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707589

Sigma-Aldrich

RuPhos Pd G1 Methyl t­-Butyl Ether Adduct

95%

Synonym(s):

(RuPhos) palladium(II) phenethylamine chloride (1:1 MTBE solvate), Chloro-(2-Dicyclohexylphosphino-2′,6′-diisopropoxy-1,1′-biphenyl)[2-(2-aminoethyl)phenyl]palladium(II) - methyl-t-butyl ether adduct, RuPhos Palladacycle, RuPhos precatalyst

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About This Item

Empirical Formula (Hill Notation):
C38H53ClNO2PPd · CH3OC4H9
CAS Number:
2361069-97-6
Molecular Weight:
816.83
MDL number:
MFCD12545955
UNSPSC Code:
12161600
PubChem Substance ID:
329762732
NACRES:
NA.22

Assay

95%

form

solid

feature

generation 1

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

180-200 °C

functional group

phosphine

SMILES string

COC(C)(C)C.NCCc1ccccc1[Pd]Cl.CC(C)Oc2cccc(OC(C)C)c2-c3ccccc3P(C4CCCCC4)C5CCCCC5

InChI

1S/C30H43O2P.C8H10N.C5H12O.ClH.Pd/c1-22(2)31-27-19-13-20-28(32-23(3)4)30(27)26-18-11-12-21-29(26)33(24-14-7-5-8-15-24)25-16-9-6-10-17-25;9-7-6-8-4-2-1-3-5-8;1-5(2,3)6-4;;/h11-13,18-25H,5-10,14-17H2,1-4H3;1-4H,6-7,9H2;1-4H3;1H;/q;;;;+1/p-1

InChI key

OMMPYFRVDWZBNR-UHFFFAOYSA-M

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions
Catalyst for Buchwald-Hartwig amination reaction.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
SHBD6094V
SHBB4745V
42096TM
63996DK

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Jaclyn L Henderson et al.
Organic letters, 12(20), 4438-4441 (2010-09-24)
Simple and efficient procedures for the Pd-catalyzed cross-coupling of primary and secondary amines with halo-7-azaindoles(pyrrolo[2,3-b]pyridine) are presented. Previously, no general method was available to ensure the highly selective reaction of the heteroaryl halide in the presence of the unprotected azaindole
Mark R Biscoe et al.
Journal of the American Chemical Society, 130(21), 6686-6687 (2008-05-02)
A new class of one-component Pd precatalysts bearing biarylphosphine ligands is described. These precatalysts are air- and thermally stable, are easily activated under normal reaction conditions at or below room temperature, and ensure the formation of the highly active monoligated
David S Surry et al.
Chemical science, 2(1), 27-50 (2011-01-01)
Dialkylbiaryl phosphines are a valuable class of ligand for Pd-catalyzed amination reactions and have been applied in a range of contexts. This review attempts to aid the reader in the selection of the best choice of reaction conditions and ligand
Ruben Martin et al.
Accounts of chemical research, 41(11), 1461-1473 (2008-07-16)
The cores of many types of polymers, ligands, natural products, and pharmaceuticals contain biaryl or substituted aromatic structures, and efficient methods of synthesizing these structures are crucial to the work of a broad spectrum of organic chemists. Recently, Pd-catalyzed carbon-carbon
David S Surry et al.
Angewandte Chemie (International ed. in English), 47(34), 6338-6361 (2008-07-30)
Palladium-catalyzed amination reactions of aryl halides have undergone rapid development in the last 12 years, largely driven by the implementation of new classes of ligands. Biaryl phosphanes have proven to provide especially active catalysts in this context. This Review discusses

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