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-tetradecane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6870 - 6873

23
[ 112-71-0 ]
[ 5117-19-1 ]
1-[2-(2-{2-[2-(2-{2-[2-(2-tetradecyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-tetradecane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6870 - 6873

24
[ 112-71-0 ]
[ 5579-66-8 ]
1-(2-{2-[2-(2-{2-[2-(2-{2-[2-(2-tetradecyloxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethoxy]-ethoxy}-ethoxy)-tetradecane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1999,vol. 64,p. 6870 - 6873

25
[ 112-71-0 ]
[ 33288-79-8 ]
4,4'-bis(tetradecyloxy)benzil [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2001,vol. 11,p. 1063 - 1071

26
[ 112-71-0 ]
[ 75154-68-6 ]
[ 338386-50-8 ]

Reference： [1]Journal of Materials Chemistry,2001,vol. 11,p. 269 - 277

27
[ 112-71-0 ]
[ 121-79-9 ]
[ 402912-75-8 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 2163 - 2173
[2]Chemistry - A European Journal,2010,vol. 16,p. 4588 - 4601
[3]Synthesis,2010,p. 953 - 958
[4]Chemistry - A European Journal,2001,vol. 7,p. 4863 - 4877
[5]Chemical Communications,2013,vol. 49,p. 10617 - 10619

28
[ 112-71-0 ]
[ 350-29-8 ]
[ 845755-16-0 ]

Reference： [1]Journal of Materials Chemistry,2002,vol. 12,p. 2214 - 2220

29
[ 112-71-0 ]
[ 98619-07-9 ]
1-(2-fluoro-4-tetradecyloxy-phenyl)-ethanone [ No CAS ]

Reference： [1]Journal of Materials Chemistry,2002,vol. 12,p. 2214 - 2220

30
[ 112-71-0 ]
[ 5315-79-7 ]
1-tetradecyl-1-pyrenyl ether [ No CAS ]

Reference： [1]Chemistry - A European Journal,2003,vol. 9,p. 1922 - 1932

31
[ 623-57-4 ]
[ 112-71-0 ]
[ 175699-94-2 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 2743 - 2746

32
[ 112-71-0 ]
[ 14714-50-2 ]
[ 850143-29-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1989 - 2007

33
[ 112-71-0 ]
[ 1478-53-1 ]
(1,1-difluoropentadecyl)phosphonic acid diethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	Stage #1: Diethyl difluoromethylphosphonate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 1-Bromotetradecane In tetrahydrofuran at 20℃;
40%	Stage #1: Diethyl difluoromethylphosphonate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 1-Bromotetradecane In tetrahydrofuran at -78℃;	5 Example 5Synthesis of (1,1-Difluoro-pentadecyl) Phosphonic Acid Diethyl Ester (10)[0153] To a solution of diethyl difluoromethanephosphonate (1.0 g, 5.316 mmol) in THF (50 mL) 2 M LDA (626 mg, 5.847 mmol) was added at -78° C. and stirred for 30 min. Tetradecyl bromide (1.474 g, 5.316 mmol) in THF (10 mL) was added to the mixture at -78° C. and the reaction mixture was stirred overnight. THF was evaporated and the residual oil was purified by flash chromatography using 30% ethyl acetate in hexane as eluent to give 817 mg (40%) of compound 10 as colorless oil. 1H NMR (CDCl3): 54.26 (m, 4H), 2.05 (m, 2H), 1.56 (m, 2H), 1.37 (t, J=6.9 Hz, 6H), 1.25 (br s, 22H), 0.87 (t, J=6.6 Hz, 3H); MS: [M+23Na] at m/z 407.2.
40%	Stage #1: Diethyl difluoromethylphosphonate With lithium diisopropyl amide In tetrahydrofuran at -78℃; Stage #2: 1-Bromotetradecane	Modified alkyl-phenyl-alkyl phosphoric acid esters and straight chain di-halo phosphonates were synthesized by methods described in U.S. patent application Ser. No. 10/963,085 (Publication No. 2006/0009507A1) and tested for activity against the LPA receptors. A preferred scheme for the synthesis of the difluoro-alkyl phosphonates and reagents (a) (i) LDA, -78° C., THF; (ii) C14H29Br, 40% (b) (i) TMSBr, CH2Cl2, 6 h., rt; (b) MeOH/H2O, 78% is shown below and effects of synthesized compounds on LPA receptor subtypes are shown in Table 4.

40%

Stage #1: Diethyl difluoromethylphosphonate With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 1-Bromotetradecane In tetrahydrofuran at -78℃;

5 To A solution of diethyl difluoromethanephosphonate (1. 0 g, 5. 316 MMOL) in THF (50 ML) 2 M LDA (626 MG, 5. 847 MMOL) was added AT-78°C and stirred for 30 min. Tetradecyl bromide (1. 474 g, 5. 316 MMOL) in THF (10 ML) was added to the mixture AT-78°C and the reaction mixture was stirred overnight. THF was evaporated and the residual oil was purified by flash chromatography using 30% ethyl acetate in hexane as eluent to give 817 mg (40%) of compound 10 as colorless oil. H NMR (CDCl3) : No. 4. 26 (M, 4H), 2. 05 (M, 2H), 1. 56 (M, 2H), 1. 37 (t, J= 6. 9 HZ, 6H), 1. 25 (BR S, 22H), 0. 87 (t, J= 6. 6 HZ, 3H) ; MS : (M + 23Na] at m/z 407. 2.

Reference： [1]Durgam, Gangadhar G.; Virag, Tamas; Walker, Michelle D.; Tsukahara, Ryoko; Yasuda, Satoshi; Liliom, Karoly; Van Meeteren, Laurens A.; Moolenaar, Wouter H.; Wilke, Nicole; Siess, Wolfgang; Tigyi, Gabor; Miller, Duane D. [Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4919 - 4930]
[2]Current Patent Assignee: RXBIO - WO2010/51053, 2010, A1 Location in patent: Page/Page column 38
[3]Current Patent Assignee: Miller, Duane D.; Tigyi, Gabor J.; Gududuru, Veeresa; Fujiwara, Yuko; Baker, Daniel; Walker, Michelle D.; Durgam, Gangadar Good - US2006/270634, 2006, A1 Location in patent: Page/Page column 6
[4]Current Patent Assignee: UNIVERSITY OF TENNESSEE - WO2005/32494, 2005, A2 Location in patent: Page/Page column 41

