Chemistry:4-Nitrochlorobenzene
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Names | |||
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Preferred IUPAC name
1-Chloro-4-nitrobenzene | |||
Other names
4-Chloro-1-nitrobenzene
4-Chloronitrobenzene p-Nitrochlorobenzene PNCBO | |||
Identifiers | |||
3D model (JSmol)
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ChemSpider | |||
KEGG | |||
PubChem CID
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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 | |||
Safety data sheet | External MSDS | ||
Flash point | 12 °C (54 °F; 285 K) | ||
Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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812 mg/kg (rat, oral) 1414 mg/kg (mouse, oral) 440 mg/kg (mouse, oral) 420 mg/kg (rat, oral)[1] | ||
LC50 (median concentration)
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164 mg/m3 (cat, 7 hr)[1] | ||
NIOSH (US health exposure limits): | |||
PEL (Permissible)
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TWA 1 mg/m3 [skin][1] | ||
REL (Recommended)
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Ca[1] | ||
IDLH (Immediate danger)
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Ca [100 mg/m3][1] | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
verify (what is ?) | |||
Infobox references | |||
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 antioxidants commonly found in rubber. Other isomers with the formula ClC6H4NO2 include 2-nitrochlorobenzene and 3-nitrochlorobenzene.
Preparation
4-Nitrochlorobenzene is prepared industrially by nitration of chlorobenzene:
- ClC
6H
5 + HNO
3 → ClC
6H
4NO
2 + H
2O
This reaction affords both the 2- and the 4-nitro derivatives, in about a 1:2 ratio. These isomers are separated by a combination of crystallization and distillation.[2] 4-Nitrochlorobenzene was originally prepared by the nitration of 4-bromochlorobenzene by Holleman and coworkers.[3]
Applications
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, fluoride, and amide displace chloride to give respectively 4-nitrophenol, 4-nitroanisole, 4-fluoronitrobenzene, and 4-nitroaniline.[2][4]
Another 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.
Safety
The U.S. National Institute for Occupational Safety and Health considers 4-nitrochlorobenzene as a potential occupational carcinogen.[5] The Occupational Safety and Health Administration set a permissible exposure limit of 1 mg/m3 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.[6][7]
References
- ↑ 1.0 1.1 1.2 1.3 1.4 1.5 1.6 NIOSH Pocket Guide to Chemical Hazards. "#0452". National Institute for Occupational Safety and Health (NIOSH). https://www.cdc.gov/niosh/npg/npgd0452.html.
- ↑ 2.0 2.1 2.2 Gerald Booth (2007). "Nitro Compounds, Aromatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a17_411. ISBN 978-3527306732.
- ↑ "The nitration of mixed dihalogen benzenes" Recueil des Travaux Chimiques des Pays-Bas et de la Belgique. Amsterdam, 1915; pp. 204-235.
- ↑ Brewster, Ray Q.; Groening, Theodore (1934). "p-Nitrodiphenyl Ether". Organic Syntheses 14: 66. doi:10.15227/orgsyn.014.0066.
- ↑ CDC - Immediately Dangerous to Life or Health Concentrations (IDLH): p-nitrochlorobenzene
- ↑ CDC - NIOSH Pocket Guide to Chemical Hazards
- ↑ New Jersey Department of Health and Senior Services - Hazardous Substance Fact Sheet
Original source: https://en.wikipedia.org/wiki/4-Nitrochlorobenzene.
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