2-Nitrochlorobenzene
| Names | |
|---|---|
| IUPAC name
1-chloro, 2-nitrobenzene
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| Identifiers | |
| ECHA InfoCard | 100.001.686 |
CompTox Dashboard (EPA)
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| Properties | |
| ClC6H4NO2 | |
| Molar mass | 157.5546 grams/mol |
| Appearance | yellow crystals |
| Density | 1.368 g/L |
| Melting point | 33 °C |
| Boiling point | 245.5 °C |
| Highly soluble In diethyl ether, benzene, and hot ethanol. Insoluble In H2O | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
|
Toxic, Irritant |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
- ^ a b Gerald Booth "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411