3-BROMO-5-HYDROXYBENZOIC ACID Chemical Properties

Melting point:

237-241 °C

Boiling point:

388.1±32.0 °C(Predicted)

Density 

1.861±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.69±0.10(Predicted)

color 

White to Light yellow to Light orange

InChI

InChI=1S/C7H5BrO3/c8-5-1-4(7(10)11)2-6(9)3-5/h1-3,9H,(H,10,11)

InChIKey

WGIBEMRBLBGETQ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

140472-69-1

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-50

Safety Statements 

61

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

HazardClass 

9

PackingGroup 

III

HS Code 

2918290090

3-BROMO-5-HYDROXYBENZOIC ACID Usage And Synthesis

Uses

3-Bromo-5-hydroxybenzoic acid is a carboxylic acid derivative and is used in organic synthesis.

Synthesis Reference(s)

[1] Leukotriene b4 inhibitors. Patent no. US20100240678A1

Synthesis

To a solution of NaOH (12.2 g; 305.8 mmol) in 300 mL of water was added 3-bromo-5-iodo-benzoic acid (20 g, 61.2 mmol) and Cu2O (866 mg, 6.1 mmol). The reaction mixture was heated at 100° C. for 24 h. After complete consumption of the starting material, the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was then acidified with 10% aq. HCl and extracted into ethyl acetate. The organic extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the 3-Bromo-5-hydroxybenzoic acid as a tan solid (12.3 g, 93% yield).

Purification Methods

The acid crystallises from H2O (m 238-239o), and with Me2SO4 it yields the 3-methoxy derivative with m 190-191o (from EtOH). [Baddar et al. J Chem Soc 469 1955, Beilstein 10 IV 333.]

References

[1] Patent: US2010/240678, 2010, A1. Location in patent: Page/Page column 22
[2] Patent: WO2009/77385, 2009, A1. Location in patent: Page/Page column 63
[3] Patent: WO2005/113494, 2005, A2. Location in patent: Page/Page column 118-119

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