1,2,3-Trichlorobenzene

Last updated
1,2,3-Trichlorobenzene
1,2,3-trichlorobenzene.svg
1,2,3-Trichlorobenzene-3D-vdW.png
Names
Preferred IUPAC name
1,2,3-Trichlorobenzene
Other names
1,2,3-TCB
Identifiers
3D model (JSmol)
956882
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.598 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-757-1
847785
KEGG
PubChem CID
RTECS number
  • DC2095000
UNII
  • InChI=1S/C6H3Cl3/c7-4-2-1-3-5(8)6(4)9/h1-3H
    Key: RELMFMZEBKVZJC-UHFFFAOYSA-N
  • C1=CC(=C(C(=C1)Cl)Cl)Cl
Properties
C6H3Cl3
Molar mass 181.44 g·mol−1
Appearancewhite crystals
Density 1.45 g/cm3
Melting point 53.5 °C (128.3 °F; 326.6 K)
Boiling point 218.5 °C (425.3 °F; 491.6 K)
Soluble
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg
Warning
H302, H410
P273, P301, P312, P330
Flash point 112.7 °C (234.9 °F; 385.8 K)
Related compounds
Related compounds
1,2,4-Trichlorobenzene
1,3,5-Trichlorobenzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

Contents

Synthesis

1,2,3-Trichlorobenzene can be prepared via dehydrohalogenation of hexachlorocyclohexane. Also, 1,3,5-trichlorobenzene is formed as a byproduct. Small amounts of 1,2,3-trichlorobenzene can also be produced while chlorinating benzene with iron(III) chloride as a catalyst. [3]

Physical properties

The compound forms white crystals with a faint aromatic odor. It is combustible [4] and poorly soluble in water. [5] The substance is irritating to eyes and the respiratory tract.

Uses

1,2,3-Trichlorobenzene is used as a herbicide. [5] [6] Also as a solvent for high-melting products, as a coolant in electrical installations and glass tempering. [7]

See also

Related Research Articles

In chemistry, a structural isomer of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term metamer was formerly used for the same concept.

<span class="mw-page-title-main">Phenyl group</span> Cyclic chemical group (–C₆H₅)

In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6H5, and is often represented by the symbol Ph. The phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen, which may be replaced by some other element or compound to serve as a functional group. A phenyl group has six carbon atoms bonded together in a hexagonal planar ring, five of which are bonded to individual hydrogen atoms, with the remaining carbon bonded to a substituent. Phenyl groups are commonplace in organic chemistry. Although often depicted with alternating double and single bonds, the phenyl group is chemically aromatic and has equal bond lengths between carbon atoms in the ring.

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.

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">Arsole</span> Chemical compound

Arsole, also called arsenole or arsacyclopentadiene, is an organoarsenic compound with the formula C4H4AsH. It is classified as a metallole and is isoelectronic to and related to pyrrole except that an arsenic atom is substituted for the nitrogen atom. Whereas the pyrrole molecule is planar, the arsole molecule is not, and the hydrogen atom bonded to arsenic extends out of the molecular plane. Arsole is only moderately aromatic, with about 40% the aromaticity of pyrrole. Arsole itself has not been reported in pure form, but several substituted analogs called arsoles exist. Arsoles and more complex arsole derivatives have similar structure and chemical properties to those of phosphole derivatives. When arsole is fused to a benzene ring, this molecule is called arsindole, or benzarsole.

<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

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

TATB, triaminotrinitrobenzene or 2,4,6-triamino-1,3,5-trinitrobenzene is an aromatic explosive, based on the basic six-carbon benzene ring structure with three nitro functional groups (NO2) and three amine (NH2) groups attached, alternating around the ring.

1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

<span class="mw-page-title-main">1,3,5-Triazido-2,4,6-trinitrobenzene</span> Chemical compound

1,3,5-Triazido-2,4,6-trinitrobenzene, also known as TATNB (triazidotrinitrobenzene) and TNTAZB (trinitrotriazidobenzene), is an aromatic high explosive composed of a benzene ring with three azido groups (-N3) and three nitro groups (-NO2) alternating around the ring, giving the chemical formula C6(N3)3(NO2)3. Its detonation velocity is 7,350 meters per second, which is comparable to TATB (triaminotrinitrobenzene).

