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	13882366 ;
ECHA InfoCard	100.002.395
KEGG	C19166 ;
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
Boiling point	220.8 °C
Solubility in water	0.05g/L
Solubility	organic solvents
Hazards
NFPA 704 (fire diamond)	4 1 0
Flash point	97.22 °C
	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]

Production and uses

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

Benzotrichloride is hydrolysed to benzoyl chloride:^[3]

C₆H₅CCl₃ + H₂O → C₆H₅C(O)Cl + 2 HCl

It is also transformed into benzotrifluoride, a precursor to pesticides:

C₆H₅CCl₃ + 3 KF → C₆H₅CF₃ + 3 KCl

References

^ Merck Index, 11th Edition, 1120.
^ Benzotrichloride Data page at Inchem.org
^ Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.

[Merck-1] Merck Index, 11th Edition, 1120.

[2] Benzotrichloride Data page at Inchem.org

[3] Manfred Rossberg, Wilhelm Lendle, Gerhard Pfleiderer, Adolf Tögel, Eberhard-Ludwig Dreher, Ernst Langer, Heinz Rassaerts, Peter Kleinschmidt, Heinz Strack, Richard Cook, Uwe Beck, Karl-August Lipper, Theodore R. Torkelson, Eckhard Löser, Klaus K. Beutel, “Chlorinated Hydrocarbons” in Ullmann’s Encyclopedia of Chemical Technology, 2007 John Wiley & Sons: New York.

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