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^Y

3D model (JSmol)

Interactive image

ChemSpider

17344583^Y

ECHA InfoCard

100.000.898

PubChem CID

6456

UNII

1D9GZ8QQXN^Y

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^Y
Key: TXMWQDFQVWGFTQ-UHFFFAOYSA-N^Y

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,^[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

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); Collective Volume, vol. 3, p. 841.
^ W. B. Renfrow Jr and C. R. Hauser (1943). "Triphenylmethylsodium". Organic Syntheses.; Collective Volume, 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.

This page was last edited on 31 October 2022, at 09:28

Triphenylmethyl chloride

From Wikipedia, the free encyclopedia

Preparation

Reactions

See also

References