Triphenylmethyl chloride

Triphenylmethyl chloride or trityl chloride (TrCl) is a white solid with the chemical formula C19H15Cl. It is an alkyl halide, sometimes used to introduce the trityl protecting group.

Triphenylmethyl chloride
Names
Preferred IUPAC name
1,1′,1′′-(Chloromethanetriyl)tribenzene
Other names
(Chloromethanetriyl)tribenzene
[Chloro(diphenyl)methyl]benzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.000.898
UNII
  • InChI=1S/C19H15Cl.C10H10.C8H8/c20-19(16-10-4-1-5-11-16,17-12-6-2-7-13-17)18-14-8-3-9-15-18;1-3-9-5-7-10(4-2)8-6-9;1-2-8-6-4-3-5-7-8/h1-15H;3-8H,1-2H2;2-7H,1H2 checkY
    Key: TXMWQDFQVWGFTQ-UHFFFAOYSA-N checkY
  • C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl
Properties
C19H15Cl
Molar mass 278.7754 g/mol
Appearance white to yellow solid
Density 1.141 g/cm3
Melting point 109 to 112 °C (228 to 234 °F; 382 to 385 K)
Boiling point 230 °C (446 °F; 503 K) (at 20 mmHg) and 374.3 °C (at 760 mmHg)
Solubility soluble in chloroform, benzene, acetone,[1] ether, THF, hexane[2]
Hazards
Flash point 177.9 °C (352.2 °F; 451.0 K)
Safety data sheet (SDS) Corvine Chemicals MSDS
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

Preparation

Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of triphenylmethanol with acetyl chloride, or by the Friedel–Crafts alkylation of benzene with carbon tetrachloride to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed.[3]

Reactions

Triphenylmethylsodium can be prepared from trityl chloride dissolved in an aprotic solvent and sodium:[4]

(C6H5)3CCl + 2 Na → (C6H5)3CNa + NaCl

Reaction with silver hexafluorophosphate gives triphenylmethyl hexafluorophosphate.

Trityl chloride reacts with zinc in nonpolar solvents (e.g. benzene) to form Gomberg's dimer.[5]

2 (C6H5)3CCl + Zn → ((C6H5)3C)2 + ZnCl2

See also

References
  1. "Archived copy". Archived from the original on 2013-01-24. Retrieved 2014-01-08.{{cite web}}: CS1 maint: archived copy as title (link)
  2. "Trityl chloride | CAS 76-83-5".
  3. W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. (1955). "Triphenylchloromethane". Organic Syntheses.{{cite journal}}: CS1 maint: multiple names: authors list (link); Collective Volume, vol. 3, p. 841.
  4. W. B. Renfrow Jr and C. R. Hauser (1943). "Triphenylmethylsodium". Organic Syntheses.; Collective Volume, vol. 2, p. 607
  5. Gomberg, M. (1900). "An Instance of Trivalent Carbon: Triphenylmethyl". Journal of the American Chemical Society. 22 (11): 757–771. doi:10.1021/ja02049a006.
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