607-01-2

Usage

Uses

Used in Chemical Synthesis:
ETHYLDIPHENYLPHOSPHINE is used as a catalyst for the following applications:
1. Three component coupling reactions of arylaldehydes with Me vinyl ketone and phthalimide, enabling the formation of complex molecules with high efficiency and selectivity.
2. Regioand stereoselective hydroalkynylation of methylenecyclopropanes, allowing for the precise control of molecular structure in the synthesis process.
3. Synthesis of oxazolidines, thiazolidines, pyrrolidines, and indoles, which are important building blocks in the pharmaceutical and chemical industries.
4. Dimer to monomer conversion, facilitating the production of specific monomers from their dimeric forms.
5. Tandem Morita-Baylis-Hillman/Michael addition reactions, providing a one-pot approach to synthesize complex molecules with multiple functional groups.
6. Platinum-catalyzed cyclization, which is crucial in the synthesis of cyclic compounds with high selectivity and yield.
7. Regioselective and stereoselective [3+2] cycloaddition, allowing for the formation of cyclic compounds with specific structural features.
8. Platinum-catalyzed intermolecular hydroamination, a key step in the synthesis of nitrogen-containing compounds.
9. Hydroformylation reactions, which are essential for the production of aldehydes from olefins, a critical component in the chemical industry.
Used in Pharmaceutical Industry:
ETHYLDIPHENYLPHOSPHINE is used as a catalyst for the synthesis of various pharmaceutical compounds, such as oxazolidines, thiazolidines, pyrrolidines, and indoles, which are important building blocks in the development of new drugs.
Used in Chemical Industry:
ETHYLDIPHENYLPHOSPHINE is used as a catalyst in the production of various chemicals, including the synthesis of complex molecules, the formation of cyclic compounds, and the production of aldehydes from olefins. Its versatility and efficiency make it a valuable asset in the chemical industry.

InChI:InChI=1/C14H15P/c1-2-15(13-9-5-3-6-10-13)14-11-7-4-8-12-14/h3-12H,2H2,1H3

Upstream product

• 925-90-6 ethylmagnesium bromide 
• 1079-66-9 chloro-diphenylphosphine 
• 557-20-0 diethylzinc 
• 17985-99-8 ethyldiphenylphosphine N-phenylimide 
• 4736-60-1 ethyltriphenylphosphonium iodide 
• 120175-90-8 Natriumdiphenylphosphinoformiat 
• 75-03-6 ethyl iodide 
• 92578-64-8 2-Diphenylphosphanyl-propionic acid 
• 74-96-4 ethyl bromide 
• 829-85-6 diphenylphosphane 
• 1733-57-9 ethydiphenylphosphine oxide 
• 310-40-7 diethyl (4-fluorophenyl)phosphonate 
• 15475-27-1 potassium diphenylphosphine 
• 65567-06-8 lithium diphenylphosphide 

Downstream Products

• 5271-36-3 P,P-diethyldibenzophospholium iodide 
• 1733-57-9 ethydiphenylphosphine oxide 
• 54807-90-8 4-(ethyl-phenyl-phosphanyl)-butan-1-ol 
• 55759-79-0 5-(ethyl-phenyl-phosphanyl)-pentan-1-ol 
• 18629-30-6 Diphenyl-aethyl-(p-benzhydryl-phenyl)-phosphoniumjodid 
• 17244-59-6 2-ethyl-2,2-diphenyl-4,4,5,5-tetrakis-trifluoromethyl-2λ⁵-[1,3,2]dioxaphospholane 
• 17244-62-1 2-ethyl-2,2-diphenyl-2λ⁵-phenanthro[9,10-d][1,3,2]dioxaphosphole 
• 96775-51-8 Hydroxymethyl-aethyl-diphenyl-phosphonium 
• 17986-05-9 N-(p-Toluolsulfonyl)-ethyl-diphenyl-phosphinimin 
• 40730-67-4 Diphenylethylphosphinfluorenylid 
• 21858-97-9 Aethyl-diphenyl-phosphordichlorid 
• 35935-13-8 C₁₄H₁₅F₂P 
• 3619-88-3 ethylphenylphosphine 
• 79731-20-7 C₁₆H₁₉N₄O₂P 

Relevant academic research and scientific papers

Decarboxylative Phosphine Synthesis: Insights into the Catalytic, Autocatalytic, and Inhibitory Roles of Additives and Intermediates

Phosphines are among the most widely used ligands, catalysts, and reagents. Current synthetic approaches to phosphines are dominated by nucleophilic displacement reactions with organometallic reagents. Here, we report a radical-based approach to phosphines that proceeds by a cross-electrophile coupling of chlorophosphines and redox-active esters. The reaction allows for the synthesis of a broad range of substituted phosphines that were not readily attainable with the present methods. Our experimental and DFT computational studies also clarified the catalytic, autocatalytic, and inhibitory roles of additives and intermediates, as well as the mechanistic details of the photocatalytic and zinc-mediated redox modes that can have implications for the mechanistic interpretation of other cross-electrophile coupling reactions.

Exploring the Reactivity of Donor-Stabilized Phosphenium Cations: Lewis Acid-Catalyzed Reduction of Chlorophosphanes by Silanes

Phosphane-stabilized phosphenium cations react with silanes to effect either reduction to primary or secondary phosphanes, or formation of P-P bonded species depending upon counteranion. This operates for in situ generated phosphenium cations, allowing catalytic reduction of P(III)-Cl bonds in the absence of strong reducing agents. Anion and substituent dependence studies have allowed insight into the competing mechanisms involved.

