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764183

Sigma-Aldrich

APhos Pd G3

greener alternative

97%

Synonym(s):

APhos-Pd-G3, Palladium G3-(4-(N,N-Dimethylamino)phenyl)di-tert-butylphosphine, [4-(Di-tert-butylphosphino)-N,N-dimethylaniline-2-(2′-aminobiphenyl)]palladium(II) methanesulfonate

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About This Item

Empirical Formula (Hill Notation):
C29H41N2O3PPdS
CAS Number:
Molecular Weight:
635.11
MDL number:
UNSPSC Code:
12161600
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

greener alternative product score

old score: 5
new score: 3
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greener alternative product characteristics

Waste Prevention
Atom Economy
Less Hazardous Chemical Syntheses
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

192-201 °C (decomposition)

functional group

phosphine

greener alternative category

SMILES string

NC1=C(C=CC=C1)C2=C([Pd]OS(C)(=O)=O)C=CC=C2.CN(C)C3=CC=C(C=C3)P(C(C)(C)C)C(C)(C)C

InChI

1S/C16H28NP.C12H10N.CH4O3S.Pd/c1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8;13-12-9-5-4-8-11(12)10-6-2-1-3-7-10;1-5(2,3)4;/h9-12H,1-8H3;1-6,8-9H,13H2;1H3,(H,2,3,4);/q;;;+1/p-1

InChI key

SNUBBUQVCDWEAV-UHFFFAOYSA-M

General description

We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives. This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Atom Economy” and “Less Hazardous Chemical Synthesis”. Click here to view its DOZN scorecard.

Application

APhos Pd G3 is a Buchwald precatalyst that can be used in cross-coupling reactions.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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Synthesis of Double-Bond-Substituted Hemithioindigo Photoswitches
Gerwien A, et al.
Organic Letters, 20(1), 232-235 (2018)
Capture of reactive monophosphine-ligated palladium (0) intermediates by mass spectrometry
Zheng Q, et al.
Journal of the American Chemical Society, 137(44), 14035-14038 (2015)

Articles

All of the preformed catalysts used in the kit are air and moisture stable complexes in their commercially available form.

Tools aid in kit setup for organic chemistry techniques, ensuring ease and success.

Tools aid in kit setup for organic chemistry techniques, ensuring ease and success.

Tools aid in kit setup for organic chemistry techniques, ensuring ease and success.

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Related Content

The Buchwald group has developed a series of highly active and versatile palladium precatalysts and biarylphosphine ligands used in cross-coupling reactions for the formation of C-C, C–N, C–O, C–F, C–CF3, and C–S bonds. The ligands are electron-rich, and highly tunable to provide catalyst systems with a diverse scope, high stability and reactivity. Furthermore, the new series of precatalysts are air-, moisture and thermally-stable and display good solubility in common organic solvents. The use of precatalysts ensures the efficient generation of the active catalytic species and allows one to accurately adjust the ligand:palladium ratio. The ligands, precatalysts and methodology developed in the Buchwald group are user friendly and have rendered previously difficult cross couplings reactions, much easier to achieve.

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