2-Amino-5-bromobenzoic acid Property

Melting point:

213-215 °C (lit.)

Boiling point:

265.51°C (rough estimate)

Density 

1.6841 (rough estimate)

refractive index 

1.6120 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in methanol and dimethyl sulfoxide.

form 

Powder

pka

4.55±0.10(Predicted)

color 

Beige

Sensitive 

Light Sensitive

Merck 

14,1405

BRN 

639028

InChI

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

InChIKey

CUKXRHLWPSBCTI-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(Br)=CC=C1N

CAS DataBase Reference

5794-88-7(CAS DataBase Reference)

NIST Chemistry Reference

2-Amino-5-bromobenzoic acid(5794-88-7)

Safety

Hazard Codes 

Xn

Risk Statements 

22-36/37

Safety Statements 

26-38-36/37

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

CB2557670

Hazard Note 

Harmful

PackingGroup 

6.1/PG 3

HS Code 

29224999

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2-Amino-5-bromobenzoic acid Chemical Properties,Usage,Production

Synthesis

A solution of bromine (7.2 g, 2 mL, 40 mmol) in 47 mL glacial acetic acid was added dropwise to sodium 2-aminobenzoate (6.4 g, 40 mmol) in 32 mL of glacial acetic acid at 15 °С and the mixture was stirred for 1 h at the same temperature. The product was filtered off, washed with benzene and dried in the dark. The bromobenzoic acids containing mixture (0.5 g) was added to 10 mL of boiling water followed by the addition of 1.3 mL of concentrated hydrochloric acid and hot filtration under vacuum. The insoluble material contained 2-amino-3,5-dibromobenzoic acid, whereas 2- amino-5-bromobenzoic acid precipitated upon cooling of the filtrate. IR (suspension in nujol, cm−1 ): 3497, 3383,  1675, 1616, 1587, 1548, 1423, 1377, 1316, 1292, 1239, 1160, 1127, 812, 748, 691.

Chemical Properties

slight yellow to white powder

Physical properties

2-Amino-5-bromobenzoic acid has 17 atoms, meaning 45 vibrational modes in three main parts: Carboxyl group, amine group, and benzene. The molecule's most mechanically active parts are the carboxyl and amine groups. They exhibit rocking, swinging, and every kind of mechanical motion beside H immigrations between each other. For this reason, the molecule is not a simple carboxylic acid nor a primary amine[1].

Uses

It is used in the preparation of hepatitis C virus NS5b RNA polymerase inhibitors. Also used in the determination of cobalt, copper, nickel, and zinc.

Uses

2-Amino-5-bromobenzoic acid is a brominated derivative of Antharilinic Acid (A679222). 2-Amino-5-bromobenzoic acid displays plant growth-regulator activity. 2-Amino-5-bromobenzoic acid is used in the preparation of hepatitis C virus NS5b RNA polymerase inhibitors.

Preparation

2-Amino-5-bromobenzoic acid is synthesized from o-aminobenzoic acid by bromination.
Synthesis of 2-amino-5-bromobenzoic acid (4c, CAS: 5794-88-7) and 2-amino3,5-dibromobenzoic acid (4d, CAS: 609-85-8): A solution of bromine (7.2 g, 2 mL, 40 mmol) in 47 mL glacial acetic acid was added dropwise to sodium 2-aminobenzoate (6.4 g, 40 mmol) in 32 mL of glacial acetic acid at 15 °С and the mixture was stirred for 1 h at the same temperature. The product was filtered off, washed with benzene and dried in the dark. The bromobenzoic acids containing mixture (0.5 g) was added to 10 mL of boiling water followed by the addition of 1.3 mL of concentrated hydrochloric acid and hot filtration under vacuum. The insoluble material contained 2-amino-3,5-dibromobenzoic acid, whereas 2- amino-5-bromobenzoic acid precipitated upon cooling of the filtrate.
2-Amino-5-bromobenzoic acid (4c) IR (suspension in nujol, cm?1 ): 3497, 3383, 1675, 1616, 1587, 1548, 1423, 1377, 1316, 1292, 1239, 1160, 1127, 812, 748, 691.

References

[1] Kunduracioglu, Ahmet . "Tautomeric Forms of 2–Amino–5–Bromobenzoic Acid: A DFT Study for Structural and Molecular Orbital Analysis." (2021).