15596-07-3

Basic information

• Product Name: (Triphenylphosphoranylidene)ketene
• Synonyms: (Triphenylphosphoranylidene)ketene;Bestmann Ylide;Ketenylidene(triphenyl)phosphorane;(Triphenylphosphoranylidene)ethenone, Bestmann ylide, Ketenylidene(triphenyl)phosphorane;Ketenylidene(triphenyl)phosphorane Bestmann Ylide;(Triphenylphosphoranylidene)ethenone
• CAS NO: 15596-07-3
• Molecular Formula: C₂₀H₁₅OP
• Molecular Weight: 302.31
• Mol File: 15596-07-3.mol
• Article Data: 16

Chemical Properties

• Melting Point: 171 °C
• Boiling Point: 455.4°C at 760 mmHg
• Flash Point: 229.2°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 1.77E-08mmHg at 25°C
• Refractive Index: 1.604
• CAS DataBase Reference: (Triphenylphosphoranylidene)ketene(CAS DataBase Reference)
• NIST Chemistry Reference: (Triphenylphosphoranylidene)ketene(15596-07-3)
• EPA Substance Registry System: (Triphenylphosphoranylidene)ketene(15596-07-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 15596-07-3(Hazardous Substances Data)

Usage

Uses

A nucleophilic two-carbon building block that participates in a variety of reactions including cycloaddition, multi-component, and domino reactions.

InChI:InChI=1/C20H15OP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-15H

Upstream product

• 1099-45-2 ethyl (triphenylphosphoranylidene)acetate 
• 103559-83-7 hexaphenylcarbodiphosphorane 
• 36050-78-9 Bis(trimethylsilyl)methylidene triphenylphosphorane 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 141293-41-6 2-(Trimethylsilyl)-2-(triphenylphosphoranyliden)essigsaeure-trimethylsilylester 
• 7533-53-1 O₂CC(PPh₃)2 

Downstream Products

• 20369-55-5 2--4-triphenyl-phosphoranyliden-cyclobutandion-(1,3) 
• 73818-39-0 (Triphenylphosphoranyliden)thioessigsaeure-S-phenylester 
• 20559-76-6 2--4-triphenyl-phosphoranyliden-cyclobutandion-(1,3) 
• 73818-40-3 1-(1-Pyrazolyl)-2-(triphenylphosphoranyliden)ethanon 
• 41693-11-2 1-(triphenylphosphoranylidene)-2-hexanone 
• 96413-04-6 11-(Tetrahydro-pyran-2-yloxy)-1-(triphenyl-λ⁵-phosphanylidene)-undecan-2-one 
• 75872-33-2 1,6-Dihydro-4-methoxy-6-oxo-1-phenyl-3-pyridazincarbonsaeure-methylester 
• 74420-99-8 (2E,4E)-Hexa-2,4-dienedioic acid bis-((1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl) ester 
• 120154-55-4 4-oxo-5-phenyl-3-triphenylphosphorano-2-pyridinethione 
• 75872-39-8 5-<1-(Benzylamino)ethyliden>-5,6-dihydro-4-methyl-1-phenyl-6-thioxo-2(1H)-pyridinon 
• 75872-41-2 5,6-Dihydro-4-methyl-5-<1-(methylamino)ethyliden>-1-phenyl-6-thioxo-2(1H)-pyridinon 
• 19753-66-3 triphenylphosphoranylidene-2-butanone 
• 96413-06-8 3-Methyl-1-(triphenyl-λ⁵-phosphanylidene)-but-3-en-2-one 
• 96413-02-4 3-Methyl-1-(triphenyl-λ⁵-phosphanylidene)-hexan-2-one 

Relevant articles and documents

Ravynic acid, an antibiotic polyeneyne tetramic acid from: Penicillium sp. elucidated through synthesis

A new antibiotic natural product, ravynic acid, has been isolated from a Penicillium sp. of fungus, collected from Ravensbourne National Park. The 3-acylpolyenyne tetramic acid structure was definitively elucidated via synthesis. Highlights of the synthetic method include the heat induced formation of the 3-acylphosphorane tetramic acid and a selective Wittig cross-coupling to efficiently prepare the natural compounds carbon skeleton. The natural compound was shown to inhibit the growth of Staphylococcus aureus down to concentrations of 2.5 g mL-1.

Synthesis of ent-halimanolides from ent-halimic acid

Three natural ent-halimanolides have been synthesized from ent-halimic acid. Their structures have been confirmed as well as their absolute configurations established. Bestmann methodology has been used for the synthesis of butenolides and for the synthes

Catalyst-Enabled Site-Divergent Stereoselective Michael Reactions: Overriding Intrinsic Reactivity of Enynyl Carbonyl Acceptors

A site-divergent stereoselective Michael reaction system is developed based on the identification of two distinct catalysts. Cinchonidine-derived thiourea catalyzes the 1,4-addition of prochiral azlactone enolates to enynyl N-acyl pyrazoles in a highly diastereo- and enantioselective manner to give stereochemically defined alkynes, while P-spiro chiral triaminoiminophosphorane catalytically controls the stereoselective 1,6-addition and the consecutive γ-protonation of the vinylogous enolate intermediate to afford Z,E-configured conjugated dienes. This 1,6-adduct serves as a valuable precursor for the synthesis of a 2-amino-2-deoxy sugar.

A cell-permeable and triazole-forming fluorescent probe for glycoconjugate imaging in live cells

A new fluorescence-forming probe, coumOCT, designed by fusing cyclooctyne with a coumarin fluorophore was successfully used for the imaging of azido-glycoconjugates in living HeLa cells. This probe is cell-permeable and generates fluorescence after triazole formation, thus minimizing the background signal and enabling the real-time intracellular imaging of glycoconjugate trafficking.