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| | 2-Amino-4-bromo-3-fluorobenzoic acid Basic information |
| Product Name: | 2-Amino-4-bromo-3-fluorobenzoic acid | | Synonyms: | 2-Amino-4-bromo-3-fluorobenzoic acid;3-BROMO-6-CARBOXY-2-FLUOROANILINE;140622;Benzoic acid, 2-amino-4-bromo-3-fluoro-;Ethanol,5-diazenyl-;2-amino-4-bromo-3-fluorobenzoicaci;2-Amino-3-fluoro-4-bromobenzoic acid;Oxymetazoline Impurity 10 | | CAS: | 1416013-62-1 | | MF: | C7H5BrFNO2 | | MW: | 234.02 | | EINECS: | | | Product Categories: | | | Mol File: | 1416013-62-1.mol |  |
| | 2-Amino-4-bromo-3-fluorobenzoic acid Chemical Properties |
| Boiling point | 332.0±42.0 °C(Predicted) | | density | 1.877±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | pka | 4.37±0.10(Predicted) | | form | powder | | color | Off white | | InChI | InChI=1S/C7H5BrFNO2/c8-4-2-1-3(7(11)12)6(10)5(4)9/h1-2H,10H2,(H,11,12) | | InChIKey | SFRJQFICUQFDFU-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC=C(Br)C(F)=C1N |
| | 2-Amino-4-bromo-3-fluorobenzoic acid Usage And Synthesis |
| Description | 2-Amino-4-bromo-3-fluorobenzoic acid is an important pharmaceutical and organic intermediate ingredient used in the synthesis of avibactam sodium, an FDA-approved non-beta-lactam β-lactamase inhibitor used in combination with ceftazidime (Avycaz). It is used for the treatment of complicated intra-abdominal infections, urinary tract infections, and pyelonephritis. | | Uses | 2-Amino-4-Bromo-3-Fluorobenzoic Acid is used in preparation of Quinazoline compounds as KRAS modulators and antitumor agents. | | Synthesis | The synthesis of 2-Amino-4-bromo-3-fluorobenzoic acid is as follows:
To a mixture of 6-bromo-7-fluoroindoline-2,3-dione (18.9 g, 77.5 mmol) in 2 N NaOH (350 mL) at 0 oC, H2O2 (30%, 40 mL) was added. The mixture was stirred at room temperature for 16 h. The mixture was quenched with Na2SO3, and the mixture was acidified with conc. HCl to adjust pH to 2. The precipitate was collected by filtration and dried to afford the desired product as a white solid (17 g, 94% yield).
 | | References | [1] Patent: WO2016/164675, 2016, A1. Location in patent: Page/Page column 231-232
[2] Patent: WO2017/98440, 2017, A1. Location in patent: Page/Page column 116
[3] Patent: WO2015/54572, 2015, A1. Location in patent: Page/Page column 253
[4] Patent: WO2017/87528, 2017, A1. Location in patent: Page/Page column 180; 181; 182
[5] Patent: WO2017/58915, 2017, A1. Location in patent: Page/Page column 102-103 |
| | 2-Amino-4-bromo-3-fluorobenzoic acid Preparation Products And Raw materials |
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