2-Nitrochlorobenzene
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| Names | |
|---|---|
| IUPAC name
1-Chloro-2-nitrobenzene | |
| Other names
2-Chloronitrobenzene | |
| Identifiers | |
| 88-73-3 | |
| 3D model (Jmol) | Interactive image |
| ChemSpider | 13853953 |
| ECHA InfoCard | 100.001.686 |
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| 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 |
| Except where otherwise noted, 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 2 Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411