Tris(3,5-dimethylphenyl)phosphine

Base Information

• Chemical Name: Tris(3,5-dimethylphenyl)phosphine
• CAS No.: 69227-47-0
• Molecular Formula: C24H27 P
• Molecular Weight: 346.452
• Hs Code.: 29310099
• European Community (EC) Number: 624-162-2
• DSSTox Substance ID: DTXSID5071969
• Nikkaji Number: J38.110A
• Wikidata: Q72515095
• Mol file: 69227-47-0.mol

Synonyms:Tris(3,5-dimethylphenyl)phosphine;69227-47-0;tris(3,5-dimethylphenyl)phosphane;Tri-3,5-xylylphosphine;Phosphine, tris(3,5-dimethylphenyl)-;C24H27P;p(3,5-xylyl)3;tris(3,5-xylyl)phosphine;tris(3,5-xylyl) phosphine;SCHEMBL503226;DTXSID5071969;C24-H27-P;MFCD03094579;AKOS015914585;CS-W013910;AS-61267;Tris(3,5-dimethylphenyl)phosphine, 96%;FT-0655401;F17206;A836402

Chemical Property of Tris(3,5-dimethylphenyl)phosphine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.06E-08mmHg at 25°C
• Melting Point: 161-164 °C
• Boiling Point: 474.1 °C at 760 mmHg
• Flash Point: 255 °C
• PSA: 13.59000
• LogP: 5.29520
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 346.185037859
• Heavy Atom Count: 25
• Complexity: 327

Purity/Quality:

99% ^*data from raw suppliers

Tris(3,5-dimethylphenyl)phosphine, 98% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-36/37/39-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC(=CC(=C1)P(C2=CC(=CC(=C2)C)C)C3=CC(=CC(=C3)C)C)C
• Uses: Catalyst for:Cu / diphosphine-catalyzed asymmetric hydrogenation of heteroaromatic ketones and enonesHighly selective rhodium-catalyzed hydrogenation reactionsClassical versus kinetic resolution in preparation of privileged silicon-stereogenic silanaphthalenesUsed for kinetic resolution of donor-functionalized secondary alcohols via Cu-H-catalyzed stereoselective silylation by dehydrogenative Si-O coupling with Si-stereogenic silanesUsed for comparative studies of conformational rigidity of silicon-stereogenic silanes in asymmetric catalysis

Technology Process of Tris(3,5-dimethylphenyl)phosphine

There total 4 articles about Tris(3,5-dimethylphenyl)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: 56.0%

tris(3,5-dimethylphenyl)phosphine oxide (381212-20-0) → tris(3,5-dimethylphenyl)phosphine (69227-47-0)

Guidance literature:

With 2,6-dimethylpyridine; oxalyl dichloride; hydrogen; tris(2,6-difluorophenyl)borane triethylphosphine oxide; In ⁽²⁾H₈-toluene; at 130 ℃; for 2h; under 3000.3 Torr; Reagent/catalyst;

DOI:10.1002/anie.201809275

Reference yield: 52.0%

3,5-dimethyphenylmagnesium bromide (34696-73-6) → tris(3,5-dimethylphenyl)phosphine (69227-47-0)

Guidance literature:

With phosphorus trichloride; In tetrahydrofuran; 0 deg C then reflux, 2 h;

DOI:10.1021/jo00011a018

Reference yield:

5-bromo-1,3-xylene (556-96-7) → tris(3,5-dimethylphenyl)phosphine (69227-47-0)

Guidance literature:

5-bromo-1,3-xylene; With magnesium; In tetrahydrofuran; for 1h; Heating;

With phosphorus trichloride; In diethyl ether; at 20 ℃; for 20h;

DOI:10.1016/S0040-4039(03)00940-7

upstream raw materials:

3,5-dimethyphenylmagnesium bromide

5-bromo-1,3-xylene

tris(3,5-dimethylphenyl)phosphine oxide

Downstream raw materials:

tris(3,5-dimethylphenyl)phosphine oxide

(2S,4S)-2,4-bis[di(3,5-dimethylphenyl)phosphino]pentane

C₈⁽¹³⁾CH₁₅BO₂

C₁₆⁽¹³⁾CH₃₀B₂O₂

Refernces

• 1、 Herseczki, Zsanett,Gergely, Ildiko,Hegedues, Csaba,Szoellosy, Aron,Bakos, Jozsef. "Electronic and steric effects of ligands as control elements for rhodium-catalyzed asymmetric hydrogenation". . p. 1673 - 1676. Retrieved 2007/10/03.
• 2、 Culcasi, Marcel,Berchadsky, Yves,Gronchi, Gerard,Tordo, Paul. "Anodic Bahavior of Crowded Triarylphosphines. ESR Study of Triarylphosphoniumyl Radicals, Ar3P.+". . p. 3537 - 3542. Retrieved 2007/10/02.