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Revision as of 15:39, 8 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEBI').← Previous edit		Latest revision as of 21:13, 31 December 2023 edit undoMichael7604 (talk | contribs)Extended confirmed users8,895 edits →Derivatives
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	{{chembox		{{chembox
	| Watchedfields = changed		|Watchedfields = changed
	| verifiedrevid = 414430668		|verifiedrevid = 443695347
	| Name = Diphenylacetylene		|Name = Diphenylacetylene
	| ImageFile = diphenylacetylene.png		|ImageFile = DiphenylacetyleneSVG.svg
	| ImageSize = 250		|ImageSize = 200
		⚫	|ImageFile1 = Diphenylacetylene-3D-balls.png
	| ImageName =
		⚫	|ImageSize1 = 200
⚫	| ImageFile1 = Diphenylacetylene-3D-balls.png
		⚫	|ImageFile2 = Diphenylacetylene-3D-vdW.png
⚫	| ImageSize1 = 250
		⚫	|ImageSize2 = 200
⚫	| ImageFile2 = Diphenylacetylene-3D-vdW.png
			|PIN = 1,1′-Ethynediyldibenzene<!-- (PIN; multiplicative name, see P-51.3) -->
⚫	| ImageSize2 =
	| IUPACName = 2-phenylethynylbenzene<!-- according to PubChem -->		|OtherNames = Tolane<br />1,2-Diphenylethyne<br />Diphenylethyne<br />2-Phenylethynylbenzene<!-- according to PubChem --><br />Tolan
		⚫	|Section1={{Chembox Identifiers
	| OtherNames = Tolan<br />Diphenylacetylene<br />1,2-diphenylethyne
		⚫	|ChEBI_Ref = {{ebicite|correct|EBI}}
⚫	| Section1 = {{Chembox Identifiers
	| ChEBI = 51579		|ChEBI = 51579
	| SMILES = c1ccc(cc1)C#Cc2ccccc2		|SMILES = c1ccc(cc1)C#Cc2ccccc2
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 9961		|ChemSpiderID = 9961
	| ChEMBL_Ref = {{ebicite|correct|EBI}}		|ChEMBL_Ref = {{ebicite|correct|EBI}}
	| ChEMBL = 223309		|ChEMBL = 223309
			|EC_number = 207-926-6
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			|UNII = Y70JA8HB75
⚫	| StdInChI = 1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
			|Beilstein = 606478
⚫	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
		⚫	|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
⚫	| StdInChIKey = JRXXLCKWQFKACW-UHFFFAOYSA-N
		⚫	|StdInChI = 1S/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
⚫	| CASNo_Ref = {{cascite|correct|CAS}}
		⚫	|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
⚫	| CASNo = 501-65-5
		⚫	|StdInChIKey = JRXXLCKWQFKACW-UHFFFAOYSA-N
⚫	| PubChem = 10390
			|CASNo_Ref = {{cascite|correct|CAS}}
⚫	| InChI = 1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
		⚫	|CASNo = 501-65-5
⚫	| InChIKey = JRXXLCKWQFKACW-UHFFFAOYAN
		⚫	|PubChem = 10390
		⚫	|InChI = 1/C14H10/c1-3-7-13(8-4-1)11-12-14-9-5-2-6-10-14/h1-10H
		⚫	|InChIKey = JRXXLCKWQFKACW-UHFFFAOYAN
		⚫	}}
		⚫	|Section2={{Chembox Properties
			|C=14|H=10
		⚫	|Appearance = Colorless solid
			|Density = 1.136 g cm<sup>−3</sup><ref name=Xray>{{cite journal |doi=10.1107/S0567740877011674|title=A Reinvestigation of Tolane|year=1977|last1=Mavridis|first1=A.|last2=Moustakali-Mavridis|first2=I.|journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry|volume=33|issue=11|pages=3612–3615}}</ref>
		⚫	|Solubility = Insoluble
			|MeltingPtC = 62.5
			|BoilingPtC = 170
			|BoilingPt_notes = at 19 mmHg
		⚫	}}
		⚫	|Section3={{Chembox Structure
		⚫	|Dipole = 0 ]
		⚫	}}
		⚫	|Section7={{Chembox Hazards
			| ExternalSDS =
		⚫	}}
		⚫	|Section8={{Chembox Related
			| OtherCompounds = ]<br />]
	}}		}}
⚫	| Section2 = {{Chembox Properties
	| Formula = C<sub>14</sub>H<sub>10</sub>
	| MolarMass = 178.24 g/mol
⚫	| Appearance = colorless solid
	| Density = 0.990 g cm<sup>-3</sup>, solid
⚫	| Solubility = insoluble
	| MeltingPt = 62.5 °C, 335.7 K, 144.5 °F
	| BoilingPt = 0–97 °C/0.3 mmHg
⚫	}}
⚫	| Section3 = {{Chembox Structure
	| MolShape = sp2 and sp at carbon
⚫	| Dipole = 0 ]
⚫	}}
⚫	| Section7 = {{Chembox Hazards
	| ExternalMSDS =
⚫	}}
⚫	| Section8 = {{Chembox Related
	| OtherCpds = ]<br />]
⚫	}}
	}}		}}
	'''Diphenylacetylene''' is the ] C<sub>6</sub>H<sub>5</sub>C≡CC<sub>6</sub>H<sub>5</sub>. The molecule consists of ] groups attached to both ends of an ]. It is a colorless crystalline material that is widely used as a building block in ] and as a ligand in ].		'''Diphenylacetylene''' is the ] C<sub>6</sub>H<sub>5</sub>C≡CC<sub>6</sub>H<sub>5</sub>. The molecule consists of two ] groups attached to a C<sub>2</sub> unit. A colorless solid, it is used as a building block in ] and as a ] in ].
