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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
Pricing and availability is not currently available.

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.[1] Also used in a ruthenium-catalyzed alkylation of active methylene compounds with alcohols.[2]
Metal chelating ligand for catalysis.[3][4]

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
0000411395
0000411395
0000382209
0000382210
0000364346

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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
Synthesis, 2794-2794 (2006)
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
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)
Tetrahedron Letters, 47, 6787-6787 (2006)
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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

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    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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