983-80-2

Basic information

• Product Name: CIS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE
• Synonyms: CIS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE;cis-vinylenebis[diphenylphosphine];cis-1,2-Bis(diphenylphosphino)ethylene,min.98%;cis-1,2-Bis(diphenylphosphino)ethylene, min. 98%;(Z)-1,2-Bis(diphenylphosphino)ethene;(Z)-1,2-Ethenediylbis(diphenylphosphine);[(Z)-1,2-Ethenediyl]bis(diphenylphosphine);[(Z)-Ethene-1,2-diyl]bis(diphenylphosphine)
• CAS NO: 983-80-2
• Molecular Formula: C₂₆H₂₂P₂
• Molecular Weight: 396.4
• EINECS: 213-569-7
• Product Categories: Ligand;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Polydentate Phosphine Ligands;organophosphine ligand;Achiral Phosphine;Aryl Phosphine
• Mol File: 983-80-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 122-124 °C(lit.)
• Boiling Point: 546.8 °C at 760 mmHg
• Flash Point: 302.7 °C
• Appearance: white/crystal
• Vapor Pressure: 1.87E-11mmHg at 25°C
• Water Solubility: Insoluble in water.
• Sensitive: Air Sensitive
• BRN: 757792
• CAS DataBase Reference: CIS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: CIS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE(983-80-2)
• EPA Substance Registry System: CIS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE(983-80-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 983-80-2(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

InChI:InChI=1/C26H22P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h1-22H/b22-21-

Upstream product

• 156-59-2 cis-1,2-Dichloroethylene 
• 829-85-6 diphenylphosphane 
• 536-74-3 phenylacetylene 
• 603-35-0 triphenylphosphine 
• 5112-95-8 bis(diphenylphosphino)acetylene 

Downstream Products

• 113088-15-6 1,1,2-tris(diphenylphosphanyl)ethene 
• 110329-67-4 α-Re2Cl4(dppee)2 
• 110329-68-5 β-Re2Cl4(dppee)2 
• 117023-98-0 β-Mo2Cl4(dppee)2 
• 117023-98-0 α-Mo2Cl4(dppee)2 
• 64645-30-3 (AuCl)2(μ-cis-1,2-bis(diphenylphosphino)ethylene) 
• 102532-72-9 {Au(cis-bis(diphenylphosphino)ethylene)2}Cl 
• 117023-99-1 β-Mo2Br4(dppee)2 
• 117024-00-7 α-Mo2Br4(dppee)2 
• 99128-42-4 Ag((cis,1,2-bis(diphenylphosphino)ethylene)2NO₃ 
• 78179-84-7 {Rh(cycloocta-1,5-diene)(cis-1,2-bis(diphenylphosphino)ethylene)}BF₄ 
• 54293-56-0 {Rh(cis-1,2-bis(diphenylphosphino)ethylene)2}BF₄ 
• 116212-41-0 1,2,3,4,5-pentafluoro-6-(2-methylallyl)benzene 
• 603-35-0 triphenylphosphine 

Relevant articles and documents

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

The well-defined NHC-copper phosphides [(NHC)CuPPh2]3 (1, NHC = 1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (IiPr); 2, NHC = N,N-di-tert-butylimidazol-2-ylidene (ItBu)) have been prepared by the reaction of simple copper halides with HPPh2 in the presence of N-heterocyclic carbenes (NHCs). Complexes 1 and 2 enabled catalytic double hydrophosphination of alkyl and aryl terminal alkynes to yield 1,2-diphosphinoethanes selectively in good yields. On the basis of these results, the most efficient and pratical in situ CuCl2/NHC catalyst has been developed. It catalyzes the selective double hydrophosphination of the alkynes with high efficiency and a wide substrate scope and exhibits even better performance than the well-defined NHC-Cu phosphides. The mechanistic studies disclosed that the formation of a copper acetylide in the catalytic cycle played an important role in the acceleration of the catalytic process.

ACETYLENIC HYDROCARBONS AND VINYL HALIDES IN THE ALKYLATION OF PH ACIDS UNDER CONDITIONS OF PHASE-TRANSFER CATALYSIS OR IN SUPERBASIC MEDIUM

By the reaction of nonactivated acetylenes with diphenylphosphine under phase-transfer catalysis or in superbasic medium the corresponding mono- and diphosphines were obtained, whereas with diphenylphosphine oxide only bis(phosphine oxides) were formed.Diphenylphosphine was found to react with 1,1- and 1,2-dichloroethenes, as well as with 1,1,2-trichloroethane, yielding 1,2-bis(diphenylphosphino)ethene.The reactions of E-1-chloro-2-phenyl- and 1-chloro-1-phenylethenes with diphenylphosphine under similar conditions lead either to E-1-diphenylphosphino-2-phenylethene or to bisphosphine with a ratio of reactants of 1:1 or 1:2 respectively.Diphenylphosphine oxide gives bis(phosphine oxides) in all the above cases.Stereochemistry and mechanism of the reactions are discussed.