5-AMINO-2-BROMOBENZOIC ACID Chemical Properties

Melting point:

171-179 °C

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

color 

Brown

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C7H6BrNO2/c8-6-2-1-4(9)3-5(6)7(10)11/h1-3H,9H2,(H,10,11)

InChIKey

FEXDUVBQBNYSQV-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

2840-02-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-36/37/38

Safety Statements 

26-36/37

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

Hazard Note 

Harmful

HazardClass 

6.1

HS Code 

2922498590

5-AMINO-2-BROMOBENZOIC ACID Usage And Synthesis

Chemical Properties

White crystalline solid

Uses

It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs and is also used in medicine.

Uses

5-Amino-2-bromobenzoic Acid can be used for FABP4 and FABP4 inhibitors to prevent or treat FABP 4/5 related diseases.

reaction suitability

reaction type: solution phase peptide synthesis

Synthesis

General procedure for the synthesis of 5-amino-2-bromobenzoic acid from 3-aminobenzoic acid: 3-aminobenzoic acid (3.00 g, 21.9 mmol) was dissolved in N,N-dimethylformamide (18.0 mL) and cooled to below 5 °C. In another vessel, a solution was prepared by mixing N,N-dimethylformamide (9.00 mL) with N-bromosuccinimide (4.09 g, 23.0 mmol). This solution was slowly added to the cooled 3-aminobenzoic acid solution, keeping the reaction temperature at 5 °C or lower. The reaction mixture was stirred at 5 °C for 1 h. After the reaction mixture was stirred for 1 h, water (60.0 mL) was added and the stirring was continued for 12 h at 5 °C. Upon completion of the reaction, the solid product was collected by filtration, and the filtrate was washed with water (5.00 mL) and dried to give 5-amino-2-bromobenzoic acid (3.68 g, 78% yield). The structure of the product was confirmed by 1H-NMR (400 MHz, DMSO-D6): δ 5.49 (s, 2H), 6.59 (dd, J = 8.5,2.9Hz, 1H), 6.93 (d, J = 2.9Hz, 1H), 7.25 (d, J = 8.5Hz, 1H), 13.04 (s, 1H).

Purification Methods

Crystallise the acid from H2O or *C6H6 (m 128o). The acetyl derivative crystallises from H2O (as monohydrate) or absolute EtOH with m 196-197o (anhydrous). [Koopal Rec Trav Chim, Pays Bas 34 148 1915, Bamberger Chem Ber 57 2090 1924, Beilstein 14 H 413, 14 II 245.]

References

[1] Patent: US2013/310576, 2013, A1. Location in patent: Paragraph 0151

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