4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

CAS 161265-03-8C39H32OP2Catalysis & Inorganic

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (CAS: 161265-03-8) is a sophisticated organophosphorus compound with a molecular weight of 578.62 g/mol. This xanthene-based phosphine ligand is highly valued for its efficacy in various transition metal-catalyzed reactions. It is particularly recognised for its role in facilitating challenging cross-coupling reactions and other synthetic transformations crucial in organic chemistry and materials science.

IUPAC: Xantphos
Synonyms: 161265-03-8Xantphos

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4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (C39H32OP2) — chemical structure, CAS 161265-03-8; Chemistry, fine chemical supplied by Tech Serve Solutions

Chemical SynthesisPhosphine Compounds

01 /Applications

Palladium-Catalyzed C-N Cross-Coupling

This ligand is employed in palladium-catalyzed C-N cross-coupling reactions, specifically for the synthesis of heterocycles. It facilitates the coupling of 3-bromothiophenes with 2-aminopyridines, enabling efficient formation of new carbon-nitrogen bonds.

Ruthenium-Catalyzed Alkylation

The compound serves as a ligand in ruthenium-catalyzed alkylation processes. It is utilized in the alkylation of active methylene compounds using alcohols, offering a versatile route for C-C bond formation.

Buchwald-Hartwig Amination

As a derivative of Xantphos, it is highly effective in Buchwald-Hartwig amination reactions, a cornerstone for forming C-N bonds in pharmaceutical and organic synthesis.

Suzuki-Miyaura Coupling

It is applicable as a ligand in Suzuki-Miyaura coupling reactions, facilitating the formation of carbon-carbon bonds between organoboron compounds and organic halides.

02 /Properties

Molecular weight	578.62
Empirical formula	C39H32OP2
Assay	97%
Application	Ligand used in a synthesis of heterocycles by palladium-catalyzed C-N cross coupling of 3-bromothiophenes with 2-aminopyridines.1 Also used in a ruthenium-catalyzed alkylation of active methylene compounds with alcohols.2
Melting point	224-228 °C(lit.)

03 /Safety & handling

Protective equipment	Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
Water hazard class (WGK, DE)	3

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

04 /Identifiers & registry

CAS number

161265-03-8

MDL number

MFCD00233866

PubChem substance

24874555

05 /Additional specifications

Ligand For	Buchwald-Hartwig Cross Coupling ReactionC-X Bond FormationHydroformylationsMiyaura Borylation ReactionStille CouplingSuzuki-Miyaura Coupling

06 /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.

07 /Frequently asked questions

What is 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene used for?

4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene is primarily used as a ligand in transition metal catalysis, particularly for palladium-catalyzed C-N cross-coupling reactions (e.g., synthesis of heterocycles from 3-bromothiophenes and 2-aminopyridines) and ruthenium-catalyzed alkylation of active methylene compounds with alcohols. It is also valuable in other cross-coupling reactions like Suzuki-Miyaura and Buchwald-Hartwig aminations.

What is the CAS number and formula for 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene?

The CAS number is 161265-03-8, and its empirical formula (Hill notation) is C39H32OP2.

What grade and purity does Tech Serve Solutions supply?

Tech Serve Solutions supplies 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene with an assay of 97%. We do not represent this product as USP, BP, EP, or any other pharmacopoeia grade.

What are the safety and handling considerations for this compound?

Appropriate personal protective equipment, including eyeshields and gloves, should be worn. In situations where dust or aerosols may be generated, use a type N95 (US) or type P1 (EN143) respirator filter. The compound is classified under WGK 2 in Germany.

How is this chemical typically packed and exported?

This chemical is carefully packed in accordance with international shipping regulations to ensure safe transit. Tech Serve Solutions is experienced in exporting fine chemicals globally.