	==Preparation==		==Preparation and structure==
			In one preparation for this compound, ] is condensed with ] to give the bis(]), which is oxidized with ].<ref name = cv4p0377>{{cite journal |author1=Cope, A. C.|author2=Smith, D. S.|author3=Cotter, R. J. | title = Diphenylacetylene |journal=Organic Syntheses | volume = 34|doi= 10.15227/orgsyn.034.0042 | year=1954|page=42}}</ref> Alternatively ] is brominated, and the resulting dibromodiphenylethane is subjected to ].<ref>{{cite journal | author1 = Lee Irvin Smith|author2= M. M. Falkof | volume= 22|page=50|doi=10.15227/orgsyn.022.0050| title = Diphenylacetylene|journal= Organic Syntheses |year=1942}}</ref> Yet another method involves the coupling of ] and the copper salt of phenylacetylene in the ]. The related ] involves the coupling of iodobenzene and ].
	Several preparations for this compound exist:
	* ] is condensed with ] to give the bis(hydrazone), which is oxidized with ].<ref name = cv4p0377>{{OrgSynth | author = Cope, A. C.; Smith, D. S.; Cotter, R. J. | title = Diphenylacetylene | collvol = 4 | collvolpages = 377 | prep = cv4p0377}}</ref>
	* ] is brominated, then ],<ref>{{OrgSynth | author = Lee Irvin Smith and M. M. Falkof | collvol = 3 | collvolpages = 350 | prep = cv3p0350 | title = Diphenylacetylene}}</ref> but the product can be contaminated with stilbene, which is difficult to remove.<ref name = cv4p0377/>
	* One method starts from ] and the copper salt of phenylacetylene in the ]
			Diphenylacetylene is a planar molecule. The central C≡C distance is 119.8 picometers.<ref name=Xray/>
	==Interesting derivatives==
⚫	*Reaction of Ph<sub>2</sub>C<sub>2</sub> with ] results in the formation of ].<ref>{{OrgSynth | author = Fieser, L. F. | title = Hexaphenylbenzene | collvol = 5 | collvolpages = 604 | prep = cv5p0604}}</ref>
			==Derivatives==
	*Reaction of Ph<sub>2</sub>C<sub>2</sub> with ] in the presence of ] affords the 3-alkoxy] which coverts to the cyclopropenium ion.<ref>{{OrgSynth | author = Xu, R. Breslow, R. | title = 1,2,3-Triphenylcyclopropendium Bromide | collvol = 9 | collvolpages = 730 | prep = cv9p0730}}</ref>
		⚫	Reaction of diphenylacetylene with ] results in the formation of ] in a ].<ref>{{cite journal | author = Fieser, L. F.| title = Hexaphenylbenzene | journal = Organic Syntheses | volume= 46|page=44|doi= 10.15227/orgsyn.046.0044 | year=1966}}</ref>
			:]
			] catalyzes ] of diphenylacetylene to form hexaphenylbenzene.<ref>{{cite journal |last1=Vij |first1=V. |last2=Bhalla |first2=V. |last3=Kumar |first3=M. |date=8 August 2016 |title=Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold |journal=] |volume=116 |issue=16 |pages=9565–9627 |doi=10.1021/acs.chemrev.6b00144}}</ref>
			:]
			Reaction of Ph<sub>2</sub>C<sub>2</sub> with ] in the presence of ] affords 3-''tert''-butoxy-1,2,3-triphenyl], which converts to 1,2,3-triphenyl] bromide after the elimination of ''tert''-butoxide.<ref>{{cite journal|first1 = Ruo|last1 = Xu|first2 = Ronald|year=1997|last2 = Breslow|title = 1,2,3-Triphenylcyclopropenium Bromide| journal=Organic Syntheses |volume = 74|pages = 72|doi = 10.15227/orgsyn.074.0072}}</ref>
	==References==		==References==
	<references/>		<references/>
	]		]
	]		]
	]
	]
	]
	]