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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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

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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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