139139-86-9

Basic information

• 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%
• CAS NO: 139139-86-9
• Molecular Formula: C₄₄H₄₀P₂
• Molecular Weight: 630.748
• Product Categories: BINAP Series;Chiral Phosphine
• Mol File: 139139-86-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 207-208°C
• Boiling Point: 745.626 °C at 760 mmHg
• Flash Point: 433.022 °C
• Appearance: off-white/Powder
• Vapor Pressure: 3.23E-21mmHg at 25°C
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: (R)-H8-BINAP(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-H8-BINAP(139139-86-9)
• EPA Substance Registry System: (R)-H8-BINAP(139139-86-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 139139-86-9(Hazardous Substances Data)

Usage

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 RhPreparation of axially chiral biaryl compounds by gold-catalyzed stereoselective intramolecular hydroarylationPreparation of chiral 3-alkyl-substituted indolines by tandem condensation-asymmetric hydrogenation of indoles with aldehydes, catalyzed by Bronsted acids and palladium BINAP complexesStereoselective preparation of hydrindanes and decalins containing up to four contiguous stereocenters via rhodium-catalyzed [2+2+2] cycloaddition of ene-allenes with allenesRhodium-catalyzed asymmetric formal olefination or cycloaddition of 1,3-dicarbonyl compounds with 1,6-diynes or 1,6-enynesStereoselective 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.

InChI:InChI=1/C44H40P2/c1-5-19-35(20-6-1)45(36-21-7-2-8-22-36)41-31-29-33-17-13-15-27-39(33)43(41)44-40-28-16-14-18-34(40)30-32-42(44)46(37-23-9-3-10-24-37)38-25-11-4-12-26-38/h1-12,19-26,29-32H,13-18,27-28H2

Upstream product

• 232264-22-1 C₂₈H₂₀F₁₈O₆S₂ 
• 159496-90-9 (R)-2-diphenylphosphinyl-2'-trifluoromethanesulfonyloxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl 
• 139139-89-2 (S)-(-)-2,2'-bis(diphenylphosphinoyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl 
• 139139-89-2 (R)-(+)-2,2'-bis(diphenylphosphinoyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl 

Relevant articles and documents

NOVEL RUTHENIUM COMPLEX AND PROCESS FOR PRODUCING OPTICALLY ACTIVE ALCOHOL COMPOUND USING SAME AS CATALYST

The present invention provides: a novel ruthenium complex which has excellent catalytic activity with respect to reactivity in the reduction of a multiple bond, in particular, in the asymmetric reduction of a carbonyl compound, enantioselectivity, etc.; a catalyst which comprises the ruthenium complex; and a process for producing optically active compound, in particular, an optically active alcohol compound, using the catalyst. The ruthenium complex has a ruthenacyclic structure. The catalyst is a catalyst for asymmetric reduction which comprises the ruthenium complex.

Method for making an optically active diphosphine ligand

The present invention provides a method for making compound (1) by reacting compound (2) with phosphine oxide (3) in the presence of a transition metal/phosphine complex and optionally reducing the reaction product: STR1 where n represents 0 or 1; the double line having a continuous line and a dotted line represents a double bond or a single bond such that the ring having the double line forms a naphthalene ring or an octahydronaphthalene ring with an adjacent benzene ring; Tf represents a trifluoromethanesulfonyl group; and Ar represents a phenyl group, a substituted phenyl group or a naphthyl group. The present invention provides an economical way to produce compound (1) as a ligand of a complex useful as a catalyst for a variety of asymmetric synthesis reactions.

Synthesis of Partially Hydrogenated BINAP Variants

Three pairs of new axially dissymmetric diphosphine ligands, (R)-(-)- and (S)-(+)-2,2'-bis(dicyclohexylphosphino)-1,1'-binaphthyl , (R)-(+)- and (S)-(-)-2,2'-bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphth