106302-03-8

Basic information

• Product Name: (3-ETHOXYCARBONYL-2-OXOPROPYL)TRIPHENYLPHOSPHONIUM CHLORIDE
• Synonyms: (3-ETHOXYCARBONYL-2-OXOPROPYL)TRIPHENYLPHOSPHONIUM CHLORIDE;(3-(ethoxycarbonyl)-2-oxopropyl)triphenyl-phospho;(3-Ethoxycarbonyl-2-oxoproply)triphenylphosphonium chloride;(4-Ethoxy-2,4-dioxo-butyl)-triphenyl-phosphonium chloride
• CAS NO: 106302-03-8
• Molecular Formula: C₂₄H₂₄O₃P*Cl
• Molecular Weight: 426.87
• Product Categories: C-C Bond Formation;Olefination;Wittig Reagents
• Mol File: 106302-03-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 160 °C (dec.)(lit.)
• Appearance: /
• CAS DataBase Reference: (3-ETHOXYCARBONYL-2-OXOPROPYL)TRIPHENYLPHOSPHONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (3-ETHOXYCARBONYL-2-OXOPROPYL)TRIPHENYLPHOSPHONIUM CHLORIDE(106302-03-8)
• EPA Substance Registry System: (3-ETHOXYCARBONYL-2-OXOPROPYL)TRIPHENYLPHOSPHONIUM CHLORIDE(106302-03-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 106302-03-8(Hazardous Substances Data)

Usage

Uses

Reactant for:Preparation of cyclic amidine-based inhibitors of ?-secretase (BACE-1)Wittig reactionsDehydrochlorination and alkylation reactions

InChI:InChI=1/C24H24O3P.ClH/c1-2-27-24(26)18-20(25)19-28(21-12-6-3-7-13-21,22-14-8-4-9-15-22)23-16-10-5-11-17-23;/h3-17H,2,18-19H2,1H3;1H/q+1;/p-1

Upstream product

• 13148-05-5 ethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate 
• 638-07-3 ethyl (2-chloroaceto)acetate 
• 603-35-0 triphenylphosphine 
• 194425-79-1 (E)-Ethyl 3-(tert-butyldimethylsilyloxy)-4-chlorobut-2-enoate 

Downstream Products

• 95005-85-9 4-(triphenylphosphoranylidene)acetoacetic acid amide 
• 27271-30-3 Cinnamoylessigester 
• 1503-99-7 ethyl 3-oxo-5-phenylpent-4-enoate 
• 13148-05-5 ethyl 3-oxo-4-(triphenylphosphoranylidene)butanoate 
• 122347-84-6 p-nitrobenzyl (2R,3R)-2-<(ethoxycarbonylmethylcarbonyl)(triphenylphosphoranylidene)methylthio>-α-isopropylidene-4-oxo-3-phenoxyacetylaminoazetidine acetate 

Relevant articles and documents

Structural, theoretical and multinuclear NMR study of mercury(II) complexes with a new ambidentate phosphorus ylide

The reaction of the new ambidentate ylide, Ph3PCHCOCH 2COOC2H5 (EAPPY), with HgX2 (X = Cl, Br and I) in equimolar ratios using methanol as the solvent leads to binuclear complexes of the type [EAPPY·H

Silyl enol ethers as new protecting groups for alkyl 4-halo-3-oxobutanoates; the preparation of pure (3-alkoxycarbonyl-2-oxopropyl)triphenylphosphonium salts

A new method has been developed for the preparation of pure (3-alkoxycarbonyl-2-oxopropyl)triphenyl-phosphonium salts 8. Alkyl 4-bromo-3-oxobutanoates and alkyl 4-chloro-3-oxobutanoates 7 are protected as the trimethylsilyl enol ethers prior to treatment of the resulting bromo(trimethylsilyl enol ether) esters 20c and 21c with triphenylphosphine in toluene and then addition of a little water to give pure (3-isopropoxycarbonyl-2-oxopropyl)triphenylphosphonium bromide 8c. Bromo(silyl enol ether) esters react more efficiently with triphenylphosphine than the chloro(silyl enol ether) esters. tert-Butyldimethylsilyl enol ethers of alkyl 4-bromo-3-oxobutanoates and alkyl 4-chloro-3-oxobutanoates 7 also react with triphenylphosphine. Protection of isopropyl 4-bromo-3-oxobutanoate 7c as the enol acetate followed by subsequent reaction with triphenylphosphine gives (Z)-(2-acetoxy-3-isopropoxycarbonylbut-2-enyl)triphenylphosphonium bromide 17.