Triphenylmethyl chloride

Triphenylmethyl chloride
Names
	Preferred IUPAC name 1,1′,1′′-(Chloromethanetriyl)tribenzene
	Other names (Chloromethanetriyl)tribenzene; [Chloro(diphenyl)methyl]benzene
Identifiers
CAS Number	76-83-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	17344583 ;
ECHA InfoCard	100.000.898
PubChem CID	6456;
UNII	1D9GZ8QQXN ;
CompTox Dashboard (EPA)	DTXSID3052511 ;
	InChI 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 Key: TXMWQDFQVWGFTQ-UHFFFAOYSA-N ;
	SMILES C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl;
Properties
Chemical formula	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, ether, THF, hexane
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). verify (what is ?) 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

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

References

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

[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); Collected Volumes, vol. 3, p. 841..

[4] W. B. Renfrow Jr and C. R. Hauser (1943). "Triphenylmethylsodium". Organic Syntheses; Collected Volumes, vol. 2, p. 607.

[Gomberg1900-5] 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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Preparation

Reactions

See also

References