2091-46-5

Usage

Uses

Used in Organic Chemistry:
PROPARGYLTRIPHENYLPHOSPHPHONIUM BROMIDE is used as a Wittig reagent for the alkylation of amines. It serves as a valuable tool in the synthesis of various organic compounds, particularly in the formation of alkenes from aldehydes and ketones through the Wittig reaction. This reaction is a widely employed method for the preparation of alkenes with high levels of stereoand regioselectivity.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, PROPARGYLTRIPHENYLPHOSPHONIUM BROMIDE is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to facilitate the formation of alkenes makes it a crucial component in the development of complex molecular structures found in many drugs.
Used in Research and Development:
PROPARGYLTRIPHENYLPHOSPHONIUM BROMIDE is also used in research and development settings, where it aids chemists in exploring new synthetic pathways and developing novel compounds with potential applications in various fields, including medicine, agriculture, and materials science.
Used in Chemical Synthesis:
In the broader field of chemical synthesis, PROPARGYLTRIPHENYLPHOSPHONIUM BROMIDE is employed as a versatile reagent for the preparation of a wide range of organic compounds. Its utility in the Wittig reaction allows for the efficient synthesis of complex molecules, making it a valuable asset in the development of new chemical products and materials.

Purification Methods

It recrystallises from 2-propanol as white plates. It also crystallises from EtOH with m 156-158o. IR has  max 1440, 1110cm
1 (P-C str). [Elter & Dediger Justus Liebigs Ann Chem 682 62 1965, Schweizer et al. J Org Chem 42 200 1977].

InChI:InChI=1/C21H18P/c1-2-18-22(19-12-6-3-7-13-19,20-14-8-4-9-15-20)21-16-10-5-11-17-21/h1,3-17H,18H2/q+1

Upstream product

• 106-96-7 propargyl bromide 
• 603-35-0 triphenylphosphine 

Downstream Products

• 62460-47-3 Triphenyl-((E)-2-piperidin-1-yl-propenyl)-phosphonium; bromide 
• 126404-82-8 1-Furyl-7-phenylhepta-1,4,6-trien-3-one 
• 126404-78-2 7-Furyl-1-phenyl-5-phenyliminohepta-1,3,6-triene 
• 126404-70-4 2-Anilino-4-(p-tolyl)buta-1,3-dienyl(triphenyl)phosphonium Bromide 
• 126404-81-7 1,7-Diphenylhepta-1,4,6-trien-3-one 
• 126404-77-1 1,7-Diphenyl-5-phenyliminohepta-1,3,6-triene 
• 126404-80-6 1-(o-Nitrophenyl)-5-phenylpenta-1,4-dien-3-one 
• 126404-76-0 1-(o-Nitrophenyl)-5-phenyl-3-phenyliminopenta-1,4-diene 
• 126404-79-3 1-Phenyl-3-phenyliminopenta-1,4-diene 
• 35225-79-7 dibenzylideneacetone 
• 126404-75-9 N-((1E,4E)-1,5-diphenylpenta-1,4-dien-3-ylidene)aniline 
• 126404-68-0 2-Anilino-4-phenylbuta-1,3-dienyl(triphenyl)phosphonium Bromide 
• 126404-74-8 2-Anilinohexa-1,3-dienyl(triphenyl)phosphonium Bromide 
• 123095-03-4 ((E)-2-Diethylamino-propenyl)-triphenyl-phosphonium; bromide 

Relevant academic research and scientific papers

An Elegant Synthesis of a New Class of 1-(Substituted)-1H-1,2,3-triazol-4-yl)methyl)diphenylphosphineoxides by Microwave Irradiation

A simple and efficient one-pot microwave-assisted click formation of 1-(substituted)-1H-1,2,3-triazol-4-yl)methyl)diphenylphosphineoxide derivatives via Huisgen regioselective [3+2]-cycloaddition of an in situ generated organic azides and diphenyl(prop-2-yn-1-yl)phosphine oxide in highly polar DMSO-H2O medium. This synthetic protocol is mild, requires shorter reaction time, and afforded products in excellent yields with high regioselectivity.

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.

Synthesis of chlorophyll-a homologs by Wittig and Knoevenagel reactions with methyl pyropheophorbide-d

The formyl group at the 3-position of methyl pyropheophorbide-d reacted with phosphorous ylides and activated methylene compounds to give efficiently the corresponding 3-(2-substituted ethenyl)chlorins compounds as a product of Wittig and Knoevenagel reactions. The trans-isomers of the synthetic chlorins, methyl 32-substituted pyropheophorbide-a had visible bands absorbing longer wavelengths than the cis-isomers and the 32-unsubstituted chlorin, methyl pyropheophorbide-a. 32,32-Disubstitution strongly affected the absorption bands compared with the bands of the 32-monosubstituted chlorins. The absorption, fluorescence and circular dichroism spectra were dependent upon the 3-substituents conjugated with the chlorin chromophore.