35
[ 112-71-0 ]
[ 187590-77-8 ]
2,3,5-tri-O-benzyl-1,4-dideoxy-1,4-[(1-tetradecyl)-(R)-episulfoniumylidene]-D-arabinitol tetrafluoroborate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With silver tetrafluoroborate; In acetonitrile; at 65℃; for 17h;	2,3,5-Tri-O-benzyl-1,4-dideoxy-1,4-[(1-tetradecyl)-(R)-episulfoniumylidene]-D-arabinitol tetrafluoroborate (66) The reaction of thioarabinitol 63 (300 mg, 0.71 mmol) with the bromide 54 (0.195 mL, 0.79 mmol) and AgBF4 (154 mg, 0.79 mmol) in dry CH3CN (8 mL) gave compound 66 as a colorless syrup (370 mg, 74%): [alpha]D +8.11 (c 0.4, MeOH); 1H NMR (CDCl3): delta 7.37-7.32 (m, 9H, Ar), 7.25-7.18 (m, 6H, Ar), 4.62 and 4.50 (2d, each 1H, Ja,b=11.9 Hz, CH2Ph), 4.61 and 4.43 (2d, each 1H, Ja,b=11.8 Hz, CH2Ph), 4.54 and 4.48 (2d, each 1H, Ja,b=11.7 Hz, CH2Ph), 4.54 (br s, 1H, H-2), 4.37 (d, 1H, J1a,1b=13.2 Hz, H-1a), 4.15 (br s, 1H, H-3), 3.78-3.75 (m, 2H, H-4 and H-5a), 3.68 (ddd, 1H, J1'a,1'b=13.1 Hz, J1'a,2'a=J1'a,2'b=8.2 Hz, H-1'a), 3.64 (dd, 1H, J5b,4=J5b,5a=11.9 Hz, H-5b), 3.64 (dd, 1H, J1b,1a=13.2 Hz, J1b,2=3.1 Hz, H-1b), 3.28-3.22 (m, 1H, H-1'b), 1.78-1.72 (m, 2H, H-2'), 1.50-1.20 (m, 22H, H-3'-H-13'), 0.88 (dd, 3H, J14',13'a=J14',13'b=6.8 Hz, H-14'); 13C NMR (CDCl3): delta 136.6, 136, 135.8 (3Cipso), 128.8-127.8 (15CAr), 82.8 (C-3), 81.8 (C-2), 73.7, 72.6, 71.9 (3 CH2Ph), 66.9 (C-5), 66.6 (C-4), 46.8 (C-1), 45.4 (C-1'), 31.9-22.7 (11C, C-3'-C-13'), 25.7 (C-2'), 14.1 (C-14'); MALDI-TOF MS: m/z 617.86 [M-BF4]+. Anal. Calcd for C40H57BF4O3S: C, 68.17; H, 8.15. Found: C, 68.14; H, 8.29.

Reference： [1]Carbohydrate Research,2007,vol. 342,p. 901 - 912
[2]Patent: US2007/244184,2007,A1 .Location in patent: Page/Page column 12; 23

36
[ 112-71-0 ]
[ 187590-77-8 ]
C₄₀H₅₇O₃S⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	In 1,1,1,3,3,3-hexafluoroisopropanol (HFIP); at 90℃; for 24h;Sealed tube;	A mixture of the thioarabinitol 63 (500 mg, 1.19 mmol) and the bromide 54 (0.357 mL, 1.31 mmol) in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP, 1 mL) was stirred and heated in a sealed tube at 90 C. for 24 h. The progress of the reaction was monitored by TLC analysis of aliquots (CHCl3/MeOH, 10:1) that showed a 30% conversion of product. Further heating did not improve the conversion rate. Hence, the mixture was cooled, and concentrated to give a syrupy residue. Purification by column chromatography (gradient of CHCl3/MeOH, 10:1) gave the purified sulfonium-ion 64 (235 mg, 47%, based on the isolation of 40% unreacted starting material 63)

Reference： [1]Carbohydrate Research,2007,vol. 342,p. 901 - 912
[2]Patent: US2007/244184,2007,A1 .Location in patent: Page/Page column 12; 22

37
[ 2425-41-4 ]
[ 112-71-0 ]
2-phenyl-5,5'-bis(tetradecyloxymethyl)-1,3-dioxane [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 7762 - 7773
[2]Chemistry - A European Journal,2007,vol. 13,p. 5585 - 5600

38
[ 112-71-0 ]
[ 2840-26-8 ]
[ 170082-19-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In methanol; water; ethyl acetate; N,N-dimethyl-formamide;	EXAMPLE 3 Synthesis of Tetradecyl 3-Amino-4-methoxybenzoate 16.7 g (0.1 mol) of <strong>[2840-26-8]3-amino-4-methoxybenzoic acid</strong> was added to 50 ml of N,N-dimethylformamide. Then 13.8 g (0.1 mol) of potassium carbonate was added to the solution obtained above, and the resulting mixture was stirred in the temperature range of from 20 to 30 C. for 30 min. 30.5 g (0.11 mol) of tetradecyl bromide was poured into the solution thus obtained, and the resulting solution was heated to 80 C., and allowed to react at the temperature for 1 hour. After completing the reaction, 50 ml of ethyl acetate, and 50 ml of water were added to the reaction mixture, and the organic layer obtained was separated, concentrated, diluted with 100 ml of methanol, and then cooled to precipitate crystals. The crystals were separated by filtration, and then dried to obtain 33.1 g (yield 91%) of the desired product. Purity 98% or higher. Melting point 54.0-56.0 C. A result of the elemental analysis of this sample was as follows:

Reference： [1]Patent: US5908955,1999,A

39
[ 98-01-1 ]
aq. NH₄ Cl [ No CAS ]
[ 112-71-0 ]
[ 25791-20-2 ]
[ 59958-20-2 ]

Yield	Reaction Conditions	Operation in experiment
	With N2; triphenylphosphine; In tetrahydrofuran; benzene;	EXAMPLE 8 Preparation of 2-(1Z-pentadecyl)furan This example describes preparation of 2-(1Z-pentadecyl)furan, compound (3), according to Scheme 2B. A mixture of 1-bromotetradecane (10) (10.0 g, 36.1 mmol), triphenylphosphine (10.5 g, 36.1 mmol) and benzene (25 ml) was refluxed for 48 h, then the mixture was concentrated under reduced pressure to a viscous oil. Addition of ether afforded a white solid, which was dried under vacuum for 24 h at 65 C., yielding 18.9 g (92%) of <strong>[25791-20-2]tetradecyltriphenylphosphonium bromide</strong> 11, which was used without further purification. Potassium hydride (2.33 g, 20.2 mmol, 35% oil dispersion) was washed with hexanes (35 ml) and pumped under vacuum. After 5 mm, the flask was filled with N2, dry THF (50 ml) was added and the reaction flask cooled in an ice bath. The phosphonium salt 11 (10 g, 18.5 mmol) was added in small portions over a 20 mm period. After stirring for 15 mm, the resulting yellow solution was warmed to room temperature and stirred for 30 mm, then cooled to -78 C. Freshly distilled furaldehyde (2.1 g, 22.2 mmol) in TIIF (25 ml) was added dropwise over 15 min. The resulting solution was stirred for 1 h, then warmed to room temperature and stirred for 18 h. The reaction was quenched with saturated aq. NH4 Cl (50 ml). The organic layer was separated and the aqueous layer was extracted with ether (320 ml). The combined organic layers were washed with saturated NaHCO3 (125 ml) and brine (125 ml), dried over MgSO4, filtered, and concentrated under vacuum. The crude product was purified by flash chromatography (hexanes), to afford 4.2 g (81%) of a mixture of furans 3 and 2 (7:3 cis/trans ratio). 1 H-NMR of major product: (CDCl3) (0.92 (3H, distorted t, J~ 7.0 Hz), 1.2-1.6 (22H, m), 2.45 (2H, apparent dq, J~ 1.8 Hz, 7.1 Hz), 5.58 (1H, dt, J 11.6, 7.1 Hz), 6.2-6.3 (2H, m), 6.40 (1H, dd, J~ 3.2, 2.0 Hz), 7.38 (1H, d, J 1.7 Hz).

