:Diazodiphenylmethane
{{Chembox
| ImageFile = Diazodiphenylmethane.svg
| ImageSize = 200px
| ImageAlt =
| PIN = [Diazo(phenyl)methyl]benzene Diazodiphenylmethane. {{PubChemLink|61230}}. Retrieved 2025-01-15.
| OtherNames = Diazodiphenylmethane
| Section1 = {{Chembox Identifiers
| CASNo = 883-40-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = VG5TWB4MMS
| PubChem = 61230
| ChemSpiderID = 55172
| SMILES = c1ccc(cc1)C(=[N+]=[N-])c2ccccc2
| StdInChI = 1S/C13H10N2/c14-15-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
| StdInChIKey = ITLHXEGAYQFOHJ-UHFFFAOYSA-N
| MeSHName = C480088
}}
| Section2 = {{Chembox Properties
| C=13 | H=10 | N=2
| Appearance = red-black solid
| Density =
| MeltingPtC = 30
| BoilingPt =
| Solubility =
| MagSus = −115·10−6{{nbsp}}cm3·mol−1
}}
| Section3 = {{Chembox Hazards
| MainHazards = unstable
| FlashPt =
| AutoignitionPt =
}}
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Diazodiphenylmethane is an organic reagent with the chemical formula C13H10N2. It exists as red-black crystals that melt just above room temperature.{{Cite web|url=http://chemyq.com/En/xz/xz1/8364rohuk.htm |title=Diphenyldiazomethane;1,1'-(Diazomethylene)bisbenzene;Diazodiphenylmethane,physical properties,suppliers,CAS,MSDS,structure,Molecular Formula, Molecular Weight ,Solubility,boiling point, melting point |website=chemyq.com |access-date=2016-06-06 |url-status=dead |archiveurl=https://web.archive.org/web/20160804033036/http://chemyq.com/En/xz/xz1/8364rohuk.htm |archivedate=2016-08-04 }}
Preparation
Diazodiphenylmethane can be synthesized via the oxidation of benzophenone hydrazone with mercury(II) oxide in diethyl ether and the presence of a basic catalyst.{{Cite journal|last=Miller|first=J|date=1959-04-01|title=Notes- Preparation of Crystalline Diphenyldiazomethane|journal=The Journal of Organic Chemistry|volume=24|issue=4|pages=560–561|doi=10.1021/jo01086a603|issn=0022-3263}} An improved procedure involves dehydrogenation with oxalyl chloride.{{Cite web|url=http://orgsyn.org/demo.aspx?prep=V85P0189|title=orgsyn.org/demo.aspx?prep=V85P0189|website=orgsyn.org|access-date=2017-03-11}}
Uses
It can be used to synthesize (diphenyl)methyl esters and ethers with carboxylic acids and alcohols respectively.{{Cite journal|last=Jovanovic |first=Bratislav |last2=Assaleh |first2=Fathi |last3=Marinkovic |first3=Aleksandar |title=Kinetics of the reaction of 5-substituted orotic acids with diazodiphenylmethane |url=http://www.doiserbia.nb.rs/Article.aspx?ID=0352-51390411949J |archive-url=https://web.archive.org/web/20200213142816/http://www.doiserbia.nb.rs/Article.aspx?ID=0352-51390411949J |url-status=dead |archive-date=2020-02-13 |journal=Journal of the Serbian Chemical Society |volume=69 |issue=11 |pages=949–953 |doi=10.2298/jsc0411949j |year=2004 |doi-access=free }}{{Cite journal|last=Petursson|first=Sigthor|date=2003-04-22|title=Tin(II) chloride catalyzed reactions of diazodiphenylmethane with vicinal diols in an aprotic solvent. The reactions with cis- and trans-1,2-cyclohexanediols and 1,2-propanediol|journal=Carbohydrate Research|volume=338|issue=9|pages=963–968|doi=10.1016/S0008-6215(03)00039-9}}
It can also generate (diphenyl)methyl carbene and nitrogen gas upon illumination by ultraviolet light or by heating.{{Cite journal|last=Parker|first=Vernon D.|last2=Bethell|first2=Donald|date=1987-08-01|title=Carbene cation radicals: the kinetics of their formation from diazoalkane cation radicals and their reactions|journal=Journal of the American Chemical Society|volume=109|issue=17|pages=5066–5072|doi=10.1021/ja00251a002|issn=0002-7863}}{{Cite book|url=https://books.google.com/books?id=FEPaBwAAQBAJ|title=Chemical Triggering: Reactions of Potential Utility in Industrial Processes|last=Sabongi|first=Gebran J.|date=2012-12-06|publisher=Springer Science & Business Media|isbn=9781461309079|language=en}} It can also be electrolyzed form a Ph2CN{{su|b=2|p=−}} anion, which can decompose to form a Ph2C− anion radical. If carried out in dimethylformamide and tetrabutylammonium perchlorate, these can react to form benzophenone azine, which has the formula Ph2C=N-N=CPh2.{{Cite journal|last=McDonald|first=Richard N.|last2=Triebe|first2=F. M.|last3=January|first3=J. R.|last4=Borhani|first4=K. J.|last5=Hawley|first5=M. D.|date=1980-12-01|title=Hypovalent radicals. 6. Electroreduction of diazodiphenylmethane - intermediacy of Ph2CN2-.cntdot. and Ph2C-.cntdot.|journal=Journal of the American Chemical Society|volume=102|issue=27|pages=7867–7872|doi=10.1021/ja00547a007|issn=0002-7863}}