Methyl (triphenylphosphoranylidene)acetate

• CAS: 2605-67-6
• Catalog Number: ACM2605676
• Category: Other Products
• Molecular Weight: 334.355g/mol
• Molecular Formula: C21H19O2P
• Synonyms: 1-(Triphenylphosphonio)-2-oxo-2-methoxyethan-1-ide; methyl(triphenylphosphoranylideneacetate); RTR-011791; NCGC00161084-02; (methoxycarbonylmethylene) triphenylphosphorane; triphenyl phosphanyliden-acetic acid methyl ester; (Carbomethoxymethylene)triphenylphosphorane; NSC-117573; Methyl (triphenyphosphoranylidene)acetate; ST2413263
• IUPAC Name: methyl 2-(triphenyl-λ5-phosphanylidene)acetate
• Canonical SMILES: COC(=O)C=P(C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3
• InChI: InChI=1S/C21H19O2P/c1-23-21(22)17-24(18-11-5-2-6-12-18,19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17H,1H3
• InChI Key: NTNUDYROPUKXNA-UHFFFAOYSA-N
• Application: (Methoxycarbonylmethylene)triphenylphosphorane is used in olefination reactions. Wittig reagent for the two-carbon homologation of aldehydes to α,β-unsaturated esters. it undergoes the Wittig reaction with aldehydes to give substituted methyl acrylates.; ; used in an efficient synthesis of pyrazoles via reaction with methyl diazoacetate in the presence of triethylamine.; ; It is used in the preparation of (triphenylphosphoranylidene)-ketene.; ; The Wittig reaction we performed in class involved the reaction of 2-nitrobenzaldehyde (1) with methyl (triphenylphosphoranylidene) acetate (2) to produce methyl (2E)-3-(2-nitrophenyl) acrylate (3) with a triphenylphosphine oxide (4) side product, and took place in a silica gel matrix to ensure even product dispersion for chromatography.
• Storage: Refrigerator (+4°C)
• Complexity: 400
• Covalently-Bonded Unit Count: 1
• EC Number: 220-018-4
• Exact Mass: 334.112g/mol
• H-Bond Acceptor: 2
• Heavy Atom Count: 24
• Monoisotopic Mass: 334.112g/mol
• NSC Number: 407395
• Rotatable Bond Count: 5
• Topological Polar Surface Area: 26.3A^2