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Diazodiphenylmethane

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Diazodiphenylmethane
Names
Preferred IUPAC name benzene
Other names Diazodiphenylmethane
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
MeSH C480088
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H10N2/c14-15-13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10HKey: ITLHXEGAYQFOHJ-UHFFFAOYSA-N
SMILES
  • c1ccc(cc1)C(==)c2ccccc2
Properties
Chemical formula C13H10N2
Molar mass 194.237 g·mol
Appearance red-black solid
Melting point 30 °C (86 °F; 303 K)
Magnetic susceptibility (χ) −115·10 cm·mol
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 , 100 kPa). Infobox references
Chemical compound

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

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. An improved procedure involves dehydrogenation with oxalyl chloride.

Uses

It can be used to synthesize (diphenyl)methyl esters and ethers with carboxylic acids and alcohols respectively.

It can also generate (diphenyl)methyl carbene and nitrogen gas upon illumination by ultraviolet light or by heating. 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.

References

  1. Diazodiphenylmethane. CID 61230 from PubChem. Retrieved 2025-01-15.
  2. "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.
  3. 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.
  4. "orgsyn.org/demo.aspx?prep=V85P0189". orgsyn.org. Retrieved 2017-03-11.
  5. 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.
  6. 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.
  7. 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.
  8. Sabongi, Gebran J. (2012-12-06). Chemical Triggering: Reactions of Potential Utility in Industrial Processes. Springer Science & Business Media. ISBN 9781461309079.
  9. 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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