Carbomethoxymethylene triphenylphosphorane, CAS No. 2605-67-6

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2605-67-6

Catalog No. EBD35223

CAS 2605-67-6

Name Carbomethoxymethylene triphenylphosphorane

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Basic Information

Synonyms: (triphenylphosphoranylidene)aceticacidmethylester auroraka-874 (carbomethoxymethylene)triphenylphosphorane (methoxycarbonylmethylene)triphenylphosphorane methyl(triphenylphosphoranylidene)acetate (2-methoxy-2-oxoethylidene)triphenylphosphorane aceticacid,(triphenylphosphoranylidene)-,methylester (triphenylphosphoranylidene)-aceticacimethylester CMMTPP carbmethoxymethylenetriphenylphosphorane methyl(triphenyl-lambda~5~-phosphanylidene)acetate Carbethoxymethylene)triphenylphosphorane Carbomethoxymethylenetriphenylphosphorane AURO

Molecular Formula: C21H19O2P

Molecular Weight: 334.35

MDL Number: MFCD00008455

Categories: Synthetic Chemistry > Basic Synthetic Reagents > C-C Bond Formation Reagents

Product Description:

Carbomethoxymethylene triphenylphosphorane is a stabilized phosphorus ylide, specifically a Wittig reagent. Its structure features a triphenylphosphonium group adjacent to a carbanion stabilized by an adjacent ester (carbomethoxy) group. This compound is a white to off-white crystalline solid, stable under normal conditions due to the resonance stabilization of the ylide. This reagent is primarily utilized in the Wittig reaction for the synthesis of ж┴,ж┬-unsaturated esters. It reacts with aldehydes and ketones to form carbon-carbon double bonds, yielding methyl (E)- or (Z)-alkenoates with high stereoselectivity. This makes it an indispensable tool in organic synthesis for constructing complex molecules, including natural products, pharmaceuticals, and fine chemicals. Its stabilized nature allows for easier handling and predictable reactivity compared to non-stabilized ylides. As a common synthetic building block, it is widely employed in research laboratories for method development and target-oriented synthesis. It serves as a key intermediate for introducing functionalized alkene moieties. While its primary application is in synthetic chemistry, it can also be used as a precursor for other phosphonium salts or in the preparation of specific pharmaceutical intermediates, though its role remains firmly within the domain of general organic synthesis reagents.

Physical Properties

Melting Point: 168-172 °C(lit.)

Boiling Point: 479.138 °C at 760 mmHg

Flash Point: 256.768 °C

Density: 1.177 g/cm3

Solubility: insoluble

Storage: Refrigerator (+4°C)

Analytical Data

Appearance: white to off-white powder