Tri-o-tolylphosphine

Base Information

• Chemical Name: Tri-o-tolylphosphine
• CAS No.: 6163-58-2
• Molecular Formula: C21H21P
• Molecular Weight: 304.371
• Hs Code.: HOSPHINE PRODUCT IDENTIFICATION
• European Community (EC) Number: 228-193-9
• NSC Number: 116667
• UNII: 5M32DK8XA8
• DSSTox Substance ID: DTXSID9064130
• Nikkaji Number: J209.007D
• Wikipedia: Tris(o-tolyl)phosphine
• Wikidata: Q60225932
• Mol file: 6163-58-2.mol

Synonyms:TOTP;tri-O-tolyphosphine;tris(2-methylphenyl)phosphine;tris(o-tolyl)phosphine;tris-O-tolyphosphine

Chemical Property of Tri-o-tolylphosphine

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Melting Point: 123-125 °C(lit.)
• Boiling Point: 412.4 °C at 760 mmHg
• Flash Point: 214.6 °C
• PSA: 13.59000
• Density: 1.16[at 20℃]
• LogP: 4.37000
• Storage Temp.: Store below +30°C.
• Sensitive.: air sensitive
• Solubility.: Chloroform, Ethyl Acetate
• Water Solubility.: Soluble in alcohol. Slightly soluble in cold water. Insoluble in water.
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 3
• Exact Mass: 304.138087668
• Heavy Atom Count: 22
• Complexity: 287

Purity/Quality:

99% ^*data from raw suppliers

Tris(2-methylphenyl)phosphine ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Phosphorus Compounds
• Canonical SMILES: CC1=CC=CC=C1P(C2=CC=CC=C2C)C3=CC=CC=C3C
• Uses: Tri(o-tolyl)phosphine is used in a ruthenium-catalyzed direct amination of alcohols. It is also used in Suzuki reaction. Further, it is used in the preparation of tri-ortho-phosphinselenide by reacting with selenium as a reagent. In addition to this, it acts as a ligand in coordination chemistry.

Technology Process of Tri-o-tolylphosphine

There total 27 articles about Tri-o-tolylphosphine 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: 96.0%

ethanol (64-17-5) + tris(2-tolyl)phosphane-borane(1:1) (878809-28-0) → triethyl borate (150-46-9) + tris-(o-tolyl)phosphine (6163-58-2)

Guidance literature:

Inert atmosphere; Reflux;

DOI:10.1016/j.tet.2009.05.063

Reference yield: 89.0%

tri-o-tolylphosphine oxide (6163-63-9) → tris-(o-tolyl)phosphine (6163-58-2)

Guidance literature:

With chloro-trimethyl-silane; magnesium; at 20 ℃; for 4h;

DOI:10.1016/j.tetlet.2014.12.132

Reference yield: 89.0%

2-methylphenyl bromide (95-46-5) → tris-(o-tolyl)phosphine (6163-58-2)

Guidance literature:

2-methylphenyl bromide; With magnesium; In tetrahydrofuran; Reflux; Inert atmosphere;

With phosphorus trichloride; In tetrahydrofuran; for 24h; Inert atmosphere;

DOI:10.1039/c7dt00727b

upstream raw materials:

ortho-tolylmagnesium bromide

2-methylphenyl bromide

Downstream raw materials:

tri-o-tolylphosphine oxide

toluene-4-sulfonamide

ethyl (2E)-3-[4-(1-{4-[(1E)-3-ethoxy-3-oxo-1-propenyl]phenyl}-5-methyl-1H-pyrrol-2-yl)phenyl]-2-propenoate

methyl 5-chloro-2-{(1E)-4-[2-(4-methoxybenzoyl)-4-methyl-1H-pyrrol-1-yl]-1-butenyl}benzoate

Refernces

• 1、 Matsumoto, Shinichi,Kawaguchi, Shinichi. "Kinetics and Equilibrium of the Reaction between Bis(trifluoroacetylacetonato)palladium(II) and Tri-o-tolylphosphine". . p. 1704 - 1707. Retrieved 1981.
• 2、 Gschwind, Ruth M.,Mende, Michael,Scott, Daniel J.,Streitferdt, Verena,Till, Marion,Wolf, Robert. "Photochemical transformation of chlorobenzenes and white phosphorus into arylphosphines and phosphonium salts". supporting information. p. 1100 - 1103. Retrieved 2022/02/03.
• 3、 Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric. "The Trityl-Cation Mediated Phosphine Oxides Reduction". supporting information. p. 3035 - 3043. Retrieved 2021/05/10.