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900349

Sigma-Aldrich

cataCXium Pd G4

Synonym(s):

[di(adamantan-1-yl)(butyl)phosphine](methanesulfonato-κO)[2′-(methylamino)-2-biphenylyl]palladium

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About This Item

Empirical Formula (Hill Notation):
C38H54NO3PPdS
CAS Number:
Molecular Weight:
742.30
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

form

powder

Quality Level

feature

generation 4

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

functional group

phosphine

SMILES string

CCCCP([C@@]12C[C@H]3C[C@@H](C1)C[C@@H](C2)C3)[C@@]4(C5)C[C@H]6C[C@H](C[C@@H]5C6)C4.CNC7=C(C8=CC=CC=C8[Pd]OS(C)(=O)=O)C=CC=C7

InChI

1S/C24H39P.C13H12N.CH4O3S.Pd/c1-2-3-4-25(23-11-17-5-18(12-23)7-19(6-17)13-23)24-14-20-8-21(15-24)10-22(9-20)16-24;1-14-13-10-6-5-9-12(13)11-7-3-2-4-8-11;1-5(2,3)4;/h17-22H,2-16H2,1H3;2-7,9-10,14H,1H3;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

ROZFJYIWIVSDBR-UHFFFAOYSA-M

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Application

A fourth generation (G4) Buchwald precatalyst that is similar to the third generation (G3) precatalysts except that the amino group on the biphenyl backbone is methylated. This modification helps to prevent the limitations found when using the third generation precatalysts. It is air, moisture, and thermally-stable and shows good solubility in common organic solvents.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3


Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

900349-BULK:
900349-250MG:
900349-1G:
900349-VAR:
900349-5G:


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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[Rupture of the pregnant uterus].
I Pardini et al.
Rivista italiana di ginecologia, 58(6), 481-502 (1977-11-01)

Articles

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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