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Merck
CN

932191

SPhos ChemBeads

greener alternative

solid

Synonym(s):

2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos, SPhos

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About This Item

Empirical Formula (Hill Notation):
C26H35O2P
CAS Number:
657408-07-6
Molecular Weight:
410.53
MDL number:
MFCD05861611
UNSPSC Code:
12352128
NACRES:
NA.22

Key Documents

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Product Name

SPhos ChemBeads,

product line

ChemBeads

Quality Level

100

form

solid

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

greener alternative product characteristics

Catalysis
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Greener Alternative Product

greener alternative category

Aligned

SMILES string

P(C4CCCCC4)(C3CCCCC3)c1c(cccc1)c2c(cccc2OC)OC

InChI

1S/C26H35O2P/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/h9-11,16-21H,3-8,12-15H2,1-2H3

InChI key

VNFWTIYUKDMAOP-UHFFFAOYSA-N

Related Categories

General description

SPhos [2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl] is an air-stable, electron-rich biaryl phosphine ligand developed by the Buchwald group to enhance the reactivity of palladium catalysis during cross-coupling reactions.
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Application

SPhos may be used as a ligand in the following processes:
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between Boc-protected aminomethyltrifluoroborate and aryl chlorides or hetaryl chlorides to form the corresponding aminomethylarenes.
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.
  • Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.
Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation.
Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.

ChemBeads are chemical coated glass beads. ChemBeads offer improved flowability and chemical uniformity perfect for automated solid dispensing and high-throughput experimentation. The method of creating ChemBeads uses no other chemicals or surfactants allowing the user to accurately dispense sub-milligram amounts of chemical.

Learn more about ChemBeads products

Product is also available as neat ligand (638072)

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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