3,5-Diaminobenzoic acid
[CAS# 535-87-5]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Other amino acid derivatives
• Name: 3,5-Diaminobenzoic acid
• Synonyms: 3,5-Diamino-benzoic acid
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152.15
• CAS Registry Number: 535-87-5
• EC Number: 208-621-0
• SMILES: C1=C(C=C(C=C1N)N)C(=O)O

Properties

• Melting point: 235-238 °C (decomp.)
• Flash point: 210 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-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
Germ cell mutagenicity	Muta.	2	H341
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

3,5-Diaminobenzoic acid is a significant compound in organic chemistry known for its diverse applications and contributions to scientific research. This aromatic amino acid derivative, also referred to as 3,5-diaminobenzoate, features two amino groups positioned meta to each other on a benzene ring, along with a carboxylic acid group.

The discovery of 3,5-diaminobenzoic acid dates back to the early 20th century when it was first synthesized and characterized for its chemical properties. Its structure, featuring both amino and carboxyl groups on the benzene ring, makes it a valuable intermediate in the synthesis of various organic compounds. The meta arrangement of the amino groups distinguishes it from other diaminobenzoic acid isomers and influences its reactivity and utility in different chemical processes.

One of the primary applications of 3,5-diaminobenzoic acid is in the synthesis of azo dyes. Its ability to form azo bonds through its amino groups allows it to be used in the creation of vibrant and stable dyes that are widely utilized in textiles, inks, and plastics. These dyes are known for their excellent colorfastness and are employed in a variety of industries to achieve desired color effects in products.

Additionally, 3,5-diaminobenzoic acid plays a crucial role in the development of pharmaceuticals and agrochemicals. It is used as a building block in the synthesis of various drugs and agricultural chemicals due to its reactivity and ability to form complex molecules. In pharmaceutical chemistry, it can be incorporated into the structure of drugs to enhance their efficacy or modify their properties.

In materials science, this compound is utilized in the production of high-performance polymers and resins. Its incorporation into polymer matrices can improve mechanical properties, thermal stability, and chemical resistance of the final materials. This makes it valuable in the production of advanced materials for aerospace, automotive, and electronic applications.

Research into 3,5-diaminobenzoic acid continues to explore new applications and enhance its utility in various fields. Its role in organic synthesis, dye chemistry, pharmaceuticals, and materials science highlights its versatility and importance in contemporary chemical research.

References

2024. Preparation of D-NCCDs and its application in fluorescent/colorimetric dual-mode discrimination of glutamine enantiomers. Microchimica Acta.
DOI: 10.1007/s00604-024-06788-1

2024. Synthesis and characterization of the hyperbranched polymers based on nanoparticles for removal of pollutant from water. Macromolecular Research.
DOI: 10.1007/s13233-024-00264-8

2011. Effect of 3,5-diaminobenzoic acid content, casting solvent, and physical aging on gas permeation properties of copolyimides containing pendant acid groups. Macromolecular Research.
DOI: 10.1007/s13233-011-0813-0