Skip to Content
Merck
All Photos(1)

Documents

936693

Sigma-Aldrich

tBuXPhos ChemBeads

new

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C29H45P
CAS Number:
564483-19-8
Molecular Weight:
424.64
MDL number:
MFCD06411306
UNSPSC Code:
12352100

Quality Level

100

form

solid

composition

, 4-6 wt. % (loading)

reaction suitability

reagent type: ligand

SMILES string

CC(C)(C)P(C(C)(C)C)C1=C(C2=C(C(C)C)C=C(C(C)C)C=C2C(C)C)C=CC=C1

InChI

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

General description

The ChemBeads product of 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. Loaded on glass beads for use in high-throughput expermentation (HTE).

Application

tBuXPhos has been used as a ligand in many C-N and C-O bond forming reactions, as well many others including:
- The palladium-catalyzed Tsuji-Trost substitution and cross-coupling of benzylic fluorides.
- The palladium-catalyzed C-N cross-coupling of sulfinamides and aryl halides.
- The protoboration of alkynes.
- ArF-alkynyl coupling with fluorinated aryls.
- The Ni & Ni/Pd reductive coupling of lignan-derived aromatics to biobased platicizers.
- The palladium-catalyzed fluorination of cyclic vinyl triflates.
ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.
For general uses, product is also available in powdered form (638080)

related product

Product No.
Description
Pricing

638080

tBuXPhos, 98%

901904

tBuXPhos, 95%

924377

Palladium(II) Acetate ChemBeads

928364

XPhos ChemBeads

931055

tBuXPhos Pd G3 ChemBeads

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Sorry, we don't have COAs for this product available online at this time.

If you need assistance, please contact Customer Support.

Already Own This Product?

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

Visit the Document Library

Lei Xu et al.
The Journal of organic chemistry, 87(21), 14879-14888 (2022-10-13)
The versions of Miyaura borylation and protoboration of alkynes catalyzed by low loadings of palladium (400 mol ppm = 0.04 mol %) have been developed. These transformations have a broad substrate scope, good functional-group compatibility, and gram-scale synthetic ability.
Xiaofei Sun et al.
The Journal of organic chemistry, 77(9), 4454-4459 (2012-03-31)
The palladium-catalyzed C-N cross coupling of sulfinamides and aryl halides is reported. In the presence of Pd(2)(dba)(3), tBuXPhos, NaOH, and a small amount of water, the C-N cross coupling of chiral tert-butanesulfinamide and aryl halides was accomplished to give N-aryl
Palladium-catalyzed substitution and cross-coupling of benzylic fluorides
Blessley G, et al.
Organic Letters, 14(11), 2754-2757 (2012)
Zhi-Ming Su et al.
ACS central science, 9(2), 159-165 (2023-02-28)
Lignin-derived aromatic chemicals offer a compelling alternative to petrochemical feedstocks, and new applications are the focus of extensive interest. 4-Hydroxybenzoic acid (H), vanillic acid (G), and syringic acid (S) are readily obtained via oxidative depolymerization of hardwood lignin substrates. Here
Yuxuan Ye et al.
Angewandte Chemie (International ed. in English), 62(15), e202300109-e202300109 (2023-02-13)
Pd-catalyzed nucleophilic fluorination reactions are important methods for the synthesis of fluoroarenes and fluoroalkenes. However, these reactions can generate a mixture of regioisomeric products that are often difficult to separate. While investigating the Pd-catalyzed fluorination of cyclic vinyl triflates, we
View All Related Papers

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