Diazodiphenylmethane

Diazodiphenylmethane
Names
	Preferred IUPAC name (Diazomethylene)dibenzene
	Other names Diazodiphenylmethane
Identifiers
CAS Number	883-40-9;
3D model (JSmol)	Interactive image;
ChemSpider	55172;
MeSH	C480088
PubChem CID	61230;
UNII	VG5TWB4MMS ;
CompTox Dashboard (EPA)	DTXSID80236941 ;
	InChI InChI=1S/C13H10N2/c14-15-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H Key: ITLHXEGAYQFOHJ-UHFFFAOYSA-N;
	SMILES c1ccc(cc1)C(=[N+]=[N-])c2ccccc2;
Properties
Chemical formula	C13H10N2
Molar mass	194.237 g·mol−1
Appearance	red-black solid
Melting point	30 °C (86 °F; 303 K)
Magnetic susceptibility (χ)	−115·10−6 cm3·mol−1
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	unstable
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Diazodiphenylmethane is an organic reagent with the chemical formula C₁₃H₁₀N₂. It exists as red-black crystals that melts just above room temperature.^[1]

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.^[2] An improved procedure involves dehydrogenation with oxalyl chloride.^[3]

Uses

It can be used to synthesise (diphenyl)methyl esters and ethers with carboxylic acids and alcohols respectively.^[4]^[5]

It can also generate the (diphenyl)methyl carbene and nitrogen gas upon illumination by ultraviolet light or heating.^[6]^[7] It can also be electrolysed to form the Ph₂CN⁻
₂ anion, which can decompose to form the 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.^[8]

References

^ "Diphenyldiazomethane;1,1'-(Diazomethylene)bisbenzene;Diazodiphenylmethane,physical properties,suppliers,CAS,MSDS,structure,Molecular Formula, Molecular Weight ,Solubility,boiling point, melting point". chemyq.com. Archived from the original on 2016-08-04. Retrieved 2016-06-06.
^ Miller, J (1959-04-01). "Notes- Preparation of Crystalline Diphenyldiazomethane". The Journal of Organic Chemistry. 24 (4): 560–561. doi:10.1021/jo01086a603. ISSN 0022-3263.
^ "orgsyn.org/demo.aspx?prep=V85P0189". orgsyn.org. Retrieved 2017-03-11.
^ Jovanovic, Bratislav; Assaleh, Fathi; Marinkovic, Aleksandar (2004). "Kinetics of the reaction of 5-substituted orotic acids with diazodiphenylmethane". Journal of the Serbian Chemical Society. 69 (11): 949–953. doi:10.2298/jsc0411949j. Archived from the original on 2020-02-13.
^ Petursson, Sigthor (2003-04-22). "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". Carbohydrate Research. 338 (9): 963–968. doi:10.1016/S0008-6215(03)00039-9.
^ Parker, Vernon D.; Bethell, Donald (1987-08-01). "Carbene cation radicals: the kinetics of their formation from diazoalkane cation radicals and their reactions". Journal of the American Chemical Society. 109 (17): 5066–5072. doi:10.1021/ja00251a002. ISSN 0002-7863.
^ Sabongi, Gebran J. (2012-12-06). Chemical Triggering: Reactions of Potential Utility in Industrial Processes. Springer Science & Business Media. ISBN 9781461309079.
^ McDonald, Richard N.; Triebe, F. M.; January, J. R.; Borhani, K. J.; Hawley, M. D. (1980-12-01). "Hypovalent radicals. 6. Electroreduction of diazodiphenylmethane - intermediacy of Ph2CN2-.cntdot. and Ph2C-.cntdot". Journal of the American Chemical Society. 102 (27): 7867–7872. doi:10.1021/ja00547a007. ISSN 0002-7863.

[1] "Diphenyldiazomethane;1,1'-(Diazomethylene)bisbenzene;Diazodiphenylmethane,physical properties,suppliers,CAS,MSDS,structure,Molecular Formula, Molecular Weight ,Solubility,boiling point, melting point". chemyq.com. Archived from the original on 2016-08-04. Retrieved 2016-06-06.

[2] Miller, J (1959-04-01). "Notes- Preparation of Crystalline Diphenyldiazomethane". The Journal of Organic Chemistry. 24 (4): 560–561. doi:10.1021/jo01086a603. ISSN 0022-3263.

[3] "orgsyn.org/demo.aspx?prep=V85P0189". orgsyn.org. Retrieved 2017-03-11.

[4] Jovanovic, Bratislav; Assaleh, Fathi; Marinkovic, Aleksandar (2004). "Kinetics of the reaction of 5-substituted orotic acids with diazodiphenylmethane". Journal of the Serbian Chemical Society. 69 (11): 949–953. doi:10.2298/jsc0411949j. Archived from the original on 2020-02-13.

[5] Petursson, Sigthor (2003-04-22). "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". Carbohydrate Research. 338 (9): 963–968. doi:10.1016/S0008-6215(03)00039-9.

[6] Parker, Vernon D.; Bethell, Donald (1987-08-01). "Carbene cation radicals: the kinetics of their formation from diazoalkane cation radicals and their reactions". Journal of the American Chemical Society. 109 (17): 5066–5072. doi:10.1021/ja00251a002. ISSN 0002-7863.

[7] Sabongi, Gebran J. (2012-12-06). Chemical Triggering: Reactions of Potential Utility in Industrial Processes. Springer Science & Business Media. ISBN 9781461309079.

[8] McDonald, Richard N.; Triebe, F. M.; January, J. R.; Borhani, K. J.; Hawley, M. D. (1980-12-01). "Hypovalent radicals. 6. Electroreduction of diazodiphenylmethane - intermediacy of Ph2CN2-.cntdot. and Ph2C-.cntdot". Journal of the American Chemical Society. 102 (27): 7867–7872. doi:10.1021/ja00547a007. ISSN 0002-7863.

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