Triphenylmethyl chloride

Triphenylmethyl chloride
Identifiers
CAS number 76-83-5 Y
PubChem 6456
ChemSpider 17344583 Y
Jmol-3D images Image 1
Properties
Molecular formula C19H15Cl
Molar mass 278.7754 g/mol
Appearance white to yellow solid
Density 1.141g/cm3
Melting point

109-112 °C, 270 K, -61 °F

Boiling point

230°C (at 20mmHg) and 374.3°C (at 760mmHg)

Solubility chloroform 0.1g/ml
Hazards
MSDS Corvine Chemicals MSDS
Flash point 177.9°C
 Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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

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.[1]

Reactions

Triphenylmethylsodium may can be prepared from trityl chloride and sodium:[2]

(C6H5)3CCl + 2 Na → (C6H5)3CNa + NaCl

Reaction with silver hexafluorophosphate gives triphenylmethyl hexafluorophosphate.

References

  1. ^ W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. (1955), "Triphenylchloromethane", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv3p0841 ; Coll. Vol. 3: 841 
  2. ^ W. B. Renfrow Jr and C. R. Hauser (1943), "Triphenylmethylsodium", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0607 ; Coll. Vol. 2: 607