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14-Bromotetradecanol

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14-Bromotetradecanol Basic information
Product Name:14-Bromotetradecanol
Synonyms:14-BROMO-1-TETRADECANOL;14-BROMO-TETRADECAN-1-OL;14-BROMOTETRADECANOL;1-Tetradecanol, 14-bromo-
CAS:72995-94-9
MF:C14H29BrO
MW:293.28
EINECS:
Product Categories:pharmacetical
Mol File:72995-94-9.mol
14-Bromotetradecanol Structure
14-Bromotetradecanol Chemical Properties
Melting point 42-43 °C(Solv: heptane (142-82-5))
Boiling point 353.6±15.0 °C(Predicted)
density 1.084±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
pka15.20±0.10(Predicted)
AppearanceWhite to yellow Solid
InChIInChI=1S/C14H29BrO/c15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16/h16H,1-14H2
InChIKeyVKXZRJZWAYBBAE-UHFFFAOYSA-N
SMILESC(O)CCCCCCCCCCCCCBr
CAS DataBase Reference72995-94-9(CAS DataBase Reference)
Safety Information
Risk Statements 36/37/38
Safety Statements 26-36/37/39
MSDS Information
14-Bromotetradecanol Usage And Synthesis
Uses14-Bromo-1-tetradecanol can be used to synthesize cyclohexenoic long chain fatty alcohols that have implications as neuronal growth stimulators.
Synthesis
1,14-Tetradecanediol

19812-64-7

14-Bromotetradecanol

72995-94-9

General procedure for the synthesis of 14-bromo-1-tetradecanol from 1,14-tetradecanediol: 1,14-tetradecanediol (1.5 g) was dissolved in 16.5 mL of cyclohexane, to which 57% aqueous hydrobromic acid solution (16.5 mL) was added. The reaction mixture was refluxed under stirring conditions for 6 hours. After completion of the reaction, the mixture was extracted three times with ether. The organic layer was neutralized with saturated sodium bicarbonate solution and subsequently washed with brine solution and dried with magnesium sulfate. After drying, it was filtered and the solvent was removed by distillation under reduced pressure. The residue was purified by rapid chromatography on silica gel (eluent ratio: hexane:ethyl acetate = 7:3) to afford 14-bromo-1-tetradecanol as white crystals in 67% yield. Molecular weight: 292.90 (C14H29BrO).TLC (unfolding agent ratio: hexane:ethyl acetate=7:3) Rf value=0.53.1H-NMR (300 MHz, CDCl3) δ: 1.26 (s, 20H, -(CH2)10-); 1.56 (qt, 2H, J=7.0 Hz, -CH2-); 1.85 (qt , 2H, J=7.1 Hz, -CH2-); 3.40 (t, 2H, J=6.9 Hz, -CH2Br); 3.64 (t, 2H, J=6.6 Hz, -CH2O-).13C-NMR (75 MHz, CDCl3) δ: 25.72; 28.17; 28.75; 29.41-32.80; 32.82; 34.05; 63.08.

References[1] Tetrahedron, 1998, vol. 54, # 27, p. 7735 - 7748
[2] Synthesis, 2006, # 5, p. 831 - 838
[3] Patent: EP1854777, 2007, A1. Location in patent: Page/Page column 18
[4] Organic Letters, 2014, vol. 16, # 3, p. 844 - 847
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 6, p. 1989 - 2007
14-Bromotetradecanol Preparation Products And Raw materials
Raw materials1,14-Tetradecanediol-->Cyclohexane-->Hydrogen bromide-->Water
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