2136-76-7

Basic information

• Product Name: 2-(triphenyl-lambda~5~-phosphanylidene)cyclopentanone
• CAS NO: 2136-76-7
• Molecular Formula: C₂₃H₂₁OP
• Molecular Weight: 344.386
• Mol File: 2136-76-7.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 514°C at 760 mmHg
• Flash Point: 264.7°C
• Density: 1.18g/cm³
• Vapor Pressure: 1.12E-10mmHg at 25°C
• Refractive Index: 1.628
• CAS DataBase Reference: 2-(triphenyl-lambda~5~-phosphanylidene)cyclopentanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(triphenyl-lambda~5~-phosphanylidene)cyclopentanone(2136-76-7)
• EPA Substance Registry System: 2-(triphenyl-lambda~5~-phosphanylidene)cyclopentanone(2136-76-7)

Safety Data

• Hazardous Substances Data: 2136-76-7(Hazardous Substances Data)

Usage

Molecular structure

Consists of a cyclopentanone ring with a phosphorus atom bonded to three phenyl groups.

Usage

Commonly used in organic synthesis as a reagent for various transformations, such as the formation of carbon-carbon or carbon-heteroatom bonds.

Metal-catalyzed reactions

Known for its use in metal-catalyzed reactions, including cross-coupling reactions and the preparation of organometallic compounds.

Biological and pharmacological activities

Studied for its potential biological and pharmacological activities.

Versatility

Considered a versatile and valuable compound in the field of chemical and pharmaceutical research.

Upstream product

• 65587-60-2 4-ethoxycarbonylbutyltriphenylphoshonium iodide 
• 41302-32-3 ethyl 5-iodopentanoate 
• 14660-52-7 ethyl 5-bromovalerate 
• 2067-33-6 5-bromopentanoic acid 

Downstream Products

• 603-35-0 triphenylphosphine 
• 71-43-2 benzene 
• 83276-32-8 [2-(2-methoxy-2-oxoethoxy)-1-cyclopenten-1-yl]triphenylphosphonium bromide 
• 83276-26-0 [2-(3-methyl-2-butenyloxy)-1-cyclopenten-1-yl]triphenylphosphonium bromide 
• 83276-20-4 [2-(1-methylethoxy)-1-cyclopenten-1-yl]triphenylphosphonium iodide 
• 83276-18-0 [2-(Phenylmethoxy)-1-cyclopenten-1-yl]triphenylphosphonium bromide 
• 83276-23-7 (2-methoxy-1-cyclopenten-1-yl)triphenylphosphonium 4-methylbenzenesulfonate 
• 104-15-4 toluene-4-sulfonic acid 
• 96013-71-7 1-(tert-Butyl-dimethyl-silanyloxy)-3-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-cyclopentylmethyl]-benzene 
• 96013-71-7 1-(tert-Butyl-dimethyl-silanyloxy)-3-[(1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-cyclopentylmethyl]-benzene 
• 96013-83-1 (1S,2S)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-cyclopentanol 
• 96013-83-1 (1R,2S)-2-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-cyclopentanol 
• 96013-83-1 2-[3-(tert-Butyl-dimethyl-silanyloxy)-benzyl]-cyclopentanol 
• 96013-73-9 1-(tert-Butyl-dimethyl-silanyloxy)-3-[2-(tert-butyl-dimethyl-silanyloxy)-cyclopent-(E)-ylidenemethyl]-benzene 

Relevant articles and documents

The value of 2JP–CO as a diagnostic parameter for the structure and thermal reactivity of carbonyl-stabilised phosphonium ylides

A survey of 20 carbonyl-stabilised phosphonium ylides with recently reported X-ray structures shows a strong correlation between the C[dbnd]P to C[dbnd]O torsion angle and the value of 2JP–CO, with high values being associated with an anti configuration and low with syn. Seven new X-ray structural determinations are reported, several for types of ylide not crystallographically characterised before, and these also conform to this pattern. The value of 2JP–CO is then correlated with whether or not thermal extrusion of Ph3PO occurs to give alkynes for over 200 ylides and an empirical rule developed that the extrusion never occurs for ylides where this value is > 11 Hz. This is used to rationalise the anomalous behaviour of some trioxo ylides and cyclic ylides, two of which afford cycloalkynes, isolated after rearrangement as the isomeric 1,3-dienes. The rule also holds for a family of novel highly fluorinated ylides which afford fluorinated alkynes in good yield upon flash vacuum pyrolysis.