| Identification | Back Directory | [Name]
Diazoacetylbenzene | [CAS]
3282-32-4 | [Synonyms]
Nsc25280
Diazoacetylbenzene
Benzoyldiazomethane
α-Diazoacetophenone
2-Diazoacetophenone
a-Diazoacetophenone
Acetophenone, 2-diazo-
2-Diazo-1-phenylethanone
.alpha.-Diazoacetophenone
.Omega.-diazoacetophenone
Phenyl diazomethyl ketone
Diazomethyl(phenyl) ketone
Ethanone, 2-diazo-1-phenyl-
2-diazonio-1-phenylethenolate | [Molecular Formula]
C8H6N2O | [MDL Number]
MFCD00033207 | [MOL File]
3282-32-4.mol | [Molecular Weight]
146.15 |
| Chemical Properties | Back Directory | [Melting point ]
49 °C | [Boiling point ]
265.75°C (rough estimate) | [density ]
1.2312 (rough estimate) | [refractive index ]
1.4900 (estimate) | [solubility ]
sol ether, THF; slightly sol pentane. | [form ]
rods | [color ]
pale yellow |
| Hazard Information | Back Directory | [Uses]
α-Diazoacetophenone is used as a precursor to carbenes and carbenoids; reagent for preparation of sulfonium, oxonium, and pyridinium
ylides; 1,3 dipole for heterocycle synthesis; reagent for Lewis acid or transition metal-mediated insertion
reactions; reagent for cyclopropanation of alkenes and for aromatic annulation. | [Preparation]
Preparative Methods of α-Diazoacetophenone: an improved method of synthesis of diazo ketones has been recently published, via
acylation of the lithium enolate of the ketone with 2,2,2-Trifluoroethyl Trifluoroacetate and subsequent
reaction with Methanesulfonyl Azide. [1] Alternatively, acylation of diazomethane with aroyl chlorides in the
presence of triethylamine provides a general method for the synthesis of aromatic diazo ketones.[2] | [storage]
diazoacetophenone is a skin irritant; therefore direct contact should be
avoided. Diazoacetophenone has shown microbial mutagenicity. | [References]
1. Danheiser, R. L.; Miller, R. F.; Brisbois, R. G.; Park, S. Z. JOC 1990, 55, 1959.
2. Bridson, J. N.; Hooz, J. OS 1973, 53, 35. |
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