N-(2-naphthyl)aniline CAS 135-88-6： Everything You Need to Know About This Chemical

Abstract

This article provides an in-depth overview of N-(2-naphthyl)aniline, a chemical compound with the CAS number 135-88-6. It delves into its chemical properties, synthesis methods, applications, safety considerations, environmental impact, and regulatory status. By exploring these aspects, the article aims to offer a comprehensive understanding of this chemical and its significance in various industries.

Introduction to N-(2-naphthyl)aniline

N-(2-naphthyl)aniline, also known as 2-naphthylaniline, is an organic compound that belongs to the aromatic amine family. It is characterized by a benzene ring substituted with a 2-naphthyl group and an amino group. This compound is widely used in the synthesis of dyes, pharmaceuticals, and other organic compounds. In this article, we will explore the various aspects of N-(2-naphthyl)aniline, including its chemical properties, synthesis, applications, safety, environmental impact, and regulatory status.

Chemical Properties of N-(2-naphthyl)aniline

N-(2-naphthyl)aniline has a molecular formula of C12H11N and a molecular weight of 169.22 g/mol. It is a white to pale yellow crystalline solid that is soluble in organic solvents such as alcohol, ether, and acetone. The compound has a melting point of approximately 114-116°C and a boiling point of around 284°C. It is also known for its distinct odor, which is often described as resembling that of coal tar.

The chemical structure of N-(2-naphthyl)aniline allows it to participate in various chemical reactions, including electrophilic aromatic substitution, nucleophilic aromatic substitution, and condensation reactions. These properties make it a versatile starting material for the synthesis of a wide range of organic compounds.

Synthesis of N-(2-naphthyl)aniline

The synthesis of N-(2-naphthyl)aniline can be achieved through several methods, including the Sandmeyer reaction, the Reimer-Tiemann reaction, and the reduction of 2-naphthyl nitro compounds. The Sandmeyer reaction involves the reaction of 2-naphthyl chloride with sodium nitrite in the presence of a copper catalyst. The Reimer-Tiemann reaction, on the other hand, involves the reaction of 2-naphthylamine with phosgene. Both methods yield N-(2-naphthyl)aniline as the primary product.

The reduction of 2-naphthyl nitro compounds is another common method for synthesizing N-(2-naphthyl)aniline. This process involves the reduction of 2-naphthyl nitro compounds using hydrogen gas or other reducing agents, such as sodium borohydride or lithium aluminum hydride.

Applications of N-(2-naphthyl)aniline

N-(2-naphthyl)aniline finds extensive use in the dye industry, where it is used as a precursor for the synthesis of various dyes, including azo dyes and anthraquinone dyes. These dyes are used in the production of textiles, leather, and plastics.

In the pharmaceutical industry, N-(2-naphthyl)aniline is used as a starting material for the synthesis of drugs, including analgesics, antipyretics, and cardiovascular agents. Its versatility in chemical reactions also makes it a valuable intermediate in the synthesis of other organic compounds.

Safety Considerations

N-(2-naphthyl)aniline is considered a hazardous substance due to its potential to cause skin irritation, allergic reactions, and respiratory problems. It is important to handle this compound with care, using appropriate personal protective equipment, such as gloves, goggles, and lab coats. In case of accidental exposure, immediate medical attention should be sought.

The compound is also flammable and should be stored in a cool, dry place away from incompatible materials. Proper ventilation is essential when working with N-(2-naphthyl)aniline to prevent the accumulation of vapors.

Environmental Impact

The environmental impact of N-(2-naphthyl)aniline is primarily associated with its potential to contaminate water sources and soil. It is classified as a priority pollutant by some regulatory agencies due to its persistence in the environment and potential for bioaccumulation. Proper waste disposal and environmental regulations are crucial to minimize the impact of this compound on ecosystems.

Regulatory Status

N-(2-naphthyl)aniline is subject to various regulations and standards, depending on the country and the specific application. In many regions, it is classified as a hazardous chemical and is subject to strict handling, storage, and disposal regulations. Compliance with these regulations is essential for businesses that use or produce this compound.

Conclusion

N-(2-naphthyl)aniline, with the CAS number 135-88-6, is a versatile organic compound with a wide range of applications. Its chemical properties, synthesis methods, and safety considerations are crucial for its proper handling and use. Understanding the environmental impact and regulatory status of this compound is essential for businesses and individuals involved in its production, distribution, and use. By exploring these aspects, this article aims to provide a comprehensive overview of N-(2-naphthyl)aniline, contributing to a better understanding of its significance in various industries.

Keywords: N-(2-naphthyl)aniline, CAS 135-88-6, chemical properties, synthesis, applications, safety, environmental impact, regulatory status.