Structure

(S)-(-)-BINAP

CAS
76189-56-5
Catalog Number
ACM76189565
Category
Organic Phosphine Compounds
Molecular Weight
622.688g/mol
Molecular Formula
C44H32P2;

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Specification

Synonyms
(+)-2,2'-bis(diphenylphosphino)-1,1'binaphthyl; (R)-(+)-2,2 bis(diphenylphosphino)-1,1-binaphthyl; 13648-EP2311831A1; (R)-(+)-(1,1'-Binaphthalene-2,2'-diyl)bis(diphenylphosphine); FT-0604001; [2'-(diphenylphosphanyl)-[1,1'-binaphthalene]-2-yl]diphenylphosphane; 1,1'-[(1R)-[1,1'-BINAPHTHALENE]-2,2'-DIYL]BIS[1,1-DIPHENYL]-PHOSPHINE; 13648-EP2286811A1; racemic-2,2'-bis(diphenylphosphino)-1,1' binaphthyl; 2,2'-Bis (diphenylphosphino)-1,1'-binaphtyl;
IUPAC Name
[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane;
Canonical SMILES
C1=CC=C(C=C1)P(C2=CC=CC=C2)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=CC=C7)C8=CC=CC=C8;
InChI
InChI=1S/C44H32P2/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/h1-32H;
InChI Key
MUALRAIOVNYAIW-UHFFFAOYSA-N;
Application
(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.
Storage
Room temperature.
Complexity
797
Covalently-Bonded Unit Count
1
EC Number
616-304-7
Exact Mass
622.198g/mol
Heavy Atom Count
46
Monoisotopic Mass
622.198g/mol
Rotatable Bond Count
7
Topological Polar Surface Area
0A^2
UNII
4F1X2F8NA3
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