| Identification | More | [Name]
Benzyltriphenylphosphonium bromide | [CAS]
1449-46-3 | [Synonyms]
BENZYLTRIPHENYLPHOSPHONIUM BROMIDE
BENZYL TRIPHENYL PHOSPHOROUS BROMIDE
TZP
Phosphonium,triphenyl(phenylmethyl)-,bromide
Benzytriphenyl Phosphonium Bromide
benzyl trphenyl phosphonium bromide
Benzyltriphenylphosphanium bromid
Triphenylbenzylphosphonium·bromide | [EINECS(EC#)]
215-908-4 | [Molecular Formula]
C25H22BrP | [MDL Number]
MFCD00031707 | [Molecular Weight]
433.32 | [MOL File]
1449-46-3.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE CRYSTALLINE POWDER | [Melting point ]
295-298 °C(lit.)
| [storage temp. ]
Inert atmosphere,Room Temperature | [form ]
solid | [color ]
White to Almost white | [Water Solubility ]
Soluble in water. | [Sensitive ]
Hygroscopic | [BRN ]
3599867 | [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 | [SMILES]
[P+](CC1C=CC=CC=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1=CC=CC=C1.[Br-] | [CAS DataBase Reference]
1449-46-3(CAS DataBase Reference) |
| Questions And Answer | Back Directory | [Preparation]
Benzyl triphenylphosphonium bromide is prepared by the following steps:To a solution of Ph3P (22 g, 0.084 mol) in toluene, BnBr (10 ml, 0.084 mol) was added dropwise with ice-cooling and stirred at room temperature for 2 hours. A solid was formed, which was filtered and washed with toluene and then dry pet ether to remove unreacted Ph3P. The salt was dried under vacuum (35 g, 96% yield). |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29319090 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE CRYSTALLINE POWDER | [Uses]
Benzyltriphenylphosphonium bromide 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. | [reaction suitability]
reaction type: C-C Bond Formation | [Synthesis]
The general procedure for the synthesis of triphenylbenzylphosphonium bromide from benzylbromide and triphenylphosphine was as follows: triphenylphosphine (7.868 g, 1.0 eq.) and benzylbromide (3.73 mL, 1.04 eq.) were dissolved in dimethylformamide (DMF) (30 mL) and the mixture was transferred to a 100 mL round bottom flask equipped with a reflux condenser. The reaction mixture was heated to reflux and kept for 1 hr and subsequently cooled to room temperature. The precipitated white crystalline solid was collected by filtration, washed with ether (100 mL) and finally dried under vacuum at 60 °C for 5 h to afford the product triphenylbenzylphosphonium bromide (12.676 g, 98% yield). | [References]
[1] Synthetic Communications, 2001, vol. 31, # 21, p. 3377 - 3382
[2] Journal of Organic Chemistry, 2018, vol. 83, # 7, p. 3529 - 3536
[3] Canadian Journal of Chemistry, 2004, vol. 82, # 9, p. 1365 - 1371
[4] Patent: WO2004/52823, 2004, A1. Location in patent: Page 8
[5] Organic Letters, 2013, vol. 15, # 22, p. 5650 - 5653 |
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