2-AMINO-3-BROMO-5-FLUOROBENZOIC ACID Chemical Properties

Melting point:

202-205°

Boiling point:

344.0±42.0 °C(Predicted)

Density 

1.877±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

pka

4.21±0.10(Predicted)

form 

Solid

Appearance

Off-white to yellow Solid

InChI

InChI=1S/C7H5BrFNO2/c8-5-2-3(9)1-4(6(5)10)7(11)12/h1-2H,10H2,(H,11,12)

InChIKey

LTOCPZGBNWZMBA-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(F)=CC(Br)=C1N

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2922498590

2-AMINO-3-BROMO-5-FLUOROBENZOIC ACID Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-3-bromo-5-fluorobenzoic acid from 2-amino-5-fluorobenzoic acid: N-bromosuccinimide (631 mg, 3.55 mmol) was added in batches to a stirred solution of 2-amino-5-fluorobenzoic acid (7,500 mg, 3.22 mmol) dissolved in acetic acid (5 mL) and the reaction mixture was stirred at room temperature overnight . The resulting precipitate was collected by filtration, washed with petroleum ether (20 mL) and dried to constant weight to afford 2-amino-3-bromo-5-fluorobenzoic acid (11,501 mg, 66.4% yield) as a clear beige solid. The product was used without further purification. The product characterization data were as follows: LCMS (t R = 1.35 min, purity = 100%), no ions detected at ESI m/z; 1H NMR (DMSO-d6) δ (ppm) 6.76 (broad single peak, 2H), 7.55 (double peak, J = 3.0 Hz, JH-F = 9.4 Hz, 1H), 7.71 (double peak, J = 3.0 Hz, JH F = 7.8 Hz, 1H), 12.72 (broad single peak, 1H); 13C NMR (DMSO-d6) δ (ppm) 109.4 (double peak, JC-F = 7.1 Hz), 111.1 (double peak, JC-F = 7.1 Hz), 116.2 (double peak, JC-F = 22.1 Hz), 124.9 (double peak, JC-F = 24.8 Hz), 145.1, 151.4 (double peaks, JC-F = 235.3 Hz), 168.1 (double peaks, JC-F = 2.7 Hz).

References

[1] Tetrahedron, 2012, vol. 68, # 2, p. 534 - 543
[2] Patent: EP3287463, 2018, A1. Location in patent: Paragraph 0203; 0208
[3] Patent: US2018/208604, 2018, A1. Location in patent: Paragraph 0502-0503
[4] Patent: WO2016/105564, 2016, A1. Location in patent: Paragraph 0288

2-AMINO-3-BROMO-5-FLUOROBENZOIC ACID(259269-84-6)Related Product Information

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