Tetrachloro-m-xylene

Tetrachloro-m-xylene
Skeletal formula 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
CAS Number	877-09-8 ;
3D model (JSmol)	Interactive image;
Abbreviations	TCMX
ChemSpider	63327 ;
ECHA InfoCard	100.011.715
EC Number	212-886-8;
PubChem CID	70139;
UNII	O8XMK3B4S9 ;
CompTox Dashboard (EPA)	DTXSID6075433 ;
	InChI InChI=1S/C8H6Cl4/c1-3-5(9)4(2)7(11)8(12)6(3)10/h1-2H3 Key: NTUBJKOTTSFEEV-UHFFFAOYSA-N ; InChI=1/C8H6Cl4/c1-3-5(9)4(2)7(11)8(12)6(3)10/h1-2H3 Key: NTUBJKOTTSFEEV-UHFFFAOYAN;
	SMILES Clc1c(c(Cl)c(c(Cl)c1Cl)C)C;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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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]

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

References

^ 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.
^ Organochlorine Pesticides by GCxGC-ECD^{[permanent dead link]}
^ 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. Bibcode:2007AcAC..602..211W. doi:10.1016/j.aca.2007.09.023. PMID 17933606.

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[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^{[permanent dead link]}

[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. Bibcode:2007AcAC..602..211W. doi:10.1016/j.aca.2007.09.023. PMID 17933606.

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