2236-01-3

Basic information

• Product Name: ACETONYL TRIPHENYLPHOSPHONIUM BROMIDE
• Synonyms: 2-OXOPROPYLTRIPHENYLPHOSPHONIUM BROMIDE;ACETONYL TRIPHENYLPHOSPHONIUM BROMIDE;2-Oxopropyltriphenylphosphonium bromide, 98+%;Acetonyltriphenylphosphonium bromide, 98+%
• CAS NO: 2236-01-3
• Molecular Formula: Br*C₂₁H₂₀OP
• Molecular Weight: 399.26
• EINECS: 218-796-5
• Mol File: 2236-01-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 226-227°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Sensitive: Hygroscopic
• BRN: 3802148
• CAS DataBase Reference: ACETONYL TRIPHENYLPHOSPHONIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: ACETONYL TRIPHENYLPHOSPHONIUM BROMIDE(2236-01-3)
• EPA Substance Registry System: ACETONYL TRIPHENYLPHOSPHONIUM BROMIDE(2236-01-3)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 2236-01-3(Hazardous Substances Data)

Usage

General Description

Acetonyl Triphenylphosphonium Bromide is a chemical compound renowned for its importance in a variety of chemical synthesis procedures, predominantly in the creation of α-alkylated ketones. As a highly potent and reactive compound, it is primarily active as a Wittig reagent. It's categorized as an organophosphorus compound, which is characterized by the presence of its phosphonium bromide functional group. The compound's effectiveness in synthesis procedures stems from its strong nucleophilic nature, which allows for successful carbon-carbon bond formation in various reaction types. Handling and use of this chemical requires careful precautions due to potential health and safety risks.

InChI:InChI=1/C21H20OP.BrH/c1-18(22)17-23(19-11-5-2-6-12-19,20-13-7-3-8-14-20)21-15-9-4-10-16-21;/h2-16H,17H2,1H3;1H/q+1;/p-1

Upstream product

• 19403-10-2 Acetyl-carbomethoxy-methyl-triphenylphosphonium-bromid 
• 2091-46-5 triphenyl(prop-2-ynyl)phosphonium bromide 
• 106-96-7 propargyl bromide 
• 603-35-0 triphenylphosphine 
• 1743-62-0 [acetyl(methoxycarbonyl)methylene]triphenylphosphorane 
• 100-51-6 benzyl alcohol 
• 100-46-9 benzylamine 
• 106-49-0 p-toluidine 
• 64-17-5 ethanol 
• 67-56-1 methanol 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 598-31-2 1-bromoacetone 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 26487-95-6 1-bromo-1-(triphenylphosphoranylidene)-2-propanone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 219916-37-7 (3E)-7-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-3-hepten-2-one 
• 33046-41-2 (E)-6-phenyl-3-hexen-2-one 
• 311808-93-2 (Z)-6-phenylhex-3-en-2-one 
• 71426-60-3 [2-(hydroxyimino)propyl](triphenyl)phosphonium bromide 
• 70351-51-8 1-methyl-3-(2-oxopropylidene)indolin-2-one 
• 882750-68-7 1-benzyl-3-(2-oxopropylidene)indolin-2-one 
• 19039-94-2 (E)-4-(3,4,5-trimethoxyphenyl)but-3-en-2-one 
• 18402-84-1 (3E)-dec-3-en-2-one 
• 4376-23-2 (E)-hex-3-en-2-one 
• 141-79-7 4-methyl-pent-3-en-2-one 
• 1392505-09-7 (E)-4-benzyl-5,5,5-trifluoro-3-penten-2-one 
• 1392505-12-2 (E)-5,5,5-trifluoro-4-(4-methoxyphenyl)-3-penten-2-one 

Relevant articles and documents

Rh(iii)-catalyzed diastereoselective cascade annulation of enone-tethered cyclohexadienonesviaC(sp2)-H bond activation

Herein, we report highly diastereoselective arylative cyclization of enone-tethered cyclohexadienonesviaRh(iii)-catalyzed C-H activation ofN-methoxybenzamides. This reaction proceeds through the formation of a five-membered rhodacycle followed by bis-Michael cascade annulation to access functionalized bicyclic scaffolds with four contiguous stereocenters with a broad substrate scope. These products have excellent functional handles, allowing further synthetic transformation to increase the structural complexity. Furthermore, mechanistic studies of arylative cyclization and a gram-scale experiment are also presented.

Synthesis and transformations of triphenylpropargylphosphonium bromide

A method of the synthesis of triphenylpropargylphosphonium bromide is developed. Its isomerization and hydration in various solvents are studied, and reactions with secondary amines, triethylamine, and triphenylphosphine are carried out. It is established that secondary amines add to the intermediate allene isomer with subsequent migration of the formed double bond to the phosphorus atom. The reaction of triethylamine with triphenylpropargyl and triphenylethynyl bromides occurs similarly to alkaline hydrolysis involving attack of the amine on the phosphorus atom. Triphenylphosphine forms with triphenylpropargylphosphonium bromide a bis-salt with a terminal methylene group. Experimental evidence is obtained showing that for phosphoxazole derivatives to form from oximes derived from triphenyl(oxomethyl)phosphonium salts that latter should bear an aryl substituent at the keto group.

A convenient method for the preparation of α-vinylfurans by phosphine-initiated reactions of various substituted enynes bearing a carbonyl group with aldehydes

α-Vinylfurans were obtained by phosphine-initiated cyclization of various enynes bearing a carbonyl group at the ene end in the presence of various aldehydes, in moderate to high yields. The reaction may consist of 1,6-addition of phosphine to the enynes, ring closure, and Wittig reaction between the ylid resulting from cyclization and an aldehyde. Thus, various aldehydes were able to be used in the reaction. The reaction was influenced greatly by the substituents at the acetylene position (R1) and the α-position of the carbonyl group (R3).