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776246

SPhos Pd G3

97%, solid

Synonym(s):

(2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl) [2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C39H48NO5PPdS
CAS Number:
1445085-82-4
Molecular Weight:
780.26
MDL number:
MFCD29472404
UNSPSC Code:
12161600
PubChem Substance ID:
329767824
NACRES:
NA.22
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Product Name

SPhos Pd G3, 97%

Quality Segment

100

product line

Buchwald precatalyst Generation 3

assay

97%

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

197-214 °C

functional group

phosphine

storage temp.

2-8°C

SMILES string

CS(=O)(=O)O[Pd]c1ccccc1-c2ccccc2N.COc3cccc(OC)c3-c4ccccc4P(C5CCCCC5)C6CCCCC6

InChI

1S/C26H35O2P.C12H10N.CH4O3S.Pd/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h9-11,16-21H,3-8,12-15H2,1-2H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

SCWODMZBSVVMRH-UHFFFAOYSA-M

General description

SPhos Pd G3 is a third-generation (G3) Buchwald precatalyst that can be used in cross-coupling reactions for the formation of C-C, C-N, C-O, C-F, C-CF3, and C-S bonds. It is air-, moisture-, and thermally stable and is highly soluble in a wide range of common organic solvents. 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

Pd catalyst for cross-coupling
SPhos Pd G3 can be used as a precatalyst in the Suzuki–Miyaura catalyst–transfer polymerization (SCTP) reaction of a wide spectrum of monomers, including electron-rich to electron-deficient (hetero)arenes. It is also used as a catalyst in the formation of a Csp3–Csp2 bond between sterically hindered boronic hemiester and quinone diazide, which is the key intermediate step in the enantioselective synthesis of azamerone.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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