1,2,3-Trichlorobenzene

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.

1,2,3-Trichlorobenzene
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
EC Number
  • 201-757-1
847785
KEGG
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
Appearance white 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:
GHS07: Exclamation markGHS09: Environmental hazard
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).
Infobox references

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
  • Chlorobenzenes—different numbers of chlorine substituents and isomeric forms.

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. doi:10.1002/14356007.o06_o03. ISBN 978-3527306732. {{cite book}}: |website= ignored (help)
  4. "ICSC 1222 - 1,2,3-TRICHLOROBENZENE". International Labour Organization. Retrieved 22 June 2023.
  5. "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.
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