2-Nitrochlorobenzene

2-Nitrochlorobenzene is an organic compound with the formula ClC6H4NO2. It is one of three isomeric nitrochlorobenzenes.[1] It is a yellow crystalline solid that is important as a precursor to other compounds due to its two functional groups.

2-Nitrochlorobenzene
Names
Preferred IUPAC name
1-Chloro-2-nitrobenzene
Other names
2-Chloronitrobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.686
EC Number
  • 201-854-9
KEGG
RTECS number
  • CZ0875000
UNII
UN number 1578
Properties
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)
Insoluble
Solubility in other solvents Highly soluble in diethyl ether, benzene, and hot ethanol
Hazards
Main hazards Toxic, Irritant
GHS pictograms
GHS Signal word Danger
H301, H302, H311, H312, H317, H331, H332, H350, H351, H361, H372, H411
P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+310, P301+312, P302+352, P304+312, P304+340, P308+313, P311, P312, P314, P321, P322, P330, P333+313, P361
Flash point 124 °C (255 °F; 397 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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 the 2-chloroaniline with Fe/HCl mixture, the Bechamp reduction. Treatment of 2-nitrochlorobenzene with sodium methoxide gives 2-nitroanisole.

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. 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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