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| | 2-Bromo-2-phenylacetic acid Basic information |
| | 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 | | pka | pK1: 2.21 (25°C) | | form | powder to crystal | | color | White to Almost white | | InChI | 1S/C8H7BrO2/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7H,(H,10,11) | | InChIKey | WAKFRZBXTKUFIW-UHFFFAOYSA-N | | SMILES | OC(=O)C(Br)c1ccccc1 | | CAS DataBase Reference | 4870-65-9(CAS DataBase Reference) | | NIST Chemistry Reference | «ALPHA»-bromophenylacetic acid(4870-65-9) |
| 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 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Eye Dam. 1
Skin Corr. 1B
STOT SE 3 |
| | 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 Preparation Products And Raw materials |
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