3-Bromo-5-nitrobenzoic acid Chemical Properties

Melting point:

159-161°C

Boiling point:

376.8±32.0 °C(Predicted)

Density 

1.892±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

powder to crystal

pka

3.09±0.10(Predicted)

color 

White to Light yellow to Light orange

BRN 

2051365

InChIKey

AXRKIZCFYZBBPX-UHFFFAOYSA-N

CAS DataBase Reference

6307-83-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,N,Xn

Risk Statements 

36/37/38-50-22

Safety Statements 

26-36/37/39-61-60-36/37-37

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

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3-Bromo-5-nitrobenzoic acid Usage And Synthesis

Chemical Properties

white to slightly yellow crystalline needles

Synthesis Reference(s)

The Journal of Organic Chemistry, 72, p. 5867, 2007 DOI: 10.1021/jo070477u

Synthesis

Part G: Preparation of 3-bromo-5-nitrobenzoic acid 3-Nitrobenzoic acid (16.7 g, 100 mmol) was dissolved in a mixed solution of trifluoroacetic acid (50 mL) and sulfuric acid (20 mL) at 50 °C. Subsequently, N-bromosuccinimide (26.7 g, 150 mmol) was added in three batches over 3 hours. The reaction mixture was stirred at 50 °C for 16 h and then cooled to room temperature. The reaction mixture was slowly poured into ice water (200 mL) and extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized by dichloromethane to give the white solid product 3-bromo-5-nitrobenzoic acid (17.7 g, 72% yield). The structure of the product was confirmed by 1H NMR (300 MHz, DMSO-d6): δ 13.8 (broad peak, 1H, carboxylic acid proton), 8.60 (single peak, 1H, aromatic proton), 8.55 (single peak, 1H, aromatic proton), 8.37 (single peak, 1H, aromatic proton).

References

[1] ChemMedChem, 2014, vol. 9, # 5, p. 973 - 983
[2] Journal of the American Chemical Society, 2017, vol. 139, # 36, p. 12579 - 12590
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 4, p. 1556 - 1564
[4] Journal of Organic Chemistry, 2007, vol. 72, # 15, p. 5867 - 5869
[5] Chemistry - A European Journal, 2011, vol. 17, # 10, p. 2987 - 2995

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