1031-93-2

Basic information

• Product Name: DIPHENYL(P-TOLYL)PHOSPHINE
• Synonyms: P-TOLYLDIPHENYLPHOSPHINE;Phosphine, (4-methylphenyl)diphenyl-;DIPHENYL(P-TOLYL)PHOSPHINE;DIPHENYL-4-TOLYLPHOSPHINE;DIPHENYL-4-METHYLPHENYLPHOSPHINE;(4-METHYLPHENYL)(DIPHENYL)PHOSPHINE;p-Tolyldiphenylphosphine,min.96%;p-Tolyldiphenylphosphine, 96+%
• CAS NO: 1031-93-2
• Molecular Formula: C₁₉H₁₇P
• Molecular Weight: 276.31
• EINECS: 213-848-3
• Product Categories: Ligand;Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds;organophosphorus ligand;Achiral Phosphine;Aryl Phosphine
• Mol File: 1031-93-2.mol
• Article Data: 31

Chemical Properties

• Melting Point: 66-68 °C(lit.)
• Boiling Point: 373.7 °C at 760 mmHg
• Flash Point: 189.3 °C
• Appearance: white/crystal
• Density: g/cm³
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Storage Temp.: 2-8°C
• BRN: 646709
• CAS DataBase Reference: DIPHENYL(P-TOLYL)PHOSPHINE(CAS DataBase Reference)
• NIST Chemistry Reference: DIPHENYL(P-TOLYL)PHOSPHINE(1031-93-2)
• EPA Substance Registry System: DIPHENYL(P-TOLYL)PHOSPHINE(1031-93-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-38-37-36
• Safety Statements: 26-37/39-39-37
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 1031-93-2(Hazardous Substances Data)

Usage

Description

Diphenyl(p-tolyl)phosphine is a white to light yellow crystalline powder that is a trivalent phosphorus compound with a phenyl group and a p-tolyl group attached to it. It is known for its unique chemical properties and versatile applications in various fields.

Uses

Used in Organic Synthesis:
Diphenyl(p-tolyl)phosphine is used as a reactant for various organic synthesis processes, including three-component cyclization, probing coordination ability via a palladium pincer complex, and chelation-assisted hydroacylation of olefins with primary alcohols. Its unique reactivity and selectivity make it a valuable building block in the synthesis of complex organic molecules.
Used in Inorganic Chemistry:
In inorganic chemistry, Diphenyl(p-tolyl)phosphine is used as a reactant for the synthesis of trinuclear ruthenium carbonyl triarylphosphine cluster complexes. These complexes have potential applications in catalysis, materials science, and as precursors for the synthesis of other metal phosphide compounds.
Used in Medicinal Chemistry:
Diphenyl(p-tolyl)phosphine is used as a reactant for the synthesis of leishmanicidal leads targeting mitochondria through the inhibition of the respiratory complex. This application highlights its potential as a precursor for the development of new therapeutic agents against parasitic diseases.
Used in Materials Science:
In materials science, Diphenyl(p-tolyl)phosphine is used as a reactant for the synthesis of InP nanofibers and metal phosphide nanostructures. These materials have potential applications in optoelectronics, photovoltaics, and sensing technologies.
Used in Physical Chemistry:
Diphenyl(p-tolyl)phosphine is used in the generation of peroxyle radical cations via pulse radiolysis one-electron oxidations. This application allows researchers to study the properties and reactivity of these highly reactive species, which can provide insights into various chemical and physical processes.

Synthesis Reference(s)

The Journal of Organic Chemistry, 52, p. 748, 1987 DOI: 10.1021/jo00381a008

InChI:InChI=1/C19H17P/c1-16-12-14-19(15-13-16)20(17-8-4-2-5-9-17)18-10-6-3-7-11-18/h2-15H,1H3

Upstream product

• 106-38-7 para-bromotoluene 
• 1079-66-9 chloro-diphenylphosphine 
• 1005-32-9 p-tolyldichlorophosphine 
• 127915-37-1 tris(diphenyl-p-tolylphosphan)(triphenylsilyl)silver(I) 
• 624-31-7 4-tolyl iodide 
• 6840-28-4 diphenyl(p-tolyl)phosphine oxide 
• 829-85-6 diphenylphosphane 
• 620-94-0 di-(p-tolyl)sulfane 
• 1213-51-0 (trimethylstannyl)diphenylphosphine 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 40841-62-1 (diphenylphosphino)(p-tolyl)methanone 
• 108-88-3 toluene 
• 106-43-4 para-chlorotoluene 
• 4376-01-6 sodium diphenylphosphide 

Downstream Products

• 60271-50-3 [4-(2-benzothiazol-2-yl-vinyl)-benzyl]-diphenyl-p-tolyl-phosphonium; bromide 
• 33082-06-3 (triphenylphosphoranediyl)aminocyclotrithiatriazene 
• 5587-39-3 diphenyl(p-tolyl)phosphine sulfide 
• 6840-28-4 diphenyl(p-tolyl)phosphine oxide 
• 93581-94-3 Pd(SCN)2((H₃CC₆H₄)P(C₆H₅)2)2 
• 86528-27-0 [Pt2H(PPh2(4-MeC6H4))(μ-dppm)]PF6 
• 1333-74-0 hydrogen 
• 87196-12-1 cis-Pd(N-thionitrosodimethylamine)(p-tolylPPh₂)Cl₂ 
• 187928-32-1 chloro(η(5)-cyclopentadienyl)bis(diphenyl-p-tolylphosphine)ruthenium 
• 184152-05-4 Rh((C₆H₅)2PCHC(O)C₆H₅)(P(C₆H₅)2C₆H₄CH₃)(CO) 

