benzyltriphenylphosphanium bromide

• ChemBase ID: 145300
• Molecular Formular: C25H22BrP
• Molecular Mass: 433.319941
• Monoisotopic Mass: 432.06424933
• SMILES: c1ccc(cc1)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: c1ccc(cc1)C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C25H22P.BrH/c1-5-13-22(14-6-1)21-26(23-15-7-2-8-16-23,24-17-9-3-10-18-24)25-19-11-4-12-20-25;/h1-20H,21H2;1H/q+1;/p-1
• InChIKey: WTEPWWCRWNCUNA-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyltriphenylphosphanium bromide
• IUPAC Traditional name: benzyltriphenylphosphanium bromide
• Synonyms: (Phenylmethyl)triphenylphosphonium bromide; Bromo(benzyl)triphenylphosphorane; NSC 54813; Benzyltriphenylphosphonium bromide; 苄基三苯基溴化膦; 苄基三苯基膦溴化物

Database IDs

• CAS Number: 1449-46-3
• EC Number: 215-908-4
• MDL Number: MFCD00031707
• Beilstein Number: 3599867
• PubChem SID: 162239507; 24866908
• PubChem CID: 2734970

CALCULATED PROPERTIES

• Acid pKa: 17.877207
• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 6.352264
• LogD (pH = 7.4): 6.352264
• Log P: 6.352264
• Molar Refractivity: 111.8338 cm^3
• Polarizability: 44.074738 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 293-298°C; 295-298 °C(lit.)

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Toxic (T); Irritant (Xi)
• UN Number: UN3464
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: II
• Risk Statements: 25-36/37/38; 36/37/38
• Safety Statements: 26-36/37/39; 26-36/37-45
• TSCA Listed: 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H300-H315-H319-H335; H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P280-P305+P351+P338-P309-P310
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (AT); 96%; 98%
• Grade: purum
• Linear Formula: C6H5CH2P(Br)(C6H5)3

DETAILS

Sigma Aldrich - 430056

Packaging
50, 250 g in glass bottle
Application
Reactant for:
• Stereoselective azidolysis of vinyl epoxides1
• Enantioselective aziridination and Friedel-Crafts cyclization for asymmetric synthesis of dihydrexidine2
• Biomimetic iron(III) mediated oxidative dimerization for synthesis of benzoquinone parvistemin A3
• Enantioselective sytnhesis of syn-diarylheptanoids from D-glucose4
• Preparation of β-amyloid plaque ligands5
• Decarboxylative cyclopropanation6

Sigma Aldrich - 13999

Application
Reactant for:
• Stereoselective azidolysis of vinyl epoxides1
• Enantioselective aziridination and Friedel-Crafts cyclization for asymmetric synthesis of dihydrexidine2
• Biomimetic iron(III) mediated oxidative dimerization for synthesis of benzoquinone parvistemin A3
• Enantioselective sytnhesis of syn-diarylheptanoids from D-glucose4
• Preparation of β-amyloid plaque ligands5
• Decarboxylative cyclopropanation6

REFERENCES

• Wittig reaction of benzylic phosphonium salts with aromatic aldehydes using solid KOH + 18-crown-6 leads to (Z)-stilbenes with good stereoselectivity: Tetrahedron Lett., 37, 4225 (1996). See Appendix 1.