2-Naphthylamine

2-Naphthylamine is an organic compound with the chemical formula C₁₀H₇NH₂. It is derived from naphthalene through the substitution of one hydrogen atom by an amine group. Historically, 2-naphthylamine was used in the manufacture of dyes, but its use has significantly declined due to its carcinogenic properties. This compound is a known human carcinogen and has been linked to bladder cancer in workers exposed to it.

Properties

2-Naphthylamine appears as a white to reddish-brown crystalline solid, with a slight, aromatic odor. It is sparingly soluble in water but more soluble in ethanol and ether. The compound's melting point is around 112°C, and it has a boiling point of 306°C.

Synthesis

2-Naphthylamine can be synthesized through several methods, including the reduction of 2-nitronaphthalene with iron and hydrochloric acid or through the amination of 2-naphthol by heating with ammonia under pressure.

Uses

Historically, 2-naphthylamine was primarily used in the synthesis of dyes and in the rubber industry. However, due to its carcinogenic nature, its industrial use has been largely phased out.

Health Effects

Exposure to 2-naphthylamine has been strongly associated with an increased risk of bladder cancer. The compound can be absorbed into the body through inhalation, ingestion, or skin contact. Once in the body, it is metabolized to form N-hydroxy-2-naphthylamine, a compound that is believed to cause DNA damage leading to cancer.

Regulation and Safety

Due to its carcinogenicity, the production and use of 2-naphthylamine are highly regulated in many countries. It is listed as a Group 1 carcinogen by the International Agency for Research on Cancer (IARC). Safety measures include the use of personal protective equipment (PPE), proper ventilation, and strict handling procedures to minimize exposure.

Environmental Impact

2-Naphthylamine can be released into the environment through industrial effluents and improper disposal of waste materials containing this compound. It is toxic to aquatic life and can cause long-term adverse effects in aquatic ecosystems.

See Also

• Naphthalene
• Amine
• Carcinogen
• Bladder cancer