677280

Sigma-Aldrich

sSPhos

Sinónimos:
[1,1′-Biphenyl]-3-sulfonic acid, 2′-(dicyclohexylphosphino)-2,6-dimethoxy- sodium salt, Sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulfonate hydrate, SPhos (water soluble)
Empirical Formula (Hill Notation):
C26H34NaO5PS · xH2O
Número de CAS:
Peso molecular:
512.57 (anhydrous basis)
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.22

reaction suitability

reaction type: Cross Couplings
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

Nivel de calidad

100

grupo funcional

phosphine

SMILES string

O.[Na+].COc1ccc(c(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4)S([O-])(=O)=O

InChI

1S/C26H35O5PS.Na.H2O/c1-30-22-17-18-24(33(27,28)29)26(31-2)25(22)21-15-9-10-16-23(21)32(19-11-5-3-6-12-19)20-13-7-4-8-14-20;;/h9-10,15-20H,3-8,11-14H2,1-2H3,(H,27,28,29);;1H2/q;+1;/p-1

InChI key

MAPQBSXKBDVINV-UHFFFAOYSA-M

Envase

2, 10 g in glass bottle
500 mg in glass bottle

Aplicación

Sulfonated ligand for palladium-catalyzed Suzuki-Miyaura coupling under aqueous conditions facilitating isolation of the organic products.

Información legal

Usage subject to US Patents 6307087 and 6395916.

pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

hazcat

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

Órganos de actuación

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Alemania

WGK 3

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

Certificado de Análisis

Certificado de origen

General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water.
Kevin W Anderson et al.
Angewandte Chemie (International ed. in English), 44(38), 6173-6177 (2005-08-13)
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...
Artículos
Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.
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