ethenyltriphenylphosphanium bromide

• ChemBase ID: 146955
• Molecular Formular: C20H18BrP
• Molecular Mass: 369.234681
• Monoisotopic Mass: 368.03294921
• SMILES: C=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• Canonical SMILES: C=C[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C20H18P.BrH/c1-2-21(18-12-6-3-7-13-18,19-14-8-4-9-15-19)20-16-10-5-11-17-20;/h2-17H,1H2;1H/q+1;/p-1
• InChIKey: VRAYVWUMBAJVGH-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: ethenyltriphenylphosphanium bromide
• IUPAC Traditional name: ethenyltriphenylphosphanium bromide
• Synonyms: Ethenyltriphenylphosphonium bromide; NSC 84065; Schweizer’s Reagent; Vinyltriphenylphosphonium bromide; Triphenylvinylphosphonium bromide; Triphenyl(vinyl)phosphonium bromide; Schweizer's Reagent; Triphenylvinylphosphonium bromide; Vinyltriphenylphosphonium bromide; Schweizer 试剂; 乙烯基三苯基溴化膦; 溴化乙烯基三苯基膦

Database IDs

• CAS Number: 5044-52-0
• EC Number: 225-740-3
• MDL Number: MFCD00011807
• Beilstein Number: 4168860
• PubChem SID: 162241147; 24848845
• PubChem CID: 2723893

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 4.8482046
• LogD (pH = 7.4): 4.8482046
• Log P: 4.8482046
• Molar Refractivity: 91.1052 cm^3
• Polarizability: 36.061058 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~180 °C; 176-178 °C(lit.); 182-186°C

Safety Information

• Storage Warning: Light Sensitive & Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• 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
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95% (AT); 95+%; 97%
• Grade: technical
• Linear Formula: CH2=CHP(Br)(C6H5)3

DETAILS

Sigma Aldrich - 150193

Application
Reagent for the synthesis of heterocycles.
Reactant involved in:
• Asymmetric conjugate addition and intramolecular cyclization1
• Condensation with benzoxazinediones2
• Intramolecular dehydrobromination3
• Schweizer reaction4
• Cycloaddition with nitro ketone Baylis-Hillman adducts5
Packaging
25 g in glass bottle

Sigma Aldrich - 93155

Other Notes
Reagent for preparing allyl amines6
Application
Reactant involved in:
• Asymmetric conjugate addition and intramolecular cyclization1
• Condensation with benzoxazinediones2
• Intramolecular dehydrobromination3
• Schweizer reaction4
• Cycloaddition with nitro ketone Baylis-Hillman adducts5

REFERENCES

• Conjugate additions of nucleophiles to the double bond give ?-substituted ethyl triphenylphosphonium salts which can be further reacted by Wittig olefination. Sequential reaction with phthalimide and an aldehyde leads, after hydrazinolysis of the resulting N-allylphthalimide, to 3-substituted allylamines: J. Org. Chem., 46, 3119 (1981). N-Alkyl allylamines can also be prepared from alkylamines: Tetrahedron Lett., 24, 3043 (1983):
  
• A variety of heterocyclic systems can be synthesized by conjugate addition and subsequent Wittig condensation: J. Am. Chem. Soc., 86, 2744, 2963 (1964); J. Org. Chem., 33, 2416 (1968). Use of carbon nucleophiles permits synthesis of carbocyclic systems: J. Org. Chem., 30, 2082 (1965).
• Conjugate addition of organocuprates leads to a new phosphonium salt which can be used in the Wittig olefination. With alkenyl cuprates this provides a stereoselective route to (Z,Z)-1,4-pentadienes: Tetrahedron Lett., 26, 1799 (1985). Sequential reactions, catalyzed by CuBr - Ag₂CO₃ or CuBr - H₂O, with Grignard reagents and Wittig olefination with an aldehyde, have also been reported: J. Org. Chem., 61,9659 (1996):