| Identification | Back Directory | [Name]
METHYL DIAZOACETATE | [CAS]
6832-16-2 | [Synonyms]
METHYL DIAZOACETATE
Diazo Methyl acetate
methyl 2-diazoacetate
2-diazonio-1-methoxyethenolate | [Molecular Formula]
C3H4N2O2 | [MOL File]
6832-16-2.mol | [Molecular Weight]
100.076 |
| Chemical Properties | Back Directory | [Boiling point ]
187.47°C (rough estimate) | [density ]
1.4457 (rough estimate) | [refractive index ]
1.5110 (estimate) | [InChI]
InChI=1S/C3H4N2O2/c1-7-3(6)2-5-4/h2H,1H3 | [InChIKey]
MIVRMHJOEYRXQB-UHFFFAOYSA-N | [SMILES]
C(OC)(=O)C=[N+]=[N-] |
| Hazard Information | Back Directory | [Uses]
Methyl Diazoacetate is used for cyclopropanation of alkenes; cyclopropenation of alkynes; addition to aromatic substrates; insertion into polar X-H bonds; condensation with carbonyls;1,3-dipolar cycloaddition with enamines and alkynes, yielding substituted pyrazolines and pyrazoles.
| [Synthesis Reference(s)]
1.Womack, E. B.; Nelson, A. B. In Organic Synthesis; Horning, E. C.; Ed.; Wiley: New York, 1955; Vol. 3, p 392.
| [Synthesis]
Methyl Diazoacetate's synthesis: from methyl glycinate hydrochloride and sodium nitrite upon treatment with a 5% solution of sulfuric acid.1
| [Precautions]
Extreme caution should be exercised in handling methyl diazoacetate since it is thermally unstable and has been found to detonate if heated rapidly or overheated (do not expose to temperatures >50 °C), emitting toxic fumes of NOx. Methyl Diazoacetate is toxic and should be handled in a well-ventilated fume hood.
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