Diphenyl(p-tolyl)phosphine

Base Information

• Chemical Name: Diphenyl(p-tolyl)phosphine
• CAS No.: 1031-93-2
• Molecular Formula: C19H17P
• Molecular Weight: 276.318
• Hs Code.: 29319090
• European Community (EC) Number: 213-848-3
• DSSTox Substance ID: DTXSID40145641
• Nikkaji Number: J217.157K
• Wikidata: Q72469392
• Mol file: 1031-93-2.mol

Synonyms:Diphenyl(p-tolyl)phosphine;1031-93-2;Diphenyl-p-tolylphosphine;Triphenylphosphine resin;p-Tolyldiphenylphosphine;(4-methylphenyl)-diphenylphosphane;Diphenyl(4-tolyl)phosphine;(4-METHYLPHENYL)DIPHENYL PHOSPHINE;EINECS 213-848-3;Diphenyl-p-tolyl phosphine;(4-Methylphenyl)(diphenyl)phosphine;Diphenyl-4-methylphenylphosphine;(4-methylphenyl)diphenylphosphane;SCHEMBL49680;Diphenyl (4-tolyl) phosphine;DTXSID40145641;Diphenyl(p-tolyl)phosphine, 96%;AMY11735;BAA03193;MFCD00008543;Phosphine, (4-methylphenyl)diphenyl-;AKOS015914280;CS-W012315;SC11156;AS-58753;FT-0625237;I10211;A800689;J-000896;DIPHENYL(4-METHYLPHENYL)PHOSPHINE;DIPHENYL(P-TOLYL)PHOSPHINE;P-TOLYLDIPHENYLPHOSPHINE

Chemical Property of Diphenyl(p-tolyl)phosphine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.89E-05mmHg at 25°C
• Melting Point: 66-68 °C(lit.)
• Boiling Point: 373.7 °C at 760 mmHg
• Flash Point: 189.3 °C
• PSA: 13.59000
• Density: g/cm³
• LogP: 3.75320
• Storage Temp.: 2-8°C
• XLogP3: 5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 276.106787540
• Heavy Atom Count: 20
• Complexity: 250

Purity/Quality:

98% ^*data from raw suppliers

p-Tolyldiphenylphosphine, min. 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-38-37-36
• Safety Statements: 26-37/39-39-37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)P(C2=CC=CC=C2)C3=CC=CC=C3
• Uses: Reactant for:Three-component cyclizationProbing coordination ability via a palladium pincer complexChelation-assisted hydroacylation of olefins with primary alcoholsReactant for synthesis of:Trinuclear ruthenium carbonyl triarylphosphine cluster complexesLeishmanicidal leads targeting mitochondria through inhibition of the respiratory complexInP nanofibers / metal phosphide nanostructuresPeroxyl radical cations via pulse radiolysis one-electron oxidations

Technology Process of Diphenyl(p-tolyl)phosphine

There total 40 articles about Diphenyl(p-tolyl)phosphine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

para-bromotoluene (106-38-7) + (diphenylphosphino)(p-tolyl)methanone (40841-62-1) → diphenyl(p-tolyl)phosphine (1031-93-2)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; caesium carbonate; In toluene; at 100 ℃; for 12h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.joc.1c00937

Reference yield: 90.0%

para-chlorotoluene (106-43-4) + (trimethylsilyl)diphenylphosphine (17154-34-6) → diphenyl(p-tolyl)phosphine (1031-93-2)

Guidance literature:

With bis(triphenylphosphine)nickel(II) chloride; potassium tert-butylate; In 1,4-dioxane; at 90 ℃; for 12h; Inert atmosphere;

DOI:10.1002/ejoc.201402660

Reference yield: 90.0%

4-tolyl iodide (624-31-7) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → diphenyl(p-tolyl)phosphine (1031-93-2)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; palladium dichloride; at 120 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tetlet.2015.12.018

upstream raw materials:

para-bromotoluene

chloro-diphenylphosphine

para-methylphenylmagnesium bromide

4-tolyl iodide

Downstream raw materials:

(P(C₆H₅)2(C₆H₄CH₃)C₆H₇)Fe(CO)3⁽¹⁺⁾*BF₄^(1-)={(P(C₆H₅)2(C₆H₄CH₃)C₆H₇)Fe(CO)3}BF₄

η2-(C,O) bis(diphenyl(p-tolyl)phosphine)(ethylphenylketene)nickel

dichloro-(perfluorobutyl)tetramethylcyclopentadienyl-diphenyl(p-tolyl)phosphine-rhodium(III)

Pd(dibutyldithiocarbamate)(PPh₂-p-tolyl)Cl

Refernces

• 1、 Budnikova, Yulia,Kargin, Yuri,Nedelec, Jean-Yves,Perichon, Jacques. "Nickel-catalysed electrochemical coupling between mono- or di-chlorophenylphosphines and aryl or heteroaryl halides". . p. 63 - 66. Retrieved 1999.
• 2、 Van Allen, Derek,Venkataraman. "Copper-catalyzed synthesis of unsymmetrical triarylphosphines". . p. 4590 - 4593. Retrieved 2003.
• 3、 Sun, Meng,Zhang, Hong-Yu,Han, Qi,Yang, Kuo,Yang, Shang-Dong. "Nickel-catalyzed C-P cross-coupling by C-CN bond cleavage". . p. 9566 - 9570. Retrieved 2011.
• 4、 Nowrouzi, Najmeh,Keshtgar, Saba,Bahman Jahromi, Enayatollah. "Ligand-free palladium catalyzed phosphorylation of aryl iodides". . p. 348 - 350. Retrieved 2016.
• 5、 Zhang, Ji-Shu,Chen, Tieqiao,Yang, Jia,Han, Li-Biao. "Nickel-catalysed P-C bond formation via P-H/C-CN cross coupling reactions". . p. 7540 - 7542. Retrieved 2015.
• 6、 Cristau, Henri-Jean,Chene, Alain,Christol, Henri. "ARYLATION CATALYTIQUE D'ORGANOPHOSPHORES. PRODUITS DE L'ARYLATION, CATALYSEE PAR LES SELS DE NICKEL (II), DE COMPOSES DU PHOSPHORE TRICOORDINE". . p. 283 - 296. Retrieved 1980.
• 7、 Ye, Yun,Zhu, Jie,Huang, Yinhua. "Diverse C-P Cross-Couplings of Arylsulfonium Salts with Diarylphosphines via Selective C-S Bond Cleavage". supporting information. p. 2386 - 2391. Retrieved 2021/04/05.