1754-88-7

Basic information

• Product Name: ethylidene(triphenyl)-lambda~5~-phosphane
• Synonyms: Phosphorane, ethylidenetriphenyl-
• CAS NO: 1754-88-7
• Molecular Formula: C₂₀H₁₉P
• Molecular Weight: 290.3386
• Mol File: 1754-88-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 441.8°C at 760 mmHg
• Flash Point: 221°C
• Density: 1.09g/cm³
• Vapor Pressure: 1.37E-07mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: ethylidene(triphenyl)-lambda~5~-phosphane(CAS DataBase Reference)
• NIST Chemistry Reference: ethylidene(triphenyl)-lambda~5~-phosphane(1754-88-7)
• EPA Substance Registry System: ethylidene(triphenyl)-lambda~5~-phosphane(1754-88-7)

Safety Data

• Hazardous Substances Data: 1754-88-7(Hazardous Substances Data)

Upstream product

• 896-33-3 ethyltriphenylphosphonium chloride 
• 7664-41-7 ammonia 
• 603-35-0 triphenylphosphine 
• 74-96-4 ethyl bromide 

Downstream Products

• 79840-20-3 ethylidenetriphenylphosphorane-borane 
• 13411-77-3 2-Dipropylphosphino-1-phenyl-propyl⁽²⁾-triphenylphosphonium-chlorid 
• 77613-59-3 4c-tert-butyl-3r-methyl-2,2,2-triphenyl-2λ⁵-[1,2]oxaphosphetane 
• 13411-70-6 Triphenylphosphin-α-dicyclohexylphosphino-aethyliden 
• 2077-29-4 (Z)-1-(4-tolyl)-1-propene 
• 2077-30-7 (E)-1-methyl-4-(prop-1-enyl)benzene 
• 873-66-5 1-propenylbenzene 
• 766-90-5 cis-1-phenyl-1-propylene 
• 637-50-3 1-phenylpropene 
• 100-51-6 benzyl alcohol 
• 25679-28-1 cis-Anethole 
• 4180-23-8 E-1-(4'-methoxyphenyl)prop-1-ene 
• 896-33-3 ethyltriphenylphosphonium chloride 
• 1450-07-3 1-benzoylethylidenetriphenylphosphorane 

Relevant articles and documents

Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters

A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.

Enantioselective palladium-catalyzed addition of malonates to 3,3-difluoropropenes

Monofluoroalkenes bearing a malonate unit at the β position can be synthesized by the enantioselective addition of diesters to 3,3-difluoropropenes. The difference in reactivity regarding the geometry and the substituents of the alkene of the 3,3-difluoropropenes, as well as the alkyl groups of the malonates, was studied and limitations were identified. The reaction was also performed with different 3,3-difluoropropenes. Further synthetic transformations of a newly functionalized monofluoroalkene were also accomplished.

Nucleophilic 1,1-Difluoroethylation with Fluorinated Phosphonium Salt

The fluorinated phosphonium salt (Ph3P+CF2CH3 BF4-) was shown to act as a nucleophilic 1,1-difluoroethylation agent to enable difluoroethylation of aldehydes and imines.