p-Tolunitrile
[CAS# 104-85-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Cyanide/nitrile
• Name: p-Tolunitrile
• Synonyms: 4-Methylbenzenecarbonitrile; p-Cyanotoluene; p-Methylbenzonitrile; 4-Methylcyanobenzene; p-Toluenenitrile; p-Toluic nitrile; p-Toluonitrile; 4-Toluyl nitrile; p-Tolylnitrile; CNT
• Molecular Formula: C₈H₇N
• Molecular Weight: 117.15
• CAS Registry Number: 104-85-8
• EC Number: 203-244-8
• SMILES: CC1=CC=C(C=C1)C#N

Properties

• Density: 0.981
• Melting point: 29.5 °C
• Boiling point: 217.6 °C
• Refractive index: 1.5285-1.5305
• Flash point: 85 °C
• Water solubility: <0.1 g/100 mL at 17 °C

Safety Data

• Hazard Symbols: GHS07;GHS08 Danger
• Risk Statements: H315-H319-H334-H335-H4112
• Safety Statements: P233-P260-P261-P264-P264+P265-P271-P273-P280-P284-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P342+P316-P362+P364-P403-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Eye irritation	Eye Irrit.	2	H319
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
Respiratory sensitization	Resp. Sens.	1	H334
Specific target organ toxicity - single exposure	STOT SE	2	H335
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

p-Tolunitrile, also known as 4-cyanotoluene, is an aromatic nitrile with the chemical formula C₈H₇NO. It is characterized by a cyano group (-CN) attached to the para position of a toluene ring. This compound is significant in organic chemistry due to its versatile applications and role as an intermediate in various chemical syntheses.

The discovery of p-tolunitrile is part of the broader exploration of aromatic nitriles, which emerged from early studies in organic chemistry. The synthesis of p-tolunitrile typically involves the reaction of p-toluidine with cyanogen chloride or by the direct cyanation of p-toluenesulfonic acid. These methods facilitate the formation of the nitrile group while maintaining the integrity of the aromatic ring.

One of the primary applications of p-tolunitrile is in the pharmaceutical industry. It serves as a key intermediate in the synthesis of various pharmaceutical compounds. For instance, p-tolunitrile is used in the production of antihypertensive drugs, where it is involved in the formation of active pharmaceutical ingredients through further chemical transformations. Its role in drug synthesis underscores its importance in developing medications with therapeutic properties.

In addition to its pharmaceutical applications, p-tolunitrile is used in the production of specialty chemicals. It acts as a building block in the synthesis of various organic compounds, including dyes, pigments, and polymers. The nitrile group in p-tolunitrile is reactive and can participate in nucleophilic addition reactions, making it a valuable intermediate in the development of complex molecules. For example, p-tolunitrile is used in the synthesis of certain high-performance polymers, which are employed in a range of industrial applications due to their superior properties.

The compound is also used in the production of agrochemicals. It serves as an intermediate in the synthesis of pesticides and herbicides, where its chemical structure contributes to the effectiveness of these compounds in managing agricultural pests and weeds. Its utility in agrochemical synthesis highlights its role in enhancing agricultural productivity and pest management.

Overall, p-tolunitrile's applications in pharmaceuticals, specialty chemicals, and agrochemicals demonstrate its versatility and importance as a chemical intermediate. Its discovery and subsequent use in various industries underscore its role in advancing chemical synthesis and industrial applications.

References

2021. Recent Advances in the Synthesis of Diverse Libraries of Small-Molecule Building Blocks in Ionic Liquids (ILs). Synlett, 32(18), 1719852.
DOI: 10.1055/s-0040-1719852

2023. Synthesis of 5-substituted-1H-tetrazoles using zinc zirconium phosphate and copper zirconium phosphate as reusable heterogeneous catalysts. Journal of the Iranian Chemical Society, 20(7), 2799.
DOI: 10.1007/s13738-023-02799-6

2024. Construction and Characterization of Magnetic Fe3O4 Nanoparticles Supported Palladium Complex: Research on Synthesis of Aryl Nitriles and Tetrazoles. Catalysis Letters, 154(8), 4812.
DOI: 10.1007/s10562-024-04812-w