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)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26

HazardClass 

IRRITANT

HS Code 

2916399090

MSDS

• Language:English Provider:ALFA

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

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