Tetrachlorobenzene

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Tetrachlorobenzene
1,2,3,4-Tetrachlorobenzene.svg
1,2,3,4-Tetrachlorobenzene
1,2,3,5-Tetrachlorobenzene.svg
1,2,3,5-Tetrachlorobenzene
1,2,4,5-Tetrachlorobenzene.svg
1,2,4,5-Tetrachlorobenzene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.032.390 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 1,2,4,5:202-466-2
  • 1,2,3,5:211-217-7
  • 1,2,3,4:211-214-0
KEGG
PubChem CID
RTECS number
  • 1,2,4,5:DB9450000
UNII
  • 1,2,4,5:InChI=1S/C6H2Cl4/c7-3-1-4(8)6(10)2-5(3)9/h1-2H
    Key: JHBKHLUZVFWLAG-UHFFFAOYSA-N
  • 1,2,3,5:InChI=1S/C6H2Cl4/c7-3-1-4(8)6(10)5(9)2-3/h1-2H
    Key: QZYNWJQFTJXIRN-UHFFFAOYSA-N
  • 1,2,3,4:InChI=1S/C6H2Cl4/c7-3-1-2-4(8)6(10)5(3)9/h1-2H
    Key: GBDZXPJXOMHESU-UHFFFAOYSA-N
  • 1,2,4,5:C1=C(C(=CC(=C1Cl)Cl)Cl)Cl
  • 1,2,3,5:C1=C(C=C(C(=C1Cl)Cl)Cl)Cl
  • 1,2,3,4:C1=CC(=C(C(=C1Cl)Cl)Cl)Cl
Properties
C6H2Cl4
Molar mass 215.88 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Tetrachlorobenzene is any of three isomeric chlorobenzenes with the molecular formula C6H2Cl4. They differ by the positions of the chlorine atoms around the ring. Tetrachlorobenzenes are colorless crystalline compounds. [1]

Contents

Properties

Selected Physical Properties of Individual Isomers
isomerm.p. (°C)b.p. (°C)m.p. (g/cm3 @100 °C)
1,2,3,4472541.539
1,2,3,551.52461.523
1,2,4,51412451.454

Synthesis

1,2,4,5-Tetrachlorobenzene can be produced by electrophilic halogenation of benzenes and some chlorobenzenes. [2] 1,2,3,4-Tetrachlorobenzene can only be produced by chlorination of 1,3,5-trichlorobenzene.

Uses

1,2,4,5-tetrachlorobenzene once was used as intermediates in the production of pesicides, [3] specifically trichlorophenols. This method has been discontinued because it also produced 2,3,7,8-tetrachlorodibenzo-p-dioxin. [1]

See also

Related Research Articles

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<span class="mw-page-title-main">1,4-Dichlorobenzene</span> Chemical compound

1,4-Dichlorobenzene (1,4-DCB, p-DCB, or para-dichlorobenzene, sometimes abbreviated as PDCB or para) is an isomer of dichlorobenzene with the formula C6H4Cl2. This colorless solid has a strong odor. The molecule consists of a benzene ring with two chlorine atoms (replacing hydrogen atoms) on opposing sites of the ring.

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In organic chemistry, an aryl halide is an aromatic compound in which one or more hydrogen atoms, directly bonded to an aromatic ring are replaced by a halide. The haloarene are different from haloalkanes because they exhibit many differences in methods of preparation and properties. The most important members are the aryl chlorides, but the class of compounds is so broad that there are many derivatives and applications.

<span class="mw-page-title-main">Chlorobenzene</span> Aromatic organochlorine compound

Chlorobenzene is 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 and a widely used intermediate in the manufacture of other chemicals.

Chloral, also known as trichloroacetaldehyde or trichloroethanal, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate, a once widely used sedative and hypnotic substance.

Hexachlorobenzene, or perchlorobenzene, is a chlorobenzene compound with the molecular formula C6Cl6. It is a fungicide formerly used as a seed treatment, especially on wheat to control the fungal disease bunt. It has been banned globally under the Stockholm Convention on Persistent Organic Pollutants.

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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–nCln, where n = 1–6 is the number of chlorine atoms. Depending on the number of chlorine substituents, there may be several constitutional isomers possible.

Iodobenzenes are a group of aryl iodides/halobenzenes consisting of one or more iodine atoms as substituents on a benzene core. They have the formula C6H6–nIn, where n = 1–6 is the number of iodine atoms. Depending on the number of bromine substituents, there may be several constitutional isomers possible.

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<span class="mw-page-title-main">Trichlorobenzene</span>

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<span class="mw-page-title-main">Hexachlorocyclohexane</span> Chemical compound

Hexachlorocyclohexane (HCH), C
6
H
6
Cl
6
, 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, which differ by the stereochemistry of the individual chlorine substituents on the cyclohexane. It is sometimes erroneously called "benzene hexachloride" (BHC). They have been used as models for analyzing the effects of different geometric positions of the large atoms with dipolar bonds on the stability of the cyclohexane conformation. The isomers are poisonous, pesticidal, and persistent organic pollutants, to varying degrees.

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C<sub>4</sub>-Benzenes Index of articles associated with the same name

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1,2,3-Trichlorobenzene is an organochlorine compound with the chemical formula C6H3Cl3. This is one of three isomers of trichlorobenzene; the two others are 1,2,4-Trichlorobenzene and 1,3,5-Trichlorobenzene.

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References

  1. 1 2 Beck, Uwe; Löser, Eckhard (2011). "Chlorinated Benzenes and Other Nucleus‐Chlorinated Aromatic Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.o06_o03. ISBN   9783527303854.
  2. "US4205014A Process for 1,2,4,5-tetrachlorobenzene". Espacenet . Retrieved 22 June 2023.
  3. NTP Toxicity Study Reports. National Toxicology Program. 1991. p. 11. Retrieved 22 June 2023.