Xantphos
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 341319

CAS#: 161265-03-8

Description: Xantphos is an organophosphorus compound derived from the heterocycle xanthene.


Price and Availability

Size
Price

1g
USD 202
Size
Price

5g
USD 420
Size
Price

25g
USD 998

Xantphos purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

img

Theoretical Analysis

MedKoo Cat#: 341319
Name: Xantphos
CAS#: 161265-03-8
Chemical Formula: C39H32OP2
Exact Mass: 578.1928
Molecular Weight: 578.6315
Elemental Analysis: C, 80.95; H, 5.57; O, 2.76; P, 10.71


Synonym: Xantphos;

IUPAC/Chemical Name: 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene

InChi Key: CXNIUSPIQKWYAI-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: CC1(C)C2=C(OC3=C1C=CC=C3P(C4=CC=CC=C4)C5=CC=CC=C5)C(P(C6=CC=CC=C6)C7=CC=CC=C7)=CC=C2


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Song T, Park JE, Chung YK. Rhodium-Catalyzed Synthesis of Imines and Esters from Benzyl Alcohols and Nitroarenes: Change in Catalyst Reactivity Depending on the Presence or Absence of the Phosphine Ligand. J Org Chem. 2018 Apr 6;83(7):4197-4203. doi: 10.1021/acs.joc.8b00197. Epub 2018 Mar 19. PubMed PMID: 29536727.

2: Satishkumar S, Poudapally S, Vuram PK, Gurram V, Pottabathini N, Sebastian D, Yang L, Pradhan P, Lakshman MK. Pd-catalyzed versus uncatalyzed, PhI(OAc)(2)-mediated cyclization reactions of N(6)-([1,1'-biaryl]-2-yl)adenine nucleosides. ChemCatChem. 2017 Nov 9;9(21):4058-4069. doi: 10.1002/cctc.201700918. Epub 2017 Oct 24. PubMed PMID: 29503672; PubMed Central PMCID: PMC5830157.

3: Redjdal W, Ibrahim N, Benmerad B, Alami M, Messaoudi S. Convergent Synthesis of N,S-bis Glycosylquinolin-2-ones via a Pd-G3-XantPhos Precatalyst Catalysis. Molecules. 2018 Feb 26;23(3). pii: E519. doi: 10.3390/molecules23030519. PubMed PMID: 29495402.

4: Keaveney ST, Schoenebeck F. Palladium-Catalyzed Decarbonylative Trifluoromethylation of Acid Fluorides. Angew Chem Int Ed Engl. 2018 Apr 3;57(15):4073-4077. doi: 10.1002/anie.201800644. Epub 2018 Mar 13. PubMed PMID: 29479784.

5: Moonshiram D, Garrido-Barros P, Gimbert-Suriñach C, Picón A, Liu C, Zhang X, Karnahl M, Llobet A. Elucidating the Nature of the Excited State of a Heteroleptic Copper Photosensitizer by using Time-Resolved X-ray Absorption Spectroscopy. Chemistry. 2018 Feb 22. doi: 10.1002/chem.201800330. [Epub ahead of print] PubMed PMID: 29470842.

6: Keller S, Prescimone A, Constable EC, Housecroft CE. Copper(i) and silver(i) complexes of 9,9-dimethyl-4,5-bis(di-tert-butylphosphino)xanthene: photophysical properties and structural rigidity under pressure. Photochem Photobiol Sci. 2018 Apr 18;17(4):375-385. doi: 10.1039/c7pp00432j. PubMed PMID: 29457807.

7: McCullough BJ, Neyhouse BJ, Schrage BR, Reed DT, Osinski AJ, Ziegler CJ, White TA. Visible-Light-Driven Photosystems Using Heteroleptic Cu(I) Photosensitizers and Rh(III) Catalysts To Produce H(2). Inorg Chem. 2018 Mar 5;57(5):2865-2875. doi: 10.1021/acs.inorgchem.7b03273. Epub 2018 Feb 15. PubMed PMID: 29446925.

8: Chehal NK, Budzelaar PHM, Hultin PG. E-Z isomerization in Suzuki cross-couplings of haloenones: ligand effects and evidence for a separate catalytic cycle. Org Biomol Chem. 2018 Feb 14;16(7):1134-1143. doi: 10.1039/c7ob02925j. PubMed PMID: 29362769.

