2,4-dichloroaniline

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2,4-Dichloroaniline is an organic compound that belongs to the class of chemical compounds known as chloroanilines. It is a white to light yellow crystalline solid with a characteristic amine odor.

Chemical Properties[edit | edit source]

2,4-Dichloroaniline is a derivative of aniline in which two of the hydrogen atoms attached to the nitrogen are replaced by chlorine atoms. It has the chemical formula C6H5Cl2N and a molecular weight of 162.02 g/mol. The compound is slightly soluble in water and more soluble in organic solvents such as ethanol and acetone.

Synthesis[edit | edit source]

2,4-Dichloroaniline can be synthesized by the nucleophilic substitution of 2,4-dichloronitrobenzene with an ammonia solution under pressure. The reaction is typically carried out in a high-pressure reactor at temperatures between 130 and 180°C.

Uses[edit | edit source]

2,4-Dichloroaniline is primarily used as an intermediate in the synthesis of dyes, pesticides, and pharmaceuticals. It is also used in the production of herbicides such as diuron and linuron.

Health Effects[edit | edit source]

Exposure to 2,4-dichloroaniline can cause irritation to the skin, eyes, and respiratory tract. It is also known to cause methemoglobinemia, a condition in which an abnormal amount of methemoglobin is produced, reducing the ability of red blood cells to deliver oxygen to tissues.

Environmental Impact[edit | edit source]

2,4-Dichloroaniline is toxic to aquatic life and can cause long-term adverse effects in the aquatic environment. It is also classified as a potential carcinogen by the International Agency for Research on Cancer (IARC).

See Also[edit | edit source]


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Contributors: Prab R. Tumpati, MD