4-Bromophenethyl alcohol Chemical Properties

Melting point:

36-38 °C(lit.)

Boiling point:

138 °C/9 mmHg (lit.)

Density 

1.436 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.573(lit.)

Flash point:

146 °F

storage temp. 

Sealed in dry,Room Temperature

form 

Liquid

pka

14.79±0.10(Predicted)

color 

Clear colorless to light yellow

BRN 

2079929

InChI

InChI=1S/C8H9BrO/c9-8-3-1-7(2-4-8)5-6-10/h1-4,10H,5-6H2

InChIKey

PMOSJSPFNDUAFY-UHFFFAOYSA-N

SMILES

C1(CCO)=CC=C(Br)C=C1

CAS DataBase Reference

4654-39-1(CAS DataBase Reference)

NIST Chemistry Reference

Benzeneethanol, 4-bromo-(4654-39-1)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

Safety Statements 

26-24/25

WGK Germany 

3

HS Code 

29052900

MSDS

• Language:English Provider:4-Bromophenethyl alcohol
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Bromophenethyl alcohol Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO LIGHT YELLOW LIQUID

Uses

4-Bromophenethyl alcohol was used in the synthesis of 4-(4-(3-(trifluoromethyl)-3H-diazirin-3-yl)phenethoxy)quinazoline.

Synthesis

General procedure for the synthesis of 4-bromophenylethanol from methyl 4-bromophenylacetate: Methyl 4-bromophenylacetate (6 g, 26.2 mmol, 1.0 eq.) was dissolved in tetrahydrofuran (THF, 100 mL) and the solution was cooled to 0 °C. Lithium borohydride (LiBH4, 2M solution in THF, 1.41 g, 52.4 mmol, 2.0 eq.) was slowly added dropwise at 0 °C. After the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. After completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate (EtOAc). The organic layers were combined, washed with saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the target product 4-bromophenethyl alcohol (4.5 g, 85.5% yield). The product was detected by LCMS, m/z: 204.8 [M + H]+. 1H NMR (400 MHz, DMSO-d6) δ 7.56-7.35 (m, 2H), 7.27-7.07 (m, 2H), 4.67 (t, J = 5.2 Hz, 1H), 3.58 (td, J = 6.8,5.4 Hz, 2H), 2.69 (t. J = 6.9Hz, 2H).

References

[1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5627 - 5631
[2] Patent: WO2015/66413, 2015, A1. Location in patent: Page/Page column 164; 165
[3] Chemistry - A European Journal, 2015, vol. 21, # 42, p. 14737 - 14741
[4] Advanced Synthesis and Catalysis, 2012, vol. 354, # 10, p. 1879 - 1884
[5] Synthesis, 2011, # 18, p. 2935 - 2940

4-Bromophenethyl alcohol(4654-39-1)Related Product Information

• Ethyl acetate
• Ethanol
• 3-Bromoanisole
• DL-1-Phenethylalcohol
• Bromoxynil octanoate
• 2-Bromofluorobenzene
• 1-Phenyl-2-nitropropene
• Bromoacetaldehyde diethyl acetal
• PIPERACETAZINE (250 MG)
• 2-Bromoethanol
• Bromoxynil
• 4'-Bromopropiophenone
• Monoethanolamine
• Phenethyl alcohol
• Phenylacetone
• 4-Bromophenylglyoxal hydrate
• 4-Bromomandelic acid
• 1-(4-BROMOPHENYL)-2-HYDROXYETHAN-1-ONE