Reference： [1]Patent: US6133313,2000,A

40
[ 112-71-0 ]
[ 19311-91-2 ]
[ 78-93-3 ]
[ 148452-71-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In chloroform;	EXAMPLE 18 N,N-Diethyl-2-(tetradecyloxy)benzamide A mixture of 25 g of <strong>[19311-91-2]N,N-diethylsalicylamide</strong>, 38.5 ml of 1-bromotetradecane, 22.35 g of potassium carbonate and 400 ml of 2-butanone is heated at reflux temperature for 16 hours. The reaction is cooled, filtered and concentrated in vacuo. The concentrate is dissolved in chloroform, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-30% ethyl acetate/hexane) to give 42.5 g of the desired product as colorless crystals. MP 31-32 C. EI-MS:m/z 390 (M+).

Reference： [1]Patent: US5208247,1993,A

41
[ 100-02-7 ]
[ 112-71-0 ]
[ 5137-55-3 ]
[ 94741-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In water; toluene;	EXAMPLE 81 4-Nitrophenyl tetradecyl ether A mixture of 75 g of 4-nitrophenol, 149.5 g of 1-bromotetradecane, 26.96 g of sodium hydroxide, 2.18 g of trioctyl methylammonium chloride, 400 ml of toluene and 400 of water is heated at reflux for 65 hours. The organic layer is separated, washed with 1N sodium hydroxide and dilute hydrochloric acid, dried and concentrated in vacuo. The residue is recrystallized from petroleum ether to give the desired product. MP 57-60 C. EI-MS:m/z 335 (M+).

Reference： [1]Patent: US5208247,1993,A

42
[ 112-71-0 ]
[ 60563-13-5 ]
[ 148452-82-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In dichloromethane; acetone;	EXAMPLE 66 3-Methoxy-4-(tetradecyloxy)benzeneacetic acid ethyl ester A mixture of 50 g of <strong>[60563-13-5]3-methoxy-4-hydroxybenzeneacetic acid ethyl ester</strong>, 66.1 g of powdered potassium carbonate, 70.57 g of 1-bromotetradecane and 500 ml of acetone is heated at reflux temperature for 76 hours. The reaction is cooled, filtered and the filtrate concentrated in vacuo. The residue is dissolved in methylene chloride, washed with 2% sodium bicarbonate and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by column chromatography (silica gel:0-10% ethyl acetate/hexane) to give 66.6 g of the desired product as colorless crystals. MP 40-41 C. EI-MS:m/z 406 (M+).

Reference： [1]Patent: US5208247,1993,A

43
[ 112-71-0 ]
[ 3316-09-4 ]
[ 156450-07-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In N,N-dimethyl-formamide; acetone;	EXAMPLE 116 3,4-Bis(tetradecyloxy)nitrobenzene A mixture of 1.0 g (6.45 mmol) of <strong>[3316-09-4]4-nitrocatechol</strong>, 4.8 ml (16.1 mmol) of 1-bromotetradecane and 2.5 g (17.4 mmol) of potassium carbonate in 20 ml of acetone and 10 ml of DMF was stirred at reflux under argon for 24 hours. The reaction mixture was filtered while hot and the filtrate was allowed to cool to room temperature and 3.5 g (99% yield, mp 64-66) of 3,4-bis(tetradecyloxy) nitrobenzene was obtained by filtration.

Reference： [1]Patent: US5324747,1994,A

44
[ 2150-45-0 ]
[ 112-71-0 ]
[ 130442-13-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; In tetrahydrofuran; N,N-dimethyl-formamide;	EXAMPLE 29 Methyl 2-hydroxy-6-(tetradecyloxy)benzoate To a suspension of 6.2 g of hexanes washed sodium hydride in 75 ml of N,N-dimethylformamide was added dropwise over 1.5 hours a solution of 20.0 g of <strong>[2150-45-0]methyl 2,6-dihydroxybenzoate</strong> in 50 ml of N,N-dimethylformamide and 24 ml of tetrahydrofuran. The resulting mixture was cooled to 0 C. and 1.78 g of sodium iodide added followed by the dropwise addition of 34.7 g of 1-bromotetradecane over 1 hour. The bath was removed and the mixture stirred at ambient temperature for 17 hours. The mixture was diluted with 500 ml of iced dilute hydrochloric acid, and extracted with ether. The ether layer was dried over magnesium sulfate and evaporated to an oil which was purified by chromatography on silica gel with ethyl acetate:hexanes giving an oil which was distilled in a Kugelrohr apparatus giving 3.0 g of the desired compound as a white solid, B.P. 130-180 C.

Reference： [1]Patent: US4983592,1991,A

45
[ 37964-17-3 ]
dimethylformamide [DMF] [ No CAS ]
[ 112-71-0 ]
ethyl 1-tetradecylpyrrole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89.0%	With sodium chloride; In water;	EXAMPLE 56 Preparation of ethyl 1-tetradecylpyrrole-3-carboxylate (Compound No.93 in Table 1) To dry dimethylformamide (DMF) (15 ml) was added 0.84 g (21 mmol) of sodium hydride (60% oil dispersion), and then 2.78 g (20 mmol) of ethyl pyrrole-3-carboxylate was added portionwise thereto under ice-cooling. After stirring at room temperature for 10 minutes, 6.65 g (24 mmol) of bromotetradecane was added dropwise under ice-cooling. The mixture was stirred for 3.5 hours at room temperature, and then 30 ml of water was added thereto. The resulting mixture was extracted with 70 ml of ethyl acetate, washed with an aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After removing the solvent, the remaining oil was purified by subjecting it to column chromatography over silica gel (eluent: ethyl acetate/hexane=1/20-1/10) to obtain 6.33 g (89.0% yield) of ethyl 1-tetradecylpyrrole-3-carboxylate as white crystals, m.p. 32-33 C. IR (KBr) cm-1: 2940, 2860, 1700, 1540. NMR (CDCl3) delta: 0.88 (3H, t), 1.25 (22H, m), 1.35 (3H, t), 1.77 (2H, m), 3.85 (2H, t), 4.26 (2H, q), 6.55 (2H, m), 7.27 (1H, m).

