3-Bromobenzoic acid Chemical Properties

Melting point:

155-158 °C(lit.)

Boiling point:

>280 °C

Density 

1,948 g/cm³

refractive index 

1.6080 (estimate)

storage temp. 

Sealed in dry,Room Temperature

solubility 

methanol: soluble50mg/mL, clear, colorless

pka

3.86(at 25℃)

form 

Powder

color 

White to light beige

Water Solubility 

0.54 g/L (32 ºC)

BRN 

2041792

InChIKey

VOIZNVUXCQLQHS-UHFFFAOYSA-N

CAS DataBase Reference

585-76-2(CAS DataBase Reference)

NIST Chemistry Reference

Benzoic acid, 3-bromo-(585-76-2)

EPA Substance Registry System

m-Bromobenzoic acid (585-76-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-37/38-36

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29163990

MSDS

• Language:English Provider:3-Bromobenzoic acid
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
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3-Bromobenzoic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder. soluble in alcohols and ethers, insoluble in water.Used as organic synthesis reagent.

Uses

3-Bromobenzoic acid was used as test solute in the determination of acidity constants by capillary zone electrophoresis. It was used as internal standard to study the retention mechanisms of an unmodified and a hydroxylated polystyrene-divinylbenzene polymer by solid-phase extraction. It was also used in synthesis of N-(1,1-dimethyl-2-hydroxyethyl)-3-bromobenzamide.

Preparation

3-Bromobenzoic acid is synthesized from 3-bromotoluene by oxidation of potassium permanganate. Mix m-bromotoluene, potassium hydroxide and water, heat to boiling, slowly add potassium permanganate, and reflux for 4 hours after adding. After acidification by filtration, the crude product was obtained by filtration. Then it is dissolved in ethanol with ammonia water, acidified with hydrochloric acid, filtered and washed with water to obtain 3-bromobenzoic acid.

Definition

ChEBI: 3-bromobenzoic acid is a bromobenzoic acid carrying a single bromo subsituent at the 3-position.

Synthesis Reference(s)

The Journal of Organic Chemistry, 15, p. 481, 1950 DOI: 10.1021/jo01149a007

Purification Methods

Crystallise the acid from acetone/water, MeOH or acetic acid. The anilide has m 137o (from EtOH/H2O). [Beilstein 9 IV 1013.]

3-Bromobenzoic acid(585-76-2)Related Product Information

• 4-Nitrobenzoic acid
• Benzoic acid
• 2-Amino-5-bromobenzoic acid
• m-Toluic acid
• 3-Hydroxybenzoic acid
• Methyl 2-bromobenzoate
• 3-Bromotoluene
• 3-Bromophenol
• Methyl 3-bromobenzoate
• 3,5-Dibromobenzoic acid
• 4-Aminobenzoic acid
• Estradiol benzoate
• Ethyl 2-(Chlorosulfonyl)acetate
• 3-Bromobenzonitrile
• 3-Chloroperoxybenzoic acid
• Hyaluronic acid
• Citric acid
• 5-Bromo-2-methylbenzoic acid