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10-Bromodecanol

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10-Bromodecanol Basic information
Product Name:10-Bromodecanol
Synonyms:10-Bromo-1-decan;DECAMETHYLENE BROMOHYDRIN;10-bromo-1-decano;10-Hydroxydecyl bromide;10-Bromo-1-decanol,95%;10-BROMO-1-DECANOL 85+%;10-BROMO-1-DECANOL, TECH., 90%;1-Decanol, 10-bromo-
CAS:53463-68-6
MF:C10H21BrO
MW:237.18
EINECS:258-572-4
Product Categories:omega-Bromoalkanols;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Linear hydrocarbon series;Alcohols;Building Blocks;C9 to C10;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;OLED materials,pharm chemical,electronic
Mol File:53463-68-6.mol
10-Bromodecanol Structure
10-Bromodecanol Chemical Properties
Boiling point 165-169 °C/10 mmHg (lit.)
density 1.19 g/mL at 25 °C (lit.)
refractive index n20/D 1.476(lit.)
Fp >230 °F
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility Chloroform (Sparingly)
pka15.20±0.10(Predicted)
form Liquid
color Clear yellow
Water Solubility It is miscible with water.
BRN 1738593
Stability:Moisture Sensitive
InChI1S/C10H21BrO/c11-9-7-5-3-1-2-4-6-8-10-12/h12H,1-10H2
InChIKeyLGZMUUBPTDRQQM-UHFFFAOYSA-N
SMILESOCCCCCCCCCCBr
CAS DataBase Reference53463-68-6(CAS DataBase Reference)
EPA Substance Registry System1-Decanol, 10-bromo- (53463-68-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
WGK Germany 3
TSCA TSCA listed
HS Code 29055900
Storage Class10 - Combustible liquids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
10-Bromodecanol Usage And Synthesis
Chemical PropertiesClear yellow liquid
Uses10-Bromo-1-decanol is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. It was also used in the synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm (Amyelois transitella).
Uses10-Bromodecanol can be used to synthesize rotaxane dendrimers. It can also be used to synthesize J2326, a molecule that induces neurite outgrowth in neuronal cells.
DefinitionChEBI: 10-Bromo-1-decanol is a primary alcohol.
Synthesis
1,10-Decanediol

112-47-0

10-Bromodecanol

53463-68-6

General procedure for the synthesis of 10-bromo-1-decanol from 1,10-decanediol: 1,10-decanediol (10 g, 57.47 mmol) was dissolved in toluene (600 mL) and transferred to a 1 L two-necked, round-bottomed flask fitted with a Dean-Stark separator. 48% hydrobromic acid (7.15 mL, 63.21 mmol) was slowly added to the reaction system and subsequently heated to reflux for 16 hours. After completion of the reaction, it was cooled to room temperature and the reaction mixture was washed sequentially with 1 N hydrochloric acid, 2 M aqueous sodium hydroxide, deionized water and saturated saline. The organic phase was separated, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (eluent: 15% ethyl acetate/hexane) to afford 10-bromo-1-decanol as a colorless transparent oil (12.7 g, 93% yield). Thin layer chromatography (TLC) Rf = 0.45 (unfolding agent: 20% ethyl acetate/hexane); 1H NMR (500 MHz, CDCl3): δ 3.63 (t, J = 5.8 Hz, 2H), 3.39 (t, J = 6.8 Hz, 2H), 1.85 (m, 2H), 1.56 (m, 2H), 1.42 (m, 2H), 1.38- 1.27 (m, 10H); 13C NMR (125 MHz, CDCl3): δ 62.9, 33.9, 32.7, 32.6, 29.3, 29.2, 29.2, 28.6, 28.0, 25.6; infrared spectra (neat sample): νmax 2927, 2856, 1738, 1593, 1449, 1367, 1241 cm-1; high-resolution mass spectrum (ESI): calculated value C10H22BrO [M + H]+ 237.0854, measured value 237.0845.

References[1] Tetrahedron, 2015, vol. 71, # 7, p. 1058 - 1067
[2] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 3, p. 1083 - 1092
[3] ACS Medicinal Chemistry Letters, 2010, vol. 1, # 6, p. 273 - 276
[4] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 1, p. 567 - 579
[5] Patent: EP1818336, 2007, A1. Location in patent: Page/Page column 7
Tag:10-Bromodecanol(53463-68-6) Related Product Information
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