m-(1-Cyanoethyl)benzoic acid
[CAS# 5537-71-3]

Identification

• Classification: API >> Synthetic anti-infective drugs >> Disinfectant antiseptic
• Name: m-(1-Cyanoethyl)benzoic acid
• Synonyms: 3-(1-Cyanoethyl)benzoic acid
• Molecular Formula: C₁₀H₉NO₂
• Molecular Weight: 175.18
• CAS Registry Number: 5537-71-3
• EC Number: 226-897-0
• SMILES: CC(C#N)C1=CC(=CC=C1)C(=O)O

Properties

• Melting point: 143-148 °C

Safety Data

• Hazard Symbols: GHS05;GHS07 Danger
• Risk Statements: H302-H317-H318
• Safety Statements: P261-P264-P264+P265-P270-P272-P280-P301+P317-P302+P352-P305+P354+P338-P317-P321-P330-P333+P317-P362+P364-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin sensitization	Skin Sens.	1	H317
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

Meta-(1-cyanoethyl)benzoic acid, commonly abbreviated as CEBA, is an important chemical compound recognized for its wide range of applications in industrial and research settings. CEBA was originally synthesized by cyanoethylation of benzoic acid derivatives under controlled conditions. The process involves the introduction of a cyanoethyl group (-CH2CH2CN) at the meta position of the benzoic acid ring, resulting in a stable crystalline compound with unique chemical properties. CEBA is characterized by the substitution of the benzoic acid core with a cyanoethyl group at the meta position. This structural modification confers it with unique properties that affect its solubility, reactivity, and interactions in chemical processes.

CEBA is a valuable intermediate in the synthesis of a wide range of organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals. Its versatility lies in facilitating complex molecular transformations through selective chemical reactions.

In polymer science, CEBA is involved in the synthesis of functionalized polymers and copolymers. Its incorporation enhances polymer properties such as adhesion, mechanical strength, and thermal stability, making it key to the development of advanced materials.

CEBA's chemical structure lends itself to surface modification processes, where it acts as a reactive agent to modify the surface properties of a substrate. This application is useful in coatings, adhesives, and electronic materials.

Researchers continue to explore the potential of CEBA in the following areas: Studying its role as a building block in drug development, using its structural features for targeted therapeutic interventions. Exploring CEBA as a catalyst or ligand in catalytic processes, aimed at improving reaction rates and selectivity in organic synthesis. Due to the unique chemical properties of CEBA derivatives, they can be used for analytical purposes, including chromatographic separations and spectroscopic analysis.

Studies of CEBA's environmental behavior and toxicological profiles highlight its safety in specific applications, ensuring regulatory compliance and sustainable use in industrial processes.

References

2011. Probing the enantioselectivity of a diverse group of purified cobalt-centred nitrile hydratases. Organic & Biomolecular Chemistry, 9(8).
DOI: 10.1039/c0ob01067g

2009. Cloning and functional expression of a nitrile hydratase (NHase) from Rhodococcus equi TG328-2 in Escherichia coli, its purification and biochemical characterisation. Applied Microbiology and Biotechnology, 85(5).
DOI: 10.1007/s00253-009-2153-y