2-Nitrochlorobenzene

{{Chembox | ImageFile = | ImageSize = | IUPACName = 1-Chloro-2-nitrobenzene | OtherNames = | Section1 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Identifiers

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3D model (JSmol)

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• Interactive image

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| ChemSpider

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• 13853953

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| ECHA InfoCard | 100.001.686 |-

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CompTox Dashboard (EPA)

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• DTXSID0020280

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InChI

• InChI=1S/C6H4ClNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H

  Key: BFCFYVKQTRLZHA-UHFFFAOYSA-N
• InChI=1/C6H4ClNO2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H

  Key: BFCFYVKQTRLZHA-UHFFFAOYAA

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SMILES

• C1=CC=C(C(=C1)[N+](=O)[O-])Cl

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2-Nitrochlorobenzene is an organic compound with the formula ClC₆H₄NO₂.It is a yellow crystalline solid that is important as a precursor to other compounds due to the two reactive sites present on the molecule.

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 30/56/14, the product mix is typically 34-36% 2-nitrochlorobenzene and 63-65% 4-nitrochlorobenzene, with only about 1% 3-nitrochlorobenzene.

Reactions

Alkylation and electrophilic aromatic substitution can occur at the chlorinated carbon center, and a diverse array of reactions can be carried out using the nitro group.2-Nitrochlorobenzene can be reduced to 2-chloroaniline with Fe/HCl mixture, the Bechamp reduction.

Applications

2-Nitrochlorobenzene is not valuable in itself but is a precursor to other useful compounds. The compound is particularly 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, itself a precursor to many dyes and pesticides.