Reference： [1]Patent: US5082856,1992,A

46
[ 3336-43-4 ]
[ 112-71-0 ]
[ 1078725-59-3 ]

Reference： [1]Synthesis,2008,p. 2551 - 2560

47
[ 2439-35-2 ]
[ 112-71-0 ]
[ 632339-53-8 ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 3201 - 3208

48
[ 63285-53-0 ]
[ 112-71-0 ]
[ 1240464-24-7 ]

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 6797 - 6809

49
[ 112-71-0 ]
[ 2043-47-2 ]
[ 1240205-64-4 ]

Reference： [1]Journal of Fluorine Chemistry,2010,vol. 131,p. 844 - 851

50
[ 16227-12-6 ]
[ 112-71-0 ]
[ 1176199-76-0 ]

Yield	Reaction Conditions	Operation in experiment
74%	In Petroleum ether; at 110℃; for 72h;	EXAMPLE 131 4-phenyl-1-(tetradec-1-yl)-(1,2,4)-triazolium bromide 0.100 g (0.0007 mol) 4-phenyl-(1,2,4)-triazole 1 and 0.572 g (0.0021 mol) 1-bromotetradecane 2 are combined in a pressure tube. The reaction mixture is stirred 3 d at 110 C. To the resulted solid 10 ml petroleum ether was added. The product is filtered off, washed with petroleum ether/THF 1:1 and diethylether, and is dried in high vacuum. M 422.53 C22H36N3Br Yield: 0.242 g (74%) 1H-NMR DM-233 (300 MHz/DMSO): (ppm)=0.85 (t, 3H, 20-H); 1.24 (m, 24H, 9-19-H); 1.94 (q, 2H, 8-H); 4.42 (t, 21-1,7-H); 7.71 (m, 3H, 5/5'/6H); 7.82 (d, 2H, 4/4'-H); 9.78 (s, 1H, 1-H); 10.79 (s, 1H, 2-H) 13C-NMR DM-233 (75.475 MHz/DMSO):

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 305 - 308
[2]Patent: US2011/105761,2011,A1 .Location in patent: Page/Page column 51

51
[ 13423-60-4 ]
[ 112-71-0 ]
[ 1176199-49-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	In tetrahydrofuran; at 110℃; for 72h;	EXAMPLE 1111-phenyl-4-(tetradec-1-yl)triazolium bromide0.300 g (0.002 mol) 1-phenyltriazole 1 and 1.500 g (0.006 mol) 1-bromotetradecane 2 were dissolved in a pressure tube in 7 ml THF.The reaction mixture was stirred 4 d at 110° C.THF was removed because of the parallel positive experiences of solvent-free synthesis and the mixture stirred for 4 h at 110° C.To the obtained solid 10 ml petroleum ether was added.The product is filtered off, washed with petroleum ether, and dried in high vacuum.M 422.53 C22H36N3BrYield: 0.4632 g (59percent)1H-NMR DM-108 (300 MHz/DMSO):(ppm)=0.86 (t, 3H, 20-H); 1.25 (m, 24H, 9-19-H); 1.94 (q, 2H, 8-H); 4.32 (t, 2H, 7-H); 7.70 (m, 3H, 5/5'/6H); 7.96 (d, 2H, 4/4'-H); 9.50 (s, 1H, 1-H); 10.97 (s, 1H, 2-H)13C-NMR DM-108 (75.475 MHz/DMSO):

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 305 - 308
[2]Patent: US2011/105761,2011,A1 .Location in patent: Page/Page column 40

52
[ 696-54-8 ]
[ 112-71-0 ]
[ 433692-36-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	In acetonitrile; for 48h;Reflux;	General procedure: The mixture of 4-pyridinealdoxime with 1-bromoalkane in CH3CN was stirred under reflux for 48 h, and the prepared salts were obtained as white crystals by crystallization from acetone, filtered, washed with acetone and allowed to dry at room temperature.

Reference： [1]Molecules,2015,vol. 20,p. 3681 - 3696
[2]Journal of Physical Organic Chemistry,2010,vol. 23,p. 519 - 525

53
[ 2301-25-9 ]
[ 112-71-0 ]
[ 1176198-72-3 ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 863 - 867

54
[ 2301-25-9 ]
[ 112-71-0 ]
[ 1286795-96-7 ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 863 - 867

55
[ 112-71-0 ]
[ 636-93-1 ]
[ 1258011-74-3 ]

Reference： [1]Chinese Chemical Letters,2010,vol. 21,p. 1415 - 1418

56
[ 112-71-0 ]
[ 33527-91-2 ]
3Br^(1-)*C₅₄H₁₁₇N₄⁽³⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	In acetonitrile; for 23h;Reflux;	To a solution of tris(2-dimethylaminoethyl)amine (0.404 g, 1.75 mmol) in acetonitrile (4 mL) was added 1-bromotetradecane (1.47 g, 5.32 mmol). Theresulting mixture was heated at reflux with stirring for 23 hours, during which time a white solid was observed. After cooling, and the addition of a cold hexanes/acetone mixture (15 mL, 1:1), to the reaction flask, the precipitate was filtered with a Buchner funnel, and rinsed with a cold hexanes/acetone mixture (20 mL, 1:1), resulting in T-14,14,14 (1.31 g, 70%) as a white powder; mp=229-258 C; ?H NMR(300 MI-Tz, CDC13) 34.10-4.02 (m, 6H), 3.63-3.54 (m, 6H), 3.39-3.22 (m, 24H), 1.73-1.61 (m, 6H), 1.36-1.06 (m, 66H), 0.84-0.77 (m, 9H); ?3C NMR (75 MHz, CD3OD) 365.3, 61.0, 50.1, 46.9, 31.7, 29.4, 29.4, 29.3, 29.3, 29.1, 29.0, 26.1, 22.5, 22.4, 13.1; high resolution mass spectrum (ESI) m/z 273.9766 ([Mj3 calculated for [C54H,,7N4j3t 273.9754). See also Yoshimura et al., 2012, Langmuir 28:9322-933 1.?H and ?3C NMR spectra of compound T-14,14,14 can be found in Figure 53.

Reference： [1]ChemBioChem,2015,vol. 16,p. 2299 - 2303
[2]Patent: WO2016/172436,2016,A1 .Location in patent: Page/Page column 127
[3]Langmuir,2012,vol. 28,p. 9322 - 9331
[4]Physical Chemistry Chemical Physics,2019,vol. 21,p. 25065 - 25071

57
[ 112-71-0 ]
[ 3934-87-0 ]
[ 1393808-52-0 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2012,vol. 60,p. 8624 - 8631

58
[ 112-71-0 ]
[ 605-32-3 ]
[ 1430074-42-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,2013,vol. 86,p. 354 - 362

59
[ 112-71-0 ]
[ 40501-41-5 ]
[ 1439362-31-8 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 5254 - 5257
Angew. Chem.,2013,vol. 125,p. 5362 - 5365,4

60
[ 112-71-0 ]
[ 17295-12-4 ]
C₂₇H₄₀O₃ [ No CAS ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 9045 - 9055

61
[ 112-71-0 ]
[ 4418-89-7 ]
[ 139056-54-5 ]

Reference： [1]Advanced Functional Materials,2014,vol. 24,p. 1703 - 1717
[2]RSC Advances,2020,vol. 10,p. 9643 - 9656

62
[ 112-71-0 ]
[ 351437-96-2 ]
1,3,5-tris(1-tetradecyl-1H-benzo[d]imidazol-2-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydroxide In acetonitrile at 80℃; for 12h;

