Xantphos

Base Information

• Chemical Name: Xantphos
• CAS No.: 161265-03-8
• Molecular Formula: C39H32OP2
• Molecular Weight: 578.63
• Hs Code.: 29319090
• European Community (EC) Number: 605-249-4
• UNII: NMU72MOG9B
• DSSTox Substance ID: DTXSID20348350
• Nikkaji Number: J1.199.378H
• Wikipedia: Xantphos
• Wikidata: Q2135551
• Mol file: 161265-03-8.mol

Synonyms:9,9-dimethyl-4,6-bis(diphenylphosphino)xanthene;xantphos

Chemical Property of Xantphos

Chemical Property:

• Appearance/Colour: white to light yellow crystals
• Vapor Pressure: 7.61E-17mmHg at 25°C
• Melting Point: 224-228 °C(lit.)
• Boiling Point: 665.7 °C at 760 mmHg
• Flash Point: 449.9 °C
• PSA: 36.41000
• LogP: 7.63460
• Storage Temp.: Room temperature.
• Solubility.: Soluble in organic solvents.
• XLogP3: 9.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 578.19283964
• Heavy Atom Count: 42
• Complexity: 731

Purity/Quality:

99% ^*data from raw suppliers

1,1''-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenyl-phosphine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 37-20/22
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2=C(C(=CC=C2)P(C3=CC=CC=C3)C4=CC=CC=C4)OC5=C1C=CC=C5P(C6=CC=CC=C6)C7=CC=CC=C7)C
• Uses: suzuki reaction 4,5-Bis(diphenylphosphino)-9, 9-dimethylxanthene is used as a bidentate ligand, which finds application in hydroformylation of alkenes. 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenyl-phosphine is an organophosphorus compound derived from the heterocycle xanthene. It is used as a bidentate ligand and is noteworthy for having a particularly wide bite angle. Such ligands are useful in the hydroformylation of alkenes.

Technology Process of Xantphos

There total 8 articles about Xantphos 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: 95.0%

9,9-dimethyl-4,6-bis(diphenyloxyphosphino)xanthene → 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (161265-03-8)

Guidance literature:

With tributylphosphine; iodine; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.166667h; Inert atmosphere;

Reference yield: 95.0%

acetone (67-64-1) + bis[2-(diphenylphosphino)phenyl] ether (166330-10-5) → 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (161265-03-8)

Guidance literature:

With trifluorormethanesulfonic acid; In toluene; at 200 ℃; for 16h; Temperature; Inert atmosphere;

Reference yield: 89.0%

1,1'-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis-1,1-diphenylphosphine oxide (808142-24-7) → 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (161265-03-8)

Guidance literature:

With bis(2-chlorophenyl)borinic acid; phenylsilane; In toluene; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1002/cctc.201700986

upstream raw materials:

9,9-dimethylxanthene

chloro-diphenylphosphine

1,1'-(9,9-dimethyl-9H-xanthene-4,5-diyl)bis-1,1-diphenylphosphine oxide

acetone

Downstream raw materials:

styrene

Rh(H)(CO)(P(C₆H₅)3)(((C₆H₅)2PC₆H₃)2OC(CH₃)2)

[(xantphos)Pd(Ph)(I)]

Refernces

• 1、 Hillebrand, Stefan,Bruckmann, Joachim,Krueger, Carl,Haenel, Matthias W.. "Bidentate Phosphines of Heteroarenes: 9,9-Dimethyl-4,5-bis(diphenylphosphino)xanthene". . p. 75 - 78. Retrieved 1995.
• 2、 Grachova, Elena,Gurzhiy, Vladislav,Koshevoy, Igor,Levin, Oleg,Luginin, Maksim,Melnikov, Alexey,Paderina, Aleksandra,Petrovskii, Stanislav,Sizov, Vladimir,Slavova, Sofia. "The Tail Wags the Dog: The Far Periphery of the Coordination Environment Manipulates the Photophysical Properties of Heteroleptic Cu(I) Complexes". . . Retrieved 2022/04/19.
• 3、 -. "Early transition metal compound and preparation method thereof and intermediate and application in olefin polymerization". Paragraph 0293-0297. . Retrieved 2019/11/13.