4-Bromo-3-nitrobenzoic acid Chemical Properties

Melting point:

202-204°C

Boiling point:

340.9±32.0 °C(Predicted)

Density 

2.0176 (rough estimate)

refractive index 

1.6200 (estimate)

storage temp. 

2-8°C

solubility 

soluble in Methanol

form 

Solid

pka

3.35±0.10(Predicted)

color 

White to yellow

CAS DataBase Reference

6319-40-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

29163990

4-Bromo-3-nitrobenzoic acid Usage And Synthesis

Chemical Properties

light yellow powder

Synthesis

The general procedure for the synthesis of 4-bromo-3-nitrobenzoic acid from 4-bromobenzoic acid is as follows: 1. prepare a nitration mixture by slowly adding fuming nitric acid (12.4 mL, 0.3 mol) to concentrated hydrochloric acid followed by sulfuric acid (30.1 mL, 0.6 mol) at 0-5 °C. 2. the cooled nitrification mixture was transferred to a beaker fitted with a mechanical stirrer and a charging funnel. 3. 4-Bromobenzoic acid (40 g, 0.2 mol) was slowly added to the nitrification mixture in batches while maintaining a temperature of 0-5°C. The dosing process lasted for 5 hours. 4. After completion of the addition, the reaction mixture was continued to be stirred at room temperature for 2 hours. 5. The reaction mixture was slowly poured into ice water to precipitate the solid product. 6. The solid product was separated by filtration, washed with water to neutrality and subsequently air dried to constant weight to give the pure 4-bromo-3-nitrobenzoic acid (white solid, 47.2 g, 96% yield). Product characterization data: 1H NMR (300 MHz, CDCl3): δ 7.85 (d, J = 12.0 Hz, 1H), 8.09 (d, J = 12.0 Hz, 1H), 8.48 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 124.2, 132.1, 135.2, 138.0, 139.8, 159.8, 171.0.

References

[1] Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2267 - 2273
[2] Patent: US2008/293736, 2008, A1. Location in patent: Page/Page column 32
[3] Patent: WO2017/7634, 2017, A1. Location in patent: Paragraph 0730; 0731; 0732
[4] Patent: WO2005/16882, 2005, A1. Location in patent: Page/Page column 13
[5] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 178 Anm. 1

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