|
|
| | 3-Bromo-2-fluorobenzoic acid Basic information |
| | 3-Bromo-2-fluorobenzoic acid Chemical Properties |
| Melting point | 168 °C | | Boiling point | 298.2±25.0 °C(Predicted) | | density | 1.789±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | form | powder to crystal | | pka | 2.88±0.10(Predicted) | | color | White to Light yellow | | InChI | InChI=1S/C7H4BrFO2/c8-5-3-1-2-4(6(5)9)7(10)11/h1-3H,(H,10,11) | | InChIKey | UVKURTLVTLRSSM-UHFFFAOYSA-N | | SMILES | C(O)(=O)C1=CC=CC(Br)=C1F | | CAS DataBase Reference | 161957-56-8(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36 | | Safety Statements | 26 | | HazardClass | IRRITANT | | HS Code | 2916399090 |
| Provider | Language |
|
ALFA
| English |
| | 3-Bromo-2-fluorobenzoic acid Usage And Synthesis |
| Chemical Properties | Off-white powder | | Uses | 3-Bromo-2-fluorobenzoic acid is used as a reagent to synthesize Dabrafenib, an inhibitor of BRAF kinase that is used to treat BRAF V600-mutation positive carcinoma. BRAF is a gene that mediates cell growth and is activated by mutations caused by cancer. 3-Bromo-2-fluorobenzoic acid is also used as a reagent to prepare Alkynlphenoxyacetic acid receptor agonists, compounds that can be potentially used for the treatment of allergic inflammatory diseases (such as allergic rhinitis). | | Synthesis | 1. n-Butyl lithium (n-BuLi, 240 mL of a 2.5 M solution, 600 mmol) was added dropwise to a tetrahydrofuran (THF, 500 mL) solution of diisopropylamine (84.3 mL, 600 mmol) at -30°C.
2. The resulting solution was stirred at -30°C for 30 minutes.
3. The mixture was added dropwise to a solution of 1-bromo-2-fluorobenzene (100 g, 571.43 mmol) in THF (500 mL) at -78° C. The solution was stirred for 30 minutes at -78° C. The mixture was then added to a solution of 1-bromo-2-fluorobenzene (100 g, 571.43 mmol).
4. After the addition, the resulting solution was stirred at -78°C for 2 hours.
5. The reaction mixture was poured over crushed solid carbon dioxide.
6. After removal of the solvent in vacuo, the resulting residue was diluted with water and washed with ether (2 x 500 mL).
7. The aqueous phase was acidified to pH 2 with 1N hydrochloric acid (HCl).
8. The precipitate was collected by filtration and dried to give 3-bromo-2-fluorobenzoic acid (90 g, 64% yield) as a white solid.
9. Mass spectrometry (MS) analysis showed m/z 221.0 (M + H+). | | References | [1] Bulletin de la Societe Chimique de France, 1996, vol. 133, # 2, p. 133 - 141
[2] Patent: WO2011/119704, 2011, A1. Location in patent: Page/Page column 39-40
[3] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 12, p. 4158 - 4181
[4] Patent: US2009/203657, 2009, A1. Location in patent: Page/Page column 47
[5] Patent: US2009/203677, 2009, A1. Location in patent: Page/Page column 50 |
| | 3-Bromo-2-fluorobenzoic acid Preparation Products And Raw materials |
|