Benzotrichloride

From Self-sufficiency
Jump to: navigation, search
Benzotrichloride
File:Benzotrichloride.png
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 98-07-7 YesY
ChemSpider 7089
RTECS number XT9275000
SMILES Script error: No such module "collapsible list".
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular 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
style="background: #F8EABA; text-align: center;" colspan="2" | Hazards
R-phrases R45 R22 R23 R37/38 R41
S-phrases S53 S45
NFPA 704
1
3
0
 YesY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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 + Cl2C6H5CH2Cl + HCl
C6H5CH2Cl + Cl2C6H5CHCl2 + 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

  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.
de:Benzotrichlorid

fr:(trichlorométhyl)benzène nl:Trichloormethylbenzeen