Diazodiphenylmethane

Diazodiphenylmethane is an organic reagent with the chemical formula C₁₃H₁₀N₂. It exists as red-black crystals that melt just above room temperature.^[2]

Diazodiphenylmethane

Names
Preferred IUPAC name [Diazo(phenyl)methyl]benzene[1]
Other names Diazodiphenylmethane
Identifiers
CAS Number	883-40-9
3D model (JSmol)	Interactive image
ChemSpider	55172
MeSH	C480088
PubChem CID	61230
UNII	VG5TWB4MMS Y
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

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.^[3] An improved procedure involves dehydrogenation with oxalyl chloride.^[4]

Uses

It can be used to synthesize (diphenyl)methyl esters and ethers with carboxylic acids and alcohols respectively.^[5][6]

It can also generate (diphenyl)methyl carbene and nitrogen gas upon illumination by ultraviolet light or by heating.^[7][8] It can also be electrolyzed form a Ph₂CN⁻
₂ 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.^[9]