Abstract

This article provides a comprehensive overview of N-(2-Naphthyl)aniline, a chemical compound with the CAS number 135-88-6. The Wikipedia page serves as the central focus, detailing its properties, uses, synthesis, safety, and environmental impact. The article delves into the chemical structure, physical and chemical properties, synthesis methods, applications, safety considerations, and environmental aspects of this compound, offering a detailed exploration of its significance in various fields.

Chemical Structure and Properties

N-(2-Naphthyl)aniline, also known as 2-naphthylaniline, is an aromatic amine derivative. It is characterized by a benzene ring substituted with a naphthyl group at the para position. The chemical formula for this compound is C13H11N. The molecular weight of N-(2-Naphthyl)aniline is 181.23 g/mol. This compound is a white to pale yellow crystalline solid that is soluble in organic solvents such as ethanol, ether, and acetone but is sparingly soluble in water. The melting point of N-(2-Naphthyl)aniline is approximately 67-68°C, and its boiling point is around 286-287°C at 760 mmHg.

The compound exhibits a characteristic odor and is known for its yellowing properties when exposed to light. It is also a reducing agent and can be used in various chemical reactions, including coupling reactions, where it serves as a coupling partner in the synthesis of dyes and pigments.

Synthesis Methods

The synthesis of N-(2-Naphthyl)aniline can be achieved through several methods, including the Sandmeyer reaction, the diazotization-coupling reaction, and the reduction of naphthyl diazonium salts. The Sandmeyer reaction involves the reaction of a diazonium salt with copper(I) cyanide in the presence of hydrochloric acid to form the desired amine. The diazotization-coupling reaction is a two-step process that involves the conversion of naphthalene to a diazonium salt followed by the coupling with an aromatic amines. The reduction of naphthyl diazonium salts is another method that utilizes a reducing agent to convert the diazonium salt into the amine.

Each method has its advantages and limitations, and the choice of synthesis route often depends on the scale of production, the desired purity of the product, and the cost considerations.

Applications

N-(2-Naphthyl)aniline finds extensive use in the dye and pigment industry. It is a key intermediate in the synthesis of various dyes, including azo dyes, triphenylmethane dyes, and anthraquinone dyes. These dyes are used in textiles, leather, and plastics for coloring purposes. Additionally, N-(2-Naphthyl)aniline is used in the pharmaceutical industry for the synthesis of certain drugs and intermediates.

The compound is also employed in the production of photographic materials, printing inks, and as a stabilizer in certain plastics. Its unique chemical properties make it a versatile intermediate in organic synthesis, contributing to its wide range of applications.

Safety Considerations

N-(2-Naphthyl)aniline is considered hazardous and requires proper handling and storage. It is classified as a toxic substance and can cause irritation to the skin, eyes, and respiratory system. Ingestion of the compound can lead to severe health effects, including liver and kidney damage. Therefore, it is crucial to use appropriate personal protective equipment (PPE) when working with this chemical.

The Occupational Safety and Health Administration (OSHA) and the National Institute for Occupational Safety and Health (NIOSH) have established guidelines for the safe handling of N-(2-Naphthyl)aniline. These guidelines include recommendations for ventilation, exposure limits, and emergency response procedures.

Environmental Impact

The environmental impact of N-(2-Naphthyl)aniline is a significant concern. The compound is persistent in the environment and can bioaccumulate in organisms. It is also toxic to aquatic life and can cause long-term ecological damage. Proper waste management and disposal procedures are essential to minimize the environmental impact of this chemical.

Regulatory agencies around the world have implemented strict regulations on the use, handling, and disposal of N-(2-Naphthyl)aniline to protect human health and the environment. These regulations aim to reduce the release of the compound into the environment and promote sustainable practices in its production and use.

Conclusion

N-(2-Naphthyl)aniline, with the CAS number 135-88-6, is a versatile chemical compound with a wide range of applications in the dye, pigment, pharmaceutical, and other industries. Its unique chemical structure and properties make it an essential intermediate in the synthesis of various products. However, its hazardous nature and environmental impact necessitate careful handling and disposal. The Wikipedia page on N-(2-Naphthyl)aniline provides valuable information on its properties, synthesis, applications, safety, and environmental considerations, serving as a comprehensive resource for anyone interested in this compound.

Keywords: N-(2-Naphthyl)aniline, CAS 135-88-6, chemical properties, synthesis methods, applications, safety, environmental impact