Cas no 84494-89-3 (Ethene-1,1-diylbis(diphenylphosphine))

Ethene-1,1-diylbis(diphenylphosphine) is a bidentate diphosphine ligand featuring a rigid ethene backbone with two diphenylphosphine groups. Its structure enables strong chelation to transition metals, enhancing stability in catalytic systems. The ligand is particularly valued for its ability to modulate electronic and steric properties in metal complexes, making it useful in homogeneous catalysis, including cross-coupling and hydrogenation reactions. The ethylene bridge provides conformational rigidity, improving selectivity in asymmetric synthesis. Its air-stable solid form facilitates handling and storage. This ligand is often employed in academic and industrial research for developing efficient and tunable catalytic processes.
Ethene-1,1-diylbis(diphenylphosphine) structure
84494-89-3 structure
Product Name:Ethene-1,1-diylbis(diphenylphosphine)
CAS No:84494-89-3
MF:C26H22P2
MW:396.400408267975
MDL:MFCD00191809
CID:720395
PubChem ID:24863495
Update Time:2025-05-27

Ethene-1,1-diylbis(diphenylphosphine) Chemical and Physical Properties

Names and Identifiers

    • Ethene-1,1-diylbis(diphenylphosphine)
    • 1,1-Bis(diphenylphosphino)ethylene
    • 1-diphenylphosphanylethenyl(diphenyl)phosphane
    • VDPP
    • 1,1′-Ethenylidenebis[1,1-diphenylphosphine] (ACI)
    • Phosphine, ethenylidenebis[diphenyl- (9CI)
    • 1,1-Bis(diphenylphosphino)ethene
    • Vinylidenebis(diphenylphosphine)
    • MFCD00191809
    • AKOS015913639
    • 84494-89-3
    • GEGLBMPXRFOXTK-UHFFFAOYSA-N
    • D94686
    • SCHEMBL1518031
    • AC-4966
    • ZB1724
    • AS-63153
    • 1,1-Bis(diphenylphosphino)ethylene, 98%
    • [1-(diphenylphosphanyl)ethenyl]diphenylphosphane
    • SY274241
    • bis(diphenylphosphino)ethene
    • DTXSID20401979
    • CS-W011709
    • MDL： MFCD00191809
    • Inchi： 1S/C26H22P2/c1-22(27(23-14-6-2-7-15-23)24-16-8-3-9-17-24)28(25-18-10-4-11-19-25)26-20-12-5-13-21-26/h2-21H,1H2
    • InChI Key： GEGLBMPXRFOXTK-UHFFFAOYSA-N
    • SMILES： C=C(P(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)C1C=CC=CC=1

Computed Properties

  • Exact Mass: 396.12000
  • Monoisotopic Mass: 396.12
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 0
  • Heavy Atom Count: 28
  • Rotatable Bond Count: 6
  • Complexity: 385
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 6.4
  • Topological Polar Surface Area: 0A^2

Experimental Properties

  • Color/Form: Not determined
  • Melting Point: 110-111?°C(lit.)
  • Boiling Point: 561.3°C at 760 mmHg
  • Flash Point: 312.2°C
  • PSA: 27.18000
  • LogP: 5.72340
  • Solubility: Not determined

Ethene-1,1-diylbis(diphenylphosphine) Security Information

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 84494-89-3 98%
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Ethene-1,1-diylbis(diphenylphosphine) Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Triethylamine Catalysts: Bis(triphenylphosphine)nickel dichloride Solvents: Dimethylformamide ;  2 h, 120 °C
Reference
FMPhos: Expanding the Catalytic Capacity of Small-Bite-Angle Bisphosphine Ligands in Regioselective Alkene Hydrofunctionalizations
Chen, Xiao-Yang ; et al, ACS Catalysis, 2020, 10(24), 14349-14358

Production Method 2

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Hexane ;  20 min, 0 °C
1.2 Solvents: Benzene ;  30 min, 0 °C
Reference
Three Isomers in Equilibrium: Phosphine Exchange of Coordinated and Pendant Phosphines in a Unique Complex, (OC)5WL (L = 1,2-Bis(diphenylphosphino)-1-di-p-tolylphosphinoethane), and Implications for Understanding the k2 Term in the Rate Law for Phosphine Substitution in Group 6 Metal Carbonyl Complexes
Van Ausdall, Bret R.; et al, Organometallics, 2018, 37(21), 3742-3749

Production Method 3

Reaction Conditions
1.1 Reagents: Lithium Solvents: Tetrahydrofuran ;  overnight, rt
1.2 Reagents: tert-Butyl chloride ;  rt
1.3 Solvents: Benzene ;  rt
Reference
Diphosphine compounds: part 1. Synthesis and electrochemistry of (Ph2P)2C=CH2 and Cis-Ph2PCH=CHPh2 when chelated to M(CO)6(M = Cr, Mo, W) and CuCl2
Hassan, Fatma S. M.; et al, Arabian Journal of Chemistry, 2008, 1(1), 67-78

Production Method 4

Reaction Conditions
1.1 Reagents: Lithium Solvents: Tetrahydrofuran ;  overnight, rt
1.2 Reagents: tert-Butyl chloride ;  rt
1.3 Solvents: Benzene ;  rt
1.4 Reagents: Hydrochloric acid Solvents: Water ;  rt
Reference
Diphosphine Compounds: Part I. Novel Biologically Active 1,1'Bis-and/or 1,2-Cis-(diphenylphosphino-)ethene and Their Complexes [M(CO)n{Ph2P(CHn)nPPh2}] & [Cu(Cl)2{Ph2P(CHn)nPPh2}], (M = W, Mo, Cr; n = 1,2....n)
Awad, Ibrahim M. A.; et al, Phosphorus, 2004, 179(7), 1251-1266

Production Method 5

Reaction Conditions
Reference
Product subclass 19: 1,1-bis(phosphorus-functionalized) alk-1-enes
Stankevic, M.; et al, Science of Synthesis, 2006, 24, 775-779

Production Method 6

Reaction Conditions
Reference
Product subclass 19: 1,1-bis(phosphorus-functionalized) alk-1-enes
Stankevic, M.; et al, Science of Synthesis, 2006, 24, 775-779

Production Method 7

Reaction Conditions
1.1 Reagents: Triethylamine Catalysts: Bis(acetylacetonato)nickel Solvents: Dimethylformamide ;  1 h, 120 °C
Reference
Nickel-catalyzed cross-coupling of diphenylphosphine with vinyl bromides and chlorides as a route to diphenylvinylphosphines
Shulyupin, Mstilsav O.; et al, Synlett, 2005, (4), 658-660

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Amadis Chemical Company Limited
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(CAS:84494-89-3)Ethene-1,1-diylbis(diphenylphosphine)
Order Number:A864118
Stock Status:in Stock
Quantity:5g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 08:44
Price ($):386.0
Tiancheng Chemical (Jiangsu) Co., Ltd
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(CAS:84494-89-3)1,1-雙(二苯基膦)乙烯
Order Number:LE2474117
Stock Status:in Stock
Quantity:25KG,200KG,1000KG
Purity:99%
Pricing Information Last Updated:Friday, 20 June 2025 12:40
Price ($):discuss personally

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Amadis Chemical Company Limited
(CAS:84494-89-3)Ethene-1,1-diylbis(diphenylphosphine)
A864118
Purity:99%
Quantity:5g
Price ($):386.0
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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:84494-89-3)1,1-雙(二苯基膦)乙烯
LE2474117
Purity:99%
Quantity:25KG,200KG,1000KG
Price ($):Inquiry
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