1,4-Bis(trichloromethyl)benzene

1,4-Bis(trichloromethyl)benzene
Names
	Other names hexachloroxylene; hexachloroparaxylene; Chloxil; Chloxyl
Identifiers
CAS Number	68-36-0 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL3182002;
ChemSpider	5997;
ECHA InfoCard	100.000.624
EC Number	200-686-3;
PubChem CID	6233;
UNII	42CH2735EU;
CompTox Dashboard (EPA)	DTXSID7026366 ;
	InChI InChI=1S/C8H4Cl6/c9-7(10,11)5-1-2-6(4-3-5)8(12,13)14/h1-4H Key: OTEKOJQFKOIXMU-UHFFFAOYSA-N;
	SMILES C1=CC(=CC=C1C(Cl)(Cl)Cl)C(Cl)(Cl)Cl;
Properties
Appearance	white solid
Density	1.778 g/cm3
Melting point	108–110 °C (226–230 °F; 381–383 K)
Boiling point	213 °C (415 °F; 486 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H311, H314, H331
Precautionary statements	P260, P261, P264, P270, P271, P280, P301+P310, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P311, P312, P321, P322, P330, P361, P363, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1,4-Bis(trichloromethyl)benzene is an organic compound with the formula C₆H₄(CCl₃)₂. A white solid, it is prepared industrially by chlorination of para-xylene. It reacts with terephthalic acid to give terephthaloyl chloride, a precursor to Kevlar.^[1] It also reacts with sulfur dioxide to give the same acid chloride and thionyl chloride.^[2] It reacts with hydrogen fluoride in 1,2-dichloroethane to form 1,4-bis(chlorodifluoromethyl)benzene in a yield of 79%.^[3]

References

^ Pfoertner, Karl-Heinz (2000). "Photochemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_573. ISBN 978-3527306732.
^ Rondestvedt, Christian S. (1976). "New Syntheses of Aromatic Acid Chlorides from Trichloromethylarenes. 1. Reaction with Sulfur Dioxide". The Journal of Organic Chemistry. 41 (22): 3569–3574. doi:10.1021/jo00884a017. S2CID 197293724.
^ Dolbier, William R.; Duan, Jian-Xin; Rong, Xiao X. (2007). "Efficient synthesis of p-bis-(chlorodifluoromethyl)benzene". Journal of Fluorine Chemistry. 128 (10). Elsevier BV: 1091–1093. Bibcode:2007JFluC.128.1091D. doi:10.1016/j.jfluchem.2007.05.007. ISSN 0022-1139.