1-bromo-2-diethoxyphosphorylethane, CAS No. 5324-30-1

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5324-30-1

Catalog No. EBD91910

CAS 5324-30-1

Name 1-bromo-2-diethoxyphosphorylethane

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Basic Information

Synonyms: Diethyl2-bromoethylphosphonate Diethyl2-bromoethanephosphonate 2-Bromoethylphosphonicaciddiethylester Diethyl2-bromoethylphosphonate,(2-Bromoethylphosphonicaciddiethylester) Diethyl-2-bromoethylphosphonate 1-bromo-2-diethoxyphosphoryl-ethane 1-bromo-2-diethoxyphosphorylethane phosphonicacid,P-(2-bromoethyl)-,diethylester diethyl(2-bromoethyl)phosphonate o,o-diethyl(2-bromoethyl)phosphonate (2-bromoethyl)phosphonicaciddiethylester phosphonicacid,(2-bromoethyl)-,diethylester(6ci,7ci,8ci,9ci)

Molecular Formula: C6H14BrO3P

Molecular Weight: 245.05

MDL Number: MFCD00000239

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

Product Description:

2-Bromoethyl diethyl phosphate is an organophosphorus compound characterized by a bromoethyl group linked to a diethyl phosphate ester. It serves as a versatile bifunctional reagent in organic synthesis, combining the reactivity of an alkyl halide with the properties of a phosphate ester. Its primary application is as a key reagent in the Wadsworth-Emmons reaction, a variant of the Horner-Wadsworth-Emmons (HWE) olefination. In this role, it acts as a phosphoryl-stabilized carbanion precursor. After deprotonation, it reacts with aldehydes or ketones to produce vinyl phosphates, which are valuable intermediates that can be further transformed into various alkenes, including terminal alkenes, upon hydrolysis or reduction. This makes it a crucial tool for constructing carbon-carbon double bonds in complex molecule synthesis, particularly in pharmaceutical and agrochemical research for building olefinic scaffolds. The compound is typically handled under inert atmosphere due to the sensitivity of the phosphonate anion precursors. It is commercially available as a reagent for specialized organic synthesis applications.

Physical Properties

Boiling Point: 75 °C/1 mmHg(lit.)

Flash Point: 110 °C

Density: 1.348 g/mL at 25 °C(lit.)

Refractivity: n20/D 1.461(lit.)

Storage: Refrigerator