1,2,4-trichlorobenzene
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1,2,4-Trichlorobenzene is an
organochlorine compound Organochlorine chemistry is concerned with the properties of organochlorine compounds, or organochlorides, organic compounds that contain one or more carbon–chlorine bonds. The chloroalkane class (alkanes with one or more hydrogens substituted ...
, one of three isomers of
trichlorobenzene Trichlorobenzene (TCB) may refer to any of three isomeric chlorinated derivatives of benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is ...
. It is a derivative of
benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
with three
chloride The term chloride refers to a compound or molecule that contains either a chlorine anion (), which is a negatively charged chlorine atom, or a non-charged chlorine atom covalently bonded to the rest of the molecule by a single bond (). The pr ...
substituents. It is a colorless liquid used as a solvent for a variety of compounds and materials.


Production and uses

Depending on the conditions and additives (e.g.,
sulfur Sulfur ( American spelling and the preferred IUPAC name) or sulphur ( Commonwealth spelling) is a chemical element; it has symbol S and atomic number 16. It is abundant, multivalent and nonmetallic. Under normal conditions, sulfur atoms ...
), it can be the main product from the chlorination of benzene. It is virtually the exclusive product from the chlorination of
1,4-dichlorobenzene 1,4-Dichlorobenzene (1,4-DCB, ''p''-DCB, or ''para''-dichlorobenzene, sometimes abbreviated as PDCB or para) is an aryl chloride and isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consist ...
. It is also the main product from the
dehydrochlorination In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halide ...
of
hexachlorocyclohexane Hexachlorocyclohexane (HCH), , is any of several polyhalogenated organic compounds consisting of a six-carbon ring with one chlorine and one hydrogen attached to each carbon. This structure has nine stereoisomers (eight diastereomers, one of whi ...
. It is useful as a high-temperature solvent, e.g. for
GPC GPC may refer to: Businesses and organisations Politics * General People's Congress (disambiguation) * Goa People's Congress, in India * Green Party of Canada * Group of Cameroonian Progressives Other businesses and organisations * Genuine ...
of polyolefines such as PE or PP which are otherwise insoluble. Aside from its use as a solvent, this compound is a useful precursor to dye and pesticides.


Safety

The
LD50 In toxicology, the median lethal dose, LD50 (abbreviation for "lethal dose, 50%"), LC50 (lethal concentration, 50%) or LCt50 is a toxic unit that measures the lethal dose of a given substance. The value of LD50 for a substance is the dose requ ...
(oral, rats) is 756 mg/kg. Animal studies have shown that 1,2,4-trichlorobenzene affects the liver and kidney, and is possibly a teratogen.CDC - NIOSH Pocket Guide to Chemical Hazards
/ref> There is no regulated occupational exposure limit for chemical exposure, but the
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 ...
recommends no greater exposure than 5 ppm, over an 8-hour workday.


See also

*
Chlorobenzenes Chlorobenzenes are a group of aryl chlorides/ halobenzenes consisting of one or more chlorine atoms as substituents on a benzene core. They have the formula C6H6–''n''Cl''n'', where ''n'' = 1–6 is the number of chlorine atoms. Depending on the ...
—different numbers of chlorine substituents and isomeric forms


References

{{DEFAULTSORT:Trichlorobenzene, 1, 2, 4- Chlorobenzenes Halogenated solvents Aromatic solvents