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638072

Sigma-Aldrich

SPhos

greener alternative

98%

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Synonym(s):
SPhos, 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, S Phos
Empirical Formula (Hill Notation):
C26H35O2P
CAS Number:
Molecular Weight:
410.53
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

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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638072

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SPhos 95%

901906

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638080

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reaction suitability

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

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, 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: catalyst
reaction type: Cross Couplings, reagent type: ligand

reaction suitability

-

reaction suitability

reaction type: Cross Couplings, reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Carboxylations, reagent type: ligand
reaction type: Decarboxylations

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

Quality Level

300

Quality Level

-

Quality Level

100

Quality Level

300

mp

164-166 °C (lit.)

mp

164-166 °C (lit.), 165.5 °C

mp

211-219 °C

mp

148-151 °C (lit.)

greener alternative product score

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

greener alternative product score

-

greener alternative product score

-

greener alternative product score

old score: 12
new score: 1
Find out more about DOZN™ Scoring

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

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)


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Highly diastereoselective arylations of substituted piperidines
Seel, Stephanie, et al.
Journal of the American Chemical Society, 133.13, 4774-4777 (2011)
Use of the SPhos Ligand to Suppress Racemization in Arylpinacolboronate Ester Suzuki Couplings Involving ?-Amino Acids. Synthesis of Biaryl Derivatives of 4-Hydroxyphenylglycine, Tyrosine, and Tryptophan
Prieto, Monica, et al.
The Journal of Organic Chemistry, 74.23, 9202-9205 (2009)
Synthesis of 1, 5-disubstituted tetrazoles via Suzuki?Miyaura cross-coupling of 5-chloro-1-phenyltetrazole
Tang, Qing, and Ryan Gianatassio
Tetrahedron Letters, 51.27, 3473-3476 (2010)
Efficient synthesis of functionalized dibenzofurans by domino `twofold Heck/6?-electrocyclization?reactions of 2, 3-di-and 2, 3, 5-tribromobenzofuran
Hussain, Munawar, Nguyen Thai Hung, and Peter Langer
Tetrahedron Letters, 50.27, 3929-3932 (2009)
What makes for a good catalytic cycle? A theoretical study of the SPhos ligand in the Suzuki?Miyaura reaction
Kozuch, Sebastian, and Jan ML Martin
Chemical Communications (Cambridge, England), 47.17, 4935-4937 (2011)

Articles

Buchwald Phosphine Ligands

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

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