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6832-16-2

6832-16-2 Structure

6832-16-2 Structure
IdentificationBack 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 PropertiesBack 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 InformationBack 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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