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526460

Sigma-Aldrich

Xantphos

97%

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Synonym(s):
4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene
Empirical Formula (Hill Notation):
C39H32OP2
CAS Number:
Molecular Weight:
578.62
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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638080763039666564
Xantphos 97%

Sigma-Aldrich

526460

Xantphos

tBuXPhos 98%

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638080

tBuXPhos

XantPhos Pd G3 95%

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763039

XantPhos Pd G3

N-XantPhos 97%

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666564

N-XantPhos

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

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Carboxylations, reagent type: ligand
reaction type: Decarboxylations

reaction suitability

-

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: ligand
reaction type: Cross Couplings

mp

224-228 °C (lit.)

mp

148-151 °C (lit.)

mp

164-167 °C (decomposition)

mp

256-262 °C

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

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

Exclamation mark

Signal Word

Warning

Hazard Statements

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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Sarah Keller et al.
Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 17(4), 375-385 (2018-02-20)
The heteroleptic complexes [Cu(tBu-xantphos)(bpy)][PF6] and [Ag(tBu-xantphos)(bpy)][PF6], where tBu-xantphos = 9,9-dimethyl-4,5-bis(di-tert-butylphosphino)xanthene and bpy = 2,2'-bipyridine have been synthesized and their photophysical properties investigated. Single crystal X-ray diffraction studies of the compounds under ambient and increased pressure are presented; increase in pressure
Joseph R Martinelli et al.
Organic letters, 8(21), 4843-4846 (2006-10-06)
[reaction: see text] The direct transformation of aryl bromides into the corresponding Weinreb amides via Pd-catalyzed aminocarbonylation at atmospheric pressure is reported.
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
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
Synthesis, 2794-2794 (2006)

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