2-Amino-5-bromobenzoic acid
[CAS# 5794-88-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: 2-Amino-5-bromobenzoic acid
• Synonyms: 5-Bromoanthranilic acid
• Molecular Formula: C₇H₆BrNO₂
• Molecular Weight: 216.03
• CAS Registry Number: 5794-88-7
• EC Number: 227-338-3
• SMILES: C1=CC(=C(C=C1Br)C(=O)O)N

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Melting point: 213-215 ºC (Expl.)
• Index of Refraction: 1.672, Calc.^*
• Boiling Point: 342.4±32.0 ºC (760 mmHg), Calc.^*
• Flash Point: 160.9±25.1 ºC, Calc.^*

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Hazard Statements: H301-H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovory and Applicatios

2-Amino-5-bromobenzoic acid is an aromatic organic compound that belongs to the class of substituted benzoic acids. This compound contains an amino group (-NH2) at the 2-position and a bromine atom (Br) at the 5-position of the benzoic acid structure. Its chemical formula is C7H6BrNO2, and it is often synthesized as a part of research into functionalized aromatic compounds. The discovery of 2-amino-5-bromobenzoic acid was part of a broader interest in the modification of benzoic acid derivatives to introduce bioactive and reactive functionalities. These modifications are useful for exploring new compounds with potential industrial, pharmaceutical, and material applications.

The synthesis of 2-amino-5-bromobenzoic acid typically involves the introduction of bromine and an amino group onto the benzoic acid backbone. A common approach for its preparation is through halogenation reactions followed by the nucleophilic substitution of the bromine atom with an amine group, often utilizing an amino acid derivative or other amine reagents. This straightforward synthetic pathway has made 2-amino-5-bromobenzoic acid an attractive target for organic chemists seeking to develop new functionalized aromatic acids.

One of the main applications of 2-amino-5-bromobenzoic acid is as an intermediate in the synthesis of pharmaceutical compounds. The amino and bromine groups present in the molecule can serve as points of reactivity, enabling further functionalization to produce bioactive compounds. These derivatives may possess important pharmacological properties, such as antibacterial, anticancer, or anti-inflammatory activities. For example, the compound can be used as a precursor in the synthesis of various drug molecules that target specific biological processes or pathways, making it valuable in drug discovery and development.

In addition to its pharmaceutical applications, 2-amino-5-bromobenzoic acid is used in the production of dyes and pigments. The amino group allows for the formation of complex coordination compounds with metal ions, which can result in the development of colorants for industrial and artistic purposes. These compounds are often used in the textile, coatings, and printing industries. The bromine atom, being a halogen, can also enhance the compound’s ability to interact with other functional groups, thus improving its utility in the synthesis of dyes and other functional materials.

Moreover, 2-amino-5-bromobenzoic acid has been employed in the development of materials with specialized electronic and optical properties. The presence of both an amino group and a halogen atom on the benzene ring makes it possible to modify the electronic characteristics of the material, thus enabling the creation of semiconducting or light-emitting materials. Research in organic electronics and optoelectronics has shown that substituted benzoic acids, such as 2-amino-5-bromobenzoic acid, can be incorporated into organic light-emitting diodes (OLEDs) and other electronic devices, where they contribute to the performance and stability of the materials.

The compound also plays a role in environmental chemistry. The reactivity of the amino group in 2-amino-5-bromobenzoic acid makes it a suitable candidate for the synthesis of compounds that can be used in environmental monitoring and remediation. For instance, the compound may be used in the development of sensors for detecting pollutants or in the synthesis of materials capable of adsorbing toxic substances from water or air.

In summary, 2-amino-5-bromobenzoic acid is a versatile compound with a range of applications in pharmaceuticals, materials science, and environmental chemistry. Its ability to undergo further functionalization due to the presence of both an amino group and a bromine atom makes it a valuable building block for the synthesis of complex organic molecules and advanced materials. The continued exploration of its reactivity and potential in various fields highlights its importance in both academic research and industrial applications.

References

1996. Chemoselectivity of 6-bromo-2-methyl-3,1-benzoxazin-4-one towards amines, Schiff bases, and azines. Monatshefte für Chemie / Chemical Monthly, 127(1).
DOI: 10.1007/bf00807415

2012. FT-IR, FT-Raman, UV spectra and DFT calculations on monomeric and dimeric structure of 2-amino-5-bromobenzoic acid. Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 88.
DOI: 10.1016/j.saa.2011.11.022

2019. 4-Hydroxy-2-quinolones: syntheses, reactions and fused heterocycles. Molecular Diversity, 23(4).
DOI: 10.1007/s11030-019-09952-5