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704946

Sigma-Aldrich

SPhos Pd G1, Methyl t-Butyl Ether Adduct

Synonym(s):

(2-Dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) chloride - methyl-t-butyl ether adduct, (SPhos) palladium(II) phenethylamine chloride (1:1 MTBE solvate), Chloro(2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl)[2-(2-aminoethylphenyl)]palladium(II) - methyl-t-butyl ether adduct, SPhos Palladacycle, SPhos precatalyst

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About This Item

Linear Formula:
C34H45ClNO2PPd · CH3OC4H9
Molecular Weight:
760.72
MDL number:
MFCD15144765
UNSPSC Code:
12161600
PubChem Substance ID:
329762493
NACRES:
NA.22

form

solid

Quality Level

100

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

160-170 °C

functional group

phosphine

SMILES string

COC(C)(C)C.NCCc1ccccc1[Pd]Cl.COc2cccc(OC)c2-c3ccccc3P(C4CCCCC4)C5CCCCC5

InChI

1S/C26H35O2P.C8H10N.C5H12O.ClH.Pd/c1-27-23-17-11-18-24(28-2)26(23)22-16-9-10-19-25(22)29(20-12-5-3-6-13-20)21-14-7-4-8-15-21;9-7-6-8-4-2-1-3-5-8;1-5(2,3)6-4;;/h9-11,16-21H,3-8,12-15H2,1-2H3;1-4H,6-7,9H2;1-4H3;1H;/q;;;;+1/p-1

InChI key

CLLOZWOLUBODPC-UHFFFAOYSA-M

Application

Application Guide for Palladium Catalyzed Cross-Coupling Reactions

Catalyst for C-N bond forming reaction.

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
SHBH1145V
SHBC5511V
SHBB5739V
SHBB5739
17796TM

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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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