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804959

Sigma-Aldrich

DavePhos-Pd-G3

95%

Synonym(s):

Methanesulfonato 2-dicyclohexylphosphino-2-(N,N-dimethylamino)biphenyl(2′-amino-1,1′-biphenyl-2-yl) palladium(II)

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About This Item

Empirical Formula (Hill Notation):
C39H49N2O3PPdS
CAS Number:
1445085-87-9
Molecular Weight:
763.28
MDL number:
MFCD27978422
UNSPSC Code:
12161600
PubChem Substance ID:
329768911
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

impurities

<5% THF

mp

183-200 °C (decomp)

functional group

phosphine

SMILES string

CN(C)C1=C(C2=C(P(C3CCCCC3)C4CCCCC4)C=CC=C2)C=CC=C1.NC5=C(C6=C([Pd]OS(C)(=O)=O)C=CC=C6)C=CC=C5

InChI

1S/C26H36NP.C12H10N.CH4O3S.Pd/c1-27(2)25-19-11-9-17-23(25)24-18-10-12-20-26(24)28(21-13-5-3-6-14-21)22-15-7-4-8-16-22;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h9-12,17-22H,3-8,13-16H2,1-2H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

FBIRGVXUSGLNQE-UHFFFAOYSA-M

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General description

DavePhos-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 solutions and are readily soluble in various organic solvents. G3- precatalysts have been employed in various C-N bond forming reactions.

Application

Pd precatalyst for cross-coupling

Pictograms

Health hazard
GHS08

Signal Word

Warning

Hazard Statements

H351

Hazard Classifications

Carc. 2

Supplementary Hazards

EUH019

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
0000214574
SHBP0518
SHBL7829
SHBH4700V
SHBH0989V

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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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Scale-Up Guide: Buchwald-Hartwig Amination

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Scale-Up Guide: Buchwald-Hartwig Amination

Preformed catalysts in the kit are stable but become air-sensitive when activated; Schlenk technique aids scale-up.

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