Dimethyl (1-Diazo-2-oxopropyl)phosphonate

• CAT Number: R030702
• CAS Number: 90965-06-3
• Molecular Formula: C₅H₉N₂O₄P
• Molecular Weight: 192.11
• Purity: ≥95%
• Synonyms: Bestmann-Ohira Reagent; 1-Diazo-1-(dimethyl phosphono)acetone; Bestmann Reagent; Dimethyl (1-Azo-2-oxopropyl)phosphonate; Dimethyl (1-azoacetonyl)phosphonate; Dimethyl (1-Diazo-2-oxopropyl)phosphonate;?Dimethyl (acetyldiazomethyl)phosphonate; Ohira-B
• Storage: Store at -20°C
• IUPAC Name: 1-diazo-1-dimethoxyphosphorylpropan-2-one
• InChI: InChI=1S/C5H9N2O4P/c1-4(8)5(7-6)12(9,10-2)11-3/h1-3H3
• InChIKey: SQHSJJGGWYIFCD-UHFFFAOYSA-N
• SMILES: CC(=O)C(=[N+]=[N-])P(=O)(OC)OC

Dimethyl (1-diazo-2-oxopropyl)phosphonate(CAT: R030702) is a diazophosphonate compound featuring a reactive diazo group adjacent to a carbonyl and phosphonate ester functionality. This unique structure makes it a versatile reagent in organic synthesis, particularly in cyclopropanation, carbene transfer, and ylide-mediated transformations. It is frequently employed in the synthesis of heterocycles, natural products, and bioactive molecules, as well as in exploring novel C–C and C–X bond-forming reactions. The phosphonate moiety enhances stability while providing a handle for further derivatization, making it a valuable tool in medicinal chemistry, agrochemical research, and method development in synthetic organic chemistry.