983-81-3

Basic information

• Product Name: TRANS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE
• Synonyms: TRANS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE;trans-vinylenebis[diphenylphosphine];(E)-1,2-Bis(diphenylphosphino)ethene;[(E)-1,2-Ethenediyl]bis(diphenylphosphine);[(E)-Ethene-1,2-diyl]bis(diphenylphosphine);[(E)-Vinylene]bis(diphenylphosphine);trans-1,2-Bis(diphenylphosphino)ethylene,97%;NSC 132587
• CAS NO: 983-81-3
• Molecular Formula: C₂₆H₂₂P₂
• Molecular Weight: 396.4
• EINECS: 213-570-2
• Product Categories: Ligand;Phosphine Ligands;Synthetic Organic Chemistry;Catalysis and Inorganic Chemistry;Phosphorus Compounds;Polydentate Phosphine Ligands
• Mol File: 983-81-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 126-130 °C(lit.)
• Boiling Point: 546.8 °C at 760 mmHg
• Flash Point: 302.7 °C
• Appearance: /Crystalline
• Density: g/cm³
• Sensitive: Air Sensitive
• BRN: 757793
• CAS DataBase Reference: TRANS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE(983-81-3)
• EPA Substance Registry System: TRANS-1,2-BIS(DIPHENYLPHOSPHINO)ETHYLENE(983-81-3)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• RIDADR: UN 3464 6.1/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 983-81-3(Hazardous Substances Data)

Usage

Description

trans-1,2-Bis(diphenylphosphino)ethylene, also known as trans-DPPE, is an organophosphorus compound characterized by a central carbon-carbon double bond flanked by two diphenylphosphino groups. This unique structure endows it with valuable properties in catalysis and coordination chemistry, making it a versatile building block for various applications.

Uses

Used in Catalyst Industry:
trans-1,2-Bis(diphenylphosphino)ethylene is used as a ligand in the development of transition metal catalysts for the coupling of primary and secondary alkyl halides with aryl Grignard reagents. Its bidentate nature and steric properties facilitate efficient catalysis and selectivity in these reactions.
Used in Carbon Capture and Utilization:
In the field of carbon capture and utilization, trans-1,2-Bis(diphenylphosphino)ethylene serves as a ligand for the homogeneous hydrogenation of carbon dioxide, mediated by ruthenium complexes. This application aids in converting CO2 into useful chemicals, thus contributing to environmental sustainability.
Used in Pharmaceutical Industry:
trans-1,2-Bis(diphenylphosphino)ethylene is used as a reactant in the preparation of cyclopalladated derivatives of benzylidene. These cyclopalladated complexes have potential applications in medicinal chemistry, particularly as anticancer agents, due to their unique reactivity and coordination properties.
Used in Antimalarial Drug Development:
In the antimalarial drug development sector, trans-1,2-Bis(diphenylphosphino)ethylene is utilized in the synthesis of cyclopalladated complexes containing tridentate thiosemicarbazone ligands. These complexes have demonstrated promising antimalarial activity, offering new avenues for the treatment of malaria.
Used in Asymmetric Catalysis:
trans-1,2-Bis(diphenylphosphino)ethylene is employed as a ligand in the catalytic asymmetric intramolecular hydroamination of alkynylamines. This reaction is an important method for the synthesis of enantioenriched amines, which are valuable building blocks in the pharmaceutical and agrochemical industries. The use of trans-DPPE in these catalysts enhances the enantioselectivity and efficiency of the process.