9: Wang GZ, Shang R, Fu Y. Irradiation-Induced Palladium-Catalyzed Decarboxylative Heck Reaction of Aliphatic N-(Acyloxy)phthalimides at Room Temperature. Org Lett. 2018 Feb 2;20(3):888-891. doi: 10.1021/acs.orglett.8b00023. Epub 2018 Jan 18. PubMed PMID: 29345954.

10: Karmel C, Li B, Hartwig JF. Rhodium-Catalyzed Regioselective Silylation of Alkyl C-H Bonds for the Synthesis of 1,4-Diols. J Am Chem Soc. 2018 Jan 31;140(4):1460-1470. doi: 10.1021/jacs.7b11964. Epub 2018 Jan 22. PubMed PMID: 29293327; PubMed Central PMCID: PMC5810544.

11: Adams GM, Colebatch AL, Skornia JT, McKay AI, Johnson HC, Lloyd Jones GC, Macgregor SA, Beattie NA, Weller AS. Dehydropolymerization of H(3)B·NMeH(2) To Form Polyaminoboranes Using [Rh(Xantphos-alkyl)] Catalysts. J Am Chem Soc. 2018 Jan 31;140(4):1481-1495. doi: 10.1021/jacs.7b11975. Epub 2018 Jan 22. PubMed PMID: 29286647.

12: Teo WJ, Ge S. Cobalt-Catalyzed Diborylation of 1,1-disubstituted Vinylarenes: A Practical Route to Branched gem-Bis(boryl)alkanes. Angew Chem Int Ed Engl. 2018 Feb 5;57(6):1654-1658. doi: 10.1002/anie.201710389. Epub 2018 Jan 10. PubMed PMID: 29193560.

13: Mao L, Bertermann R, Emmert K, Szabó KJ, Marder TB. Synthesis of Vinyl-, Allyl-, and 2-Boryl Allylboronates via a Highly Selective Copper-Catalyzed Borylation of Propargylic Alcohols. Org Lett. 2017 Dec 15;19(24):6586-6589. doi: 10.1021/acs.orglett.7b03294. Epub 2017 Nov 28. PubMed PMID: 29181971.

14: Al-Shuaeeb RAA, Dejean C, Alami M, Messaoudi S. Controllable Activation of Pd-G3 Palladacycle Precatalyst in the Presence of Thiosugars: Rapid Access to 1-Aminobiphenyl Thioglycoside Atropoisomers at Room Temperature. Chem Asian J. 2017 Dec 14;12(24):3114-3118. doi: 10.1002/asia.201701415. Epub 2017 Nov 21. PubMed PMID: 29071808.

15: Schulz M, Reichardt C, Müller C, Schneider KRA, Holste J, Dietzek B. Excited State Properties of Heteroleptic Cu(I) 4H-Imidazolate Complexes. Inorg Chem. 2017 Nov 6;56(21):12978-12986. doi: 10.1021/acs.inorgchem.7b01680. PubMed PMID: 29064681.

16: Mita T, Hanagata S, Michigami K, Sato Y. Co-Catalyzed Direct Addition of Allylic C(sp(3))-H Bonds to Ketones. Org Lett. 2017 Nov 3;19(21):5876-5879. doi: 10.1021/acs.orglett.7b02871. PubMed PMID: 29048908.

17: Chandrasekhar A, Sankararaman S. Selective Synthesis of 3-Arylbenzo-1,2,3-triazin-4(3H)-ones and 1-Aryl-(1H)-benzo-1,2,3-triazoles from 1,3-Diaryltriazenes through Pd(0) Catalyzed Annulation Reactions. J Org Chem. 2017 Nov 3;82(21):11487-11493. doi: 10.1021/acs.joc.7b02023. PubMed PMID: 28984453.

18: Gao S, Hu X. Nickel-catalyzed ring-opening of α-hydroxycyclobutenones with a remarkable ligand effect. Chem Commun (Camb). 2017 Sep 21;53(76):10540-10543. doi: 10.1039/c7cc03340k. PubMed PMID: 28890958.

19: Niu ZG, Wang XY, Chen HH, Wang X, Wei S, Wu DM, Chen GY, Qin J, Li GN. Synthesis and Properties of two CuI Complexes Involving Tetrathia-fulvalene-Fused Phenanthroline Ligand. Acta Chim Slov. 2017 Sep;64(3):633-637. PubMed PMID: 28862301.

20: Mukherjee P, Das AR. One-flask synthesis of pyrazolone thioethers involving catalyzed and uncatalyzed thioetherification pathways of pyrazolones. Org Biomol Chem. 2017 Sep 13;15(35):7267-7271. doi: 10.1039/c7ob01754e. PubMed PMID: 28832050.