Benzotrichloride

Benzotrichloride
Skeletal formula of benzotrichloride
Ball-and-stick model of the benzotrichloride molecule
Names
IUPAC name
(Trichloromethyl)benzene
Other names
Toluene trichloride
Phenyl chloroform
alpha,alpha,alpha-Trichlorotoluene
PhCCl3
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.395
KEGG
RTECS number XT9275000
UNII
Properties
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)
0.05g/L
Solubility organic solvents
Hazards
R-phrases (outdated) R45 R22 R23 R37/38 R41
S-phrases (outdated) S53 S45
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
1
4
0
Flash point 97.22 °C (207.00 °F; 370.37 K)
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).
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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

  1. 1 2 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.
  2. ↑ Merck Index, 11th Edition, 1120.
  3. ↑ Benzotrichloride Data page at Inchem.org
  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.
  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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