Triphenylmethyl chloride

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Triphenylmethyl chloride
Triphenylmethyl chloride.png
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
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
Safety data sheet Corvine Chemicals MSDS
Flash point 177.9 °C (352.2 °F; 451.0 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

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.

Preparation[edit]

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[edit]

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.

See also[edit]

References[edit]

  1. ^ http://www.sciencelab.com/msds.php?msdsId=9925340
  2. ^ https://www.scbt.com/scbt/product/trityl-chloride-76-83-5
  3. ^ W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. (1955). "Triphenylchloromethane". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 3, p. 841
  4. ^ W. B. Renfrow Jr and C. R. Hauser (1943). "Triphenylmethylsodium". Organic Syntheses.; Collective Volume, 2, p. 607