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ChemicalBook--->CAS DataBase List--->53463-68-6

53463-68-6

53463-68-6 Structure

53463-68-6 Structure
IdentificationMore
[Name]

10-Bromodecanol
[CAS]

53463-68-6
[Synonyms]

10-BROMO-1-DECANOL
10-BROMODECANOL
DECAMETHYLENE BROMOHYDRIN
10-bromo-1-decano
10-BROMO-1-DECANOL, TECH., 90%
10-BROMODECAN-1-OL
10-BROMO-1-DECANOL 85+%
10-Hydroxydecyl bromide
[EINECS(EC#)]

258-572-4
[Molecular Formula]

C10H21BrO
[MDL Number]

MFCD00041681
[Molecular Weight]

237.18
[MOL File]

53463-68-6.mol
Chemical PropertiesBack Directory
[Appearance]

Clear yellow liquid
[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. ]

−20°C
[solubility ]

Chloroform (Sparingly)
[form ]

Liquid
[pka]

15.20±0.10(Predicted)
[color ]

Clear yellow
[Water Solubility ]

It is miscible with water.
[BRN ]

1738593
[Stability:]

Moisture Sensitive
[InChIKey]

LGZMUUBPTDRQQM-UHFFFAOYSA-N
[CAS DataBase Reference]

53463-68-6(CAS DataBase Reference)
[EPA Substance Registry System]

1-Decanol, 10-bromo- (53463-68-6)
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
[WGK Germany ]

3
[TSCA ]

Yes
[HS Code ]

29055900
Hazard InformationBack Directory
[Chemical Properties]

Clear yellow liquid
[Uses]

10-Bromo-1-decanol was used in the synthesis of (11Z,13Z)-11,13-hexadecadienal, the female sex pheromone of the navel orangeworm (Amyelois transitella).
[Uses]

10-Bromo-1-decanol is used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff.
[Definition]

ChEBI: 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
Spectrum DetailBack Directory
[Spectrum Detail]

10-Bromodecanol(53463-68-6)MS
10-Bromodecanol(53463-68-6)1HNMR
10-Bromodecanol(53463-68-6)IR1
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

10-Bromo-1-decanol,95%(53463-68-6)
[Alfa Aesar]

10-Bromo-1-decanol, 95%(53463-68-6)
[Sigma Aldrich]

53463-68-6(sigmaaldrich)
[TCI AMERICA]

10-Bromo-1-decanol,>85.0%(GC)(53463-68-6)
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