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1449-46-3 Usage


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).

Chemical Properties



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.

Check Digit Verification of cas no

The CAS Registry Mumber 1449-46-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,4,4 and 9 respectively; the second part has 2 digits, 4 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 1449-46:
83 % 10 = 3
So 1449-46-3 is a valid CAS Registry Number.

1449-46-3 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (B2025)  Benzyltriphenylphosphonium Bromide  >98.0%(HPLC)(T)

  • 1449-46-3

  • 25g

  • 350.00CNY

  • Detail
  • TCI America

  • (B2025)  Benzyltriphenylphosphonium Bromide  >98.0%(HPLC)(T)

  • 1449-46-3

  • 250g

  • 2,160.00CNY

  • Detail
  • Alfa Aesar

  • (B24567)  Benzyltriphenylphosphonium bromide, 98%   

  • 1449-46-3

  • 10g

  • 201.0CNY

  • Detail
  • Alfa Aesar

  • (B24567)  Benzyltriphenylphosphonium bromide, 98%   

  • 1449-46-3

  • 50g

  • 794.0CNY

  • Detail
  • Alfa Aesar

  • (B24567)  Benzyltriphenylphosphonium bromide, 98%   

  • 1449-46-3

  • 250g

  • 1891.0CNY

  • Detail
  • Aldrich

  • (430056)  Benzyltriphenylphosphoniumbromide  96%

  • 1449-46-3

  • 430056-50G

  • 986.31CNY

  • Detail
  • Aldrich

  • (430056)  Benzyltriphenylphosphoniumbromide  96%

  • 1449-46-3

  • 430056-250G

  • 3,925.35CNY

  • Detail



According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017


1.1 GHS Product identifier

Product name Benzyltriphenylphosphonium bromide

1.2 Other means of identification

Product number -
Other names (Phenylmethyl)triphenylphosphonium bromide Bromo(benzyl)triphenylphosphorane

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1449-46-3 SDS

1449-46-3Relevant articles and documents

Kinetics and mechanistic investigation of epoxy-anhydride compositions cured with quaternary phosphonium salts as accelerators

Amirova, Lyaysan R.,Burilov, Alexander R.,Amirova, Liliya M.,Bauer, Ingmar,Habicher, Wolf D.

, p. 1088 - 1097 (2016)

Mechanism and curing kinetics of bisphenol A epoxy resin-iso-methyltetrahydrophthalic anhydride compositions using quaternary phosphonium salts as accelerators were investigated by differential scanning calorimetry (DSC) and electrospray mass-spectrometry (ESI-MS). The DSC method was applied to investigate curing kinetics and apparent activation energy values for the overall curing process. The DSC results showed that some of the phosphonium salts lead to a lower activation energy, that means they are more effective accelerators for the curing of epoxy-anhydride systems. The mechanism of curing was studied by ESI-MS using the model reaction of epichlorohydrin (E) with phthalic anhydride (PA) in the presence of phosphonium salts or 2-methylimidazole. Products containing the alkyl moiety of the phosphonium salt in form of alkyl esters could be identified. This suggests that the phosphonium salts activate the anhydride by electrophilic attack.

Investigating Variation of the Pnicogen Nucleophilic Heteroatom on Ionic Liquid Solvent Effects in Bimolecular Nucleophilic Substitution Processes

Schaffarczyk McHale, Karin S.,Haines, Ronald S.,Harper, Jason B.

, p. 534 - 539 (2019)

A series of nucleophiles containing Group 15 nucleophilic heteroatoms has been used to expand and develop the current understanding of ionic liquid solvent effects on bimolecular nucleophilic substitution processes. It was found that when using arsenic-, antimony- and bismuth-based nucleophiles, rate constant enhancement was observed for all solvent compositions containing ionic liquids. This rate constant enhancement was driven by ionic liquid/transition state interactions, which contrasts with previous studies on earlier Group 15 nucleophiles. This study provides a holistic understanding and augments the predictive framework for the effects of ionic liquids on bimolecular nucleophilic substitution processes, with the potential for these periodic trends to be broadly applied.

Functionalized Cyclopropanes as Versatile Intermediates for the Diversity-Oriented Synthesis of γ-Lactones, γ-Lactams and δ-Lactams

Maximiano, Adrielle P.,Ramos, Giovana S.,Marques, Marcelo V.,Sá, Marcus M.

