638080

Sigma-Aldrich

tBuXPhos

greener alternative

98%

Synonym(s):
t-Bu XPhos, 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl, tBuXPhos, tert-Butyl XPhos
Empirical Formula (Hill Notation):
C29H45P
CAS Number:
Molecular Weight:
424.64
MDL number:
PubChem Substance ID:

Quality Level

assay

98%

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

greener alternative product score

old score: 12
new score: 1
Find out more about DOZN™ Scoring.

greener alternative product characteristics

Atom Economy
Design for Energy Efficiency
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

mp

148-151 °C (lit.)

functional group

phosphine

greener alternative category

Re-engineered

SMILES string

CC(C)c1cc(C(C)C)c(c(c1)C(C)C)-c2ccccc2P(C(C)(C)C)C(C)(C)C

InChI

1S/C29H45P/c1-19(2)22-17-24(20(3)4)27(25(18-22)21(5)6)23-15-13-14-16-26(23)30(28(7,8)9)29(10,11)12/h13-21H,1-12H3

InChI key

SACNIGZYDTUHKB-UHFFFAOYSA-N

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General description

tBuXPhos [2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.

Application

tBuXPhos is a ligand for Pd-catalyzed C-O and C-N bond formation.
It can be used in the following reactions:
  • Palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.
  • Palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.
  • Palladium-catalyzed rapid methoxylation and deuteriomethoxylation of bromo-chalcones.

tBuXPhos has been used in the preparation of [tBuXPhosAu(MeCN)]BAr4F, a gold catalyst for the intermolecular [2+2] cycloaddition of terminal arylalkynes with substituted alkenes to form functionalized cyclobutenes with high regioselectivity.

Packaging

1, 5, 25, 100, 500 g in glass bottle

Legal Information

Usage subject to Patents: EP 1097158; JP 5758844; CA 2336691

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Intermolecular [2+ 2] Cycloaddition of Alkynes with Alkenes Catalyzed by Gold (I).
de Orbe ME and Echavarren AM.
Organic Syntheses, 93, 115-126 (2016)
Palladium-Catalyzed C?N Cross Coupling of Sulfinamides and Aryl Halides.
Sun X, et al.
The Journal of Organic Chemistry, 77(9), 4454-4459 (2012)
Palladium?Catalyzed Rapid Methoxylation and Deuteriomethoxylation of Bromo?chalcones: Uncovering the Catalytic Activity of the Pd/tBuXPhos Catalyst System.
Rangarajan T M, et al.
ChemistrySelect, 1(21), 6894-6901 (2016)
Kevin W Anderson et al.
Journal of the American Chemical Society, 128(33), 10694-10695 (2006-08-17)
The direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd(2)dba(3) and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H(2)O. We have also...
Palladium-catalyzed substitution and cross-coupling of benzylic fluorides.
Blessley G, et al.
Organic Letters, 14(11), 2754-2757 (2012)
Articles
Buchwald Phosphine Ligands
Read More
Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.
Read More

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