(Acetylmethylene)triphenylphosphorane, 99%, Thermo Scientific Chemicals

Description

(Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
(Acetylmethylene)triphenylphosphorane is used as a Wittig reagent in synthetic chemistry, especially for the synthesis of functionalized pyrrolidines and cyclobutanones. It plays as a vital role in asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin.It is also employed as a reactant in the preparation of 1,2-dioxanes with antitrypanosomal activity. Further, it is used in the preparation of amphibian pyrrolizidine alkaloids through allylic aminations and silicon-containing acyclic dienone musk odorants. In addition to this, it is involved in Domino Suzuki/Heck coupling reactions to prepare fluorenylidenes.

Solubility
Soluble in chloroform. Slightly soluble in methanol.

Notes
Air sensitive. Incompatible with strong oxidizing agents.

Specifications

Chemical Identifiers

• CAS: 1439-36-7
• Molecular Formula: C21H19OP
• Molecular Weight (g/mol): 318.36
• MDL Number: MFCD00008774
• InChI Key: KAANTNXREIRLCT-UHFFFAOYSA-N
• Synonym: acetylmethylene triphenylphosphorane, 1-triphenylphosphoranylidene propan-2-one, 1-triphenylphosphoranylidene-2-propanone, 1-triphenylphosphoranylidene acetone, 2-propanone, 1-triphenylphosphoranylidene, acetonylidenetriphenyl phosphorane, acetylmethylene triphenylphosphine, triphenylacetylmethylene phosphorane, 2-propanone, triphenylphosphoranylidene, triphenylphosphoranylidene-2-propanone
• PubChem CID: 15038
• IUPAC Name: 1-(triphenyl-$l^{5}-phosphanylidene)propan-2-one
• SMILES: CC(=O)C=P(C1=CC=CC=C1)(C1=CC=CC=C1)C1=CC=CC=C1

• Melting Point: 204°C to 209°C
• Quantity: 250 g
• Beilstein: 750077
• Sensitivity: Air sensitive
• Solubility Information: Soluble in chloroform. Slightly soluble in methanol.
• Formula Weight: 318.36
• Percent Purity: 99%
• Chemical Name or Material: (Acetylmethylene)triphenylphosphorane

Safety and Handling

EINECSNumber	215-878-2
RTECSNumber	UC3900000
TSCA	No
Recommended Storage	Keep cold

SDS

RUO – Research Use Only