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ChemicalBook--->CAS DataBase List--->139139-86-9

139139-86-9

139139-86-9 Structure

139139-86-9 Structure
IdentificationBack Directory
[Name]

(R)-H8-BINAP
[CAS]

139139-86-9
[Synonyms]

(R)-H8-BINAP
(R)-H8-BINAP >=94%
(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)-(+)-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]
[Molecular Formula]

C44H40P2
[MDL Number]

MFCD01630795
[MOL File]

139139-86-9.mol
[Molecular Weight]

630.748
Chemical PropertiesBack Directory
[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
Safety DataBack Directory
[Hazard Codes ]

Xi
[Risk Statements ]

36/38
[Safety Statements ]

26
[WGK Germany ]

3
Questions And AnswerBack Directory
[Reaction]

  1. Biaryl bisphosphine ligand. The H8-BINAP ligand, as the ruthenium complex, catalyzes hydrogenation of unsaturated carboxylic acids to a higher ee than does BINAP.
  2. The ruthenium catalyzed hydrogenation of aryl propenoic acid to produce the drug Ibuprofen.
  3. Rhodium catalyzed asymmetric regioselective 1,4-addition of arylboronic acids to 3-substituted maleimides.
  4. Ligand for palladium-catalyzed enantioselective hydrogenation of substituted indoles.
  5. Rhodium-catalyzed enantioselective cyclization of γ-alkynylaldehydes with acyl phosphonates.
  6. Enantioselective synthesis of axially chiral 1-arylisoquinolines by Rh-catalyzed [2+2+2] cycloaddition.
  7. Enantioselective synthesis of 2,3-disubstituted indolines through Bronsted acid/Pd-complex-promoted tandem reactions.
  8. Dehydration triggered asymmetric hydrogenation of 3-(α-hydroxyalkyl)indoles
  9. Iridium-catalyzed [2+2+2] cycloaddition of α,ω-diynes with arylisocyanates
  10. Asymmetric hydrogenation of 3-(toluenesulfonamidoalkyl)-indoles
  11. Asymmetric Rh(I)-catalyzed intramolecular [3+2] cycloaddition of 1-yne-vinylcyclopropanes for bicyclo[3.3.0] compounds with a chiral quaternary carbon stereocenter.
  12. Enantioselective intermolecular [2+2+2] cycloadditions of ene-allenes with allenoates.
  13. Rh-catalyzed one-pot intermolecular [2+2+2] trimerization/asymmetric intramolecular [4+2] cycloaddition of two aryl ethynyl ethers and 5-alkynals.
  14. Rh-catalyzed regio-, diastereo-, and enantioselective [2+2+2] cycloaddition of 1,6-enynes with acrylamides.
Reactions of 139139-86-9_1
Reactions of 139139-86-9_2
Reactions of 139139-86-9_3
Reactions of 139139-86-9_4
Reactions of 139139-86-9_5
Hazard InformationBack Directory
[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.
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