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    7396-44-3

    Catalog No. EBD1077815

    CAS 7396-44-3

    Name diethyl [(benzyloxycarbonyl)methyl]phosphonate

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    Basic Information

    Synonyms: diethyl[(benzyloxycarbonyl)methyl]phosphonate (diethoxyphosphoryl)aceticacidbenzylester benzylO,O-diethylphosphonoacetate benzyldiethylphosphorylacetate benzyldiethoxyphosphonoacetate benzyldiethylphosphonoacetate diethyl(benzyloxycarbonylmethyl)phosphonate

    Molecular Formula: C13H19O5P

    Molecular Weight: 286.26

    Categories: Synthetic Chemistry > Organic Building Blocks > Phosphorus Compounds Synthetic Chemistry > Basic Synthetic Reagents > C-C Bond Formation Reagents

    Product Description:
    Diethyl [(benzyloxycarbonyl)methyl]phosphonate is an organophosphorus compound characterized by a phosphonate ester group and a benzyl-protected carboxylic acid equivalent. It serves as a versatile synthetic building block, specifically as a stabilized phosphonate anion equivalent of glycine. This compound is a key reagent in the Horner-Wadsworth-Emmons (HWE) olefination reaction. Its primary application is in organic synthesis for the construction of α,β-unsaturated esters, amides, and related compounds. The phosphonate moiety acts as a stabilized carbanion precursor, which reacts with aldehydes or ketones to form alkenes with high (E)-selectivity under mild conditions. This makes it a valuable tool for introducing dehydroamino acid units and other unsaturated structures into target molecules. While not a final product itself, it is a fundamental reagent in medicinal chemistry research for synthesizing peptide mimetics and in materials science for preparing conjugated systems. Its utility stems from its stability, ease of handling compared to some other phosphorus ylides, and the predictability of the HWE reaction outcome.
    Physical Properties

    Boiling Point: 386.9°C at 760 mmHg

    Flash Point: 201.3°C

    Density: 1.167g/cm3

    mg g kg ml l t