CAS:1449-46-3 | Benzyltriphenylphosphonium Bromide
Molecular Formula: C25H22BrP
Molecular Weight:433.33
EINECS:215-908-4
Purity:98%
Package:5g/10g/25g/50g/bulk package
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Product Introduction
Name | Benzyltriphenylphosphonium bromide |
MDL No | MFCD00031707 |
Melting point | 295-298 °C(lit.) |
Flash Point | 295 °C |
PSA | 13.59 |
LogP | 2.18 |
Appearance | White to off-white powder,crystals and/or chunks |
Sensitivity | Hygroscopic |
Storage condition | Keep container tightly sealed. Store in cool, dry conditions in well sealed containers |
InChI | InChI=1/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 |
Smiles | C1=CC=C(C=C1)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-] |
Application:
Benzyltriphenylphosphonium bromide(CAS:1449-46-3) is used as a reactant for stereoselective azidolysis of vinyl epoxides, enantioselective aziridination and Friedel-Crafts cyclization for asymmetric synthesis of dihydrexidine, biomimetic iron(III) mediated oxidative dimerization for synthesis of benzoquinone parvistemin A, enantioselective synthesis of syn-diarylheptanoids from D-glucose, preparation of β-amyloid plaque ligands and decarboxylative cyclopropanation. It react with 4-methyl-oxetan-2-one to produce 4-hydroxy-1-phenyl-1-(triphenyl-l5-phosphanylidene)-pentan-2-one.
References:
Saumen Hajra, Sukanta Bar. Catalytic enantioselective synthesis of A-86929, a dopamine D1 agonist. Chemical Communications. 2011, 47 (13), 3981-3982.
Marcus J Smith, Christopher C Nawrat, Christopher J Moody. Synthesis of parvistemin A via biomimetic oxidative dimerization. Organic Letters. 2011, 13 (13), 3396-3398.
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.
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