All Photos(4)

678740

Sigma-Aldrich

Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)

Synonym(s):
Pd(amphos)Cl2, (A-taPhos)2PdCl2
Empirical Formula (Hill Notation):
C32H56Cl2N2P2Pd
CAS Number:
Molecular Weight:
708.07
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

functional group

phosphine

SMILES string

Cl[Pd]Cl.CN(C)c1ccc(cc1)P(C(C)(C)C)C(C)(C)C.CN(C)c2ccc(cc2)P(C(C)(C)C)C(C)(C)C

InChI

1S/2C16H28NP.2ClH.Pd/c2*1-15(2,3)18(16(4,5)6)14-11-9-13(10-12-14)17(7)8;;;/h2*9-12H,1-8H3;2*1H;/q;;;;+2/p-2

InChI key

DWOZNANUEDYIOF-UHFFFAOYSA-L

Application

Higly active, air-stable catalyst for Suzuki-Miyaura cross-coupling with aryl halides including 5- and 6-membered heteroaryl chlorides.

Packaging

1, 5, 50 g in glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Arkady Krasovskiy et al.
Journal of the American Chemical Society, 131(43), 15592-15593 (2009-10-16)
Mix in water, stir. That is all that is required in this new approach to sp(3)-sp(2) cross-couplings between an alkyl iodide and an aryl bromide, both potentially bearing functionality. They react under catalysis by Pd(0) in the presence of zinc...
Anil S Guram et al.
Organic letters, 8(9), 1787-1789 (2006-04-21)
[reaction: see text] New air-stable PdCl(2){P(t)Bu(2)(p-R-Ph)}(2) (R = H, NMe(2), CF(3),) complexes represent simple, general, and efficient catalysts for the Suzuki-Miyaura cross-coupling reactions of aryl halides including five-membered heteroaryl halides and heteroatom-substituted six-membered heteroaryl chlorides with a diverse range of...

Articles

A-Phos

A-Phos Palladium Complexes for Efficient Suzuki Coupling

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