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

• 40612-18-8 (E)-1,2-bis(diphenylphosphoryl)ethene 
• 1079-66-9 chloro-diphenylphosphine 
• 156-60-5 trans-1,2-dichloroethylene 
• 4376-01-6 sodium diphenylphosphide 
• 1031-93-2 diphenyl(p-tolyl)phosphine 
• 603-35-0 triphenylphosphine 
• 7650-91-1 benzyldiphenylphosphane 
• 6002-34-2 tert-butyldiphenylphosphine 
• 6372-40-3 isopropyldiphenylphosphine 
• 15475-27-1 potassium diphenylphosphine 
• 983-80-2 cis-1,2-bis-(diphenylphosphino)ethene 
• 536-74-3 phenylacetylene 
• 829-85-6 diphenylphosphane 
• 5112-95-8 bis(diphenylphosphino)acetylene 

Downstream Products

• 99396-97-1 (AuCl)2(μ-trans-1,2-bis(diphenylphosphino)ethylene) 
• 272458-79-4 Fe(C₅H₅)(C₃₆H₃₂NP₂O₂) 
• 421549-92-0 [(Ag2(μ-O2CCF3)2(μ-trans-Ph2PCH=CHPPh2))(x)] 
• 426213-22-1 [4-BrC6H4CH(4-C6H4OCH2CCAu)2(μ-trans-bis(diphenylphosphino)ethylene)] 
• 78149-28-7 Ir3(CO)7(μ3-cis-PhPCH=CHPPh2) 

Relevant articles and documents

The ambiguous behaviour of diphosphines towards the quasilinear iron(i) complex [Fe(N(SiMe3)2)2]--between inertness, P-C bond cleavage and C-C double bond isomerisation

Chelating phosphines are widely used as robust and reliable ligands in catalysis. We show that the anionic iron(i) complex [FeI(N(SiMe3)2)2]- is able to selectively cleave a P-aryl bond of 1,2-bis(diphenylphosphino)benzene. Furthermore, the related cis-1,2-bis(diphenylphosphino)-ethylene (dppee) binds not to the P donors but to the ethylene unit, and is (catalytically) transformed to the trans-isomer.

Ready Approach to Organophosphines from ArCl via Selective Cleavage of C-P Bonds by Sodium

The preparation, application, and reaction mechanism of sodium phosphide R2PNa and other alkali metal phosphides R2PM (M = Li and K) have been studied. R2PNa could be prepared, accurately and selectively, via the reactions of SD (sodium finely dispersed in mineral oil) with phosphinites R2POR′ and chlorophosphines R2PCl. R2PNa could also be prepared from triarylphosphines and diarylphosphines via the selective cleavage of C-P bonds. Na was superior to Li and K for these reactions. R2PNa reacted with a variety of ArCl to efficiently produce R2PAr. ArCl is superior to ArBr and ArI since they only gave low yields of the products. In addition, Ph2PNa is superior to Ph2PLi and Ph2PK since Ph2PLi did not produce the coupling product with PhCl, while Ph2PK only gave a low yield of the product. An electron-withdrawing group on the benzene ring of ArCl greatly accelerated the reactions with R2PNa, while an alkyl group reduced the reactivity. Vinyl chloride and alkyl chlorides RCl also reacted efficiently. While t-BuCl did not produce the corresponding product, admantyl halides could give the corresponding phosphine in high yields. A wide range of phosphines were prepared by this method from the corresponding chlorides. Unsymmetric phosphines could also be conveniently generated in one pot starting from Ph3P. Chiral phosphines were also obtained in good yields from the reactions of menthyl chlorides with R2PNa. Possible mechanistic pathways were given for the reductive cleavage of R3P by sodium generating R2PNa and the substitution reactions of R2PNa with ArCl generating R2PAr.

Synthesis of (R,R)- and (S,S)-Norphos

Oxidation of (E)-1,2-bis(diphenylphosphanyl)ethene with hydrogen peroxide gave (E)-1,2-bis(diphenylphosphoryl)ethene. Diels-Alder reaction of (E)-1,2-bis(diphenylphosphoryl)ethene with cyclopentadiene yielded 2,3-bis(diphenylphosphoryl)bicyclo[2.2.1]hept-5-ene (NorphosO). rac-NorphosO was resolved with O,O-dibenzoyltartaric acid. (R,R)- and (S,S)-NorphosO were reduced with trichlorosilane to give 2,3-bis(diphenylphosphanyl)bicyclo[2.2.1] hept-5-ene [(R,R)- and (S,S)-Norphos]. Georg Thieme Verlag Stuttgart.