benzyl 2-(triphenyl-λ5-phosphanylidene)acetate

• ChemBase ID: 148623
• Molecular Formular: C27H23O2P
• Molecular Mass: 410.444081
• Monoisotopic Mass: 410.14356661
• SMILES: c1ccc(cc1)COC(=O)C=P(c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: O=C(C=P(c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C27H23O2P/c28-27(29-21-23-13-5-1-6-14-23)22-30(24-15-7-2-8-16-24,25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-20,22H,21H2
• InChIKey: INKMLGJBBDRIQR-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• IUPAC Traditional name: benzyl 2-(triphenyl-λ^5-phosphanylidene)acetate
• Synonyms: (Benzyloxycarbonylmethylene)triphenylphosphorane; 2-(Triphenylphosphoranylidene)acetic acid phenylmethyl ester; Benzyl(triphenylphosphoranylidene)acetate; benzyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate; Benzyl 2-(triphenylphosphoranylidene)acetate; 苄基(三苯基膦)乙酸酯

Database IDs

• CAS Number: 15097-38-8
• MDL Number: MFCD00191787
• PubChem SID: 162242798; 24866098
• PubChem CID: 3862746

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 7.6722
• LogD (pH = 7.4): 7.6722
• Log P: 7.6722
• Molar Refractivity: 123.0617 cm^3
• Polarizability: 48.39908 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 120-122 °C(lit.); 122 - 124°C
• Hydrophobicity(logP): 7.901

Safety Information

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

Product Information

• Purity: 95%; 95+%; 97%
• Linear Formula: (C6H5)3P=CHCO2CH2C6H5

DETAILS

Sigma Aldrich - 419206

Packaging
5, 25 g in glass bottle
Application
Reactant for:
• Tributylphosphine-mediated vinylogous Wittig reactions1
• Synthesis of 1,2-dioxanes for antitrypanosomal activity2
• Organocatalytic Michael-type reactions / Wittig reactions of phosphorus ylides and unsaturated ketones3
• Stereoselective phosphine-catalyzed cycloaddition to form spirocyclopenteneoxindoles4
• Enantioselective synthesis of pantothenic acid5
• Preparation of phosphorus ylides from phosphoranes and acetic anhydride6