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SPhos

Name: SPhos
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

24882907

UNSPSC Code:

12352128

MDL number:

MFCD05861611

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Properties

Quality Level

300

product line

Buchwald Ligand

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.

sustainability

Greener Alternative Product

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

Description

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

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.

Learn more about Buchwald Phosphine Ligands

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

Highly universal ligand for Suzuki-Miyaura coupling; aryl chlorides, hindered biaryls, heterobiaryls.

Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation.

Legal Information

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

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Storage Class

13 - Non Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Articles

Buchwald Phosphine Ligands

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