Reference： [1]Xiong, Jin-Feng; Li, Jian-Xiao; Mo, Guang-Zhen; Huo, Jing-Pei; Liu, Jin-Yan; Chen, Xiao-Yun; Wang, Zhao-Yang [Journal of Organic Chemistry, 2014, vol. 79, # 23, p. 11619 - 11630]

63
[ 112-71-0 ]
[ 6217-22-7 ]
C₄₄H₆₆O₂ [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 23952 - 23956

64
[ 112-71-0 ]
[ 125414-41-7 ]
tert-butyl N-[2-tetradecyloxy-1-(tetradecyloxymethyl)ethyl]carbamate [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 1068 - 1081

65
[ 112-71-0 ]
[ 155370-03-9 ]
C₂₉H₃₈FNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
29%		General procedure: To a solution of 2-(2-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (4), 2-(3-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one (5), and <strong>[155370-03-9]2-(4-fluorophenyl)-2,3-dihydroquinolin-4(1H)-one</strong> (6) (2.41 g, 0.01 mol for each) in DMF (10mL each) was added KOH (1.12 g, 0.02 mol each) and the resulting mixture was stirred at room temperature for 1 h. Then alkyl bromide (0.03 mol each) was added dropwise, and the reaction mixture was stirred overnight at room temperature. Then the reaction mixture was poured into 20 mL of water. The resulting mixture was extracted with CH2Cl2 (2 x 20 mL). The combined organic layer was washed with brine, dried over Na2SO4 , filtered, and concentrated in a vacuum to give crude products 7a-k, 8a-k, and 9a-k, which were purified by column chromatography using a mixture of n-hexane-chloroform (8.5:0.5) as eluent (yields are in Tables 1, 4, and 7).

Reference： [1]Turkish Journal of Chemistry,2015,vol. 39,p. 850 - 866

66
[ 112-71-0 ]
[ 96556-05-7 ]
C₂₃H₅₀N₃⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	In acetonitrile; for 19h;Reflux;	To a solution of <strong>[96556-05-7]1,4,7-trimethyl-1,4,7-triazacyclononane</strong> (0.203 g, 1.19mmol) in acetonitrile (4 mL) was added 1-bromotetradecane (0.702 g, 2.53 mmol).The resulting colorless solution was heated at reflux with stirring for 19 hours, during which time the solution turned yellow. The reaction mixture was concentrated in vacuo, resulting in a yellow-white crude solid, which was triturated with hot hexanes (35 mL), then washed with cold hexanes (50 mL), resulting in C-14,0,0 (0.382 g,72%) as a white powder; mp=153-168 C; ?H NMR (300 MI-Tz, CDC13) oe 4.37-4.24(m, 2H), 4.08-3.80 (m, 2H), 3.60-3.51 (m, 2H), 3.26 (s, 3H), 2.87-2.67 (m, 4H), 2.47(s, 4H), 2.38 (s, 6H), 1.68-1.56 (m, 2H), 1.38-1.04 (m, 22H), 0.84-0.77 (m, 3H); ?3CNMR (75 MHz, CD3OD) oe 63.3, 60.2, 59.2, 54.3, 47.5, 46.6, 31.6, 29.3, 29.2, 29.1,29.0, 28.8, 26.1, 22.3, 21.6, 13.0; high resolution mass spectrum (ESI) m/z 368.4000([Mf calculated for [C23H5oN3f: 368.3999). ?H and ?3C NMR spectra of compound C- 14,0,0 can be found in Figure 37.

Reference： [1]ChemBioChem,2015,vol. 16,p. 2299 - 2303
[2]Patent: WO2016/172436,2016,A1 .Location in patent: Page/Page column 118

67
[ 112-71-0 ]
[ 2050-16-0 ]
C₂₆H₃₈N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium carbonate In N,N-dimethyl-formamide at 90℃; for 12h;

Reference： [1]Tan, Xiaoping; Zhang, Ruilin; Guo, Chunxiang; Cheng, Xiaohong; Gao, Hongfei; Liu, Feng; Bruckner, Johanna R.; Giesselmann, Frank; Prehm, Marko; Tschierske, Carsten [Journal of Materials Chemistry C, 2015, vol. 3, # 42, p. 11202 - 11211]

68
[ 112-71-0 ]
[ 403-01-0 ]
C₂₆H₄₃FO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 g		To <strong>[403-01-0]methyl 3-fluoro-4-hydroxybenzoate</strong> (851 mg) and potassium carbonate (3.5 g), 1,3-dimethyl-2-imidazolidinone(10 mL) was added, and the mixture was stirred at 70°C for 15 minutes, then 1-bromooctadecane (2.3 mL) wasadded thereto, and the mixture was stirred at 70°C for 10 hours. Water was added to the reaction liquid, the solutionwas stirred, and then the precipitate was collected by suction filtration, and the obtained solid was washed with waterand acetonitrile to obtain the compound (E15) (2.0 g). 1H NMR (500 MHz, CDCl3) delta 7.78-7.80 (1 H,m), 7.73 (1 H, dd J = 11.5, 2.3 Hz), 6.96 (1 H, t J = 8.0 Hz), 4.07(2 H, t J = 6.3 Hz), 3.89 (3 H,s), 1.81-1.87 (2 H, m), 1.44-1.50 (2 H, m), 1.22-1.38 (28 H, br), 0.88 (3 H, t J = 7.0 Hz).

Reference： [1]Patent: EP2921499,2015,A1 .Location in patent: Paragraph 0168; 0169; 0170

