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763004

Sigma-Aldrich

CPhos Pd G3

95%

Synonym(s):

CPhos-G3-Palladacycle, CPhos-Pd-G3, [(2-Dicyclohexylphosphino-2′,6′-bis(N,N-dimethylamino) -1,1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C41H54N3O3PPdS
CAS Number:
1447963-73-6
Molecular Weight:
806.34
UNSPSC Code:
12161600
PubChem Substance ID:
329767018
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

feature

generation 3

reaction suitability

core: palladium
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

176-178 °C (decomposition)

functional group

phosphine

SMILES string

CS(=O)(=O)O[Pd]c1ccccc1-c2ccccc2N.CN(C)c3cccc(N(C)C)c3-c4ccccc4P(C5CCCCC5)C6CCCCC6

InChI

1S/C28H41N2P.C12H10N.CH4O3S.Pd/c1-29(2)25-19-13-20-26(30(3)4)28(25)24-18-11-12-21-27(24)31(22-14-7-5-8-15-22)23-16-9-6-10-17-23;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h11-13,18-23H,5-10,14-17H2,1-4H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

SMFSVINURNWOPR-UHFFFAOYSA-M

Related Categories

General description

CPhos Pd G3 is a modified G3 precatalyst (G3′). It has been synthesized by Buchwald and coworkers from second generation (G2) precatalyst by methylation of the amino group present on biphenyl backbone. It is a useful catalyst for various cross-coupling reactions. They are versatile catalysts. They have long life in solution and are readily soluble in various organic solvents. G3- precatalysts have been employed in various C-N bond forming reactions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBJ1719
SHBH4622V
SHBG7368V
SHBG0815V
SHBF1960V

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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)

Articles

Scale-Up Guide: Buchwald-Hartwig Amination Reaction

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form. Once activated by base under the reaction conditions they become sensitive to air. To best enable scale-up success, the use of standard Schlenk technique is recommended.

KitAlysis™ C-N (Buchwald-Hartwig) High-Throughput Screening Kit

All contents in the foil bag are weighed, plated, packed, and sealed in a glove box under nitrogen.

G3 and G4 Buchwald Precatalysts

G3 and G4 Buchwald palladium precatalysts are the newest air, moisture, and thermally stable crossing-coupling complexes used in bond formation for their versatility and high reactivity.

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