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901904

tBuXPhos

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

Greener Alternative

95%, powder or crystals

Synonym(s):

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

NACRES:

NA.22

UNSPSC Code:

12352002

MDL number:

MFCD06411306

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Properties

Product Name

tBuXPhos, 95%

assay

95%

form

powder or crystals

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: catalyst
reaction type: Cross Couplings, reagent type: ligand

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

148-151 °C (lit.), 150 °C

functional group

phosphine

greener alternative category

Aligned

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

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives. This bulky dialkylbiaryl phosphine (Buchwald ligand) is used for palladium-catalyzed Buchwald-Hartwig amination and Suzuki-Miyaura coupling reactions. Its large cone angle promotes formation of highly reactive monoligated species, providing exceptional activity for challenging C-N and C-C bond-forming reactions, thus aligning with Green Chemistry principle "Catalysis". Click here for more information.

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 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.

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