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

Chemical Properties

white to light yellow crystal powde

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

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

• 829-85-6 diphenylphosphane 
• 5112-95-8 bis(diphenylphosphino)acetylene 
• 156-60-5 trans-1,2-dichloroethylene 
• 40612-18-8 (E)-1,2-bis(diphenylphosphoryl)ethene 
• 1079-66-9 chloro-diphenylphosphine 
• 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 

Downstream Products

• 99396-97-1 (AuCl)2(μ-trans-1,2-bis(diphenylphosphino)ethylene) 
• 18433-72-2 (diphos)2CoH 
• 14647-23-5 cis-[NiCl₂(1,2-bis(diphenylphosphino)ethane)] 

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.