158755

1-(Triphenylphosphoranylidene)-2-propanone

99%

• Synonym(s): (2-Oxopropylidene)triphenylphosphorane, Acetylmethylene-triphenylphosphorane, Methyl (triphenylphosphoranylidene)methyl ketone, NSC 407394
• Linear Formula: CH₃COCH=P(C₆H₅)₃
• CAS Number: 1439-36-7
• Molecular Weight: 318.35
• Beilstein: 750077
• EC Number: 215-878-2
• MDL number: MFCD00008774
• UNSPSC Code: 12352115
• PubChem Substance ID: 24849772
• NACRES: NA.22

Properties

• Assay: 99%
• form: solid
• reaction suitability: reaction type: C-C Bond Formation
• mp: 203-205 °C (lit.)
• functional group: ketone; phosphine
• SMILES string: CC(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3
• InChI: 1S/C21H19OP/c1-18(22)17-23(19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21/h2-17H,1H3
• InChI key: KAANTNXREIRLCT-UHFFFAOYSA-N

Description

Application

Reactant for:

• Cascade reactions of enals for enantioselective synthesis of indane derivatives
• Enantioselective conjugate addition for synthesis of α-branched indoles
• Synthesis of 1,2-dioxanes with antitrypanosomal activity
• Asymmetric allylboration for enantioselective synthesis of (+)-awajanomycin
• Domino Suzuki / Heck coupling reactions for preparation of fluorenylidenes
• Synthesis of amphibian pyrrolizidine alkaloids via allylic aminations
• Synthesis of silicon-containing acyclic dienone musk odorants

Wittig reagent used recently in the syntheses of functionalized pyrrolidines and cyclobutanones.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves