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901906

SPhos

Name: SPhos
Brand: ALDRICH

95%, powder or crystals

Synonym(s):

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

UNSPSC Code:

12161600

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Properties

Product Name

SPhos, 95%

assay

95%

form

powder or crystals

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

greener alternative product characteristics

Catalysis
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sustainability

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mp

164-166 °C (lit.), 165.5 °C

functional group

phosphine

greener alternative category

Aligned

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.

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Application

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

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

Legal Information

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

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

WXBD5936V

WXBD0196V

WXBC7953V

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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)

Synthesis and Suzuki?Miyaura Cross-Coupling Reactions of Potassium Boc-Protected Aminomethyltrifluoroborate with Aryl and Hetaryl Halides

Molander, Gary A., and Inji Shin.

Organic Letters, 13.15, 3956-3959 (2011)

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Global Trade Item Number

SKU	GTIN
901906-1G	04061835511150
901906-250G	04061835519859
901906-25G	04061835559947
901906-5G	04061835511181