69
[ 112-71-0 ]
[ 3376-59-8 ]
(±)-2,3-bis-(tetradecyloxy)propyl benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a stirred suspension of sodium hydride (0.273 g, 0.68mol, 60% in oil) in anhydrous THF (100 mL) under a nitrogenatmosphere at 0C, a solution of (±)-1 (33.3 g, 0.17 mol)in anhydrous THF (150 mL) was added over a period of 1 hmaintaining the internal temperature below 5C. After stirringat room temperature for 12 h, 1-bromotetradecane(187.7 g, 0.68 mol) was added at 0C over a period of 1 h.After complete addition, the reaction mixture was stirred for2 h at room temperature and this was gradually increasedwhen reaching reflux, and then stirred for 24 h. A LiOH solution(10% wt/v,100 mL) was added, and stirring and thetemperature were maintained for 12 h. The mixture was dilutedwith saturated ammonium chloride (300 mL). Theaqueous layer was extracted with dichloromethane (700 mL),washed with water (3 150 mL), and dried over Na2SO4.The unreacted 1-bromotetradeane was removed by distillationunder reduced pressure (1 mm of Hg and 125 C). Theresidue was purified by column chromatography eluting withhexane to obtain (±)-2 (39.5 g, 48%) as a white solid, mp.43-45 C (lit. 42.5-43.5C) [18]. 1H NMR (CDCl3, 200MHz) 0.87 (t, J = 6.7 Hz, 6H, C12-C12H3), 1.25 (br s, 44H,C11-C11H2), 1.58-1.61 (m, 4H, C10-C10H2), 3.37-3.73(m, 9H; C9-C9-C3-C2H2, C1H); 13C NMR (CDCl3,200MHz) 14.1 (C16-16), 22.8 (C15-15), 27.6 (C12-12),29.1-29.5 (C13-13), 29.7 (C11-11), 32.5 (C14-14), 32.8(C10-10), 64.3 (3C), 65.5 (C1), 71.0 (C9), 70.9(C9),72.0(C3), 78.4 (C2). EI-LR-MS, m/z, M+: 484.
		To a stirred suspension of sodium hydride (0.273 g, 0.68mol, 60% in oil) in anhydrous THF (100 mL) under a nitrogenatmosphere at 0C, a solution of (±)-1 (33.3 g, 0.17 mol)in anhydrous THF (150 mL) was added over a period of 1 hmaintaining the internal temperature below 5C. After stirringat room temperature for 12 h, 1-bromotetradecane(187.7 g, 0.68 mol) was added at 0C over a period of 1 h.After complete addition, the reaction mixture was stirred for2 h at room temperature and this was gradually increasedwhen reaching reflux, and then stirred for 24 h. A LiOH solution(10% wt/v,100 mL) was added, and stirring and thetemperature were maintained for 12 h. The mixture was dilutedwith saturated ammonium chloride (300 mL). Theaqueous layer was extracted with dichloromethane (700 mL),washed with water (3 150 mL), and dried over Na2SO4.The unreacted 1-bromotetradeane was removed by distillationunder reduced pressure (1 mm of Hg and 125 C). Theresidue was purified by column chromatography eluting withhexane to obtain (±)-2 (39.5 g, 48%) as a white solid, mp.43-45 C (lit. 42.5-43.5C) [18]. 1H NMR (CDCl3, 200MHz) 0.87 (t, J = 6.7 Hz, 6H, C12-C12H3), 1.25 (br s, 44H, C11-C11H2), 1.58-1.61 (m, 4H, C10-C10H2), 3.37-3.73(m, 9H; C9-C9-C3-C2H2, C1H); 13C NMR (CDCl3,200MHz) 14.1 (C16-16), 22.8 (C15-15), 27.6 (C12-12),29.1-29.5 (C13-13), 29.7 (C11-11), 32.5 (C14-14), 32.8(C10-10), 64.3 (3C), 65.5 (C1), 71.0 (C9), 70.9(C9),72.0(C3), 78.4 (C2). EI-LR-MS, m/z, M+: 484.

Reference： [1]Letters in Organic Chemistry,2016,vol. 13,p. 71 - 75
[2]Letters in Organic Chemistry,2016,vol. 13,p. 71 - 75

70
[ 110-95-2 ]
[ 112-71-0 ]
C₃₅H₇₆N₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	General procedure: Polymethylene-alpha,omega-bis(dimethyltetradecylammonium)dibromides were synthesized by reacting thecorresponding N,N,N',N'-tetramethyl-alpha,omega-polymethylenediamine with excess n-tetradecylbromide in acetone, with subsequent recrystallization fromethyl alcohol twice, according to the procedure in[26].

Reference： [1]Russian Journal of Physical Chemistry,2016,vol. 90,p. 339 - 343
Zh. Fiz. Khim.,2016,vol. 90,p. 211 - 215,5
[2]Food Chemistry,2019,vol. 277,p. 407 - 413

71
[ 112-71-0 ]
[ 638-66-4 ]
tetradecyl-octadecanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-Bromotetradecane With iodine; magnesium In tetrahydrofuran for 2h; Reflux; Stage #2: n-Octadecanal In tetrahydrofuran at 20℃; for 0.5h;	59.1 Step 1 (0836) To a round bottomed flask is added magnesium metal (0.201 g, 8.27 mmol) and a catalytic amount of iodine, followed by tetrahydrofuran (30 mL) and 1-bromotetradecane (2.17 g, 7.82 mmol). The mixture is refluxed for 2 h and then cooled to rt. A solution of octadecyl aldehyde (0.600 g, 2.24 mmol) in tetrahydrofuran (5 mL) is added, and the reaction mixture is stirred for 30 min at rt. The reaction is diluted with ethyl acetate, washed with 1 M HCl, dried with sodium sulfate and concentrated. The crude product is further purified by flash chromatography on silica with a heptane/ethyl acetate gradient. The product containing fractions are identified by TLC, combined and concentrated: 310 mg, 29.7%.

Reference： [1]Current Patent Assignee: Novartis (w/o Sandoz); NOVARTIS AG - US9301923, 2016, B2 Location in patent: Page/Page column 125

72
[ 112-71-0 ]
[ 33329-35-0 ]
C₅₇H₁₂₃N₄⁽³⁺⁾*3Br^(1-) [ No CAS ]

Reference： [1]ChemMedChem,2016,vol. 11,p. 1401 - 1405
[2]Physical Chemistry Chemical Physics,2019,vol. 21,p. 25065 - 25071

73
[ 112-71-0 ]
[ 33329-35-0 ]
C₆₀H₁₂₈N₄⁽⁴⁺⁾*4Br^(1-) [ No CAS ]

Reference： [1]ChemMedChem,2016,vol. 11,p. 1401 - 1405

74
[ 112-71-0 ]
[ 39503-61-2 ]
1-(5-bromo-4-methoxy-2-(tetradecyloxy)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With potassium carbonate; In N,N-dimethyl-formamide; acetone; at 60℃; for 3.0h;	General procedure: Toa solution of Compound 2 3 mmol, in DMF 10 ml and acetone 10ml, wasadded K2CO3 0.5 g and the corresponding bromoalkanes 3mmol. The reaction mixture was refluxed for 3 hours in 60. After the reactionhas been completed, to remove the solid (K2CO3) byfiltration and then washed several times with acetone. The mixture was concentrated in vacuo and generated a large amount of solid precipitated by adda small amount of water, filtrated and dried. The products (3a-h) wereobtained.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5218 - 5221

