2-Nitrochlorobenzene

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2-Nitrochlorobenzene
IUPAC name

1-Chloro-2-nitrobenzene

Identifiers
CAS number 88-73-3
ChemSpider 13853953
Jmol-3D images {{#if:C1=CC=C(C(=C1)[N+](=O)[O-])Cl|Image 1
Properties
Molecular formula C6H4ClNO2
Molar mass 157.55 g mol−1
Appearance Yellow crystals
Density 1.368 g/mL
Melting point 33 °C; 91 °F; 306 K
Boiling point 245.5 °C; 473.9 °F; 518.6 K
Solubility in water Insoluble
Solubility in other solvents Highly soluble in diethyl ether, benzene, and hot ethanol
Hazards
Main hazards Toxic, Irritant
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

2-Nitrochlorobenzene is an organic compound with the formula ClC6H4NO2.[1] 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.[1] 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.

References

  1. ↑ 1.0 1.1 Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411
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