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526460

Sigma-Aldrich

Xantphos

97%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C39H32OP2
CAS Number:
161265-03-8
Molecular Weight:
578.62
MDL number:
MFCD00233866
UNSPSC Code:
12352005
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

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
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

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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Certificates of Analysis (COA)

Lot/Batch Number
WXBD4701V
WXBC8838V
SHBK1999
SHBJ9388

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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
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
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.
Guang-Yao Gao et al.
Organic letters, 6(11), 1837-1840 (2004-05-21)
A series of meso-amidoporphyrins were facilely synthesized by direct reactions of meso-brominated porphyrins with amides via palladium-catalyzed amidation reaction. Using a combination of palladium precursor Pd(OAc)(2) or Pd(2)(dba)(3) and phosphine ligand Xantphos, both 5-bromo-10,20-diphenylporphyrin and 5,15-dibromo-10,20-diphenylporphyrin, as well as their
Synthesis, 2794-2794 (2006)
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