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Sigma-Aldrich

tBuXPhos Pd G3

98%

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Synonym(s):
tBuXPhos-Pd-G3, [(2-Di-tert-butylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate
Empirical Formula (Hill Notation):
C42H58NO3PPdS
CAS Number:
1447963-75-8
Molecular Weight:
794.37
MDL number:
MFCD22666411
UNSPSC Code:
12352300
PubChem Substance ID:
329766956
NACRES:
NA.22

Quality Level

100

Assay

98%

form

solid

feature

generation 3

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

mp

130-140 °C

functional group

phosphine

SMILES string

CS(=O)(=O)O[Pd]c1ccccc1-c2ccccc2N.CC(C)c3cc(C(C)C)c(c(c3)C(C)C)-c4ccccc4P(C(C)(C)C)C(C)(C)C

InChI

1S/C29H45P.C12H10N.CH4O3S.Pd/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;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h13-21H,1-12H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

SQQOHCLJPLSJGX-UHFFFAOYSA-M

Related Categories

General description

tBuXPhos Pd G3 is a third generation (G3) Buchwald precatalyst. It is air, moisture and thermally-stable and is highly soluble in a wide range of common organic solvents. It has long life in solutions. tBuXPhos Pd G3 is an excellent reagent for Buchwald-Hartwig cross-coupling reaction. Some of its unique features include lower catalyst loadings, shorter reaction time, efficient formation of the active catalytic species and accurate control of ligand: palladium ratio.

Application

tBuXPhos Pd G3 may be used to synthesize 4-cyano-7-azaindole from 4-chloro-7-azaindole by cyanation reaction. It may also be used for the α-arylation reaction of acetate esters at room temperature.

For small scale and high throughput uses, product is also available as ChemBeads (931055)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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2-Aminobiphenyl Palladacycles: The ?Most Powerful? Precatalysts in C-C and C-Heteroatom Cross-Couplings.
Bruneau A, et al.
ACS Catalysis, 5(2), 1386-1396 (2015)

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