607-01-2

Basic information

• Product Name: ETHYLDIPHENYLPHOSPHINE
• Synonyms: DIPHENYLETHYLPHOSPHINE;ETHYLDIPHENYLPHOSPHINE;Ethyldiphenylphosphine,98%;Ethyldiphenylphosphine,99%;Silicagel, functionalized, Diphenylphosphinoethyl, 0.7 mmol/g;(Diphenylphosphino)ethane;1-(Diphenylphosphino)ethane;NSC 151254
• CAS NO: 607-01-2
• Molecular Formula: C₁₄H₁₅P
• Molecular Weight: 214.24
• EINECS: 1592732-453-0
• Product Categories: Phosphine Ligands;Synthetic Organic Chemistry;organophosphorus ligand;Achiral Phosphine;Aryl Phosphine
• Mol File: 607-01-2.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 293 °C(lit.)
• Flash Point: >230 °F
• Appearance: Clear colorless/Liquid
• Density: 1.048 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00231mmHg at 25°C
• Refractive Index: n20/D 1.614(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Sensitive: Air Sensitive
• BRN: 744253
• CAS DataBase Reference: ETHYLDIPHENYLPHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYLDIPHENYLPHOSPHINE(607-01-2)
• EPA Substance Registry System: ETHYLDIPHENYLPHOSPHINE(607-01-2)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• RIDADR: 3278
• WGK Germany: 3
• RTECS: SY9242500
• F: 10-13-23
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 607-01-2(Hazardous Substances Data)

Usage

Description

ETHYLDIPHENYLPHOSPHINE is a clear colorless liquid that serves as a versatile and efficient catalyst in various chemical reactions due to its unique chemical properties.

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

• 17985-99-8 ethyldiphenylphosphine N-phenylimide 
• 4736-60-1 ethyltriphenylphosphonium iodide 
• 310-40-7 diethyl (4-fluorophenyl)phosphonate 
• 15475-27-1 potassium diphenylphosphine 
• 1605-53-4 diethyl-phenyl-phosphine 
• 1079-66-9 chloro-diphenylphosphine 
• 617-86-7 triethylsilane 
• 719-80-2 Ethyl diphenylphosphinite 
• 21776-15-8 diphenyl(vinyl)phosphine sulfide 
• 1017-98-7 ethyldiphenylphosphine sulfide 
• 74-85-1 ethene 
• 829-85-6 diphenylphosphane 
• 587-85-9 diphenylmercury(II) 
• 644-97-3 Dichlorophenylphosphine 

Downstream Products

• 5271-36-3 P,P-diethyldibenzophospholium iodide 
• 1733-57-9 ethydiphenylphosphine oxide 
• 54807-90-8 4-(ethyl-phenyl-phosphanyl)-butan-1-ol 
• 334932-58-0 C₂₆H₂₅NO₃P₂ 
• 6372-42-5 cyclohexyldiphenylphosphine 
• 1486-28-8 diphenyl(methyl)phosphine 
• 1038-95-5 Tri(p-tolyl)phosphine 
• 71564-17-5 manganese pentacarbonyl 
• 47315-22-0 (CO)4Mn(P(C₆H₅)2(C₂H₅)) 
• 61943-36-0 HMn(CO)3(P(C₆H₅)2(C₂H₅))2 
• 15444-76-5 Mn₂(CO)8(ethyldiphenylphosphine)2 
• 51684-12-9 iron(II)(carbonyl)2((phenyl)2ethylphosphine)2Br₂ 
• 36870-06-1 trans-Fe(CO)3(PPh₂Et)2 
• 22671-03-0 mer-{OsCl₃(PEtPh₂)3} 

Relevant articles and documents

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.

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).

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.