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| | (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Basic information | | Reaction |
| Product Name: | (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl | | Synonyms: | (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene puriss.;(S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-biphthyl;(S)-BINAP,99%e.e.;(S)-(-)-2,2'-Bis(diphenylphoshino)-1,1'-binaphthyl for synthesis;2-(diphenylphosphino)-1-(2-(diphenylphosphino)naphthalen-1-yl)naphthalene;(+/-)-BINAP;(+/-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE;S(-)-(1,1'-BINAPHTHALENE-2,2'-DIYL)BIS(DIPHENYLPHOSPHINE) | | CAS: | 76189-56-5 | | MF: | C44H32P2 | | MW: | 622.69 | | EINECS: | 616-305-2 | | Product Categories: | Aromatics;Catalyst;Asymmetric Synthesis;Phosphine Ligands;Synthetic Organic Chemistry;Chiral Reagents;Peptide;Chiral Compound;chiral;BINAP Series;Chiral Phosphine | | Mol File: | 76189-56-5.mol |  |
| | (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Chemical Properties |
| Melting point | 283-286 °C(lit.) | | Boiling point | 724.3±55.0 °C(Predicted) | | alpha | -240 º (c=0.3, toluene) | | refractive index | -235 ° (C=0.3, Toluene) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Benzene (Slightly), Chloroform (Slightly) | | form | Crystals or Crystalline Powder | | color | White to light yellow | | optical activity | [α]20/D -222, c = 0.5 in benzene | | Sensitive | Air Sensitive | | Merck | 14,1223 | | BRN | 5321444 | | CAS DataBase Reference | 76189-56-5(CAS DataBase Reference) |
| | (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Usage And Synthesis |
| Reaction |
- (R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester.
- Useful ligand in asymmetric Heck processes.
- Ligand employed in palladium-catalyzed asymmetric arylation of ketones.
- Ligand employed in rhodium-catalyzed 1,4-additions to enones.
- Ligand employed in palladium-catalyzed hydroamination of styrene derivatives.
- Ligand employed in silver-catalyzed asymmetric Sakuri-Hosomi allylation and Mukaiyama aldol reaction.
- Ligand employed in rhodium-catalyzed kinetic resolution of enynes.
- Ligand employed in asymmetric rhodium-catalyzed hydroboration of cyclopropenes.
- Ligand employed in silver-catalyzed a-hydroxylation of stannyl enol ethers.
- Ligand employed in palladium-catalyzed synthesis of chiral allenes.
| | Chemical Properties | white to light yellow crystal powde | | Uses | 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Ligand used in a palladium-catalyzed, asymmetric, tandem Heck reaction-carbanion capture process leading to a synthesis of a tricyclic sesquiterpene. Also used in a ruthenium-catalyzed asymmetric hydrogenation of α,β-unsaturated acids. | | Uses | Reactant involved in:
- Enantioselective and diastereoselective unpoled carbonyl allylation
- Syntehsis of organophophine oxides as anittumor agents
- SN2 halogenation of hydroxy groups
- Synthesis of BINAP complexes
- Studies of conformational flexibility of BINAP chelates
| | Uses | Chiral ligand for metal mediated asymmetric catalysis. |
| | (S)-(-)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Preparation Products And Raw materials |
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