Tricyclohexylphosphine oxide

Base Information

• Chemical Name: Tricyclohexylphosphine oxide
• CAS No.: 13689-19-5
• Molecular Formula: C18H33OP
• Molecular Weight: 296.433
• Hs Code.: 2902199090
• European Community (EC) Number: 677-887-1
• NSC Number: 222417
• DSSTox Substance ID: DTXSID90160001
• Nikkaji Number: J50.219G
• Wikidata: Q72510529
• Mol file: 13689-19-5.mol

Synonyms:Tricyclohexylphosphine oxide;13689-19-5;PHOSPHINE OXIDE, TRICYCLOHEXYL-;dicyclohexylphosphorylcyclohexane;(dicyclohexylphosphoroso)cyclohexane;NSC 222417;BRN 2808763;C18H33OP;MFCD00014298;4-16-00-01009 (Beilstein Handbook Reference);NSC222417;SCHEMBL517951;DTXSID90160001;C18-H33-O-P;AKOS026670088;NSC-222417;AS-60467;SY106349;LS-106038;CS-0155317;FT-0636939;T3430;F10270;A886604;Y-200026;F8880-3373

Chemical Property of Tricyclohexylphosphine oxide

Chemical Property:

• Appearance/Colour: White crystalline
• Vapor Pressure: 1.95E-08mmHg at 25°C
• Melting Point: 155-157 °C
• Refractive Index: 1.492
• Boiling Point: 466.6 °C at 760 mmHg
• Flash Point: 236 °C
• PSA: 26.88000
• Density: 1 g/cm³
• LogP: 6.34760
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility.: Soluble in most organic solvents. Insoluble in water.
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 296.226902670
• Heavy Atom Count: 20
• Complexity: 281

Purity/Quality:

98%, ^*data from raw suppliers

Tricyclohexylphosphine Oxide ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(CC1)P(=O)(C2CCCCC2)C3CCCCC3
• Uses: Tricyclohexylphosphine oxide is used as a ligand for a range of metal-catalyzed organic transformations. Ligand used in the Pd-catalyzed coupling of malononitrile with aryl halides.1 Bulky phosphine ligand used with a Pd(0)-triolefinic macrocycle catalyst for Suzuki coupling of aryl bromides and chlorides. This ligand is applied with Ni as a key intermediate in the formation of cylcopentane compounds.

Technology Process of Tricyclohexylphosphine oxide

There total 32 articles about Tricyclohexylphosphine oxide 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: 99.0%

tricyclohexylphosphine (2622-14-2) → tricyclohexylphosphine oxide (13689-19-5)

Guidance literature:

With water; Selectfluor; In acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1016/j.tetlet.2016.06.078

Reference yield: 96.0%

Triphenylphosphine oxide (791-28-6) → tricyclohexylphosphine oxide (13689-19-5)

Guidance literature:

With hydrogen; In tetrahydrofuran; at 120 - 150 ℃; under 187519 Torr;

Reference yield: 58.0%

(p-cymene)Ru(μ-Cl)3RuCl(C2H4)(PCy3) (850167-17-8) → C20H28Cl6Ru3 + tricyclohexylphosphine oxide (13689-19-5)

Guidance literature:

With dinitrogen monoxide; In tetrahydrofuran; at 60 ℃; for 24h;

DOI:10.1021/om300786f

upstream raw materials:

tricyclohexylphosphine

cyclohexane

dicyclohexylphosphine oxide

dicyclohexylphosphinoyl chloride

Downstream raw materials:

dichlorotricyclohexyl phosphorous

Co(tricyclohexylphosphine oxide)2Cl₂

Refernces

• 1、 Poh, Scott,Hernandez, Raquel,Inagaki, Mayuko,Jessop, Philip G.. "Oxidation of phosphines by supercritical nitrous oxide". . p. 583 - 585. Retrieved 1999.
• 2、 Yamada, Tohru,Suzuki, Kyosuke,Hashimoto, Kentaro,Ikeno, Taketo. "N2O oxidation of phosphines catalyzed by low-valent nickel complexes". . p. 1043 - 1044. Retrieved 1999.
• 3、 Mutule, Ilga,Joo, Beomjun,Medne, Zane,Kalnins, Toms,Vedejs, Edwin,Suna, Edgars. "Stereoselective synthesis of the diazonamide a macrocyclic core". . p. 3058 - 3066. Retrieved 2015.
• 4、 Swart, Marthinus R.,Twigge, Linette,Erasmus, Elizabeth,Marais, Charlene,Bezuidenhoudt, Barend C. B.. "Olefin Metathesis, p-Cresol, and the Second Generation Grubbs Catalyst: Fitting the Pieces". . p. 1752 - 1762. Retrieved 2021/05/06.