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Revision as of 03:41, 19 April 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit		Latest revision as of 04:43, 11 February 2024 edit undoMaxim Masiutin (talk | contribs)Extended confirmed users, IP block exemptions, Pending changes reviewers30,619 edits Add: bibcode, authors 1-1. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. | #UCB_Other
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	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 406054165
			| Watchedfields = changed
	| ImageFile = Tetraphenylmethane.svg
		⚫	| verifiedrevid = 424798390
	| ImageSize = 100px
	| IUPACName = Tetraphenylmethane		| ImageFileL1 = Tetraphenylmethane.svg
			| ImageSizeL1 = 120px
			| ImageFileR1 = Tetraphenylmethane-from-xtal-view-1-Mercury-3D-bs.png
			| ImageSizeR1 = 120px
			| PIN = 1,1′,1′′,1′′′-Methanetetrayltetrabenzene
	| OtherNames =		| OtherNames =
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo = 630-76-2
	| PubChem =		| CASNo = 630-76-2
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| SMILES = c1ccccc1C(c2ccccc2)(c3ccccc3)c4ccccc4
			| UNII = CM2Q9C446P
			| EC_number = 211-144-0
			| PubChem = 12424
		⚫	| SMILES = c1ccccc1C(c2ccccc2)(c3ccccc3)c4ccccc4
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
			| ChemSpiderID = 11917
			| InChI = 1/C25H20/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
			| InChIKey = PEQHIRFAKIASBK-UHFFFAOYAS
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChI = 1S/C25H20/c1-5-13-21(14-6-1)25(22-15-7-2-8-16-22,23-17-9-3-10-18-23)24-19-11-4-12-20-24/h1-20H
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChIKey = PEQHIRFAKIASBK-UHFFFAOYSA-N
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>25</sub>H<sub>20		| Formula = C<sub>25</sub>H<sub>20</sub>
	| MolarMass = 320.44 g/mol		| MolarMass = 320.44 g/mol
	| Appearance =		| Appearance =
	| Density =		| Density =
	| MeltingPt = 272 °C		| MeltingPtC = 282
	| BoilingPt =		| BoilingPt = 431 °C
	| Solubility =		| Solubility =
	}}		}}
	| Section3 = {{Chembox Hazards		|Section3={{Chembox Structure
			| Structure_ref = <ref>{{Cite journal|last1=Robbins|first1=A.|last2=Jeffrey|first2=G. A.|last3=Chesick|first3=J. P.|last4=Donohue|first4=J.|last5=Cotton|first5=F. A.|last6=Frenz|first6=B. A.|last7=Murillo|first7=C. A.|date=1975-10-01|title=A refinement of the crystal structure of tetraphenylmethane: three independent redeterminations|url=http://scripts.iucr.org/cgi-bin/paper?S0567740875007686|journal=Acta Crystallographica Section B: Structural Crystallography and Crystal Chemistry|volume=31|issue=10|pages=2395–2399|doi=10.1107/S0567740875007686|bibcode=1975AcCrB..31.2395R |issn=0567-7408}}</ref>
⚫	| MainHazards =
			| CrystalStruct = tetragonal
⚫	| FlashPt =
			| PointGroup = S<sub>4</sub>
	| Autoignition =
			| SpaceGroup = P{{overline|4}}2<sub>1</sub>c, No. 114
			| LattConst_a = 10.896 Å
			| LattConst_c = 7.280 Å
			| LattConst_Comment = (20 °C)
			| UnitCellFormulas = 2
	}}		}}
			| Section4 = {{Chembox Hazards
			| GHSPictograms = {{GHS08}}
			| GHSSignalWord = Danger
			| HPhrases = {{H-phrases|350}}
			| PPhrases = {{P-phrases|201|202|281|308+313|405|501}}
		⚫	| MainHazards =
		⚫	| FlashPt =
			| AutoignitionPt =
			}}
	}}		}}
	'''Tetraphenylmethane''' is an ] consisting of a ] core with four ] ]s. It was first synthesized by ] in 1898.		'''Tetraphenylmethane''' is an ] consisting of a ] core with four ] ]s. It was first synthesized by ] in 1898.
			== Synthesis ==
	Gomberg's classical ] in ''scheme 1'' starts by reacting triphenylmethylbromide '''1''' with ] '''2''' to the ] '''3'''. ] with ] then produces the ] '''4''' from which on heating above the ], ] gas evolves with formation of tetraphenylmethane '''5'''.<ref>{{cite journal | title = On tetraphenylmethane | author = M. Gomberg | journal = ] | year = 1898 | volume = 20 | issue = 10 | pages = 773–780 | doi= 10.1021/ja02072a009}}</ref>		Gomberg's classical ] shown below starts by reacting triphenylmethyl bromide '''1''' with ] '''2''' to the ] '''3'''. ] with ] then produces the ] '''4''' from which on heating above the ], ] gas evolves with formation of tetraphenylmethane '''5'''.<ref>{{cite journal | title = On tetraphenylmethane | first= M. |last=Gomberg | journal = ] | year = 1898 | volume = 20 | issue = 10 | pages = 773–780 | doi= 10.1021/ja02072a009| url= https://zenodo.org/record/1428930 }}</ref>
	:]		:]
	Gomberg was able to distinguish this compound from ] (] was not an option given the small differences in the hydrogen fractions of 6.29% and 6.60%) by ] of '''5''' with ] to '''6'''.		Gomberg was able to distinguish this compound from ] (] was not an option given the small differences in the hydrogen fractions of 6.29% and 6.60%) by ] of '''5''' with ] to '''6'''. A strong ] would be able to abstract the methine proton of the nitrated triphenylmethyl compound if present, forming a strongly colored compound.
		⚫	He obtained further evidence for the formation of tetraphenylmethane by reducing the nitro groups to ] groups with ] dust in ] to the ] '''7''', which on exposure to ] eliminates ] to the known compound ] '''8'''.
	A strong ] would be able to abstract the methine proton of the nitrated triphenylmethyl compound if present, forming a strongly colored compound.
		⚫	Gomberg's success in synthesizing tetraphenylmethane set him on the attempt to prepare the next homologue ], which led him to the discovery of the ].
⚫	He obtained further evidence for the formation of tetraphenylmethane by reducing the nitro groups to ] groups with ] dust in ] to the ] '''7''' which on exposure to ] eliminates ] to the known compound ] '''8'''.
⚫	Gomberg's success in synthesizing tetraphenylmethane set him on the attempt to prepare the next homologue ] which led him to the discovery of the ].
	== See also==		== See also==
			* ]
	* ]		* ]
	* ]		* ]
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