Raney-Ni reduction of phosphine sulfides

A variety of tertiary phosphine sulfides have been reduced by Raney-Ni to give the corresponding phosphineswith high efficiency and undermild conditions. Alkyl, aryl, acyclic, cyclic, aswell as sterically crowded phosphine sulfides are reduced with equal facility. Optically active P-stereogenic phosphine sulfides are reduced stereospecifically with clean retention of configuration at P. Reductions of unsaturated phosphinesulfides is not fully chemoselective and takes place with concomitant partial reduction of the double bond. Clean reduction of the unsaturated phosphine sulfides to the corresponding fully saturated phosphines can be achieved in one step by running the reduction under H2atmosphere (balloon).

Reduction of phosphine oxides to the corresponding phosphine derivatives in Mg/Me3SiCl/DMI system

Direct reductions of phosphine oxides to the corresponding phosphines were performed successfully by using Mg/Me3SiCl/DMI system. The reduction proceeded under mild conditions and was applicable to a wide range of phosphine oxides; triarylphosphine oxides, alkyldiarylphosphine oxides, and dialkylarylphosphine oxides gave the corresponding phosphines in good to excellent yields.

Highly efficient reduction of tertiary phosphine oxides and sulfides with amine-assisted aluminum hydrides under mild conditions

Reduction of tertiary phosphine oxides and sulfides into the corresponding phosphines with amine-assisted aluminum hydrides has been studied. The method is characterized by mild conditions, short reaction time, high efficiency, and expanded substrate scope. The new method is an alternative to the currently used methods of reducing phosphine oxides or recycling phosphines engaged in organic reactions.

Terminal phosphanido rhodium complexes mediating catalytic P-P and P-C bond formation

Complexes with terminal phosphanido (M-PR2) functionalities are believed to be crucial intermediates in new catalytic processes involving the formation of P-P and P-C bonds. We showcase here the isolation and characterization of mononuclear phosphanide rhodium complexes ([RhTp(H)-(PR2)L]) that result from the oxidative addition of secondary phosphanes, a reaction that was also explored computationally. These compounds are active catalysts for the dehydrocoupling of PHPh2 to Ph 2P-PPh2. The hydrophosphination of dimethyl maleate and the unactivated olefin ethylene is also reported. Reliable evidence for the prominent role of mononuclear phosphanido rhodium species in these reactions is also provided.

An acidity scale of tetrafluoroborate salts of phosphonium and iron hydride compounds in [D2]dichIoromethane

Equilibrium constants (K) for reactions between acids and the conjugate base forms of a number of phosphonium salts, [HPR3][BF4], and iron hydrides, [Fe(CO)3H(PR3)2][BF 4], in CD2Cl2 have been determined by means of 31P and 1H NMR spectroscopy at 20°C. The anchor compound chosen for pKCD2Cl2 determinations was [HPCy 3][BF4] with a pKCD2Cl2 value of 9.7, as assigned by literature convention (Cy: cyclohexyl). A continuous scale of pKCD2Cl2 values covering the range from 9.7 to -3 was created and correlated with the ΔH values reported by Angelici and co-workers and literature pKa values. The pKCD2Cl2 values for 15 other hydride or dihydrogen complexes of the iron group elements and of diethyl ether were also placed on this scale. The crystal structures of [Fe(CO) 3H(PCy2Ph)2][BF4] and [Fe(CO) 3(PCy2Ph)2] revealed that the frans-oriented, bulky, unsymmetrical phosphane ligands distort the equatorial plane of the complexes. The acidity of iron carbonyl hydrides is an important feature of the reactions of iron hydrogenase enzymes.

CsOH-promoted P-alkylation: A convenient and highly efficient synthesis of tertiary phosphines

A mild and efficient method for the synthesis of tertiary phosphines and ditertiary phosphines has been developed. In the presence of cesium hydroxide, molecular sieves and DMF at room temperature, various secondary phosphines and alkyl bromides were examined, and the results have demonstrated that this methodology offers a general synthetic procedure to produce tertiary phosphines in moderate to high yields. Optically active tertiary phosphine synthesis is also described.

Synthesis of 1,2-dihydro-1,3-diaza-2λ5,4λ5-2,4- diphosphorine 2-oxides

The reaction of lithium (N-diphenylphosphoryl)phosphazenes with nitriles afforded 1,2-dihydro-1,3-diaza-2λ5,4λ5-2,4- diphosphorine 2-oxides through a C-regioselective addition to the cyano linkage followed by in situ cyclocondensation. The new heterocycles were designed to mimic thymine and are promising chemotherapeutic anticancer agents. As an exception, for p-nitrobenzonitrile a SNAr reaction was exclusively observed with the nucleophile entering in the ortho position of the nitro substituent in a process directed by the strong electron withdrawing effect of the NO2 group.

New synthetic approach to phosphonium salts derived from 4,5-bis(diphenylphosphino)-1-phenylpyridazin-6-one and quantum-chemical calculations of their formation

4,5-Bis(diphenylphosphino)-1-phenylpyridazin-6-one reacts with ethyl iodide, 1,2-dichloroethane, 1,2-dibromomehtane, and o-dibromobenzene to give the corresponding bis-phosphonium salts which, depending on the halogen derivative, can undergo further trans