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Dimethyl (1-diazo-2-oxopropyl)phosphonate solution

ALDRICH/742724 - ~10% in acetonitrile (H-NMR), ≥96% (HPLC)

Synonym: Bestmann-Ohira Reagent; Dimethyl (1-azoacetonyl)phosphonate solution; Dimethyl (acetyldiazomethyl)phosphonate solution

CAS Number: 90965-06-3
Empirical Formula (Hill Notation): C5H9N2O4P
Molecular Weight: 192.11
MDL Number: MFCD07368360
Linear Formula: C5H9N2O4P
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-742724-10ML 10 mL
 $502.00
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assay ≥96% (HPLC)
concentration ~10% in acetonitrile (H-NMR)
density 0.800-0.850 g/mL at 20 °C
form liquid
functional group ketone
  phosphonate
InChI 1S/C5H9N2O4P/c1-4(8)5(7-6)12(9,10-2)11-3/h1-3H3
InChI key SQHSJJGGWYIFCD-UHFFFAOYSA-N
Quality Level 100 
reaction suitability reaction type: C-C Bond Formation
refractive index n20/D 1.352-1.354
SMILES string COP(=O)(OC)C(=[N+]=[N-])C(C)=O
storage temp. 2-8°C
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.
Purity ≥96% (HPLC)
Density 0.800-0.850 g/mL at 20 °C
Refractive Index n20/D 1.352-1.354
Storage Temp. 2-8°C
UNSPSC 12352108

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