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684821

Sigma-Aldrich

1,2-Bis(phenylsulfinyl)ethane palladium(II) acetate

greener alternative

Synonym(s):

White catalyst

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About This Item

Empirical Formula (Hill Notation):
C18H20O6PdS2
CAS Number:
858971-43-4
Molecular Weight:
502.90
MDL number:
MFCD09842752
UNSPSC Code:
12161600
PubChem Substance ID:
329760926
NACRES:
NA.22

form

powder

reaction suitability

core: palladium
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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: C-H Activation

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

greener alternative category

Aligned,

storage temp.

−20°C

SMILES string

CC(=O)O[Pd]OC(C)=O.O=S(CCS(=O)c1ccccc1)c2ccccc2

InChI

1S/C14H14O2S2.2C2H4O2.Pd/c15-17(13-7-3-1-4-8-13)11-12-18(16)14-9-5-2-6-10-14;2*1-2(3)4;/h1-10H,11-12H2;2*1H3,(H,3,4);/q;;;+2/p-2

InChI key

SNNYSJNYZJXIFE-UHFFFAOYSA-L

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Find details here.

Application

White Catalyst: A Catalyst for Allylic C–H Oxidation and Amination
Macrolactonization via Hydrocarbon Oxidation
Catalyst for allylic C-H oxidation, useful for preparation of branched allylic esters, macrocycles, and amino alcohol derivatives.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H318

Precautionary Statements

P280 - P305 + P351 + P338

Hazard Classifications

Eye Dam. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBC3239V
14696KKV
14696KK
50996JJ
04111DH

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Kenneth J Fraunhoffer et al.
Journal of the American Chemical Society, 128(28), 9032-9033 (2006-07-13)
A novel Pd/sulfoxide-catalyzed macrolactonization reaction of linear omega-alkenoic acids is reported that proceeds via serial ligand-catalyzed allylic C-H oxidation. The scope of this macrolactonization appears to be very broad. Aryl, alkyl, and (Z)-alpha,beta-unsaturated acids are all competent nucleophiles for this
syn-1,2-Amino alcohols via diastereoselective allylic C-H amination.
Kenneth J Fraunhoffer et al.
Journal of the American Chemical Society, 129(23), 7274-7276 (2007-05-23)

Articles

White Catalyst

Developed by Professor M. Christina White and co-workers at the University of Illinois–Urbana, the “White catalyst” (684821) has been shown to be an exceptional catalyst for the functionalization of allylic carbon centers.

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