4-Nitrochlorobenzene – Wikipedia
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Names | |||
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Preferred IUPAC name | |||
Other names
4-Chloro-1-nitrobenzene |
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Identifiers | |||
ChemSpider | |||
ECHA InfoCard | 100.002.554 | ||
KEGG | |||
UNII | |||
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Properties | |||
C6H4ClNO2 | |||
Molar mass | 157.55 g·mol−1 | ||
Appearance | Light yellow solid | ||
Odor | sweet[1] | ||
Density | 1.52 g/cm3 (20 °C) | ||
Melting point | 83.6 °C (182.5 °F; 356.8 K) | ||
Boiling point | 242.0 °C (467.6 °F; 515.1 K) | ||
Insoluble | |||
Solubility in other solvents | Soluble in toluene, ether, acetone, hot ethanol | ||
Vapor pressure | 0.2 mmHg (30°C)[1] | ||
Hazards | |||
Flash point | 12 °C (54 °F; 285 K) | ||
Lethal dose or concentration (LD, LC): | |||
812 mg/kg (rat, oral) 1414 mg/kg (mouse, oral) 440 mg/kg (mouse, oral) 420 mg/kg (rat, oral)[1] |
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164 mg/m3 (cat, 7 hr)[1] | |||
NIOSH (US health exposure limits): | |||
TWA 1 mg/m3 [skin][1] | |||
Ca[1] | |||
Ca [100 mg/m3][1] | |||
Safety data sheet (SDS) | External MSDS | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound
4-Nitrochlorobenzene is the organic compound with the formula ClC6H4NO2. It is a pale yellow solid. 4-Nitrochlorobenzene is a common intermediate in the production of a number of industrially useful compounds, including common antioxidants found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.
Preparation[edit]
4-Nitrochlorobenzene is prepared industrially by nitration of chlorobenzene:[2]
This reaction affords both the 2- and the 4-nitro derivatives, in about a 1:2 ratio. These isomers are separated by distillation.[citation needed] 4-Nitrochlorobenzene was originally prepared by the nitration of 4-bromochlorobenzene by Holleman and coworkers.[3]
Applications[edit]
4-Nitrochlorobenzene is an intermediate in the preparation of a variety of derivatives. Nitration gives 2,4-dinitrochlorobenzene, and 3,4-dichloronitrobenzene. Reduction with iron metal gives 4-chloroaniline. The electron-withdrawing nature of the appended nitro-group makes the benzene ring especially susceptible to nucleophilic aromatic substitution, unlike related chlorobenzene. Thus, the strong nucleophiles hydroxide, methoxide, and amide displace chloride to give respectively 4-nitrophenol, 4-nitroanisole, 4-nitroaniline.[2]
Another major use of 4-nitrochlorobenzene is its condensation with aniline to produce 4-nitrodiphenylamine. Reductive alkylation of the nitro group affords secondary aryl amines, which are useful antioxidants for rubber.
The National Institute for Occupational Safety and Health considers 4-nitrochlorobenzene as a potential occupational carcinogen that may be absorbed through the skin.[4] The Occupational Safety and Health Administration set a permissible exposure limit of 1 mg/m3, while the American Conference of Governmental Industrial Hygienists recommends an airborne exposure limit of 0.64 mg/m3, over a time-weighted average of eight hours.[5][6]
References[edit]
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