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Sigma-Aldrich

SPhos

greener alternative

98%

Synonym(s):

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

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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
PubChem Substance ID:
24882907
NACRES:
NA.22

Quality Level

300

assay

98%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Cross Couplings
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: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction
reagent type: ligand
reaction type: Heck Reaction
reagent type: ligand
reaction type: Kumada Coupling
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

greener alternative product score

old score: 10
new score: 1
Find out more about DOZN™ Scoring

greener alternative product characteristics

Waste Prevention
Less Hazardous Chemical Syntheses
Inherently Safer Chemistry for Accident Prevention
Learn more about the Principles of Green Chemistry.

mp

164-166 °C (lit.)

functional group

phosphine

greener alternative category

Re-engineered,

SMILES string

COc1cccc(OC)c1-c2ccccc2P(C3CCCCC3)C4CCCCC4

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

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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.
We are committed to bringing you Greener Alternative Products, which adhere to one of the four categories of Greener Alternatives . This product belongs to category of Re-engineered products, showing key improvements in Green Chemistry Principles “Waste Prevention”, “Less Hazardous Chemical Syntheses” and “Inherently Safer Chemistry for Accident Prevention”. Click here to view its DOZN scorecard.

Application

Learn more about Buchwald Phosphine Ligands

For small scale and high throughput uses, product is also available as ChemBeads (932191)
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.

Legal Information

Usage subject to Patents: US 6307087; EP 1097158; JP 5758844; CA 2336691

related product

Product No.
Description
Pricing

918008

GPhos, ≥95%

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of riccardin C and its seven analogues. Part 1: The role of their phenolic hydroxy groups as LXRa agonists.
Hioki H, et al.
Bioorganic & Medicinal Chemistry Letters, 19(3), 738-741 (2009)
Seel S, et al.
Journal of the American Chemical Society, 133(13), 4774-4777 (2011)
Sustainable Fe?ppm Pd nanoparticle catalysis of Suzuki-Miyaura cross-couplings in water
Handa, Sachin, et al.
Science, 349.6252, 1087-1091 (2015)
Pd-catalyzed Suzuki?Miyaura reactions of aryl halides using bulky biarylmonophosphine ligands
Altman, Ryan A., and Stephen L. Buchwald
Nature Protocols, 2.12 (2007)
A general solution for unstable boronic acids: slow-release cross-coupling from air-stable MIDA boronates
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