The Blanc chloromethylation is the chemical reaction of aromatic rings with formaldehyde and hydrogen chloride to form chloromethyl arenes. The reaction is catalyzed by Lewis acids such as zinc chloride. The reaction was discovered by Gustave Louis Blanc (1872-1927) in 1923

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

Trimesic acid, also known as benzene-1,3,5-tricarboxylic acid, is an organic compound with the formula C6H3(CO2H)3. It is one of three isomers of benzenetricarboxylic acid. A colorless solid, trimesic acid has some commercial value as a precursor to some plasticizers.

1,2,4-Trichlorobenzene is an organochlorine compound, one of three isomers of trichlorobenzene. It is a derivative of benzene with three chloride substituents. It is a colorless liquid used as a solvent for a variety of compounds and materials.

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

Trichlorobenzene (TCB) may refer to any of three isomeric chlorinated derivatives of benzene with the molecular formula C6H3Cl3. Trichlorobenzenes are man-made chemical compounds that occur in three different forms. Even though the forms have the same molecular weight and molecular formulae, they are structurally different by the positions of the chlorine atoms attached to the benzene ring. 1,2,3-Trichlorobenzene and 1,3,5-trichlorobenzene are colorless solids, but 1,2,4-trichlorobenzene is a colorless oil. The isomers may also have different chemical and toxicological properties.

<span class="mw-page-title-main">Benzene</span> Hydrocarbon compound consisting of a 6-sided ring

Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, benzene is classed as a hydrocarbon.

<span class="mw-page-title-main">1,3,5-Trinitrobenzene</span> Chemical compound

1,3,5-Trinitrobenzene is an organic compound with the formula C6H3(NO2)3. It is one of three trinitrated benzene-derivatives. A pale yellow solid, the compound is highly explosive.

<span class="mw-page-title-main">Trihydroxybenzenes</span> Index of chemical compounds with the same name

The trihydroxybenzenes (or benzenetriols) are organic compounds with the formula C6H3(OH)3. Also classified as polyphenols, they feature three hydroxyl groups substituted onto a benzene ring. They are white solids with modest solubility in water.

<span class="mw-page-title-main">1,3,5-Trichlorobenzene</span> Chemical compound

1,3,5-Trichlorobenzene is an organochlorine compound. It is one of the three isomers of trichlorobenzene. Being more symmetrical than the other isomers, it exists as colourless crystals whereas the other isomers are liquids at room temperature.

C<sub>3</sub>-Benzenes Index of articles associated with the same name

The C3-benzenes are a class of organic aromatic compounds which contain a benzene ring and three other carbon atoms. For the hydrocarbons with no further unsaturation, there are four isomers. The chemical formula for all the saturated isomers is C9H12.

<span class="mw-page-title-main">1,3,5-Triethylbenzene</span> Chemical compound

1,3,5-Triethylbenzene is a chemical compound of the group of aromatic hydrocarbons.

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

References

  1. "1,2,3-Trichlorobenzene". Sigma Aldrich . Retrieved 22 June 2023.
  2. "1,2,3-Trichlorobenzene". Thermo Fisher . Retrieved 22 June 2023.
  3. Beck, Uwe; Löser, Eckhard (15 October 2011). "Chlorinated Benzenes and Other Nucleus-Chlorinated Aromatic Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KGaA. doi:10.1002/14356007.o06_o03. ISBN   978-3527306732.
  4. "ICSC 1222 - 1,2,3-TRICHLOROBENZENE". International Labour Organization . Retrieved 22 June 2023.
  5. 1 2 "GESTIS-Stoffdatenbank". gestis.dguv.de. Retrieved 22 June 2023.
  6. Montgomery, John H. (23 August 1991). Groundwater Chemicals Field Guide. CRC Press. p. 193. ISBN   978-0-87371-554-6 . Retrieved 22 June 2023.
  7. National Study of Chemical Residues in Fish: Volume I. DIANE Publishing. 1992. p. C-240. ISBN   978-1-4289-0620-4 . Retrieved 22 June 2023.