2-(triphenyl-$l^{5}-phosphanylidene)acetonitrile

• ChemBase ID: 74856
• Molecular Formular: C20H16NP
• Molecular Mass: 301.321501
• Monoisotopic Mass: 301.10203615
• SMILES: P(=CC#N)(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: N#CC=P(c1ccccc1)(c1ccccc1)c1ccccc1
• InChI: InChI=1S/C20H16NP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15,17H
• InChIKey: APISVOVOJVZIBA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(triphenyl-$l^{5}-phosphanylidene)acetonitrile; 2-(triphenyl-λ^5-phosphanylidene)acetonitrile
• IUPAC Traditional name: 2-(triphenyl-$l^{5}-phosphanylidene)acetonitrile; 2-(triphenyl-λ^5-phosphanylidene)acetonitrile
• Synonyms: (Triphenylphosphoranylidene)acetonitrile; Cyanomethylene triphenylphosphorane; Cyanomethyltriphenylphosphonium ylide; NSC 135204; (Cyanomethylene)triphenylphosphorane; (Triphenylphosphoranylidene)acetonitrile; (Cyano)(triphenylphosphoranylidene)methane; (氰亚甲基)三苯基膦; (三苯基膦)乙腈

Database IDs

• CAS Number: 16640-68-9
• EC Number: 240-689-7
• MDL Number: MFCD00567633
• PubChem SID: 24856944; 162039774
• PubChem CID: 85524

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.5014
• LogD (pH = 7.4): 5.5014
• Log P: 5.5014
• Molar Refractivity: 92.6593 cm^3
• Polarizability: 36.051704 Å^3
• Polar Surface Area: 23.79 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 189-195 °C(lit.); 189-195°C

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: 97%
• Linear Formula: (C6H5)3P=CHCN

DETAILS

Sigma Aldrich - 280429

Application
Wittig reagent for the preparation of α,β, unsaturated nitriles from carbonyl compounds.9
Reactant for
• Preparation of antitrypanosomal activity1
• Direct Michael addition of alkenes2
• Synthesis of 1,6-enynes3
• Beta-umpolung addition of nucleophiles to activated disubstituted alkyl allenes4
• Stereoselective analysis of β-homoproline derivatives5
• Stereoselective olefination of N-sulfonyl imines6
• Palladacycle mediated synthesis of cyano-functionalized chiral diphosphines7
• Horner-Wadsworth-Emmons reactions8
Packaging
5 g in glass bottle