Diazodiphenylmethane is an organic reagent with the chemical formula C13H10N2. It exists as red-black crystals that melts just above room temperature.[1]
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Preferred IUPAC name
(Diazomethylene)dibenzene | |
Other names
Diazodiphenylmethane
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Identifiers | |
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3D model (JSmol)
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MeSH | C480088 |
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CompTox Dashboard (EPA)
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Properties | |
C13H10N2 | |
Molar mass | 194.237 g·mol−1 |
Appearance | red-black solid |
Melting point | 30 °C (86 °F; 303 K) |
−115·10−6 cm3·mol−1 | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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unstable |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
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]