Other grades of this product :
| Product Name: | (R)-H8-BINAP | | Synonyms: | (R)-H8-BINAP;(R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl(R)-H8-BINAP;(R)-(+)-2,2μ-Bis(diphenylphospino)-5,5μ,6,6μ,7,7μ,8,8μ-octahydro-1,1μ-binaphthyl, [(1R)-5,5μ,6,6μ,7,7μ,8,8μ-octahydro-[1,1μ-binaphthalene]-2,2μ-diyl]bis[diphenylphosphine];(R)-(+)-2,2'-Bis(diphenylphospino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl;(R)-(+)-2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl;(R)-H8-BINAP >=94%;(R)-(+)-2,2-Bis(diphenylphosphino)-5,5,6,6,7,7,8,8-octahydro-[1,1-binaphthalene]-2,2-diyl]bis[diphenylphosphine];(R)-2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthalene | | CAS: | 139139-86-9 | | MF: | C44H40P2 | | MW: | 630.74 | | EINECS: | | Product Categories: | BINAP Series;Chiral Phosphine | | Mol File: | 139139-86-9.mol |
| (R)-H8-BINAP Chemical Properties |
| Melting point | 207-208°C | | Boiling point | 745.6±60.0 °C(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | form | Powder | | color | off-white | | optical activity | [α]20/D +74°, c = 0.5 in toluene | | CAS DataBase Reference | 139139-86-9 |
| Hazard Codes | Xi | | Risk Statements | 36/38 | | Safety Statements | 26 | | WGK Germany | 3 |
| (R)-H8-BINAP Usage And Synthesis |
| Reaction |
- Biaryl bisphosphine ligand. The H8-BINAP ligand, as the ruthenium complex, catalyzes hydrogenation of unsaturated carboxylic acids to a higher ee than does BINAP.
- The ruthenium catalyzed hydrogenation of aryl propenoic acid to produce the drug Ibuprofen.
- Rhodium catalyzed asymmetric regioselective 1,4-addition of arylboronic acids to 3-substituted maleimides.
- Ligand for palladium-catalyzed enantioselective hydrogenation of substituted indoles.
- Rhodium-catalyzed enantioselective cyclization of γ-alkynylaldehydes with acyl phosphonates.
- Enantioselective synthesis of axially chiral 1-arylisoquinolines by Rh-catalyzed [2+2+2] cycloaddition.
- Enantioselective synthesis of 2,3-disubstituted indolines through Bronsted acid/Pd-complex-promoted tandem reactions.
- Dehydration triggered asymmetric hydrogenation of 3-(α-hydroxyalkyl)indoles
- Iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes with arylisocyanates
- Asymmetric hydrogenation of 3-(toluenesulfonamidoalkyl)-indoles
- Asymmetric Rh(I)-catalyzed intramolecular [3+2] cycloaddition of 1-yne-vinylcyclopropanes for bicyclo[3.3.0] compounds with a chiral quaternary carbon stereocenter.
- Enantioselective intermolecular [2+2+2] cycloadditions of ene-allenes with allenoates.
- Rh-catalyzed one-pot intermolecular [2+2+2] trimerization/asymmetric intramolecular [4+2] cycloaddition of two aryl ethynyl ethers and 5-alkynals.
- Rh-catalyzed regio-, diastereo-, and enantioselective [2+2+2] cycloaddition of 1,6-enynes with acrylamides.
| | Uses | Catalytic ligand used for:- Enantioselective synthesis of dihydrobenzofurans and dihydronaphthofurans via olefin isomerization/enantioselective intramolecular Alder-ene reaction of enynes catalyzed by Rh
- Preparation of axially chiral biaryl compounds by gold-catalyzed stereoselective intramolecular hydroarylation
- Preparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Bronsted acids and palladium BINAP complexes
- Stereoselective preparation of hydrindanes and decalins containing up to four contiguous stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of ene-allenes with allenes
- Rhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynes
- Stereoselective preparation of 2,3-substituted indolines via Pd-catalyzed hydrogenation of (α-hydroxyalkyl)indoles
| | General Description | The product is a diphenylphosphinobenzoic acid (DPPBA) based ligand for the palladium-catalyzed asymmetric allylic alkylation with a high degree of enantioselectivity. |
| (R)-H8-BINAP Preparation Products And Raw materials |
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