2-Bromo-2-phenylacetic acid Chemical Properties

Melting point:

82-83 °C(lit.)

Boiling point:

120-121 °C(Press: 0.02 Torr)

Density 

1.643±0.06 g/cm3(Predicted)

storage temp. 

Store below +30°C.

solubility 

soluble in Methanol

form 

powder to crystal

pka

pK1: 2.21 (25°C)

color 

White to Almost white

CAS DataBase Reference

4870-65-9(CAS DataBase Reference)

NIST Chemistry Reference

«ALPHA»-bromophenylacetic acid(4870-65-9)

Safety Information

Hazard Codes 

C

Risk Statements 

34-36/37

Safety Statements 

26-27-28-36/37/39-45

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

HazardClass 

8

PackingGroup 

III

HS Code 

29163900

MSDS

• Language:English Provider:2-Bromo-2-phenylacetic acid
• Language:English Provider:SigmaAldrich

2-Bromo-2-phenylacetic acid Usage And Synthesis

Chemical Properties

Beige crystalline powder

Uses

α-Bromophenylacetic acid can be used as a reactant to prepare:

• Polymandelide by reacting with triethylamine.
• α-Mercaptophenylacetic acid by treating with sodium hydrosulfide (NaSH·H₂O).
• β-Lactams by reacting with imines in the presence of triphenylphosphine as a mediator.

Uses

2-Bromo-2-phenylacetic Acid can be used as an inhibitor of mammalian collagenase and elastase.

Synthesis

General procedure for the synthesis of α-bromophenylacetic acid from phenylacetic acid: 2-phenylacetic acid (376 mg, 2.7 mmol), N-bromosuccinimide (540 mg, 3.05 mmol), and carbon tetrachloride (5.5 mL) were added to a dry two-necked flask fitted with a condensing unit. Azobisisobutyronitrile (23 mg, 0.14 mmol) was added with stirring and the reaction was heated to reflux at 77°C with stirring for 2 hours. The progress of the reaction was monitored by nuclear magnetic resonance spectroscopy (1H NMR) until 2-phenylacetic acid was completely consumed. Upon completion of the reaction, the reaction was cooled naturally to room temperature, and the reaction mixture was diluted with hexane (10.0 mL) and filtered. The solvent was removed by rotary evaporation and purified by silica gel column chromatography (eluent: n-hexane/ether, 2:1, v/v) to afford α-bromophenylacetic acid as a white solid (95% yield).

References

[1] Patent: CN105384703, 2016, A. Location in patent: Paragraph 0014
[2] Journal of Organic Chemistry, 2016, vol. 81, # 20, p. 9620 - 9629
[3] Journal of Medicinal Chemistry, 1999, vol. 42, # 1, p. 50 - 59
[4] Journal of Medicinal Chemistry, 2003, vol. 46, # 20, p. 4333 - 4341
[5] Tetrahedron Letters, 2004, vol. 45, # 26, p. 5151 - 5154

2-Bromo-2-phenylacetic acid(4870-65-9)Related Product Information

• 2-Bromofluorobenzene
• 4'-Bromopropiophenone
• Hyaluronic acid
• Bromoxynil
• Ethyl 2-(Chlorosulfonyl)acetate
• 3-Bromoanisole
• Folic acid
• 4-Bromobenzaldehyde
• Bromoxynil octanoate
• Citric acid
• α-Lipoic Acid
• Ascoric Acid
• Phenylacetic acid
• 2-BROMO-2-PHENYLACETIC ACID METHYL ESTER
• 2'-BROMO-3,4-DICHLOROPHENYLACETIC ACID METHYL ESTER
• ALPHA-BROMO-3-CHLOROBENZENEACETIC ACID ETHYL ESTER
• Ethyl α-bromophenylacetate
• alpha-Bromo-2-chlorophenylacetic acid