75
[ 112-71-0 ]
[ 137618-48-5 ]
tert-butyl (2,3-bis(tetradecyloxy)propyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With tetra-(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In water; toluene; at 60℃;	Tert-butyl-(2,3-dihydroxypropyl)carbamate (5) (1 g; 5.299 mmol) and 1-bromotetradecane (10.31 mL; 36.605 mmol) were dissolved in 10 mL of toluene. Subsequently, aqueous NaOH 50% (w/w) were added (10 mL) along with tetrabutylammonium hydrogensulphate (0.89 g; 2.615 mmol). The reaction mixture was heated at 60 C and vigorously stirred overnight. AcOEt (25 mL) was added to the reaction mixture and the organic phase was washed with (3x15 mL) of brine. The organic phase was dried with anhydrous MgSO4, filtrated and concentrated under reduced pressure. Crude was purified by flash chromatography TLC from hexane to 5% AcOEt (v/v) affording a colourless oily product (53% yield). Rf = 0.2 (Hexane:AcOEt 97:3); 1H-NMR (400 MHz, CDCl3) delta 4.88 (1H, broad s, Boc-NH-CH2CH(OC14H29)CH2(OC14H29)); 3.8-3.2 (9H, m, X-CHn where X= N,O ); 1.55 (4H, m, -CH(OCH2CH2CH2R)CH2(OCH2CH2CH2R) ); 1.44 (9H, s, (CH3)3C-O-CO-NH-R)); 1.26 (44H, s, aliphatic chains); 0.88 (6H, t, J = 6.8 Hz, R-CH2CH3) ppm. MS (ESI, low res. positive mode). Calcd. for [M+H]+ = 584.5619. Found: [M+H]+ = 584.5605. Calcd. for [M+Na]+ = 606.5432. Found: [M+Na]+ = 606.5425. Calcd for [2M+Na]+ = 1190.0971. Found: [2M+Na]+ = 1190.0966
44%	With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide; In water; toluene; at 65℃;Sealed tube;	In a 50 mL sealed cap glass vial, a mixture of <strong>[137618-48-5]tert-butyl (2,3-dihydroxypropyl)carbamate</strong> (1.15 g, 6.0 mmol) in toluene (6.0 mL) was treated sequentially with 1-bromotetradecane (10.71 mL, 36 mmol), sodium hydroxide (50% aq.; 6.0 mL) and tetrabutylammonium bisulfate (1.02 g, 3.0 mmol). The vial was sealed and heated at 65 C with vigorous stirring overnight. The mixture was cooled to room temperature (rt) and extracted with toluene (2 x 25 mL). The combined organic layers were washed with water, dried over sodium sulfate, and evaporated. The resulting colorless liquid was purified by silica gel column chromatography (hexane-ethyl acetate (0-25%)) to give the title compound as a colorless liquid (1.52 g, 44% yield). 1H NMR (500 MHz, Chloroform-d) delta 4.88 (s, 1H), 3.57 (dt, J = 9.3, 6.7 Hz, 1H), 3.52 - 3.29 (m, 7H), 3.17 (dt, J = 12.1, 5.7 Hz, 1H), 1.63 - 1.48 (m, 5H), 1.44 (s, 9H), 1.25 (s, 44H), 0.88 (t, J = 6.9 Hz, 6H); ESI-MS m z (0352) [M+H]+ calc'd for C36H73N04, 585; found, 585.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 175 - 186
[2]Patent: WO2018/26866,2018,A1 .Location in patent: Paragraph 0157

76
[ 2055-21-2 ]
[ 112-71-0 ]
C₃₆H₇₀N₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

Reference： [1]ChemMedChem,2017,vol. 12,p. 1931 - 1934

77
[ 112-71-0 ]
[ 599-61-1 ]
C₂₆H₄₀N₂O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a round-bottom flask attached to a reflux condenser was added K2CO3 (276 mg, 2 mM) and 3,30-sulfonyldianiline(248 mg, 1 mM) in 25 mL acetone; the mixture was stirred for 40 min at 80 C. Either 1-bromotetradecane (0.29 mL,1 mM for DAP-T) or 1-bromodecane (0.2 mL, 1 mM forDAP-D) was then added, and the reaction mixture was refluxed for a further 8 h at 80 C. The reaction was monitored with thin-layer chromatography (TLC) usingethyl acetate and n-hexane (4:6, v/v) as the solvent system.Upon completion of the reaction, the reaction mixture was cooled to room temperature and excess acetone was evaporated under reduced pressure using a rotary evaporator. The mixture was washed with water, filtered, dried,and subjected to silica gel column chromatography to obtain pure solid products using ethyl acetate and n-hexane(1.5:8.5, v/v) as the solvent system. Yields 81% and 77% for DAP-T and DAP-T,respectively.

Reference： [1]Journal of Surfactants and Detergents,2017,vol. 20,p. 1367 - 1375

78
[ 112-71-0 ]
[ 22916-47-8 ]
1-(2-((2,4-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-3-tetradecyl-1H-imidazol-3-ium bromide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4288 - 4294

79
[ 108-16-7 ]
[ 112-71-0 ]
(2-Hydroxy-propyl)-dimethyl-tetradecyl-ammonium; bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
Ca. 70%	In acetonitrile; for 24h;Heating;	General procedure: N-(hydroxyalkyl)-N,N- dimethyl n-alkyl ammonium bromide (Scheme 1), referred to as CnEtOH, CnPrOH, and CniPrOH (n= 12 and 14, EtOH = ethanol, PrOH = propanol, and iPrOH = iso-propanol) were synthesized using a simple alkylation of the amino alcohol (3-(dimethyl amino) propan-1-ol, 1-(dimethyl amino) propan-2-ol, or 2-(dimethyl amino)ethan-1-ol)) with alkyl bromide (1-Bromododecane or 1-Bromotetradecane) in acetonitrile: a mixture of bromoalkane (25 mmol) and amino alcohol (20 mmol) in acetonitrile (20 mL) was heated for 24 h. The excess of amine was eliminated by vacuum evaporation. The products obtained were washed three times with a mixture of ether and hexane for purification. The yield of the reaction was about 70%. The purity of the compounds was determined by chromatography, using a thin layer chromatography (TLC) plate on silica gel immersed in a solution of 8% of NaBr prepared in methanol. The eluent used was methanol/dichloromethane (1:9, by vol); the examination of the spots on the plate was done by the ultra violet (UV) light (245 nm) using bismuth nitrate as a revelator.

Reference： [1]Journal of Surfactants and Detergents,2019,vol. 22,p. 663 - 672

80
[ 112-71-0 ]
[ 23351-91-9 ]
5-bromoisophthalic acid ditetradecyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Add 3g to 50mL DMF solvent <strong>[23351-91-9]5-bromoisophthalic acid</strong> (0.012 mol) and 4.8 g potassium bicarbonate(0.048 mol), stirred at room temperature to form a potassium salt.8.32g of n-bromotetradecane (0.03mol) was added to the mixed solution,The reaction was stirred at 90 C for 12 hours. Stop the reaction and allow the solution to cool to room temperature.It was poured into 300 mL of water and extracted with ethyl acetate.Dry over anhydrous sodium sulfate, filter and then dry the solvent.Petroleum ether/ethyl acetate for crude products (15/1)Column chromatography for the eluent gave a white solid.

Reference： [1]Patent: CN109956869,2019,A .Location in patent: Paragraph 0105-0108

81
[ 1615-14-1 ]
[ 112-71-0 ]
1-(2-hydroxyethyl)-3-tetradecyl-1H-imidazol-3-ium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	In acetonitrile; for 24h;Reflux;	The mixture containing 1.0 g (8.9 mmol) of 1-(2-hydroxyethyl)imidazole and 2.72 g (9.8 mmol) of 1-tetradecyl bromide dissolved in 10 mL of acetonitrile was boiled with reflux condenser for 24 h. The precipitate formed during cooling was filtered, purified by recrystallization from ethyl acetate and dried under vacuum. Yield: 2.70 g (73%). Mp= 40-42 C.IR-spectrum (KBr), cm-1: 3532, 3330, 3134, 3069, 2917, 2850, 1564,1472, 1379, 1165,1071, 873, 792, 720. 1H NMR spectrum, 400 MHz (CDCl3), delta, ppm, J/Hz: 0.87 t (3H, J=6.8), 1.25-1.33m (22 H),1.87-1.91m (2 H), 3.98 t (2H, J=4.9), 4.26 t (2H, J=7.5), 4.53 t (2H,J=4.9), 7.31 s (1 H), 7.63 s (1 H), 9.73 s (1 H). ESI MS, m/z: 309.5 [MBr]+.Calculated, %: C19H37 N2 OBr: C 58.60; H 9.57; N 7.19; Br 20.52;found, %: C 58.02; H 10.05; N 7.21; Br 19.99.

