Butyltriphenylphosphonium bromide

Base Information

• Chemical Name: Butyltriphenylphosphonium bromide
• CAS No.: 1779-51-7
• Deprecated CAS: 1091621-45-2,2197129-37-4
• Molecular Formula: C22H24BrP
• Molecular Weight: 399.31
• Hs Code.: HOSPHONIUM BROMIDE PRODUCT IDENTIFICATION
• European Community (EC) Number: 918-205-7,217-219-4
• NSC Number: 59684
• UNII: 97KU95HRS8
• DSSTox Substance ID: DTXSID90883581
• ChEMBL ID: CHEMBL4792223
• Mol file: 1779-51-7.mol

Synonyms:butyltriphenylphosphonium;butyltriphenylphosphonium bromide

Chemical Property of Butyltriphenylphosphonium bromide

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 240-243 °C(lit.)
• PSA: 13.59000
• LogP: 1.78460
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Solubility.: Chloroform, Methanol
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 398.07990
• Heavy Atom Count: 24
• Complexity: 273

Purity/Quality:

99% ^*data from raw suppliers

n-ButyltriphenylphosphoniumBromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 21/22-36/37/38
• Safety Statements: 36/37-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCC[P+](C1=CC=CC=C1)(C2=CC=CC=C2)C3=CC=CC=C3.[Br-]
• Uses: suzuki reaction Reactant for: Free radical 5-exo-dig cyclization Intramolecular hydroacylalkoxylation Wittig reactions for stereoselective synthesis of alkenes Dimerization of α-olefins Alkylidenation of hydrazides for synthesis of indoles Tandem cyclization and 1,2-thiolate shift of nitrogen ylides n-Butyltriphenylphosphonium Bromide is used in the synthesis of inhibitors of tubulin polymerization thus expressing antimitotic and antitubulin properties. Also used in the synthesis of 3-phenylpropanoic acids as peroxisome proliferator-activated receptor dual agonists affecting the mitochondrial carnitine system.

Technology Process of Butyltriphenylphosphonium bromide

There total 8 articles about Butyltriphenylphosphonium 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: 97.7%

1-bromo-butane (109-65-9) + triphenylphosphine (603-35-0) → n-butyl(triphenyl)phosphonium bromide (1779-51-7)

Guidance literature:

In 5,5-dimethyl-1,3-cyclohexadiene; for 6h; Inert atmosphere; Reflux;

Reference yield: 97.0%

triphenylphosphine (603-35-0) + butan-1-ol (71-36-3) → n-butyl(triphenyl)phosphonium bromide (1779-51-7)

Guidance literature:

With hydrogen bromide; at 110 ℃; for 48h;

Reference yield: 65.0%

n-Butyl chloride (109-69-3) + triphenylphosphine hydrobromide (6399-81-1) → n-butyl(triphenyl)phosphonium bromide (1779-51-7)

Guidance literature:

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

upstream raw materials:

1-bromo-butane

triphenylphosphine

n-Butyl chloride

triphenylphosphine hydrobromide

Downstream raw materials:

non-5-en-1-ol

(Z)-9-Tridecensaeure-aethylester

13-acetoxy-tridec-4c-ene

2-methyl-4-(triphenyl-λ⁵-phosphanylidene)-heptan-3-one

Refernces

• 1、 Mechoulam,Sondheimer. "-". . p. 4386. Retrieved 1958.
• 2、 da Silva, Maycon R.,Vidal, Diogo M.,Figueiredo, Leonardo,Bandeira, Pamela T.,Bergmann, Jan,Zarbin, Paulo H. G.. "Tergal Gland Secretion of the Rove Beetle Aleochara pseudochrysorrhoa (Staphylinidae: Aleocharinae): Chemical Composition and Biological Roles". . . Retrieved 2020.
• 3、 Deng, Tianning,Mazumdar, Wrickban,Yoshinaga, Yuki,Patel, Pooja B.,Malo, Dana,Malo, Tala,Wink, Donald J.,Driver, Tom G.. "Rh2(II)-Catalyzed intermolecular N-Aryl aziridination of olefins using nonactivated N atom precursors". supporting information. p. 19149 - 19159. Retrieved 2021/11/23.