Benzyltriphenylphosphonium bromide

Base Information

• Chemical Name: Benzyltriphenylphosphonium bromide
• CAS No.: 1449-46-3
• Molecular Formula: C25H22BrP
• Molecular Weight: 433.327
• Hs Code.: 29319090
• European Community (EC) Number: 215-908-4
• NSC Number: 54813
• DSSTox Substance ID: DTXSID50932443
• ChEMBL ID: CHEMBL172390
• Mol file: 1449-46-3.mol

Synonyms:Benzyltriphenylphosphonium bromide;1449-46-3;Benzyl triphenyl phosphonium bromide;benzyl(triphenyl)phosphanium;bromide;EINECS 215-908-4;NSC 54813;benzyl triphenylphosphonium bromide;PHOSPHONIUM, TRIPHENYL(PHENYLMETHYL)-, BROMIDE;Phosphonium, triphenyl(phenylmethyl)-, bromide (1:1);C25H22BrP;Benzyltriphenylphosphoniumbromide;Bromo(benzyl)triphenylphosphorane;benzyltriphenylphosphanium bromide;benzyl(triphenyl)phosphanium bromide;benzyl(triphenyl)phosphonium bromide;(Phenylmethyl)triphenylphosphonium bromide;C25H22P.Br;SCHEMBL163158;CHEMBL172390;C25-H22-P.Br;DTXSID50932443;benzyl-triphenylphosphonium bromide;WTEPWWCRWNCUNA-UHFFFAOYSA-M;AMY42218;BAA44946;NSC54813;Benzyl-Triphenyl-Phosphonium Bromide;MFCD00031707;NSC-54813;Phosphonium, benzyltriphenyl- bromide;AKOS001064828;phenylmethyltriphenylphosphonium bromide;CS-W011620;JC10093;Phenylmethyl-triphenylphosphonium bromide;B2025;FT-0604864;EN300-173909;F17169;A808297;W-108144;Z56762358;(PHENYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE;BENZYL TRIPHENYL PHOSPHOROUS BROMIDE;BENZYLTRIPHENYLPHOSPHONIUM BROMIDE;BROMO(BENZYL)TRIPHENYLPHOSPHORANE;TRIPHENY(PHENYLMETHYL)PHOSPHONIUM BROMIDE

Chemical Property of Benzyltriphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: White crystalline powder
• Melting Point: 295-298 °C(lit.)
• PSA: 13.59000
• LogP: 2.18470
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 432.06425
• Heavy Atom Count: 27
• Complexity: 347

Purity/Quality:

99% ^*data from raw suppliers

Benzyltriphenylphosphonium bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: C1=CC=C(C=C1)C[P+](C2=CC=CC=C2)(C3=CC=CC=C3)C4=CC=CC=C4.[Br-]
• 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.

Technology Process of Benzyltriphenylphosphonium bromide

There total 17 articles about Benzyltriphenylphosphonium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

benzyl bromide (100-39-0) + triphenylphosphine (603-35-0) → benzyltriphenylphosphonium bromide (1449-46-3)

Guidance literature:

In xylene; for 0.00833333h; Heating; microwave irradiation;

DOI:10.1081/SCC-100106048

Reference yield: 95.0%

triphenylphosphine (603-35-0) → benzyltriphenylphosphonium bromide (1449-46-3)

Guidance literature:

With benzyl bromide; In benzene; for 12h; Reflux;

DOI:10.1002/chem.200802466

Reference yield: 24.0%

benzyl chloride (100-44-7) + triphenylphosphine (603-35-0) → benzyltriphenylphosphonium bromide (1449-46-3)

Guidance literature:

In N,N-dimethyl-formamide; at 70 ℃; for 1h;

upstream raw materials:

benzyl bromide

triphenylphosphine

Triphenylphosphine oxide

triphenylphosphine hydrobromide

Downstream raw materials:

(benzoylphenylmethylene)triphenylphosphorane

(3E,4E)-3,4-dibenzylidenecyclopentane

(E)-2-bromo-1-methyl-4-styrylbenzene

2-Ethoxy-1-phenyl-3,3,3-trifluoroprop-1-ene

Refernces

• 1、 Zhao, Xiaolei,Zheng, Wei,Zhang, Yi,Huang, Wei. "Cis alkenes stabilized by intramolecular sulphur?π interactions". . p. 814 - 817. Retrieved 2020.
• 2、 Hübner,Wulff-Molder,Vogt,Meisel. "Synthesis and crystal structures of (Benzyl)triphenylphosphonium Bromides, [C6H5-CH2P(C6H5) 3]+Br- and [C6H5-CH2P(C6H5) 3]+Br3-". . p. 1321 - 1324. Retrieved 1997.
• 3、 Halilovic, Dzeneta,Budanovi?, Maja,Wong, Zeng R.,Webster, Richard D.,Huh, June,Stuparu, Mihaiela C.. "Photochemical Synthesis and Electronic Properties of Extended Corannulenes with Variable Fluorination Pattern". . p. 3529 - 3536. Retrieved 2018.
• 4、 Walsh, Mark P.,Kitching, Matthew O.. "Supramolecular Recognition of Quaternary Phosphonium Cations". . . Retrieved 2021/12/06.
• 5、 Abaev, Vladimir T.,Chalikidi, Petrakis N.,Demidov, Oleg P.,Gutnov, Andrey V.,Magkoev, Taimuraz T.,Trushkov, Igor V.,Uchuskin, Maxim G.. "One-Step Synthesis of Triphenylphosphonium Salts from (Het)arylmethyl Alcohols". . p. 9838 - 9846. Retrieved 2021/07/28.