1779-51-7

Basic information

• Product Name: Butyltriphenylphosphonium bromide
• Synonyms: butyltriphenyl-phosphoniubromide;Phosphonium,butyltriphenyl-,bromide;N-BUTYLTRIPHENYLPHOSPHONIUM BROMIDE;BUTYLTRIPHENYLPHOSPHONIUM BROMIDE;BUTYL TRIPHENYL PHOSPHOROUS BROMIDE;BTPPBR;(1-BUTYL)TRIPHENYLPHOSPHONIUM BROMIDE;Butylriphenylphosphonium Bromide
• CAS NO: 1779-51-7
• Molecular Formula: Br*C₂₂H₂₄P
• Molecular Weight: 399.3
• EINECS: 217-219-4
• Product Categories: Pharmaceutical Intermediates;Phosphonium Compounds;Synthetic Organic Chemistry;Wittig & Horner-Emmons Reaction;Wittig Reaction
• Mol File: 1779-51-7.mol

Chemical Properties

• Melting Point: 240-243 °C(lit.)
• Appearance: White/Crystalline Powder
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol
• Water Solubility: soluble
• Sensitive: Hygroscopic
• BRN: 3580224
• CAS DataBase Reference: Butyltriphenylphosphonium bromide(CAS DataBase Reference)
• NIST Chemistry Reference: Butyltriphenylphosphonium bromide(1779-51-7)
• EPA Substance Registry System: Butyltriphenylphosphonium bromide(1779-51-7)

Safety Data

• Hazard Codes: Xn
• Statements: 21/22-36/37/38
• Safety Statements: 36/37-36/37/39-26
• RIDADR: 3464
• WGK Germany: 3
• RTECS: TA1855200
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1779-51-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Butyltriphenylphosphonium bromide is used as a reagent for various chemical reactions, including the Suzuki reaction, free radical 5-exo-dig cyclization, intramolecular hydroacylalkoxylation, Wittig reactions for stereoselective synthesis of alkenes, dimerization of α-olefins, and alkylidenation of hydrazides for the synthesis of indoles.
Used in Pharmaceutical Industry:
Butyltriphenylphosphonium bromide is used as a reactant in the synthesis of inhibitors of tubulin polymerization, which express antimitotic and antitubulin properties. These inhibitors have potential applications in the development of new drugs for the treatment of cancer and other diseases.
Used in Drug Delivery Systems:
In the pharmaceutical industry, Butyltriphenylphosphonium bromide is also used in the synthesis of 3-phenylpropanoic acids as peroxisome proliferator-activated receptor dual agonists. These agonists affect the mitochondrial carnitine system and have potential applications in the treatment of various metabolic disorders.
Used in Organic Chemistry:
Butyltriphenylphosphonium bromide is used as a catalyst in tandem cyclization and 1,2-thiolate shift of nitrogen ylides, which are important reactions in the synthesis of complex organic molecules.

InChI:InChI=1/C22H25P.BrH/c1-2-3-19-23(20-13-7-4-8-14-20,21-15-9-5-10-16-21)22-17-11-6-12-18-22;/h4-18,23H,2-3,19H2,1H3;1H

Upstream product

• 109-65-9 1-bromo-butane 
• 603-35-0 triphenylphosphine 
• 109-69-3 n-Butyl chloride 
• 6399-81-1 triphenylphosphine hydrobromide 
• 71-36-3 butan-1-ol 
• 23626-32-6 {C₁₈H₁₅PC₄H₉}{NiBr₃(Triphenylphosphin)} 

Downstream Products

• 31502-17-7 non-5-en-1-ol 
• 17631-10-6 [1-(hydroxyimino-phenyl-methyl)-butyl]-triphenyl-phosphonium; bromide 
• 749-19-9 Diphenyl-<2-(1-phenyl-butyl)-phenyl>-phosphin 
• 17620-94-9 3-chloro-5-(triphenyl-λ⁵-phosphanylidene)-octan-4-one 
• 58257-45-7 methyl tridec-9-enoate 
• 56219-08-0 (Z)-9-Tridecensaeure-aethylester 
• 35835-78-0 13-acetoxy-tridec-4c-ene 
• 750-31-2 Diphenyl-(2-<6-methoxy-2-(1-phenyl-butyl)-phenyl>)-phosphin 
• 6048-24-4 Triphenyl-<1-(γ-phenyl-butyryl)-butyliden>-phosphoran 
• 6129-02-8 1-cyclobutyl-2-(triphenylphosphoranylidene)pentan-1-one 
• 19060-27-6 Triphenyl-<1-(cyclopropylcarbonyl)-butyliden>-phosphoran 
• 70435-86-8 1-Benzyloxy-3-(1,1-dimethyl-2-hexenyl)-benzol 
• 4233-13-0 butyldiphenylphosphine oxide 
• 14670-41-8 (Z)-1-chloro-4-(pent-1-en-1-yl)benzene 

