| Identification | More | [Name]
2-Bromo-2-phenylacetic acid | [CAS]
4870-65-9 | [Synonyms]
2-BROMO-2-PHENYLACETIC ACID
A-BROMOPHENYLACETIC ACID
ALPHA-BROMOPHENYLACETIC ACID
DL-ALPHA-BROMOPHENYLACETIC ACID
LABOTEST-BB LT00455397
TIMTEC-BB SBB007654
Benzeneacetic acid, alpha-bromo-
Bromo(phenyl)acetic acid
(S)-2-Bromo-2-Phenylacetic Acid
ALPHA-BROMO-ALPHA-PHENYLACETIC ACID
a-Bromophenylacetic acid, Pract.
a-Bromo-a-phenylacetic acid
a-Bromobenzeneacetic acid
DL-a-Bromophenylacetic acid
Phenylbromoacetic acid
α-Bromobenzeneacetic acid | [EINECS(EC#)]
225-477-4 | [Molecular Formula]
C8H7BrO2 | [MDL Number]
MFCD00004206 | [Molecular Weight]
215.04 | [MOL File]
4870-65-9.mol |
| Safety Data | Back Directory | [Hazard Codes ]
C | [Risk Statements ]
R34:Causes burns.
R36/37:Irritating to eyes and respiratory system . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 3261 8/PG 2
| [WGK Germany ]
3
| [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29163900 |
| Hazard Information | Back Directory | [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.
| [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 |
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