84494-89-3

Basic information

• Product Name: 1,1-BIS(DIPHENYLPHOSPHINO)ETHYLENE
• Synonyms: 1,1-BIS(DIPHENYLPHOSPHINO)ETHYLENE;Ethene-1,1-diylbis(diphenylphosphine);VDPP;Vinylidenebis(diphenylphosphine);1,1-Bis(diphenylphosphino)ethylene98%
• CAS NO: 84494-89-3
• Molecular Formula: C₂₆H₂₂P₂
• Molecular Weight: 396.4
• Product Categories: Phosphines;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Polydentate Phosphine Ligands;Achiral Phosphine;Aryl Phosphine
• Mol File: 84494-89-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 110-111 °C(lit.)
• Boiling Point: 561.3°C at 760 mmHg
• Flash Point: 312.2°C
• Appearance: /Solid
• Vapor Pressure: 4.75E-12mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 1,1-BIS(DIPHENYLPHOSPHINO)ETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-BIS(DIPHENYLPHOSPHINO)ETHYLENE(84494-89-3)
• EPA Substance Registry System: 1,1-BIS(DIPHENYLPHOSPHINO)ETHYLENE(84494-89-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 84494-89-3(Hazardous Substances Data)

Usage

General Description

1,1-Bis(diphenylphosphino)ethylene, also known as dppe, is a chemical compound with the formula C26H24P2. It is a white solid that is soluble in organic solvents. 1,1-BIS(DIPHENYLPHOSPHINO)ETHYLENE is a bidentate ligand, meaning it can coordinate with two atoms in a coordination complex. It is commonly used in organic and coordination chemistry as a ligand in metal catalyzed reactions, particularly in catalytic hydrogenation and cross-coupling reactions. 1,1-Bis(diphenylphosphino)ethylene is known for stabilizing metal complexes and enhancing their reactivity, making it a valuable tool in synthetic chemistry.

InChI:InChI=1/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

Upstream product

• 14633-92-2 bis(diphenylthiophosphoryl)methane 
• 588-72-7 [(E)-2-bromoethenyl]benzene 
• 829-85-6 diphenylphosphane 
• 75-35-4 1,1-Dichloroethylene 
• 603-35-0 triphenylphosphine 
• 1079-66-9 chloro-diphenylphosphine 
• 97106-56-4 vinylidenebis(diphenylphosphine) disulfide 

Downstream Products

• 106210-83-7 Cl₂Pd(((C₆H₅)2P)2CHCH₂OC₄H₉) 
• 105988-35-0 1,1,1,1,2,2,2,3,3,3-decacarbonyl-2,3-μ-{vinylidenebis(diphenylphosphine)-P,P'}-triangulo-triruthenium(0) 
• 84534-91-8 (CO)4W(PPh₂C(=CH₂)PPh₂) 
• 96453-02-0 [vinylidenebis(diphenylphosphine)]chlorocopper(I) 
• 96452-99-2 [vinylidenebis(diphenylphosphine)]chlorogold(I) 
• 96453-00-8 bis[vinylidenebis(diphenylphosphine)]dichlorodigold(I) 
• 187848-26-6 (C₆F₅)2Au(Cl)(P(C₆H₅)2C(CH₂)P(C₆H₅)2) 
• 1268517-88-9 [Pd(2,5-Me₂C₆H₂CHC(H)=N(2,4,6-Me₃C₆H₂)-C₆,N)(Ph₂PC(=CH₂)PPh₂-P,P)][PF₆] 
• 1268517-97-0 [Pd(1-CH₂-2-(HC=N(2,4,6-Me₃C₆H₂))-4-MeC₆H₃-C,N)(Ph₂PC(=CH₂)PPh₂-P,P)][PF₆] 

Relevant articles and documents

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)nPPh 2}], (M = W, Mo, Crn = 1,2...n)

Interaction of [Ph2PC(=CH2)PPh2] (A) 1-3 and/or [Ph2P (CH=CH) PPh2](B) ligands in different molar ratio with hexacarbonyl metals M(CO)6 gives [M(CO)nPh2PC(=CH2)PPh2] and/or [M(CO)nPh2P (CH=CH)PPh2 where M=Cr, Mo or W, n = 2 and/or 4]. The carbon diphosphine complexes of type (A) which form four heteromemebered rings and/or type (B) form five heteromembered rings which reacts (addition reaction) with some different amines (methyl arnine, dimethyl anime), phenyl hydrazine and/or some of amino acids (glycine, alanine, aspartic acid, serene). The structures of A and/or B complexes and their amino derivatives have been characterized by using elemental analysis, IR spectra, 1HNMR,1H-{31P}-NMR, and mass spectra. Ligands and their complexes were screened in vitro to investigate the biological activities (antibacterial and antifungi). Interestingly, complexes are having strong and remarkable activities increases than the free ligands.

Reactivity of carbanions stabilized by two alpha phosphorus groups

The stabilized anion {[Ph2P(S)]2CH}- with lithium as counter cation 1a reacts with formaldehyde or benzaldehyde to give vinylidene phosphine sulfides [Ph2P(S)]2C=CHR, where R is H or Ph, respectively