4-Amino-3-bromobenzoic acid
[CAS# 6311-37-1]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: 4-Amino-3-bromobenzoic acid
• Synonyms: ZR BE DVQ
• Molecular Formula: C₇H₆BrNO₂
• Molecular Weight: 216.03
• CAS Registry Number: 6311-37-1
• EC Number: 627-791-0
• SMILES: C1=CC(=C(C=C1C(=O)O)Br)N

Properties

• Density: 1.8±0.1 g/cm³, Calc.^*
• Melting point: 211-215 °C (Expl.)
• Index of Refraction: 1.672, Calc.^*
• Boiling Point: 368.5±32.0 °C (760 mmHg), Calc.^*
• Flash Point: 176.7±25.1 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H315-H319-H335
• Safety 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
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

• Transport Information: UN 2811

Discovery and Applications

4-Amino-3-bromobenzoic acid is an organic compound with a benzene ring substituted by an amino group at the para position and a bromine atom at the meta position. This compound belongs to the class of aromatic carboxylic acids and is of significant interest due to its versatile applications in organic synthesis and material science. Its discovery is tied to the broader exploration of substituted benzoic acids, which have been widely studied due to their chemical reactivity and ability to form complex molecules with various functional properties.

The synthesis of 4-amino-3-bromobenzoic acid can be traced back to the ongoing efforts in modifying the properties of aromatic acids to serve as intermediates in the creation of bioactive and functional materials. The incorporation of the bromine atom into the aromatic ring is known to enhance the electrophilic properties of the compound, making it more reactive and useful in subsequent chemical transformations. The amino group, on the other hand, serves as a nucleophilic site for further functionalization, allowing the synthesis of diverse derivatives with varying applications.

One of the main applications of 4-amino-3-bromobenzoic acid is in the synthesis of pharmaceutical compounds. Its structure, which combines both an amino group and a carboxylic acid group, makes it a useful building block in the creation of complex molecules with biological activity. The ability of 4-amino-3-bromobenzoic acid to undergo electrophilic aromatic substitution reactions, particularly with electrophilic reagents such as acyl and alkyl groups, facilitates the development of a variety of bioactive derivatives. These derivatives can be explored for their potential as antibiotics, anti-inflammatory agents, and other therapeutic compounds.

In addition to its role in pharmaceutical chemistry, 4-amino-3-bromobenzoic acid is also employed in materials science. It has been studied as a potential precursor for the synthesis of organic semiconductors and polymers. The bromine atom on the aromatic ring can participate in halogen bonding, which plays a crucial role in the formation of organized molecular structures necessary for electronic applications. These properties make 4-amino-3-bromobenzoic acid and its derivatives of interest in the development of organic light-emitting diodes (OLEDs) and other optoelectronic devices.

Furthermore, 4-amino-3-bromobenzoic acid has potential applications in agrochemicals. The functionalization of its structure can lead to the development of herbicides and pesticides, where the amino and carboxyl groups serve as points of attachment for other bioactive functionalities. Its use in the agrochemical industry is centered on its ability to modify and enhance the effectiveness of existing chemical agents, providing new ways to combat plant diseases and pests.

Despite its broad range of applications, the handling of 4-amino-3-bromobenzoic acid must be done with caution, particularly due to the presence of the bromine atom, which can pose environmental and health risks. Proper safety measures should be in place when working with this compound to mitigate exposure and prevent harm. However, its versatility as a chemical intermediate and its role in various industries highlight its importance in chemical synthesis and material development.

In conclusion, 4-amino-3-bromobenzoic acid is an important compound with diverse applications in the pharmaceutical, materials science, and agrochemical industries. Its ability to undergo various chemical reactions, combined with its reactivity and structural properties, makes it a valuable building block in the synthesis of complex molecules and functional materials. As research into its potential applications continues, 4-amino-3-bromobenzoic acid is likely to remain a key compound in chemical synthesis.

References

1954. Investigation into the tuberculostatic activity of some derivatives of p. amino-benzoic acid. Antonie van Leeuwenhoek, 20(1).
DOI: 10.1007/bf02543731

2009. 4-Amino-3-bromo-benzoic acid. Acta crystallographica. Section E, Structure reports online, 65(3).
DOI: 10.1107/s1600536809006825

2020. Pd-Catalyzed Functionalization of Aryl Amines on a Soluble Polymer Support. Synlett, 31(14).
DOI: 10.1055/s-0040-1707261