Reference： [1]Chemistry and Physics of Lipids,2019,vol. 223

82
[ 112-71-0 ]
[ 33527-91-2 ]
C₅₄H₁₁₇N₄⁽³⁺⁾*3C₂F₆NO₄S₂^(1-) [ No CAS ]

Reference： [1]Physical Chemistry Chemical Physics,2019,vol. 21,p. 25065 - 25071

83
[ 79418-41-0 ]
[ 112-71-0 ]
C₂₃H₃₅NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of 3-amino 7-hydroxycoumarin (1.0 eq) in dimethylformamide (DMF) (20 mL) was added anhy. K2CO3 (2.5 eq) and stirredat room temperature for 10-15 min. To this mixture, alkyl bromide(1.0 mmol) was added and resulting solution was stirred at room temperature(rt) for 22-24 h. The completion of reaction was checked byTLC. After completion of reaction, the reaction mixture was pouredinto ice-cold water to give solid. The solid was filtered, washed withwater, dried and recrystallized from ethanol to give compound 13 asoffwhite solid. These compounds 14a-lwere directly used for next step.

Reference： [1]Journal of Molecular Liquids,2020,vol. 297

84
[ 7295-76-3 ]
[ 112-71-0 ]
3-methoxy-1-tetradecylpyridinium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In acetonitrile for 48h; Reflux;	6.1.2. General procedure for synthesis of monoquaternary salts 1-15 General procedure: 1-Bromoalkane (28.93 mmol)was added to nitrogen-containingheterocycles compound (20.67 mmol) in acetonitrile (30 mL) underroom temperature conditions. The reaction mixture was then stirredunder reflux for 48 h. The solvent was evaporated underreduced pressure, and the crude product purified by crystallizationfrom diethyl ether, filtered, washed with diethyl ether and allowedto dry at room temperature. The salts 6 and 8 were purified bycrystallization from acetone. See the Supplementary Informationfor more details and NMR spectra for each of the novel compound.6.1.2.1. 4-Carbamoyl-1-dodecylpyridinium bromide (1a).Compound 1a was isolated as white solid; Yield 89%

Reference： [1]Benkova, Marketa; Bostik, Pavel; Bostikova, Vanda; Dolezal, Rafael; Gunde-Cimerman, Nina; Hobzova, Lenka; Hympanova, Michaela; Jun, Daniel; Korabecny, Jan; Malinak, David; Marek, Jan; Markova, Aneta; Prchal, Lukas; Ryskova, Lenka; Salajkova, Sarka; Sleha, Radek; Soukup, Ondrej; Sepčić, Kristina [European Journal of Medicinal Chemistry, 2020, vol. 206]

85
[ 112-71-0 ]
[ 16218-28-3 ]
C₄₁H₆₄I₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With tetrabutylammomium bromide In water; toluene at 20℃; Inert atmosphere;

Reference： [1]Zhang, Deling; Liu, Yuantao; Gao, Hongfei; Chang, Qing; Cheng, Xiaohong [Journal of Materials Chemistry C, 2020, vol. 8, # 48, p. 17474 - 17481]

86
[ 112-71-0 ]
[ 3598-30-9 ]
3,3’,4,4’-tetrakis(tetradecyloxy)-1,1’-biphenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate; zinc In N,N-dimethyl-formamide at 100℃; for 24h;

Reference： [1]Hang, Jun-Fang; Lin, Hang; Zhao, Ke-Qing; Hu, Ping; Wang, Bi-Qin; Monobe, Hirosato; Zhu, Chenhui; Donnio, Bertrand [European Journal of Organic Chemistry, 2021, vol. 2021, # 13, p. 1989 - 2002]

87
[ 934-90-7 ]
[ 112-71-0 ]
C₂₂H₄₆NO⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile;Reflux;	General procedure: 0.1mol of N-2-hydroxypropyl piperidine and 30ml of acetonitrile were placed in a flat-bottomed double-necked flask. After the proper homogenization, 0.1mol of 1-bromononane (1-bromodecane, 1-bromododecane or 1-bromotetradecane) was added to it. The reaction was conducted in a flask equipped with a magnetic stirrer at reflux condition of acetonitrile for 30-35h. The scheme of obtaining ILSs can be shown as follows (Scheme 2 ). The synthesized cationic ILS was distilled in a vacuum to purify the reaction mixture. In this case, the ILSs were separated from the solvent and the unreacted 1-bromoalkane. For purification of the synthesized gemini surfactants, they were crystallized in acetone thrice. The yield of the synthesized ILSs was 94-95%. They are miscible in ethanol, acetone, ethyl acetate, and partially dissolved in water. The structure of the cationic ILSs was elucidated by NMR and IR spectroscopic methods. 1-bromododecane based ILS: IR ν, cm-1: 3288, 3256 ν (OH), 2919 and 2852 ν (C-H), 1462 and 1373 δ (C-H), 1263 ν (C-N), 1081 and 1043 ν (C-O), 722 δ -(CH2)-x (Fig. S3). 1H NMR, (300.13MHz, D2O), δ (ppm): 0.77 (t, 3H), 1.16-1.18 (d, 3H), 1.26-1.32 (m 18H), 1.58-178 (m, 6H), 3.22-3.47 (m, 6H), 4.31 (m,1H) (Fig. S4).

Reference： [1]Journal of Molecular Liquids,2021,vol. 344

88
[ 112-71-0 ]
[ 85-86-9 ]
C₃₆H₄₄N₄O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	Stage #1: Sudan III With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 0.166667h; Stage #2: 1-Bromotetradecane In N,N-dimethyl-formamide at 60 - 80℃; for 96h;

Reference： [1]Honda, Akinori; Kakihara, Shunta; Kawai, Masato; Miyamura, Kazuo; Takahashi, Tomomi [Crystal Growth and Design, 2021, vol. 21, # 11, p. 6223 - 6229]

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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. 112-71-0 ] {[proInfo.proName]}

Quality Control of [ 112-71-0 ]

Related Doc. of [ 112-71-0 ]

Product Details of [ 112-71-0 ]

Calculated chemistry of [ 112-71-0 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 112-71-0 ]

Application In Synthesis of [ 112-71-0 ]

[ 112-71-0 ] Synthesis Path-Upstream 1~8

[ 112-71-0 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 112-71-0 ]

Aliphatic Chain Hydrocarbons

Bromides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 112-71-0 ]