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4-Nitrochlorobenzene is the
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
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
antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...
s commonly found in
rubber Rubber, also called India rubber, latex, Amazonian rubber, ''caucho'', or ''caoutchouc'', as initially produced, consists of polymers of the organic compound isoprene, with minor impurities of other organic compounds. Types of polyisoprene ...
. Other
isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...
s with the formula ClC6H4NO2 include
2-nitrochlorobenzene 2-Nitrochlorobenzene is an organic compound with the formula ClC6H4NO2. It is one of three isomeric nitrochlorobenzenes. It is a yellow crystalline solid that is important as a precursor to other compounds due to its two functional groups. Sy ...
and 3-nitrochlorobenzene.


Preparation and reactions

4-Nitrochlorobenzene is prepared industrially by nitration of
chlorobenzene Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent a ...
: : 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. 4-Nitrochlorobenzene was originally prepared by the
nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...
of 4-bromochlorobenzene by Holleman and coworkers. The chloride substituent in 4-nitrochlorobenzene is more labile than in
chlorobenzene Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent a ...
. For example, it is readily displaced by sulfide nucleophiles, leading the way to
4-nitrothiophenol 4-Nitrothiophenol is an organosulfur compound with the formula . It exists as a yellow solid that is soluble in several organic solvents. It is one of three isomers of nitrothiophenol. It was originally prepared by sulfidation of 4-nitrochlorobe ...
. In another example, 4-nitrochlorobenzene is a favored substrate for
cross-coupling reaction In organic chemistry, a cross-coupling reaction is a reaction where two different fragments are joined. Cross-couplings are a subset of the more general coupling reactions. Often cross-coupling reactions require metal catalysts. One important re ...
s.


Applications

4-Nitrochlorobenzene is an intermediate in the preparation of a variety of derivatives.
Nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between Alcohol ...
gives
2,4-dinitrochlorobenzene 2,4-Dinitrochlorobenzene (DNCB) is an organic compound with the chemical formula (O2N)2C6H3Cl. It is a yellow solid that is soluble in organic solvents. It is an intermediate for the industrial production of other compounds. Preparation and reac ...
, and
3,4-dichloronitrobenzene 1,2-Dichloro-4-nitrobenzene is an organic compound with the formula 1,2-ClCH-4-NO. This pale yellow solid is related to 1,2-dichlorobenzene by the replacement of one H atom with a nitro functional group. This compound is an intermediate in the s ...
. 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 A nucleophilic aromatic substitution (SNAr) is a substitution reaction in organic chemistry in which the nucleophile displaces a good leaving group, such as a halide, on an aromatic ring. Aromatic rings are usually nucleophilic, but some aromatic c ...
, unlike related chlorobenzene. Thus, the strong
nucleophile In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are ...
s hydroxide, methoxide,
fluoride Fluoride (). According to this source, is a possible pronunciation in British English. is an Inorganic chemistry, inorganic, Monatomic ion, monatomic Ion#Anions and cations, anion of fluorine, with the chemical formula (also written ), whose ...
, and
amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...
displace chloride to give respectively
4-nitrophenol 4-Nitrophenol (also called ''p''-nitrophenol or 4-hydroxynitrobenzene) is a phenolic compound that has a nitro group at the opposite position of the hydroxyl group on the benzene ring. Properties 4-nitro phenol is a slightly yellow, crystalline ...
, 4-nitroanisole,
4-fluoronitrobenzene 4-Fluoronitrobenzene is an organic compound with the formula FC6H4NO2. It is one of three isomeric fluoronitrobenzenes.Gerald Booth, "Nitro Compounds, Aromatic" in ''Ullmann's Encyclopedia of Industrial Chemistry'', Wiley-VCH: Weinheim, 2005. ...
, and
4-nitroaniline 4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. A yellow solid, it is one of three isomers of nitroaniline. It is an intermediate in the production of dyes, antioxidants, pharmaceuticals, ...
. 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 The National Institute for Occupational Safety and Health (NIOSH, ) is the List of United States federal agencies, United States federal agency responsible for conducting research and making recommendations for the prevention of work-related occ ...
considers 4-nitrochlorobenzene as a potential occupational carcinogen. The
Occupational Safety and Health Administration The Occupational Safety and Health Administration (OSHA; ) is a regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. The United States Congress established ...
set a permissible exposure limit of 1 mg/m3 The
American Conference of Governmental Industrial Hygienists The American Conference of Governmental Industrial Hygienists (ACGIH) is a professional association of industrial hygienists and practitioners of related professions, with headquarters in Cincinnati, Ohio. One of its goals is to advance worker pr ...
recommends an airborne exposure limit of 0.64 mg/m3 over a time-weighted average of eight hours.New Jersey Department of Health and Senior Services - Hazardous Substance Fact Sheet
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References

{{DEFAULTSORT:Nitrochlorobenzene, 4- 4-Chlorophenyl compounds Nitrobenzene derivatives Substances discovered in the 1910s IARC Group 2B carcinogens