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

CAS 153305-67-0C48H40P2Catalysis & Inorganic

2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl (CAS: 153305-67-0) is a chiral phosphine ligand with a molecular weight of 678.78. This compound is a key reagent in various catalytic applications, particularly in organic synthesis. Its unique structure facilitates stereoselective transformations and is employed in sophisticated cross-coupling reactions and cycloadditions. Supplied with an assay of 97%, it serves as a vital component for researchers and industrial chemists.

IUPAC: rac-Tol-BINAP
Synonyms: 153305-67-0C48H40P2rac-Tol-BINAP

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2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl (C48H40P2) — chemical structure, CAS 153305-67-0; Chemistry, fine chemical supplied by Tech Serve Solutions

Chemical SynthesisPhosphine Compounds

01 /Applications

Catalysis in Cycloaddition Reactions

This phosphine ligand is utilised in rhodium-catalysed 2+2+2 cycloaddition reactions, enabling the formation of complex cyclic structures. It also plays a role in the regioselective intermolecular cyclotrimerization of alkynes when complexed with cationic rhodium(I) species.

Cross-Coupling Reactions

The compound finds application in palladium-catalysed coupling reactions, including the amination of aromatic iodides or bromides. It is also involved in palladium-catalyzed ether formation from aryl halides, facilitating the synthesis of various organic molecules.

Decarboxylative Coupling

It is a component in catalyst systems, such as copper-palladium-phenanthroline-Tol-BINAP, used for decarboxylative coupling of carboxylic acids. This expands its utility in synthetic transformations.

Preparation of Methylenesultams

This ligand assists in the preparation of methylenesultams through intramolecular Heck cyclization of bromovinylsulfonamides, followed by a Michael addition reaction of sultams with thiols.

02 /Properties

Molecular weight	678.78
Empirical formula	C48H40P2
Assay	97%
Application	Used in:• Rhodium-catalyzed 2+2+2 cycloaddition reactions1• Decarboxylative coupling of carboxylic acids using copper-palladium-phenanthroline-Tol-BINAP catalyst system2• Palladium-catalyzed coupling of aromatic iodides or bromides and tin-thiolates under microwave conditions3• Preparation of methylenesultams via intramolecular Heck cyclization of bromovinylsulfonamides and subsequent Michael addition reaction of sultams with thiols4• Regioselective intermolecular cyclotrimerization of alkynes in complex with cationic rhodium(I)5• Palladium-catalyzed amination reactions6• Palladium-catalyzed ether formation from aryl halides7
Melting point	267-271 °C

03 /Safety & handling

GHS hazard pictogram: Harmful / irritant (GHS07) — Harmful / irritant

Warning

Hazard statements

H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust, fume, gas or vapours
P305IF IN EYES

Protective equipment	dust mask type N95 (US), Eyeshields, Gloves
Water hazard class (WGK, DE)	3
Hazard codes (EU)	Xi
Risk statements (R)	36/37/38
Safety statements (S)	26

Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.

04 /Identifiers & registry

CAS number

153305-67-0

MDL number

MFCD01311709

05 /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.

06 /Frequently asked questions

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

2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl is primarily used as a ligand in various catalytic reactions, including rhodium-catalysed 2+2+2 cycloadditions, palladium-catalysed cross-coupling reactions (amination, ether formation), decarboxylative coupling, and in the preparation of methylenesultams.

What are the CAS number and formula for this compound?

The CAS number is 153305-67-0, and the empirical formula (Hill notation) is C48H40P2.

What grade and purity does Tech Serve Solutions supply?

Tech Serve Solutions supplies this compound with an assay of 97%. This product is not represented as USP, BP, EP, or any pharmacopoeia grade.

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

According to GHS, this compound is a Warning. It causes skin irritation (H315), serious eye irritation (H319), and may cause respiratory irritation (H335). Recommended personal protective equipment includes a dust mask type N95 (US), eyeshields, and gloves. Handle in a well-ventilated area.

How is this chemical packed, shipped, and exported?

Tech Serve Solutions offers this chemical in appropriate packaging for safe transport, adhering to international shipping regulations. We are a global supplier and exporter of fine chemicals.

How can I request a sample or quote?

To request a sample or a quote for 2,2′-Bis(di-p-tolylphosphino)-1,1′-binaphthyl, please contact our sales team through the website or via direct inquiry, providing your specific requirements.