5-DIAZOMELDRUM'S ACID Chemical Properties

Melting point:

95 °C

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

solubility 

sol ether, dichloromethane, and acetonitrile.

form 

powder to crystal

color 

White to Orange to Green

CAS DataBase Reference

7270-63-5

Safety Information

RIDADR 

1325

HS Code 

2932.99.9090

HazardClass 

4.1

PackingGroup 

III

5-DIAZOMELDRUM'S ACID Usage And Synthesis

Uses

5-Diazomeldrum's acid is a reagent useful in the synthesis of α-oxyketenes and in [2 + 2] cycloaddition reactions with olefins.

Preparation

Most commonly by diazo transfer to Meldrum's acid. A number of procedures involving the use of sulfonyl azide reagents have been reported.Typical procedures involve the addition of the sulfonyl azide to a solution of Meldrum's acid containing a tertiary amine base. Aqueous workup followed by chromatography on silica gel provide the diazo compound in yields ranging from 40 to 76%. A modification using KF on alumina is reported to provide a 90% yield of 5-Diazomeldrum's acid. Diazo compounds are potentially explosive as are certain sulfonyl azides, such as tosyl azide. For this reason, extreme care must be observed in the synthesis and use of this compound, with all operations being conducted behind a blast shield in a fume hood.

storage

In addition to the previously mentioned explosion hazard which this  reagent presents, there are health related hazards that must also be considered. Diazo compounds, as a class,  are toxic and irritating and can be sensitizers. They must be used in a well-ventilated fume hood and not  come in contact with skin. For a description of the hazards associated with this class of compounds, see the  handling and storage precautions listed for Diazomethane.

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