, (2021)

A two-step procedure for the preparation of cyclopropanecarboxaldehyde-1,1-diester from a γ,δ-epoxyester and its synthetic versatility are described herein. The epoxide ring-opening/cyclopropanation process occurs in the presence of Mg(ClO 4) 2under heating, resulting in cyclopropanemethanol-1,1-diester in 65% yield. A mild TEMPO-mediated oxidation of this substrate readily generated the corresponding aldehyde in 75% yield, which was applied in the one-pot synthesis of four cyclopropylidene-γ-lactams and three δ-lactams. In addition, vinylcyclopropanes were obtained through the Wittig reaction of the aldehyde with phosphonium salts and used as precursors for tetrahydrofurans.

Catalyst-free room-temperature iClick reaction of molybdenum(II) and tungsten(II) azide complexes with electron-poor alkynes: Structural preferences and kinetic studies

Schmid, Paul,Maier, Matthias,Pfeiffer, Hendrik,Belz, Anja,Henry, Lucas,Friedrich, Alexandra,Sch?nfeld, Fabian,Edkins, Katharina,Schatzschneider, Ulrich

, p. 13386 - 13396 (2017)

Two isostructural and isoelectronic group VI azide complexes of the general formula [M(η3-allyl)(N3)(bpy)(CO)2] with M = Mo, W and bpy = 2,2′-bipyridine were prepared and fully characterized, including X-ray structure analysis. Both reacted smoothly with electron-poor alkynes such as dimethyl acetylenedicarboxylate (DMAD) and 4,4,4-trifluoro-2-butynoic acid ethyl ester in a catalyst-free room-temperature iClick [3 + 2] cycloaddition reaction. Reaction with phenyl(trifluoromethyl)acetylene, on the other hand, did not lead to any product formation. X-ray structures of the four triazolate complexes isolated showed the monodentate ligand to be N2-coordinated in all cases, which requires a 1,2-shift of the nitrogen from the terminal azide to the triazolate cycloaddition product. On the other hand, a 19F NMR spectroscopic study of the reaction of the fluorinated alkyne with the tungsten azide complex at 27 °C allowed detection of the N1-coordinated intermediate. With this method, the second-order rate constant was determined as (7.3 ± 0.1) × 10-2 M-1 s-1, which compares favorably with that of first-generation compounds such as difluorocyclooctyne (DIFO) used in the strain-promoted azide-alkyne cycloaddition (SPAAC). In contrast, the reaction of the molybdenum analogue was too fast to be studied with NMR methods. Alternatively, solution IR studies revealed pseudo-first order rate constants of 0.4 to 6.5 × 10-3 s-1, which increased in the order of Mo > W and F3C-CC-COOEt > DMAD.

Synthesis of Indoles by Reductive Cyclization of Nitro Compounds Using Formate Esters as CO Surrogates

Ahmed Fouad, Manar,Ferretti, Francesco,Formenti, Dario,Milani, Fabio,Ragaini, Fabio

supporting information, p. 4876 - 4894 (2021/09/20)

Alkyl and aryl formate esters were evaluated as CO sources in the Pd- and Pd/Ru-catalyzed reductive cyclization of 2-nitrostyrenes to give indoles. Whereas the use of alkyl formates requires the presence of a ruthenium catalyst such as Ru3(CO)12, the reaction with phenyl formate can be performed by using a Pd/phenanthroline complex alone. Phenyl formate was found to be the most effective CO source and the desired products were obtained in excellent yields, often higher than those previously reported using pressurized CO. The reaction tolerates many functional groups, including sensitive ones like a free aldehydic group or a pendant pyrrole. Detailed experiments and kinetic studies allow to conclude that the activation of phenyl formate is base-catalyzed and that the metal doesn't play a role in the decarbonylation step. The reactions can be performed in a single thick-walled glass tube with as little as 0.2 mol-% palladium catalyst and even on a 2 g scale. The same protocol can be extended to other nitro compounds, affording different heterocycles.

Reactions of benzyltriphenylphosphonium salts under photoredox catalysis

Boldt, Andrew M.,Dickinson, Sidney I.,Ramirez, Jonathan R.,Benz-Weeden, Anna M.,Wilson, David S.,Stevenson, Susan M.

supporting information, p. 7810 - 7815 (2021/09/28)

The development of benzyltriphenylphosphonium salts as alkyl radical precursors using photoredox catalysis is described. Depending on substituents, the benzylic radicals may couple to form C-C bonds or abstract a hydrogen atom to form C-H bonds. A natural product, brittonin A, was also synthesized using this method.

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