Relevant articles and documents

Two Are Better Than One: A Design Principle for Ultralong-Persistent Luminescence of Pure Organics

Because of their innate ability to store and then release energy, long-persistent luminescence (LPL) materials have garnered strong research interest in a wide range of multidisciplinary fields, such as biomedical sciences, theranostics, and photonic devices. Although many inorganic LPL systems with afterglow durations of up to hours and days have been reported, organic systems have had difficulties reaching similar timescales. In this work, a design principle based on the successes of inorganic systems to produce an organic LPL (OLPL) system through the use of a strong organic electron trap is proposed. The resulting system generates detectable afterglow for up to 7 h, significantly longer than any other reported OLPL system. The design strategy demonstrates an easy methodology to develop organic long-persistent phosphors, opening the door to new OLPL materials.

Tergal Gland Secretion of the Rove Beetle Aleochara pseudochrysorrhoa (Staphylinidae: Aleocharinae): Chemical Composition and Biological Roles

Aleochara pseudochrysorrhoa has a glandular complex known as the tergal gland. Generally, the tergal gland secretion (TGS) has been described to have defensive function, but some reports point to a possible secondary function of this complex. For example, the TGS of the related species A. curtula has been demonstrated to possess an important role in intraspecies communication. In this work, we describe the chemical composition of the TGS of A. pseudochrysorrhoa males and females. Eleven compounds were identified based on GC/MS and GC-FT-IR analyses, retention indexes and derivatization products. Furthermore, a brief study regarding the biological function of the TGS in mating behavior is provided, in which the stimulation of male grasping response reaction by female TGS proved to be dependent on concentration.

Lipophilic ion aromaticity is not important for permeability across lipid membranes

To clarify the contribution of charge delocalization in a lipophilic ion to the efficacy of its permeation through a lipid membrane, we compared the behavior of alkyl derivatives of triphenylphosphonium, tricyclohexylphosphonium and trihexylphosphonium bo

Rh2(II)-Catalyzed intermolecular N-Aryl aziridination of olefins using nonactivated N atom precursors

The development of the first intermolecular Rh2(II)-catalyzed aziridination of olefins using anilines as nonactivated N atom precursors and an iodine(III) reagent as the stoichiometric oxidant is reported. This reaction requires the transfer of an N-aryl nitrene fragment from the iminoiodinane intermediate to a Rh2(II) carboxylate catalyst; in the absence of a catalyst only diaryldiazene formation was observed. This N-aryl aziridination is general and can be successfully realized by using as little as 1 equiv of the olefin. Di-, tri-, and tetrasubstituted cyclic or acylic olefins can be employed as substrates, and a range of aniline and heteroarylamine N atom precursors are tolerated. The Rh2(II)-catalyzed N atom transfer to the olefin is stereospecific as well as chemo- and diastereoselective to produce the N-aryl aziridine as the only amination product. Because the chemistry of nonactivated N-aryl aziridines is underexplored, the reactivity of N-aryl aziridines was explored toward a range of nucleophiles to stereoselectively access privileged 1,2-stereodiads unavailable from epoxides, and removal of the N-2,4-dinitrophenyl group was demonstrated to show that functionalized primary amines can be constructed.

Phosphonium-based ionic liquids: Economic and efficient catalysts for the solvent-free cycloaddition of CO2 to epoxidized soybean vegetable oil to obtain potential bio-based polymers precursors

A series of phosphonium-based ionic liquids have been prepared in one step in a simple way from inexpensive feedstocks. The prepared ionic liquids have been successfully tested as catalysts in the solvent-free cycloaddition reaction of CO2 to an epoxidized soybean oil to obtain carbonated soybean oil that can be potentially employed as bio-monomer in the synthesis for bio-based polymers. The catalytic performance of these ionic liquids was compared to the widely used and benchmark catalyst in CO2 cycloaddition to epoxides reaction, namely tetrabutylammonium bromide at different reaction conditions. The influence of some reaction parameters such as temperature, CO2 pressure, reaction time and catalyst amount was studied. It has been found that the solubility of the prepared ionic liquids in the reaction media (epoxidized soybean oil) is a key factor that limits the catalytic performance of some of the synthesized ionic liquids. All prepared ionic liquids have shown higher thermal stability that the benchmark catalyst and three of them have shown superior catalytic performance. The best results in terms of conversion and selectivity have been obtained with dodecyltriphenylphosphonium bromide (5) achieving almost full conversion (99.8%) and excellent selectivity (84.0%) after 5 h reaction at 160 oC and 40 bar of CO2. Outstanding results compared to those reported in the literature with similar catalysts in the solvent-free CO2 cycloaddtion to an epoxidized soybean oil to obtain the corresponding carbonated oil have been achieved. Considering the facile synthesis of catalyst 5, the large availability and non-expensive of the feedstocks and its catalytic performance it can be considered a valuable and green alternative for CO2 fixation to epoxidized vegetable oil.

