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2-Nitrochlorobenzene

2-Nitrochlorobenzene is an organic compound with the formula ClC6H4NO2. It is one of three isomeric nitrochlorobenzenes. It is a yellow crystalline solid that is important as a precursor to other compounds due to its two functional groups.

Synthesis
Nitrochlorobenzene is typically synthesized by nitration of chlorobenzene in the presence of sulfuric acid: :C6H5Cl + HNO3 → O2NC6H4Cl + H2O This reaction affords a mixture of isomers. Using an acid ratio of 30% nitric acid, 56% sulfuric acid and 14% water, the product mix is typically 34-36% 2-nitrochlorobenzene and 63-65% 4-nitrochlorobenzene, with only about 1% 3-nitrochlorobenzene. ==Reactions==
Reactions
2-Nitrochlorobenzene can be reduced to the 2-chloroaniline with Fe/HCl mixture, the Bechamp reduction. : Similarly, it reacts with sodium methoxide to give 2-nitroanisole. Substitution of chloride by fluoride is also practiced commercially to convert 2-nitrochlorobenzene to 2-fluoronitrobenzene. The Halex process uses potassium fluoride in polar solvents like sulfolane : : ==Applications==
Applications
2-Nitrochlorobenzene is useful because both of its reactive sites can be utilized to create further compounds that are mutually ortho. Its derivative 2-chloroaniline is a precursor to 3,3’-dichlorobenzidine, a precursor to dyes and pesticides. ==References==
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