Benzotrichloride

Benzotrichloride
Names
	IUPAC name (Trichloromethyl)benzene
	Other names Toluene trichloride; Phenyl chloroform; alpha,alpha,alpha-Trichlorotoluene
Identifiers
CAS Number	98-07-7 ;
3D model (JSmol)	Interactive image;
ChemSpider	7089 ; 13882366 ;
ECHA InfoCard	100.002.395
KEGG	C19166 ;
PubChem CID	7367;
RTECS number	XT9275000;
UNII	U62VHG99AM ;
CompTox Dashboard (EPA)	DTXSID1020148 ;
	InChI InChI=1S/C7H5Cl3/c8-7(9,10)6-4-2-1-3-5-6/h1-5H Key: XEMRAKSQROQPBR-UHFFFAOYSA-N ;
	SMILES ClC(Cl)(Cl)c1ccccc1;
Properties
Chemical formula	C7H5Cl3
Molar mass	195.48
Appearance	Clear liquid
Density	1.3756 g/mL
Melting point	−5.0 °C (23.0 °F; 268.1 K)
Boiling point	220.8 °C (429.4 °F; 493.9 K)
Solubility in water	0.05g/L
Solubility	organic solvents
Hazards
NFPA 704 (fire diamond)	4 1 0
Flash point	97.22 °C (207.00 °F; 370.37 K)
Autoignition; temperature	420 °C (788 °F; 693 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

Benzotrichloride, also known as trichlorotoluene is an organic compound with the formula C₆H₅CCl₃. It is principally used as an intermediate in the preparation of other chemical products such as dyes.^[1]^[2]^[3]

It is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.^[4]

Preparation

Benzotrichloride is produced by the free radical chlorination of toluene, catalysed by light or radical initiators such as dibenzoyl peroxide. Two intermediates are observed:

C₆H₅CH₃ + Cl₂ → C₆H₅CH₂Cl + HCl

C₆H₅CH₂Cl + Cl₂ → C₆H₅CHCl₂ + HCl

C₆H₅CHCl₂ + Cl₂ → C₆H₅CCl₃ + HCl

Uses

Benzotrichloride is partially hydrolysed to benzoyl chloride:^[1]

C₆H₅CCl₃ + H₂O → C₆H₅C(O)Cl + 2 HCl

It is also transformed into benzotrifluoride, a precursor to pesticides:^[5]

C₆H₅CCl₃ + 3 KF → C₆H₅CF₃ + 3 KCl

References

^ ^a ^b Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry: 139. doi:10.1002/14356007.a06_233.pub2.
^ Merck Index, 11th Edition, 1120.
^ Benzotrichloride Data page at Inchem.org
^ "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: postscript (link)
^ Bonath, B.; Förtsch, B.; Saemann, R. (1966). "Kinetische Untersuchung einer Seitenkettenchlorierung unter Verwendung eines Analogcomputers". Chemie Ingenieur Technik. 38 (7): 739–742. doi:10.1002/cite.330380711.

[Ullmann-1] Rossberg, Manfred; Lendle, Wilhelm; Pfleiderer, Gerhard; Tögel, Adolf; Dreher, Eberhard-Ludwig; Langer, Ernst; Rassaerts, Heinz; Kleinschmidt, Peter; Strack, Heinz; Cook, Richard; Beck, Uwe; Lipper, Karl-August; Torkelson, Theodore R.; Löser, Eckhard; Beutel, Klaus K.; Mann, Trevor (2006). "Chlorinated Hydrocarbons". Ullmann's Encyclopedia of Industrial Chemistry: 139. doi:10.1002/14356007.a06_233.pub2.

[Merck-2] Merck Index, 11th Edition, 1120.

[3] Benzotrichloride Data page at Inchem.org

[gov-right-know-4] "40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities" (PDF) (July 1, 2008 ed.). Government Printing Office. Retrieved October 29, 2011. {{cite journal}}: Cite journal requires |journal= (help)CS1 maint: postscript (link)

[5] Bonath, B.; Förtsch, B.; Saemann, R. (1966). "Kinetische Untersuchung einer Seitenkettenchlorierung unter Verwendung eines Analogcomputers". Chemie Ingenieur Technik. 38 (7): 739–742. doi:10.1002/cite.330380711.

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