4-Aminobenzonitrile
[CAS# 873-74-5]

Identification

• Classification: Organic raw materials >> Nitrile compound
• Name: 4-Aminobenzonitrile
• Synonyms: 4-Cyanoaniline; p-Cyanoaniline
• Molecular Formula: C₇H₆N₂
• Molecular Weight: 118.14
• CAS Registry Number: 873-74-5
• EC Number: 212-850-1
• SMILES: C1=CC(=CC=C1C#N)N

Properties

• Melting point: 83-87 °C
• Boiling point: 167 °C (1.1 mmHg)

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H302-H311-H315-H319-H331-H335
• Safety Statements: P261-P262-P264-P264+P265-P270-P271-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P316-P319-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	3	H301
Eye irritation	Eye Irrit.	2	H319
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	3	H311
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412
Germ cell mutagenicity	Muta.	2	H341
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

4-Aminobenzonitrile is a significant chemical compound within the realm of organic chemistry, valued for its unique structure and diverse applications. This compound is an aromatic nitrile with an amino group attached to the benzene ring, specifically positioned at the para position relative to the nitrile group. Its synthesis and utilization span various fields, including pharmaceuticals, materials science, and chemical synthesis.

The discovery of 4-aminobenzonitrile can be traced back to the early 20th century, a period marked by significant advancements in organic chemistry and the development of new synthetic methods. The compound is synthesized through the reaction of 4-chlorobenzonitrile with ammonia or an amine in the presence of a catalyst. This reaction exemplifies the broader trend in chemical research focused on modifying aromatic compounds to introduce functional groups that impart specific chemical properties.

One of the primary applications of 4-aminobenzonitrile is in the pharmaceutical industry. The compound serves as a valuable intermediate in the synthesis of various drugs. Its role as a building block in medicinal chemistry is linked to its ability to participate in further chemical transformations, leading to the creation of complex drug molecules. For example, 4-aminobenzonitrile has been used in the synthesis of analgesic and anti-inflammatory agents, where its functional groups are essential for imparting the desired biological activity.

In addition to its role in drug synthesis, 4-aminobenzonitrile is employed in the development of dyes and pigments. The nitrile and amino groups in the molecule enable it to participate in coupling reactions, which are crucial for forming azo dyes. These dyes are widely used in textiles and other applications where vivid colors are required. The ability of 4-aminobenzonitrile to form stable complexes with metal ions further extends its utility in colorant applications.

The compound also finds application in the field of materials science. Its chemical properties allow it to be used as a precursor in the synthesis of various polymeric materials. By incorporating 4-aminobenzonitrile into polymer chains, researchers can enhance the mechanical and thermal properties of the resulting materials. The compound's reactivity with other monomers makes it a valuable component in the design of advanced polymers with specific attributes.

Moreover, 4-aminobenzonitrile has been investigated for its potential in agrochemical formulations. The compound's ability to interact with biological targets makes it a candidate for developing herbicides and pesticides. Its chemical structure can be modified to improve its efficacy and selectivity in pest control applications.

The continued research into 4-aminobenzonitrile highlights its importance as a versatile chemical entity with wide-ranging applications. Its role as a synthetic intermediate, dye precursor, and material component underscores its significance in both industrial and research settings. The compound's discovery and subsequent applications illustrate the ongoing efforts to leverage organic chemistry for practical and innovative solutions.

References

2024. Regioselective C-C bond cleavage/aminocarbonylation cascade under copper catalysis. Science China Chemistry, 67(8).
DOI: 10.1007/s11426-024-2255-5

2022. Palladium-Catalyzed Cyanation of Arenediazonium Tetrafluoroborate Derivatives with 2-(Piperidin-1-yl)acetonitrile as the Cyano Source. Synthesis, 54(8).
DOI: 10.1055/a-1770-8592

1985. The Metabolism of 4-Cyano-N,N dimethyl-[14C] aniline (CDA) by Rats and Mice. Comparative Genetic Toxicology.
DOI: 10.1007/978-1-349-07901-8_65