triphenyl(prop-2-en-1-yl)phosphanium bromide

• ChemBase ID: 108935
• Molecular Formular: C21H20BrP
• Molecular Mass: 383.261261
• Monoisotopic Mass: 382.04859927
• SMILES: [Br-].C=CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1
• Canonical SMILES: C=CC[P+](c1ccccc1)(c1ccccc1)c1ccccc1.[Br-]
• InChI: InChI=1S/C21H20P.BrH/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21;/h2-17H,1,18H2;1H/q+1;/p-1
• InChIKey: FWYKRJUVEOBFGH-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: triphenyl(prop-2-en-1-yl)phosphanium bromide
• IUPAC Traditional name: triphenyl(prop-2-en-1-yl)phosphanium bromide
• Synonyms: ALLYLTRIPHENYLPHOSPHONIUM BROMIDE; 2-Propenyltriphenylphosphonium bromide; NSC 110609; NSC 59815; Allyltriphenylphosphonium bromide; 烯丙基三苯基溴化膦; 烯丙基三苯基溴化鏻

Database IDs

• CAS Number: 1560-54-9
• EC Number: 216-332-6
• MDL Number: MFCD00011808
• Beilstein Number: 3579053
• PubChem SID: 162094639; 24890798
• PubChem CID: 197740

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 5.3590407
• LogD (pH = 7.4): 5.3590407
• Log P: 5.3590407
• Molar Refractivity: 96.3839 cm^3
• Polarizability: 37.899105 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 222-225 °C(lit.); 222-225°C

Safety Information

• Storage Warning: Hygroscopic
• RTECS: TA1843000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R:36/37/38
• Safety Statements: 26-37; 26-37/39; S:20-25-26-37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%; 99%
• Linear Formula: H2C=CHCH2P(C6H5)3Br

DETAILS

MP Biomedicals - 05209285

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A36603

Packaging
100 g in poly bottle
Application
Reactant for:
• Preparation of a diol and carbamate chemistry library for common functional groups1
• Regioselective synthesis of alkenes via semihydrogenation and semihydrogenation-oxidation of dienes2
• Alkene addition of frustrated Lewis pairs3
• Olefination of N-sulfonyl imines for stereoselective synthesis of vinyl arenes4
• Wittig olefination of aldehydes for preparation of conjugated dienes5
• Tandem Michael addition / ylide olefination reactions for the synthesis of highly functionalized cyclohexadienes6

REFERENCES

• Wittig reaction (see Appendix 1) with aldehydes, using K₂CO₃ in toluene, gives dienes: Synth. Commun., 22, 1421 (1992). The derived phosphorane also reacts with ?-chloroacrylates to give conjugated phosphoranes, convertible to trienes: Tetrahedron Lett., 1359 (1975):
  
• Michael addition of the phosphorane to ɑ?-unsaturated ketones, followed by intramolecular Wittig reaction, gives cyclohexa-1,3-dienes: Tetrahedron Lett., 4425 (1973). Further lithiation of the phosphorane in the presence of TMEDA, followed by reaction of the ylide anion with an aldehyde, provides a route to (E,E)-?-hydroxy-1,3-dienes: Tetrahedron Lett., 32, 4353 (1991).