N-methoxy-N-methyl-2-(triphenyl-λ5-phosphanylidene)acetamide

• ChemBase ID: 74877
• Molecular Formular: C22H22NO2P
• Molecular Mass: 363.389341
• Monoisotopic Mass: 363.13881558
• SMILES: P(=CC(=O)N(C)OC)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: CON(C(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1)C
• InChI: InChI=1S/C22H22NO2P/c1-23(25-2)22(24)18-26(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h3-18H,1-2H3
• InChIKey: DGBLSOOPDBHHRX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-methoxy-N-methyl-2-(triphenyl-λ^5-phosphanylidene)acetamide; N-methoxy-N-methyl-2-(triphenyl-$l^{5}-phosphanylidene)acetamide
• IUPAC Traditional name: N-methoxy-N-methyl-2-(triphenyl-λ^5-phosphanylidene)acetamide; N-methoxy-N-methyl-2-(triphenyl-$l^{5}-phosphanylidene)acetamide
• Synonyms: (N-Methoxymethylaminocarbonylmethylene)triphenylphosphorane; N-Methoxy-N-methyl(triphenylphosphoranylidene)acetamide; N-Methoxy-N-methyl-2-(triphenylphosphoranylidene)acetamide; (N-甲氧基甲基氨基羰基亚甲基)三苯基正膦; N-甲氧基-N-甲基(三苯基正膦亚基)乙酰胺

Database IDs

• CAS Number: 129986-67-0
• MDL Number: MFCD00134433
• Beilstein Number: 4198472
• PubChem SID: 162039795; 24863472
• PubChem CID: 2773656

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.0633
• LogD (pH = 7.4): 5.0633
• Log P: 5.0633
• Molar Refractivity: 106.6458 cm^3
• Polarizability: 41.736538 Å^3
• Polar Surface Area: 29.54 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 173-175 °C(lit.)

Safety Information

• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: (C6H5)3P=CHCON(OCH3)CH3

DETAILS

Sigma Aldrich - 376876

Packaging
5, 25 g in glass bottle
Application
Reactant for:
• Synthesis of electron-deficient alkenes via stereoselective olefination of N-sulfonyl imines1
• Phosphine-catalyzed asymmetric addition reactions2
• Cysteine-catalyzed enantioselective intramolecular Rauhut-Currier reaction3
• Wittig olefination4
• Synthesis of aigialomycin D, a Protein Kinase inhibitor and a potential anticancer agent5