2-BROMOPHENETHYLALCOHOL Chemical Properties

Boiling point:

97 °C/0.7 mmHg (lit.)

Density 

1.483 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.577(lit.)

Flash point:

>230 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO, Ethyl Acetate

pka

14.70±0.10(Predicted)

form 

Liquid

Specific Gravity

1.483

color 

Clear slightly yellow

InChI

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

InChIKey

ADLOWZRDUHSVRU-UHFFFAOYSA-N

SMILES

C1(CCO)=CC=CC=C1Br

Safety Information

Safety Statements 

24/25

WGK Germany 

3

HS Code 

29062990

MSDS

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

2-BROMOPHENETHYLALCOHOL Usage And Synthesis

Chemical Properties

clear slightly yellow liquid

Uses

2-Bromophenethyl alcohol is used as an end capping reagent during the synthesis of rod-coil block copolymers and also as a test compound in the study to evaluate the potential Aedes aegypti repellent chemotype.

Uses

2-Bromophenethyl alcohol is a brominated phenethanol derivative used as a building block in the preparation or bicyclic and tricyclic heterocycles.

General Description

2-Bromophenethyl alcohol is a phenethyl alcohol derivative. It participates in the preparation of novel P-chirogenic phosphines with a sulfur-chelating arm (P*,S-hybrid ligand).

Synthesis

General method: anhydrous CaCl2 (1.12 g, 10.2 mmol) was dissolved in ethanol (50 mL) in a three-necked round-bottomed flask under argon protection. The solution was cooled to 0 °C, followed by slow addition of NaBH4 (0.19 g, 5.1 mmol) at the same temperature. The resulting suspension was stirred at 0 °C for 30 min, after which an ethanol solution (60 mL) of methyl 2-(2-bromophenyl)acetate (S5a, 1.0 g, 3.4 mmol) was added dropwise at the same temperature. The reaction mixture was continued to be stirred at 0 °C for 30 min, and then raised to room temperature and stirred for 15 h. The reaction was carried out at 0 °C. Upon completion of the reaction, 50 mL of a mixture of water and dichloromethane (1:1, v/v) was added to the mixture and sonicated for 1 hour. The mixture was vacuum filtered through diatomaceous earth and the filtrate was concentrated under reduced pressure. The crude product was dissolved in 50 mL of water and extracted with dichloromethane (3 x 30 mL). The organic phases were combined, dried with anhydrous Na2SO4 and the solvent was evaporated under reduced pressure to give the target product 2-(2-bromophenyl)ethanol (S6a-S6d). The products were characterized as follows: 2-(2-bromo-4,5-dimethoxyphenyl)ethanol (S6a): brown oil in 60% yield (2.56 g); 2-(2-bromo-5-methoxyphenyl)ethanol (S6b): colorless transparent oil in 42% yield (1.29 g); 2-(2-bromo-4-methoxyphenyl)ethanol (S6c): colorless transparent oily substance, yield 55% (1.03 g); 2-(2-bromophenyl)ethanol (S6d): colorless transparent oily substance, yield 55% (2.41 g).

References

[1] Tetrahedron, 2013, vol. 69, # 42, p. 8914 - 8920

2-BROMOPHENETHYLALCOHOL(1074-16-4)Related Product Information

• Ethyl 2-(2-bromophenyl)acetate
• 2-Bromophenylacetic acid
• 2-BROMOPHENETHYLALCOHOL
• 2-Bromo-5-chlorophenylacetic acid
• 2-Bromo-4-methoxyphenylacetic acid
• 2-BROMO-4,5-DIMETHOXYPHENYLACETIC ACID
• 3-BROMOPHENETHYL ALCOHOL
• 4-Bromophenethyl alcohol
• AMINO-(1-BROMO-NAPHTHALEN-2-YL)-ACETIC ACID
• (7-BROMO-2,3-DIHYDRO-1,4-BENZODIOXIN-6-YL)ACETIC ACID
• (2-BROMO-4,5-DIETHOXYPHENYL)ACETIC ACID
• AMINO(2-BROMOPHENYL)ACETIC ACID
• 2-BROMO-4-HYDROXY-5-METHOXYPHENYLACETIC ACID
• α-(p-bromophenyl)ethyl alcohol
• m-bromobenzeneethanol
• AKOS AU36-M431
• AKOS AU36-M435
• AKOS AU36-M430