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677280

Sigma-Aldrich

sSPhos

Synonym(s):

SPhos (water soluble), Sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulfonate hydrate, [1,1′-Biphenyl]-3-sulfonic acid, 2′-(dicyclohexylphosphino)-2,6-dimethoxy- sodium salt

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About This Item

Empirical Formula (Hill Notation):
C26H34NaO5PS · xH2O
CAS Number:
1049726-96-6
Molecular Weight:
512.57 (anhydrous basis)
MDL number:
MFCD07781994
UNSPSC Code:
12352103
PubChem Substance ID:
24885361
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

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

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

Application

Learn more about Buchwald Phosphine Ligands

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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.
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
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

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