Skip to Content
MilliporeSigma
All Photos(7)

Documents

638080

Sigma-Aldrich

tBuXPhos

greener alternative

98%

Synonym(s):

tBuXPhos, 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl, t-Bu XPhos, tert-Butyl XPhos

Sign Into View Organizational & Contract Pricing
All Photos(7)

About This Item

Empirical Formula (Hill Notation):
C29H45P
CAS Number:
564483-19-8
Molecular Weight:
424.64
MDL number:
MFCD06411306
UNSPSC Code:
12352002
PubChem Substance ID:
24882908

Quality Level

300

assay

98%

form

solid

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Atom Economy”, “Use of Renewable Feedstock” and “Design for Energy Efficiency”. Click here to view its DOZN scorecard.

Learn more about Buchwald Phosphine Ligands

Application

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.
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.

Legal Information

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

related product

Product No.
Description
Pricing

918008

GPhos, ≥95%

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Customers Also Viewed

Slide 1 of 6

1 of 6

SPhos 98%

Sigma-Aldrich

638072

SPhos

RuPhos 98%

Sigma-Aldrich

663131

RuPhos

DavePhos 97%

Sigma-Aldrich

638021

DavePhos

tBuMePhos

Sigma-Aldrich

695211

tBuMePhos

tBuBrettPhos Pd G3 96%

Sigma-Aldrich

745979

tBuBrettPhos Pd G3

CyJohnPhos 97%

Sigma-Aldrich

638099

CyJohnPhos

Arkaitz Correa et al.
Journal of the American Chemical Society, 131(44), 15974-15975 (2009-11-06)
A novel protocol for the direct carbon dioxide insertion (CO(2)) into aryl halides in a catalytic manner is presented herein. Unlike other carboxylation methods using CO(2), there is no need for the synthesis of the corresponding organometallic intermediates. Additionally, and
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)
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 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)
View All Related Papers

Articles

Buchwald Phosphine Ligands

Buchwald Phosphine Ligands

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Buchwald Phosphine Ligands

Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service