cis-1,2-Bis(diphenylphosphino)ethylene

Base Information

• Chemical Name: cis-1,2-Bis(diphenylphosphino)ethylene
• CAS No.: 983-81-3
• Molecular Formula: C26H22 P2
• Molecular Weight: 396.408
• Hs Code.: 29310099
• European Community (EC) Number: 213-569-7
• NSC Number: 132588,132587
• DSSTox Substance ID: DTXSID601283879
• Nikkaji Number: J298.582I
• Wikipedia: 1,2-Bis(diphenylphosphino)ethylene
• Wikidata: Q72445356
• ChEMBL ID: CHEMBL2114057
• Mol file: 983-81-3.mol

Synonyms:983-80-2;cis-1,2-Bis(diphenylphosphino)ethylene;(Z)-1,2-Bis(diphenylphosphino)ethene;[(Z)-2-diphenylphosphanylethenyl]-diphenylphosphane;cis-Vinylenebis(diphenylphosphine);EINECS 213-569-7;trans-1,2-Bis(diphenylphosphinyl)ethylene;cis-vinylenebis[diphenylphosphine];dppv;C26H22P2;C26-H22-P2;Phosphine, trans-;Phosphine, vinylenebis(diphenyl-, (E)-;Phosphine, (E)-;Phosphine, 1,2-ethenediylbis[diphenyl-, (E)-;[(Z)-2-diphenylphosphanylvinyl]-diphenyl-phosphane;SCHEMBL338474;CHEMBL2114057;NCKJIJSEWKIXAT-DQRAZIAOSA-N;DTXSID601283879;1,2-bis(diphenylphosphino)ethylene;NSC132587;NSC132588;cis-1,2-Bis(diphenylphosphino)ethene;AKOS002263216;CS-W009728;NSC 132588;NSC-132587;NSC-132588;Phosphine, vinylenebis(diphenyl-, trans-;AS-62969;Phosphine,2-ethenediylbis[diphenyl-, (E)-;cis-1,2-Bis(diphenylphosphino)ethylene, 97%;A845853;[(1Z)-2-(diphenylphosphanyl)ethenyl]diphenylphosphane;[(Z)-2-(Diphenylphosphino)ethenyl](diphenyl)phosphine #

Chemical Property of cis-1,2-Bis(diphenylphosphino)ethylene

Chemical Property:

• Appearance/Colour: WHITE POWDER OR CRYSTALLINE POWDER
• Melting Point: 126-130 °C(lit.)
• Boiling Point: 546.8 °C at 760 mmHg
• Flash Point: 302.7 °C
• PSA: 27.18000
• Density: g/cm³
• LogP: 5.72340
• Sensitive.: Air Sensitive
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 6
• Exact Mass: 396.11967470
• Heavy Atom Count: 28
• Complexity: 371

Purity/Quality:

98%,99%, ^*data from raw suppliers

trans-1,2-bis(Diphenylphosphino)ethylene ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)P(C=CP(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)P(/C=C\P(C2=CC=CC=C2)C3=CC=CC=C3)C4=CC=CC=C4
• Uses: Catalyst for:Coupling of primary and secondary alkyl halides with aryl grignard reagentsHomogeneous hydrogenation of Carbon Dioxide mediated by RutheniumReactant for:Preparation of cyclopalladated derivatives of benzylidenePreparation of cyclopalladated complexes containing tridentate thiosemicarbazone ligands as antimalarial agentsCatalytic asymetric intramolecular hydroamination of alkynylamines

Technology Process of cis-1,2-Bis(diphenylphosphino)ethylene

There total 15 articles about cis-1,2-Bis(diphenylphosphino)ethylene 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: 91.0%

trans-1,2-dichloroethylene (156-60-5,43695-79-0) + diphenylphosphane (829-85-6) → trans-1,2-bis(diphenylphosphino)ethylene (983-81-3)

Guidance literature:

With triethylamine; bis(triphenylphosphine)nickel(II) chloride; In N,N-dimethyl-formamide; at 120 ℃; for 7h;

DOI:10.1055/s-2005-863714

Reference yield: 83.0%

trans-1,2-dichloroethylene (156-60-5,43695-79-0) + chloro-diphenylphosphine (1079-66-9,74391-44-9) → trans-1,2-bis(diphenylphosphino)ethylene (983-81-3)

Guidance literature:

chloro-diphenylphosphine; With potassium; In 1,4-dioxane; for 10h; Heating;

trans-1,2-dichloroethylene; In 1,4-dioxane; at 20 ℃; for 10h; Further stages.;

DOI:10.1055/s-2008-1032133

Reference yield: 81.0%

trans-1,2-dichloroethylene (156-60-5,43695-79-0) + sodium diphenylphosphide (4376-01-6) → trans-1,2-bis(diphenylphosphino)ethylene (983-81-3)

Guidance literature:

In tetrahydrofuran; at 25 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/acs.organomet.0c00295

upstream raw materials:

diphenylphosphane

bis(diphenylphosphino)acetylene

trans-1,2-dichloroethylene

chloro-diphenylphosphine

Downstream raw materials:

(AuCl)2(μ-trans-1,2-bis(diphenylphosphino)ethylene)

1,3-C6H4(Mn(CO)4)2(μ-dppen)

Refernces

• 1、 Landais, Yannick,Laye, Claire,Lusseau, Jonathan,Robert, Frédéric. "The Trityl-Cation Mediated Phosphine Oxides Reduction". supporting information. p. 3035 - 3043. Retrieved 2021/05/10.
• 2、 Yuan, Jia,Zhu, Lizhao,Zhang, Jianying,Li, Jianfeng,Cui, Chunming. "Sequential Addition of Phosphine to Alkynes for the Selective Synthesis of 1,2-Diphosphinoethanes under Catalysis. Well-Defined NHC-Copper Phosphides vs in Situ CuCl2/NHC Catalyst". supporting information. p. 455 - 459. Retrieved 2017/04/26.