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Xantphos

Name: Xantphos
Brand: ALDRICH

97%

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Synonym(s):

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

Empirical Formula (Hill Notation):

C₃₉H₃₂OP₂

CAS Number:

161265-03-8

Molecular Weight:

578.62

MDL number:

MFCD00233866

PubChem Substance ID:

24874555

NACRES:

NA.22

Quality Level

300

Assay

97%

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: C-X Bond Formation
reagent type: ligand
reaction type: Hydroformylations
reagent type: ligand
reaction type: Miyaura Borylation Reaction
reagent type: ligand
reaction type: Stille Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

224-228 °C (lit.)

functional group

phosphine

SMILES string

CC1(c2c(Oc3c1cccc3P(c4ccccc4)c5ccccc5)c(P(c6ccccc6)c7ccccc7)ccc2)C

InChI

1S/C39H32OP2/c1-39(2)33-25-15-27-35(41(29-17-7-3-8-18-29)30-19-9-4-10-20-30)37(33)40-38-34(39)26-16-28-36(38)42(31-21-11-5-12-22-31)32-23-13-6-14-24-32/h3-28H,1-2H3

InChI key

CXNIUSPIQKWYAI-UHFFFAOYSA-N

Related Categories

Buchwald Catalysts & Ligands

Phosphine Ligands

General description

Xantphos is a bidentate ligand that is employed in various metal-catalyzed reactions, including cross-couplings, Buchwald-Hartwig cross-coupling reactions, C-X bond formation, hydroformylation, Miyaura borylation reaction, Stille coupling, Suzuki-Miyaura coupling, (hetero)arylation, amination, and amidation.

For small scale and high throughput uses, product is also available as ChemBeads (928356)

Application

Ligand used in a synthesis of heterocycles by palladium-catalyzed C-N cross coupling of 3-bromothiophenes with 2-aminopyridines. Also used in a ruthenium-catalyzed alkylation of active methylene compounds with alcohols.

Metal chelating ligand for catalysis.

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Precautionary Statements

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Tetrahedron Letters, 47, 6787-6787 (2006)

Ligand Bite Angle Effects in Metal-catalyzed C-C Bond Formation.

P W van Leeuwen et al.

Chemical reviews, 100(8), 2741-2770 (2001-12-26)

Synthesis, 2794-2794 (2006)

Development of Novel Analogs of the Monocarboxylate Transporter Ligand FACH and Biological Validation of One Potential Radiotracer for Positron Emission Tomography (PET) Imaging.

Masoud Sadeghzadeh et al.

Molecules (Basel, Switzerland), 25(10) (2020-05-20)

Monocarboxylate transporters 1-4 (MCT1-4) are involved in several metabolism-related diseases, especially cancer, providing the chance to be considered as relevant targets for diagnosis and therapy. [18F]FACH was recently developed and showed very promising preclinical results as a potential positron emission

A new synthesis of naphthyridinones and quinolinones: palladium-catalyzed amidation of o-carbonyl-substituted aryl halides.

Peter J Manley et al.

Organic letters, 6(14), 2433-2435 (2004-07-02)

[reaction: see text] An alternative to the Friedlander condensation for the synthesis of naphthyridinones and quinolinones has been discovered. Palladium-catalyzed amidation of halo aromatics substituted in the ortho position by a carbonyl functional group or its equivalent with primary or

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