Dimethyl (1-Diazo-2-oxopropyl)phosphonate

Description

Dimethyl (1-diazido-2-oxopropyl)phosphonate is a liquid-added organophosphorus flame retardant with good solubility with water, common organic solvents, and inorganic salts flame retardants, with excellent flame retardant properties, low price and low additive amount and other advantages.

Chemical Properties

Light yellow liquid

Application

Dimethyl (1-diazo-2-oxopropyl)phosphonate can be used as a reagent for the synthesis of:
Ethynyl compounds (alkynes) from aldehydes.
Isoquinoline and pyridine N-oxides by cyclization with oximes in the presence of Rh catalyst.
Dimethyl(diazomethyl)phosphonate through methanolysis, which is further employed as a reagent in the synthesis of enol ethers or alkynes.
Five-member heterocyclic scaffolds of pyrazoles, triazoles, and oxazoles via cycloaddition reaction and multicomponent reaction.

Uses

Reagent for transformation of aldehydes to terminal alkynes and ketones to methyl enol ethers.

reaction suitability

reaction type: C-C Bond Formation

Synthesis

Dissolve NaH (0.67 g, 60% w/w, 16.75 mmol) in benzene (45 mL) and dry THF (15 mL). Cool the mixture on ice. A solution of dimethyl (2-oxopropyl) phosphonate (15.3 mmol) in dry benzene (15 mL) was added. A white solid was formed. The reaction mixture was stirred at room temperature for 1 hour. To the mixture was added a solution of toluidic acid hydrazide (16.23 mmol) in dry benzene (7.5 mL). The mixture was stirred at room temperature overnight. The mixture was filtered with Hyflo. The mixture was concentrated in a vacuum to give dimethyl (1-diazido-2-oxopropyl)phosphonate.