3-BROMOPHENETHYL ALCOHOL Chemical Properties

Boiling point:

107-110 °C/1 mmHg (lit.)

Density 

1.478 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.5732(lit.)

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

pka

14.83±0.10(Predicted)

color 

Clear colorless

Safety Information

Hazard Codes 

Xi

Safety Statements 

24/25

WGK Germany 

3

Hazard Note 

Harmful/Irritant/Keep Cold

HS Code 

29062990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

3-BROMOPHENETHYL ALCOHOL Usage And Synthesis

Chemical Properties

clear colorless liquid

Uses

3-Bromophenethyl alcohol may be used as a starting material in the synthesis of its mesylate derivative (m-Br-C₆H₄CH₂CH₂OMs) by treatment with mesyl chloride.

General Description

3-Bromophenethyl alcohol is a phenethyl alcohol derivative. Its enthalpy of vaporization at boiling point has been determined.

Synthesis

The general procedure for the synthesis of 3-bromophenylethanol using 3-bromophenylacetic acid as starting material was as follows: to a solution of 3-bromophenylacetic acid (2.00 g, 9.3 mmol) was slowly added BH3-Me2S (7 mL of a 2M THF solution, 14.0 mmol) at 0 °C. The reaction mixture was gradually warmed up to room temperature with continuous stirring for 20 hours. Upon completion of the reaction, the mixture was again cooled to 0 °C and water (10 mL) was added dropwise to quench the reaction. Subsequently, the organic layer was separated, washed with brine (20 mL), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure to give a colorless oily crude product. Purification by column chromatography (eluent: 50% EtOAc in heptane solution) resulted in 3-bromophenethyl alcohol as a colorless oil (1.47 g, 79% yield). The product was detected by mass spectrometry showing m/z 224/226 [M + H]+, and the 1H NMR (300 MHz, CDCl3) data were as follows: δ 7.41-7.35 (2H, m), 7.23-7.16 (2H, m), 3.87 (2H, t, J = 6.5 Hz), 2.86 (2H, t, J = 6.5 Hz).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3018 - 3022
[2] Journal of Labelled Compounds and Radiopharmaceuticals, 2007, vol. 50, # 3, p. 183 - 188
[3] Patent: WO2008/53136, 2008, A1. Location in patent: Page/Page column 38
[4] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2882 - 2891
[5] Journal of Medicinal Chemistry, 1998, vol. 41, # 3, p. 358 - 378

3-BROMOPHENETHYL ALCOHOL(28229-69-8)Related Product Information

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