2-Nitrochlorobenzene: Difference between revisions
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'''2-Nitrochlorobenzene''' is an [[organic compound]] with the formula ClC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub>.<ref name=Ullmann>Gerald Booth, "Nitro Compounds, Aromatic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH: Weinheim, 2005. {{DOI|10.1002/14356007.a17_411}}</ref> It is a yellow crystalline solid that is important as a precursor to other compounds due to |
'''2-Nitrochlorobenzene''' is an [[organic compound]] with the formula ClC<sub>6</sub>H<sub>4</sub>NO<sub>2</sub>. It is one of three isomeric [[nitrochlorobenzene]]s.<ref name=Ullmann>Gerald Booth, "Nitro Compounds, Aromatic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH: Weinheim, 2005. {{DOI|10.1002/14356007.a17_411}}</ref> It is a yellow crystalline solid that is important as a precursor to other compounds due to its two functional groups. |
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==Synthesis== |
==Synthesis== |
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==Reactions== |
==Reactions== |
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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.<ref name=Ullmann/> 2-Nitrochlorobenzene can be reduced to [[2-chloroaniline]] with Fe/HCl mixture, the [[Bechamp reduction]]. Treatment with [[sodium methoxide]] gives [[O-Nitroanisole| |
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.<ref name=Ullmann/> 2-Nitrochlorobenzene can be reduced to the [[chloroaniline|2-chloroaniline]] with Fe/HCl mixture, the [[Bechamp reduction]]. Treatment of 2-nitrochlorobenzene with [[sodium methoxide]] gives [[O-Nitroanisole|2-nitroanisole]]. |
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==Applications== |
==Applications== |
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Revision as of 16:00, 19 January 2018
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| Names | |
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| Preferred IUPAC name
1-Chloro-2-nitrobenzene | |
| Other names
2-Chloronitrobenzene
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.001.686 |
CompTox Dashboard (EPA)
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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 | |
| Occupational safety and health (OHS/OSH): | |
Main hazards
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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. 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.
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
- ^ a b Gerald Booth, "Nitro Compounds, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH: Weinheim, 2005. doi:10.1002/14356007.a17_411