CAS 76189-55-4 (R)-(+)-BINAP - Catalysts / Alfa Chemistry

Synonyms

-Bis(diphenylphosphino)-1,1; AK-46295; (s)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphtyl; (S)-(-)-2,2'-BIS(DIPHENYLPHOSPHINO)-1'1-BINAPHTHYL; 98327-87-8; PubChem12874; MUALRAIOVNYAIW-UHFFFAOYSA-N; (rac)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl; 156196-EP2284169A1; (R)-(+)-2,2'-Bis(diphenyphosphino)-1,1'-binaphthyl;

IUPAC Name

[1-(2-diphenylphosphanylnaphthalen-1-yl)naphthalen-2-yl]-diphenylphosphane;

Molecular Weight

622.688g/mol

Molecular Formula

C44H32P2;

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;

Storage

Room temperature.

Complexity

797

Covalently-Bonded Unit Count

EC Number

616-304-7

Exact Mass

622.198g/mol

Heavy Atom Count

Monoisotopic Mass

622.198g/mol

Rotatable Bond Count

Topological Polar Surface Area

0A^2

UNII

4F1X2F8NA3

Application

(R)-(+)-BINAP, a chiral ligand available as a white to light yellow crystalline powder, is extensively used in metal-mediated asymmetric catalysis. This compound serves as a critical component in transition metal-catalyzed reactions, such as hydrogenation and disilylation, owing to its ability to form highly selective homogeneous catalysts when combined with rhodium and ruthenium derivatives. These catalysts demonstrate remarkable efficacy in the reduction of aryl ketones, β-keto esters, and α-amino ketones, and they excel in facilitating asymmetric hydrogenation and hydroformylation of olefins, as well as asymmetric Heck reactions and isomerizations of allyls. In addition, (R)-BINAP, in combination with Ag(I), catalyzes asymmetric aldol reactions and enantioselective hetero-Diels-Alder reactions. It is also an essential precursor in NOYORI CATALYST SYSTEMS when paired with dichloro(1,5-cyclooctadiene)ruthenium, renowned for their high catalytic activity and enantioselectivity across diverse substrates. The ligand is crucial in a wide array of processes including the asymmetric Heck process, palladium-catalyzed arylation, rhodium-mediated 1,4-additions, and many other intricate catalytic applications involving cyclopropenes, enynes, stannyl enol ethers, and alkyl alcohols.

December 15, 2024

Exceptional Performance in Asymmetric Catalysis

I've been using (R)-(+)-BINAP from Alfa Chemistry in our lab's asymmetric catalysis projects. Its effectiveness in rhodium-catalyzed enantioselective hydrogenation is outstanding, enhancing our synthesis processes remarkably with high selectivity and activity.