| Revision as of 14:23, 10 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,074 edits Saving copy of the {{chembox}} taken from revid 451902671 of page Triphenylmethyl_chloride for the Chem/Drugbox validation project (updated: ''). |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 451499930 |
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| verifiedrevid = 470616841 |
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|ImageFile=Triphenylmethyl_chloride.png |
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| ImageFile = Triphenylmethyl_chloride.png |
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|ImageSize= |
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| ImageSize = |
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| ImageFileL2 = Triphenylmethyl-chloride-from-xtal-3D-bs.png |
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|IUPACName=benzene |
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| ImageSizeL2 = 145 |
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|OtherNames= |
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| ImageFileR2 = Triphenylmethyl-chloride-from-xtal-3D-sf.png |
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| PIN = 1,1′,1′′-(Chloromethanetriyl)tribenzene |
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| OtherNames = (Chloromethanetriyl)tribenzene<br />benzene |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=76-83-5 |
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| CASNo =76-83-5 |
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| CASNo_Ref = {{cascite}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem=6456 |
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| UNII = 1D9GZ8QQXN |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| PubChem =6456 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 17344583 |
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| ChemSpiderID = 17344583 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = TXMWQDFQVWGFTQ-UHFFFAOYSA-N |
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| StdInChIKey = TXMWQDFQVWGFTQ-UHFFFAOYSA-N |
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| SMILES=C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl |
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| SMILES =C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3)Cl |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>19</sub>H<sub>15</sub>Cl |
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| Formula =C<sub>19</sub>H<sub>15</sub>Cl |
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| MolarMass=278.7754 g/mol |
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| MolarMass =278.7754 g/mol |
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| Appearance=white to yellow solid |
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| Appearance =white to yellow solid |
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| Density= 1.141g/cm<sup>3</sup> |
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| Density = 1.141 g/cm<sup>3</sup> |
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| MeltingPtC=109-112 |
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| MeltingPtC =109 to 112 |
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| BoilingPtC = 230 |
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| BoilingPt=230°C (at 20]) and 374.3°C (at 760mmHg) |
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| BoilingPt_notes = (at 20 ]) and 374.3 °C (at 760 mmHg) |
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| Solubility= |
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| Solubility = |
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| SolubleOther=chloroform 0.1g/ml |
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| SolubleOther =soluble in ], ], ],<ref>{{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 }}</ref> ], ], ]<ref>{{Cite web|url=https://www.scbt.com/scbt/product/trityl-chloride-76-83-5|title=Trityl chloride | CAS 76-83-5}}</ref><!-- --> |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| ExternalMSDS = |
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| ExternalSDS = |
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| FlashPt=177.9°C |
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| FlashPtC = 177.9 |
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| AutoignitionPtC = |
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| Autoignition= |
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'''Triphenylmethyl chloride''' or '''trityl chloride (TrCl)''' is a white solid with the chemical formula C<sub>19</sub>H<sub>15</sub>Cl. It is an ], sometimes used to introduce the trityl ]. |
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==Preparation== |
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Triphenylmethyl chloride is commercially available. It may be prepared by the reaction of ] with ], or by the ] of ] with ] to give the trityl chloride-aluminium chloride adduct, which is then hydrolyzed.<ref>{{OrgSynth | author = W. E. Bachmann; C. R. Hauser; Boyd E. Hudson, Jr. | title = Triphenylchloromethane | collvol = 3 | collvolpages = 841 | prep = cv3p0841 | year = 1955}}.</ref> |
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==Reactions== |
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] can be prepared from trityl chloride dissolved in an aprotic solvent and ]:<ref>{{OrgSynth | author = W. B. Renfrow Jr and C. R. Hauser | title = Triphenylmethylsodium | collvol = 2 | collvolpages = 607| year = 1943 | prep = CV2P0607}}</ref> |
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:(C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>CCl + 2 Na → (C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>CNa + NaCl |
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Reaction with ] gives ]. |
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Trityl chloride reacts with zinc in nonpolar solvents (e.g. ]) to form ].<ref name="Gomberg1900">{{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}}</ref> |
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:2 (C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>CCl + Zn → ((C<sub>6</sub>H<sub>5</sub>)<sub>3</sub>C)<sub>2</sub> + ZnCl<sub>2</sub> |
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==See also== |
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* ] |
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* ] |
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* ] |
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* ] |
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* ] |
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==References== |
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<references/> |
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] |
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] |
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] |