2-(triphenyl-λ5-phosphanylidene)propanal

• ChemBase ID: 151423
• Molecular Formular: C21H19OP
• Molecular Mass: 318.348721
• Monoisotopic Mass: 318.11735186
• SMILES: CC(=P(c1ccccc1)(c1ccccc1)c1ccccc1)C=O
• Canonical SMILES: O=CC(=P(c1ccccc1)(c1ccccc1)c1ccccc1)C
• InChI: InChI=1S/C21H19OP/c1-18(17-22)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
• InChIKey: VHUQEFAWBCDBSC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(triphenyl-λ^5-phosphanylidene)propanal
• IUPAC Traditional name: 2-(triphenyl-λ^5-phosphanylidene)propanal
• Synonyms: 1-Formylethylidenetriphenylphosphorane; 2-(Triphenylphosphoranylidene)propionaldehyde; 2-(三苯基正膦基)丙醛

Database IDs

• CAS Number: 24720-64-7
• MDL Number: MFCD00075596
• PubChem SID: 24863304; 162245577
• PubChem CID: 4280987

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.7111
• LogD (pH = 7.4): 5.7111
• Log P: 5.7111
• Molar Refractivity: 97.2311 cm^3
• Polarizability: 38.11993 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 219-221 °C(lit.)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%
• Linear Formula: (C6H5)3P=C(CH3)CHO

DETAILS

Sigma Aldrich - 374377

Packaging
1, 10 g in glass bottle
Application
Reactant for:
• Preparation of acitretin analogs with antitumor activity1
• Stereoselective synthesis of essential building blocks of phorboxazole A via hetero Diels-Alder and stereoselective hetero-Michael addition/equilibration2
• Preparation of C1-C14 fragment of sarcoglaucol-16-one via Z-selective ando-type Horner-Wadsworth-Emmons olefination3
• Wittig reactions4
• Synthesis of ring-expanded and epothilone-hybridized macrosphelide analogs as apoptosis-inducing agents5
• Preparation of phosphonic acid-containing analogs of mycophenolic acid as inhibitors of IMPDH6