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2-Amino-5-bromobenzoic acid

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2-Amino-5-bromobenzoic acid Basic information

Product Name:
2-Amino-5-bromobenzoic acid
Synonyms:
  • 2-amnio-5-bromo-benzoic acid
  • 2-AMino-5-broMobenzoic acid, 97% 5GR
  • 2-Amino-5-bromobenzoic acid,97%
  • 2 - aMino - 5 - broMine benzoic acid
  • 2-amino-5-bromo-benzoicaci
  • 5-bromo-anthranilicaci
  • Anthranilic acid, 5-bromo-
  • Benzoic acid, 2-amino-5-bromo-
CAS:
5794-88-7
MF:
C7H6BrNO2
MW:
216.03
EINECS:
227-338-3
Product Categories:
  • Anilines, Amides & Amines
  • Bromine Compounds
  • Carboxylic Acids
  • Phenyls & Phenyl-Het
  • Benzoic acid series
  • Four-membered heterocyclic compound,Others
  • FINE Chemical & INTERMEDIATES
  • Amino Acids and Derivatives
  • Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts
  • Carboxylic Acids
  • Phenyls & Phenyl-Het
  • Benzoic acid
  • Organic acids
  • Acids & Esters
  • bc0001
Mol File:
5794-88-7.mol
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2-Amino-5-bromobenzoic acid Chemical Properties

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)
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Safety Information

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

MSDS

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2-Amino-5-bromobenzoic acid Usage And Synthesis

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).

2-Amino-5-bromobenzoic acid Preparation Products And Raw materials

Preparation Products

Raw materials

2-Amino-5-bromobenzoic acidSupplier

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