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

Description

(Triphenylphosphoranylidene)ketene is an organic compound characterized by its unique structure, featuring a ketene group with a triphenylphosphoranylidene substituent. This molecule is known for its reactivity and versatility in organic synthesis, making it a valuable intermediate in the formation of various complex organic molecules.

Uses

Used in Organic Synthesis:
(Triphenylphosphoranylidene)ketene is used as a nucleophilic two-carbon building block for its ability to participate in a variety of reactions, including cycloaddition, multi-component, and domino reactions. Its unique reactivity allows for the creation of complex molecular structures that are otherwise difficult to synthesize, making it a valuable tool in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (Triphenylphosphoranylidene)ketene is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its ability to form a wide range of products through different reaction pathways makes it a versatile building block for the development of new drugs and therapeutic agents.
Used in Material Science:
(Triphenylphosphoranylidene)ketene is also utilized in material science for the development of novel materials with specific properties. Its reactivity and structural diversity enable the creation of materials with tailored characteristics, such as improved mechanical strength, thermal stability, or chemical resistance, depending on the desired application.
Used in Chemical Research:
In the field of chemical research, (Triphenylphosphoranylidene)ketene serves as an important model compound for studying reaction mechanisms and exploring new synthetic methodologies. Its unique reactivity allows researchers to gain insights into various chemical processes and develop innovative strategies for the synthesis of complex organic molecules.

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

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

Downstream Products

• 20369-54-4 2--4-triphenyl-phosphoranyliden-cyclobutandion-(1,3) 
• 20369-53-3 2--4-triphenyl-phosphoranyliden-cyclobutandion-(1,3) 
• 73818-39-0 (Triphenylphosphoranyliden)thioessigsaeure-S-phenylester 
• 74163-33-0 [2-Furan-2-yl-4,6-dioxo-5-(triphenyl-λ⁵-phosphanylidene)-5,6-dihydro-4H-pyran-3-yl]-triphenyl-phosphonium; chloride 
• 57674-94-9 1-Phenyl-3H-pyrrolizin-3-on 
• 96413-02-4 3-Methyl-1-(triphenyl-λ⁵-phosphanylidene)-hexan-2-one 
• 75508-95-1 4-Thioxo-2-p-tolyl-5-(triphenyl-λ⁵-phosphanylidene)-4,5-dihydro-[1,3]oxazin-6-one 
• 120154-55-4 4-oxo-5-phenyl-3-triphenylphosphorano-2-pyridinethione 
• 75508-93-9 2-Methyl-4-thioxo-5-(triphenyl-λ⁵-phosphanylidene)-4,5-dihydro-[1,3]oxazin-6-one 
• 91957-34-5 3-benzyl-5,5-dimethyl-4-methylene-2-oxazolidinone 
• 100192-61-8 3-benzyl-5,5-dimethyloxazolidine-2,4-dione 
• 186135-55-7 4-Ethoxy-2H,5H-1-benzoxepin-2-one 
• 186135-56-8 4-Ethoxy-2H,5H-1-benzazepin-2-one 
• 100192-62-9 5-methyl-3-(α-phenylethyl)-2,4-oxazolidinedione 

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.