(R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl

CAS 99646-28-3C48H40P2Chemical Synthesis

(R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl (CAS: 99646-28-3) is a chiral phosphine ligand with the molecular formula C48H40P2 and a molecular weight of 678.78 g/mol. It is primarily utilised as a crucial component in asymmetric synthesis, serving as a catalyst or precursor for various catalytic systems. Its specific chiral properties make it invaluable for controlling stereochemistry in organic reactions, particularly in the synthesis of enantiomerically pure compounds.

IUPAC: (R)-Tol-BINAP
Synonyms: 99646-28-3C48H40P2(R)-Tol-BINAP

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(R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl (C48H40P2) — chemical structure, CAS 99646-28-3; Chemistry, fine chemical supplied by Tech Serve Solutions

Asymmetric SynthesisBINAPsChemical SynthesisChiral CatalystsLigandsand Reagents

01 /Applications

Catalyst in Asymmetric Conjugate Addition

This compound serves as a catalyst in studies exploring the role of excess phosphine ligands in the enantioselective conjugate addition of ethylmagnesium bromide to α,β-unsaturated esters.

Precursor for Reductive Amination Catalysts

It acts as a reactant in the preparation of catalysts used for the efficient reductive amination of ketones, a key transformation in pharmaceutical synthesis.

Ligand in Rhodium-Catalyzed Hydrogenation

The phosphine is employed as a ligand in Rh(I)-catalyst systems for the asymmetric hydrogenation of acetamidoacrylic acid derivatives, yielding chiral amines.

Component of Chiral Platinum Catalysts

It is used in the development of chiral platinum catalysts for the asymmetric Baeyer-Villiger oxidation of cyclic ketones, enabling enantioselective lactone formation.

Ligand in Copper-Catalyzed Michael Reactions

This BINAP derivative forms CuI-Tol-BINAP catalysts, which are effective for the enantioselective Michael reactions involving Grignard reagents and unsaturated esters.

02 /Properties

Molecular weight	678.78
Empirical formula	C48H40P2
Assay	97%
Optical activity	[α]20/D +162°, c = 0.5 in benzene
Application	Catalyst involved in studies of the role of excess phosphine ligand in enantioselective conjugate addition of ethylmagnesium bromide and α,β-unsaturated ester1Reactant serving as a precursor for: • Catalysts used for reductive amination of ketones2• Rh(I)-catalyst for hydrogenation of acetamidoacrylic acid derivatives3• Chiral platinum catalysts for asymmetric Baeyer-Villiger oxidation of cyclic ketones4• CuI-Tol-BINAP catalysts for enantioselective Michael reactions of Grignard reagents to unsaturated esters5• BINAP Pt Dications for cation trapping6
Melting point	254-258 °C

03 /Identifiers & registry

CAS number

99646-28-3

MDL number

MFCD01311709

04 /Quality & supply

Documentation

Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.

Supply & logistics

Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.

05 /Frequently asked questions

What is (R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl used for?

This compound is primarily used as a chiral phosphine ligand in asymmetric synthesis, acting as a catalyst or a precursor for various catalytic systems in enantioselective reactions such as conjugate addition, reductive amination, hydrogenation, Baeyer-Villiger oxidation, and Michael reactions.

What is the CAS number and formula for this chemical?

The CAS number is 99646-28-3 and the empirical formula (Hill notation) is C48H40P2.

What grade and purity does Tech Serve Solutions supply?

Tech Serve Solutions supplies this chemical with an assay of 97%. It is intended for research and laboratory use and is not supplied as USP, BP, EP, or any pharmacopoeia grade.

How should (R)-(+)-2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl be handled safely?

This compound is classified under WGK 3 (Germany), indicating a high hazard to water. Handle with appropriate personal protective equipment in a well-ventilated area to avoid exposure. Refer to the Safety Data Sheet for detailed handling and safety information.

How is this chemical packed, shipped, and exported?

Tech Serve Solutions ensures secure and compliant packaging for global export, adhering to all necessary regulations for the safe transport of fine chemicals.

How can I request a sample or quote?

To request a sample or a quotation, please contact our sales department through the website or by phone, providing the product name and CAS number (99646-28-3).