Mechanism-Inspired Design of Bifunctional Catalysts for the Alternating Ring-Opening Copolymerization of Epoxides and Cyclic Anhydrides

Advances in catalysis have enabled the ring-opening copolymerization of epoxides and cyclic anhydrides to afford structurally and functionally diverse polyesters with controlled molecular weights and dispersities. However, the most common systems employ b

Ionic liquid functionalized acid orange for organic solvent and preparation method thereof

The invention relates to ionic liquid functionalized acid orange for an organic solvent and a preparation method thereof. The preparation method for the ionic liquid functionalized acid orange for theorganic solvent provided by the invention comprises the following steps: first, first, reacting triphenylphosphine and slightly excessive bromoalkane, and washing and purifying by using ethyl acetateto prepare alkyl triphenyl bromide; performing neutral reaction on acidified acid orange and silver carbonate, and washing and drying to prepare acid orange silver salt; then, respectively performingion exchange on the prepared acid orange silver salt and different alkyl triphenyl bromide to prepare a series of novel ionic liquid functionalized acid orange which can be dissolved in a plurality of organic solvents. The synthesis reaction conditions are mild and the post-treatment is simple. The type of ionic liquid functionalized acid orange has good solubility in the plurality of the organicsolvents, and is an azo dye and an acid base indicator which can be used for the organic solvent.

Exploring London Dispersion and Solvent Interactions at Alkyl–Alkyl Interfaces Using Azobenzene Switches

Interactions on the molecular level control structure as well as function. Especially interfaces between innocent alkyl groups are hardly studied although they are of great importance in larger systems. Herein, London dispersion in conjunction with solvent interactions between linear alkyl chains was examined with an azobenzene-based experimental setup. Alkyl chains in all meta positions of the azobenzene core were systematically elongated, and the change in rate for the thermally induced Z→E isomerization in n-decane was determined. The stability of the Z-isomer increased with longer chains and reached a maximum for n-butyl groups. Further elongation led to faster isomerization. The origin of the intramolecular interactions was elaborated by various techniques, including 1H NOESY NMR spectroscopy. The results indicate that there are additional long-range interactions between n-alkyl chains with the opposite phenyl core in the Z-state. These interactions are most likely dominated by attractive London dispersion. This work provides rare insight into the stabilizing contributions of highly flexible groups in an intra- as well as an intermolecular setting.

Iron-Nickel Dual-Catalysis: A New Engine for Olefin Functionalization and the Formation of Quaternary Centers

Alkene hydroarylation forms carbon-carbon bonds between two foundational building blocks of organic chemistry: olefins and aromatic rings. In the absence of electronic bias or directing groups, only the Friedel-Crafts reaction allows arenes to engage alkenes with Markovnikov selectivity to generate quaternary carbons. However, the intermediacy of carbocations precludes the use of electron-deficient arenes, including Lewis basic heterocycles. Here we report a highly Markovnikov-selective, dual-catalytic olefin hydroarylation that tolerates arenes and heteroarenes of any electronic character. Hydrogen atom transfer controls the formation of branched products and arene halogenation specifies attachment points on the aromatic ring. Mono-, di-, tri-, and tetra-substituted alkenes yield Markovnikov products including quaternary carbons within nonstrained rings.

The compound, composition, and display device

PROBLEM TO BE SOLVED: To provide a compound capable of elevating an upper limit temperature where a SmC (smectic-C) phase of a liquid crystal can exist, broadening a temperature width of the SmC phase or enlarging a tilt angle of the SmC phase, and to provide a liquid crystal composition comprising the compound and a display element including the liquid crystal composition.SOLUTION: [1] The compound is expressed by general formula (i) shown below. In general formula (i), R and R' each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 9 carbon atoms; A1, A2 and A3 each independently represent a 1,4-phenylene group or a 2,3-difluoro-1,4-phenylene group; m represents an integer of 1 to 10; and Y represents a cyclohexylene group, a phenylene group, a bicyclooctylene group or a dialkylsilylene group.