Triphenylmethyl chloride
{{chembox
| Watchedfields = changed
| verifiedrevid = 470616841
| ImageFile = Triphenylmethyl_chloride.png
| ImageSize =
| ImageFileL2 = Triphenylmethyl-chloride-from-xtal-3D-bs.png
| ImageSizeL2 = 145
| ImageFileR2 = Triphenylmethyl-chloride-from-xtal-3D-sf.png
| PIN = 1,1′,1′′-(Chloromethanetriyl)tribenzene
| OtherNames = (Chloromethanetriyl)tribenzene
[Chloro(diphenyl)methyl]benzene
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo =76-83-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1D9GZ8QQXN
| PubChem =6456
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 17344583
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TXMWQDFQVWGFTQ-UHFFFAOYSA-N
| SMILES =C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl
}}
|Section2={{Chembox Properties
| Formula =C19H15Cl
| MolarMass =278.7754 g/mol
| Appearance =white to yellow solid
| Density = 1.141 g/cm3
| MeltingPtC =109 to 112
| BoilingPtC = 230
| BoilingPt_notes = (at 20 mmHg) and 374.3 °C (at 760 mmHg)
| Solubility =
| SolubleOther =soluble in chloroform, benzene, acetone,{{Cite web |url=http://www.sciencelab.com/msds.php?msdsId=9925340 |title=Archived copy |access-date=2014-01-08 |archive-date=2013-01-24 |archive-url=https://web.archive.org/web/20130124031450/http://www.sciencelab.com/msds.php?msdsId=9925340 |url-status=dead }} ether, THF, hexane{{Cite web|url=https://www.scbt.com/scbt/product/trityl-chloride-76-83-5|title=Trityl chloride | CAS 76-83-5}}
}}
|Section3={{Chembox Hazards
| ExternalSDS = [http://www.corvinechemicals.com/products-Triphenylmethyl%20Chloride.htm Corvine Chemicals MSDS]
| FlashPtC = 177.9
| AutoignitionPtC =
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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.{{OrgSynth | author = W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. | title = Triphenylchloromethane | collvol = 3 | collvolpages = 841 | prep = cv3p0841 | year = 1955}}.
Reactions
Triphenylmethylsodium can be prepared from trityl chloride dissolved in an aprotic solvent and sodium:{{OrgSynth | author = W. B. Renfrow Jr and C. R. Hauser | title = Triphenylmethylsodium | collvol = 2 | collvolpages = 607| year = 1943 | prep = CV2P0607}}
:(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.{{cite journal |last1=Gomberg |first1=M. |title=An Instance of Trivalent Carbon: Triphenylmethyl |journal=Journal of the American Chemical Society |date=1900 |volume=22 |issue=11 |pages=757–771 |doi=10.1021/ja02049a006 |url=https://pubs.acs.org/doi/abs/10.1021/ja02049a006|url-access=subscription }}
:2 (C6H5)3CCl + Zn → ((C6H5)3C)2 + ZnCl2