14799-82-7

Basic information

• Product Name: (CYCLOPROPYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE
• Synonyms: (CYCLOPROPYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE;(CYCLOPROPYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE, 98+%;cyclopropylmethyl(triphenyl)phosphanium
• CAS NO: 14799-82-7
• Molecular Formula: Br*C₂₂H₂₂P
• Molecular Weight: 397.29
• EINECS: 238-862-7
• Mol File: 14799-82-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 182-183°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive: Hygroscopic
• BRN: 4068302
• CAS DataBase Reference: (CYCLOPROPYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (CYCLOPROPYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE(14799-82-7)
• EPA Substance Registry System: (CYCLOPROPYLMETHYL)TRIPHENYLPHOSPHONIUM BROMIDE(14799-82-7)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 14799-82-7(Hazardous Substances Data)

Usage

Synthesis

Triphenylphosphine (3.9 g, 14.8 mmoles) was placed into a 300 mL round bottom flask, equipped with a condenser which was cooled with tap water. Dry benzene (100 mL) (distilled over sodium/benzophenone) was cannulated into the reaction vessel, and a positive pressure of argon and magnetic stirring were maintained throughout the reaction sequence. Cyclopropylmethyl bromide (2.0 g, 14.8 mmoles) was added to the solution via syringe. The reaction mixture was heated at reflux for 10 days producing insoluble cyclopropylmethyltriphenylphosphonium bromide.

InChI:InChI=1/C22H22P.BrH/c1-4-10-20(11-5-1)23(18-19-16-17-19,21-12-6-2-7-13-21)22-14-8-3-9-15-22;/h1-15,19H,16-18H2;1H/q+1;/p-1

Upstream product

• 7051-34-5 cyclopropylcarbinyl bromide 
• 603-35-0 triphenylphosphine 
• 2516-33-8 Cyclopropylmethanol 

Downstream Products

• 14799-59-8 (2-cyclopropylethene-1,1-diyl)dibenzene 
• 14902-13-7 1.2-Dicyclopropyl-1-phenyl-aethylen 
• 16958-36-4 cis-1-Cyclopropyl-2-(o-hydroxyphenyl)-ethylen 
• 16958-37-5 trans-1-Cyclopropyl-2-(o-hydroxyphenyl)-ethylen 
• 16958-38-6 Cyclohexyliden-cyclopropyl-methan 
• 14799-61-2 cyclopropylmethyldiphenylphosphine oxide 
• 14799-60-1 1-phenyl-2-cyclopropylethylene 
• 16958-34-2 (Z)-1-cyclopropyl-2-phenyl ethylene 
• 16958-35-3 (E)-1-cyclopropyl-2-phenyl ehtylene 
• 14902-14-8 -triphenyl-phosphoran 
• 14799-62-3 <2-Hydroxy-2,2-diphenyl-aethyl>-diphenyl-phosphinoxid 
• 929041-98-5 3-(2-cyclopropylvinyl)-5-[methyl(methylsulfonyl)amino]benzoic acid 

Relevant articles and documents

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A biosynthetically inspired route to substituted furans using the Appel reaction: Total synthesis of the furan fatty acid F5

Appel reaction conditions have been harnessed to affect a mild biosynthetically inspired dehydration of endoperoxides to deliver multi-substituted electron rich furans. Unlike traditional dehydrative procedures, this method is metal and acid free, and can be achieved under redox neutral conditions. It is general for a range of aryl and alkyl substituted endoperoxides, and is functional group tolerant. Furthermore, this procedure has been used to deliver an effective total synthesis of the furan fatty acid (FFA) F5.

Reductive and brominative termination of alkenol cyclization in aerobic cobalt-catalyzed reactions

(Chemical Equation Presented) Tetrahydrofur-2-ylmethyl radicals were stereoselectively generated from substituted pent-4-en-1-ols in aerobic cobalt(II)-catalyzed oxidations. Intermediates were trapped with cyclohexa -1,4-diene, γ-terpinene, BrCCl3, diethyl dibromomalonate, or electron-deficient olefins such as acrylonitrile or dimethyl fumarate to afford functionalized tetrahydrofurans in synthetically useful yields.