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638080

tBuXPhos

Name: <I>t</I>BuXPhos
Brand: ALDRICH

98%, solid

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):

C₂₉H₄₅P

CAS Number:

564483-19-8

Molecular Weight:

424.64

UNSPSC Code:

12352002

PubChem Substance ID:

24882908

NACRES:

NA.22

MDL number:

MFCD06411306

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Properties

Product Name

tBuXPhos, 98%

product line

Buchwald Ligand

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.

sustainability

Greener Alternative Product

mp

148-151 °C (lit.)

functional group

phosphine

greener alternative category

Re-engineered,

SMILES string

CC(P(C(C=CC=C1)=C1C(C(C(C)C)=CC(C(C)C)=C2)=C2C(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

Description

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

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Articles

Buchwald Phosphine Ligands

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