(2-oxopropyl)triphenylphosphanium bromide

• ChemBase ID: 74879
• Molecular Formular: C21H20BrOP
• Molecular Mass: 399.260661
• Monoisotopic Mass: 398.04351389
• SMILES: [P+](c1ccccc1)(c1ccccc1)(c1ccccc1)CC(=O)C.[Br-]
• Canonical SMILES: CC(=O)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C21H20OP.BrH/c1-18(22)17-23(19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21;/h2-16H,17H2,1H3;1H/q+1;/p-1
• InChIKey: KZBWHCFTAAHIJJ-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-oxopropyl)triphenylphosphanium bromide
• IUPAC Traditional name: (2-oxopropyl)triphenylphosphanium bromide
• Synonyms: (2-Oxopropyl)triphenylphosphonium bromide; Acetonyltriphenylphosphonium bromide; 丙酮基三苯基溴化膦

Database IDs

• CAS Number: 2236-01-3
• EC Number: 218-796-5
• MDL Number: MFCD00051863
• Beilstein Number: 3802148
• PubChem SID: 162039797
• PubChem CID: 638158

CALCULATED PROPERTIES

• Acid pKa: 18.218384
• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 4.2278438
• LogD (pH = 7.4): 4.2278438
• Log P: 4.2278438
• Molar Refractivity: 96.9553 cm^3
• Polarizability: 38.132767 Å^3
• Polar Surface Area: 17.07 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 226-227°C

Safety Information

• Storage Warning: Hygroscopic; Irritant/Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98+%

REFERENCES

• Wittig intermediate for formation of methyl alkenyl ketones. Efficient catalyst for protection and deprotection of alcohols, e.g. THP ethers are formed rapidly in DCM and cleaved in MeOH: Tetrahedron Lett., 40, 2389 (1999). Reagent for the acylation of alcohols, phenols, thiols and amines, and for 1,1-diacylation of alkdehydes under solvent-free conditions: Eur. J. Org. Chem., 2782 (2005).