Relevant articles and documents

A general synthesis of aryl phosphines by palladium catalyzed phosphination of aryl bromides using triarylphosphines

Palladium catalyzed phosphination of substituted aryl bromides using triarylphosphines as the phosphinating agents has been developed; this method tolerates ketone, aldehyde, ester, nitrile, ether and chloride functional groups.

Photochemical Anion-Promoted Carbon-Sulfur Cleavage Reactions of Diaryl Sulfides, Alkyl Aryl Sulfides, and Related Sulfoxides and Sulfones

Diaryl sulfides and the related sulfoxides and sulfones react with substances such as diethyl phosphite anion, pinacolone enolate, and diphenylphosphide anion under irradiation to cleave one carbon-sulfur bond and form diethyl arylphosphonates, arylmethyl tert-butyl ketones, and aryldiphenylphosphines.Alkyl aryl sulfides and the related sulfones also experience carbon-sulfur bond cleavage under these conditions to produce arenethiols.Generally, these reactions occur in synthetically useful yields.The reactions of the anions with these sulfides, sulfoxides, and sulfones all require irradiation, but is notable that the reactions of diphenylphosphide anion occur in the visible region of the spectrum.Several lines of evidence suggest that the reaction proceeds via the familiar SRN1 pathway and that the photochemically-induced electron transfer occurs in an arene-anion complex.Thermochemical considerations dictate the cleavage direction in the anion radicals of unsymmetrical sulfides.

Application of palladium-catalyzed Pd-aryl/P-aryl exchanges: Preparation of functionalized aryl phosphines by phosphination of aryl bromides using triarylphosphines

Palladium-catalyzed Pd-aryl/P-aryl interchange reaction was applied in the synthesis of various functionalized arylphosphines. This phosphination used inexpensive, readily available and air stable triarylphosphines as the phosphinating agents. Broad functional groups were compatible including keto, aldehyde, ester, nitrile, ether, chloride, pyridyl and thiophenyl groups. Halides were found to be good promoter for the rates and yields of the reaction.

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Efficient potassium hydroxide promoted P-arylation of aryl halides with diphenylphosphine

A simple synthetic method of triarylphosphine compounds by KOH-promoted P-Arylation reaction of aryl halides with diphenylphosphine is presented. Notably, this transformation could smoothly proceed with high yields under transition-metal-free and mild reaction conditions. In addition, this protocol is valuable for industrial application due to the convenient operation and readily accessible aromatic halides. A possible explanation of the reaction mechanism was proposed based on the experimental data.

Palladium-Catalyzed C-P(III) Bond Formation by Coupling ArBr/ArOTf with Acylphosphines

Palladium-catalyzed C-P bond formation reaction of ArBr/ArOTf using acylphosphines as differential phosphination reagents is reported. The acylphosphines show practicable reactivity with ArBr and ArOTf as the phosphination reagents, though they are inert to the air and moisture. The reaction affords trivalent phosphines directly in good yields with a broad substrate scope and functional group tolerance. This reaction discloses the acylphosphines' capability as new phosphorus sources for the direct synthesis of trivalent phosphines.

Ready Approach to Organophosphines from ArCl via Selective Cleavage of C-P Bonds by Sodium

The preparation, application, and reaction mechanism of sodium phosphide R2PNa and other alkali metal phosphides R2PM (M = Li and K) have been studied. R2PNa could be prepared, accurately and selectively, via the reactions of SD (sodium finely dispersed in mineral oil) with phosphinites R2POR′ and chlorophosphines R2PCl. R2PNa could also be prepared from triarylphosphines and diarylphosphines via the selective cleavage of C-P bonds. Na was superior to Li and K for these reactions. R2PNa reacted with a variety of ArCl to efficiently produce R2PAr. ArCl is superior to ArBr and ArI since they only gave low yields of the products. In addition, Ph2PNa is superior to Ph2PLi and Ph2PK since Ph2PLi did not produce the coupling product with PhCl, while Ph2PK only gave a low yield of the product. An electron-withdrawing group on the benzene ring of ArCl greatly accelerated the reactions with R2PNa, while an alkyl group reduced the reactivity. Vinyl chloride and alkyl chlorides RCl also reacted efficiently. While t-BuCl did not produce the corresponding product, admantyl halides could give the corresponding phosphine in high yields. A wide range of phosphines were prepared by this method from the corresponding chlorides. Unsymmetric phosphines could also be conveniently generated in one pot starting from Ph3P. Chiral phosphines were also obtained in good yields from the reactions of menthyl chlorides with R2PNa. Possible mechanistic pathways were given for the reductive cleavage of R3P by sodium generating R2PNa and the substitution reactions of R2PNa with ArCl generating R2PAr.