2,5-Dibromobenzoic acid Chemical Properties

Melting point:

156-159 °C(lit.)

Boiling point:

344.6±32.0 °C(Predicted)

Density 

1.9661 (rough estimate)

refractive index 

1.4970 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

2.46±0.10(Predicted)

color 

White to Yellow to Orange

BRN 

1868193

InChI

InChI=1S/C7H4Br2O2/c8-4-1-2-6(9)5(3-4)7(10)11/h1-3H,(H,10,11)

InChIKey

SQQKOTVDGCJJKI-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(Br)=CC=C1Br

CAS DataBase Reference

610-71-9(CAS DataBase Reference)

NIST Chemistry Reference

2,5-Dibromobenzoic acid(610-71-9)

Safety Information

Hazard Codes 

Xi,C

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

DG6290000

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,5-Dibromobenzoic acid Usage And Synthesis

Chemical Properties

off-white powder

Uses

2,5-Dibromobenzoic Acid is an intermediate used to prepare benzo[c]chromenone and benzo[c]chromene derivatives as estrogen β-receptor-selective agonists in comparison with effusol and estradiol. It is also used in the synthesis of aminopyridine-based c-Jun N-terminal kinase inhibitors with cellular activity and minimal cross-kinase activity.

Synthesis

First, sodium periodate solution was prepared: 4.3 g (19.9 mmol) of sodium periodate was dissolved in a solvent mixture of 30 mL of water and 18 mL of acetic acid. Subsequently, 10 g (49.7 mmol) of o-bromobenzoic acid and 5.1 g (49.7 mmol) of sodium bromide were added to the reaction flask with the above prepared sodium periodate solution. The reaction mixture was heated to 30°C, at which temperature 4.4 mL of concentrated sulfuric acid was slowly added dropwise. After the dropwise addition was completed, the reaction temperature was raised to 50 °C and the reaction was kept at this temperature for 2-3 hours. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the mixture was cooled to room temperature and poured into ice water to precipitate the solid product. The solid was collected by filtration and the filter cake was washed several times with cold water to give 11.9 g of 2,5-dibromobenzoic acid in 85.6% yield.

Purification Methods

Crystallise the acid from water or EtOH. [Beilstein 9 H 358, 9 I 147, 9 II 237, 9 III 1428, 9 IV 1027.]

References

[1] Patent: CN107954852, 2018, A. Location in patent: Paragraph 0029-0031
[2] Justus Liebigs Annalen der Chemie, 1891, vol. 266, p. 203
[3] Journal of the Indian Chemical Society, 1980, vol. 57, # 6, p. 640 - 642

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