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(R)-Tol-BINAP

Catalog Number
ACM99646283-3
Product Name
(R)-Tol-BINAP
Structure
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CAS
99646-28-3
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IUPAC Name
[1-[2-bis(4-methylphenyl)phosphanylnaphthalen-1-yl]naphthalen-2-yl]-bis(4-methylphenyl)phosphane;
Molecular Weight
678.796g/mol
Molecular Formula
C48H40P2;
Canonical SMILES
CC1=CC=C(C=C1)P(C2=CC=C(C=C2)C)C3=C(C4=CC=CC=C4C=C3)C5=C(C=CC6=CC=CC=C65)P(C7=CC=C(C=C7)C)C8=CC=C(C=C8)C;
InChI
InChI=1S/C48H40P2/c1-33-13-23-39(24-14-33)49(40-25-15-34(2)16-26-40)45-31-21-37-9-5-7-11-43(37)47(45)48-44-12-8-6-10-38(44)22-32-46(48)50(41-27-17-35(3)18-28-41)42-29-19-36(4)20-30-42/h5-32H,1-4H3;
InChI Key
IOPQYDKQISFMJI-UHFFFAOYSA-N;
Complexity
897
Covalently-Bonded Unit Count
1
Exact Mass
678.261g/mol
Heavy Atom Count
50
Monoisotopic Mass
678.261g/mol
Rotatable Bond Count
7
Topological Polar Surface Area
0A^2
Application
(R)-Tol-BINAP, a white to cream powder, serves as a versatile chiral catalyst ligand with a wide range of applications in asymmetric synthesis. As a complex derived from rhodium precursors, (R)-Tol-BINAP is utilized for the asymmetric hydroformylation of vinyl acetate and plays a crucial role in the reductive amination of ketones. It also functions as a ligand for Pt dications in cation trapping and supports Rh(I)-catalyzed hydrogenation of acetamidoacrylic acid derivatives. This chiral catalyst can be applied to the allylation of N-tosyl α-imino esters and is an effective ligand in palladium-catalyzed carbon-oxygen bond formation and α-arylation of ketones. Additionally, it serves as a ligand for copper-catalyzed asymmetric conjugate reduction, dienolate addition to aldehydes, and the enantioselective reduction of lactones and lactams. (R)-Tol-BINAP also aids in the enantioselective cycloaddition of allenylsilanes with α-imino esters and catalyzes the Aldol reaction to ketones. In rhodium catalysis, it facilitates the [2+2+2] cycloaddition reactions of alkenes and alkynes, and in copper catalysis, it is instrumental in asymmetric conjugate additions of alkyl Grignard reagents on α,β-unsaturated esters as well as in the synthesis of cyclopropanes through tandem conjugate addition and intramolecular enolate trapping. Furthermore, the p-Tol-BINAP·AgF complex has been reported to catalyze the asymmetric Mukaiyama-type aldol reaction, highlighting its functionality based on its bis-naphthalene backbone with diverse phosphine derivatives.
January 21, 2025

Exceptional Chiral Catalyst for Research Applications

I've been using (R)-Tol-BINAP from Alfa Chemistry in my lab experiments for asymmetric hydroformylation and cycloaddition reactions. The powder's efficacy as a chiral catalyst ligand is outstanding, proving vital for our research needs.

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