Tetrachloro-m-xylene

Tetrachloro-m-xylene (tetrachlorometaxylene, or TCMX) is the organochlorine compound with the formula C6Cl4(CH3)2. It is the chlorinated derivative of m-xylene in which the four aromatic hydrogen atoms are replaced by chlorine. It is prepared by ferric chloride-catalyzed reaction of the xylene with chlorine.[1]

Tetrachloro-m-xylene
Skeletal formula of TCMX
Skeletal formula of TCMX
Ball-and-stick model of TCMX
Ball-and-stick model of TCMX
Names
Preferred IUPAC name
1,2,3,5-Tetrachloro-4,6-dimethylbenzene
Other names
Tetrachlorometaxylene
2,4,5,6-Tetrachlorometaxylene
Identifiers
3D model (JSmol)
Abbreviations TCMX
ChemSpider
ECHA InfoCard 100.011.715
EC Number
  • 212-886-8
UNII
  • InChI=1S/C8H6Cl4/c1-3-5(9)4(2)7(11)8(12)6(3)10/h1-2H3 checkY
    Key: NTUBJKOTTSFEEV-UHFFFAOYSA-N checkY
  • InChI=1/C8H6Cl4/c1-3-5(9)4(2)7(11)8(12)6(3)10/h1-2H3
    Key: NTUBJKOTTSFEEV-UHFFFAOYAN
  • Clc1c(c(Cl)c(c(Cl)c1Cl)C)C
Properties
C8H6Cl4
Molar mass 243.94524
Appearance colorless or white solid
Melting point 223 °C (433 °F; 496 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

TCMX is used as an internal standard in the analysis of organochlorides, particularly organochloride pesticides.[2][3]

References
  1. Riegger, Paul; Steffen, Klaus Dieter (1979). "Chlorination of xylenes and secondary Products. I. Chlorination of the nucleus and Side Chains of Xylenes". Chemiker-Zeitung. 103: 1-7.
  2. Organochlorine Pesticides by GCxGC-ECD
  3. Wang, Wentao; Meng, Bingjun; Lu, Xiaoxia; Liu, Yu; Tao, Shu (2007). "Extraction of polycyclic aromatic hydrocarbons and organochlorine pesticides from soils: A comparison between Soxhlet extraction, microwave-assisted extraction and accelerated solvent extraction techniques". Analytica Chimica Acta. 602 (2): 211–222. doi:10.1016/j.aca.2007.09.023.
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