Benzyltriphenylphosphonium bromide
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Benzyltriphenylphosphonium bromide
structure -
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CAS No:
1449-46-3
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Formula:
C25H22BrP
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Chemical Name:
Benzyltriphenylphosphonium bromide
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Synonyms:
Phosphonium,triphenyl(phenylmethyl)-,bromide;benzyl trphenyl phosphonium bromide;Benzytriphenyl Phosphonium Bromide;Benzyltriphenylphosphanium bromid;Triphenylbenzylphosphonium·bromide;triphenyl-(phenylmethyl)phosphonium bromide;Benzyl Triphenyl Phosphonium Bromide ( Btppb );Benzyltriphenylphosphonium bromide,97%
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CAS No:
Benzyltriphenylphosphonium bromide Basic Attributes
433.32
432.064240
3599867
215-908-4
54813
White to Almost white
29319090
Characteristics
0
2.18470
white to off-white crystal
295-298 °C(lit.)
Soluble in water.
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from moisture.
Inert atmosphere,Room Temperature
Safety Information
III
6.1
NONH for all modes of transport
3
Xi
26-36/37/39
Xi
Stable under normal shipping and handling conditions.
P261-P305 + P351 + P338
36/37/38
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 44 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Benzyltriphenylphosphonium bromide Use and Manufacturing
Triphenylphosphine (7.868 g, 1.0 equivalent) and benzyl bromide (3.73 ml, 1.04 equivalent) were dissolved in dimethyl formamide (DMF) (30 ml) and added to a 100 ml round-bottomed flask equipped with a reflux condenser. The reaction mixture was heated to reflux for 1 h and then cooled to room temperature. The precipitated white crystalline solid was collected by filtration, washed with diethyl ether (100 ml) and dried at 60°C under vacuum for 5 h (12.676 G, 98 percent).General procedure: To a solution of benzylbromide (33 mmol) in toluene (20 mL) was added a solution of triphenylphosphine (36.3 mmol) in toluene (25 mL). After being heated at reflux for 5 h, the reaction mixture was cooled at room temperature and a first crop of product was collected by filtration. The filtrate was then refluxed for additional 5 h and a second crop of product precipitated (10-20percent). The collected crops were crystallized from ethanol to give pure phosphonium bromide in high yield.A solution of PPhGeneral procedure: Triphenylphosphine (5 mmol) was added to a solution of 4-substituted-benzyl halide (5 mmol) in toluene (50 mL). The mixture was heated to reflux for 6 h and then cooled to room temperature. The precipitate was collected, recrystallized from ethanol to give the products.To a solution of triphenylphosphine (10 g, 38.1 mmol) in toluene (150 mL) was added benzyl bromide (7.1 g, 42 mmol, 1.1 equiv) at room temperature. The reaction mixture was stirred at 110 °C for 16 h. After completion, the obtained solid was filtered and washed with toluene to afford 10 g of benzylidenetriphenyl-15-phosphane (Yield = 74percent).Step-(i): Synthesis of benzyltriphenylphosphonium bromide (1.1) To a stirred solution of triphenyl phosphine (30 g, 114.23 mmol) in toluene (300 mL) was added benzyl bromide (29.3 g, 171.34 mmol) at 20-35°C and the reaction mixture was allowed to stir at 110°C for 24h. The reaction mixture was cooled to 20-35 °C, obtained solid was filtered and washed with toluene to get the desired compound as a white solid (30 g, 60percent);
Pharmaceutical intermediates
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.
Computed Properties
Molecular Weight:433.3
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:5
Exact Mass:432.06425
Monoisotopic Mass:432.06425
Heavy Atom Count:27
Complexity:347
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes
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Benzyltriphenylphosphonium bromide
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