677280

Sigma-Aldrich

sSPhos

Synonym(s):
[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
CAS Number:
Molecular Weight:
512.57 (anhydrous basis)
MDL number:
PubChem Substance ID:
NACRES:
NA.22

reaction suitability

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

Quality Level

functional group

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

Packaging

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

Application

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

Legal Information

Usage subject to US Patents 6307087 and 6395916.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

hazcat

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

Target Organs

Respiratory system

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
Articles
Buchwald phosphine ligands for C-C, C-N, and C-O bond formation.
Read More

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service