[2-(benzyloxy)-2-oxoethyl]triphenylphosphanium bromide

• ChemBase ID: 148569
• Molecular Formular: C27H24BrO2P
• Molecular Mass: 491.356021
• Monoisotopic Mass: 490.06972864
• SMILES: c1ccc(cc1)COC(=O)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: O=C(C[P+](c1ccccc1)(c1ccccc1)c1ccccc1)OCc1ccccc1.[Br-]
• InChI: InChI=1S/C27H24O2P.BrH/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;/h1-20H,21-22H2;1H/q+1;/p-1
• InChIKey: AVQABZVTPWROCF-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: [2-(benzyloxy)-2-oxoethyl]triphenylphosphanium bromide
• IUPAC Traditional name: [2-(benzyloxy)-2-oxoethyl]triphenylphosphanium bromide
• Synonyms: (Benzyloxycarbonylmethyl)triphenylphosphonium bromide; (苄氧羰基甲基)三苯基溴化膦

Database IDs

• CAS Number: 78385-36-1
• MDL Number: MFCD00191780
• PubChem SID: 24866100; 162242744
• PubChem CID: 11214019

CALCULATED PROPERTIES

• Acid pKa: 19.348608
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 5.7685857
• LogD (pH = 7.4): 5.7685857
• Log P: 5.7685857
• Molar Refractivity: 122.7859 cm^3
• Polarizability: 48.41347 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 124 °C (dec.)(lit.)

Safety Information

• 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: C6H5CH2O2CCH2P(C6H5)3Br

DETAILS

Sigma Aldrich - 419230

Packaging
10 g in glass bottle
Application
Reactant for:
• Atypical aza-Morita-Baylis-Hillman mechanism1
• Thermal decomposition2
• Double aza-Michael reaction3
• Cyclodextrin derivatives4
• Stereoselective preparation of α,β-unsaturated carbonyl compounds via stereoselective Wittig olefination with aldehydes under solventless conditions or ultrasonication5
• Synthesis of [difluoro(alkenylphenyl)methyl]phosphonic acids on non-crosslinked polystyrene as inhibitors of PTP-1B via Wittig reaction6