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901906

SPhos

95%, powder or crystals

greener alternative

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Synonym(s):

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

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1 g

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$58.70
$44.02
5 g

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$159.00
25 g

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$742.00
$556.50

About This Item

Empirical Formula (Hill Notation):
C26H35O2P
CAS Number:
Molecular Weight:
410.53
NACRES:
NA.22
UNSPSC Code:
12161600
MDL number:

$44.02

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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

Greener Alternative Product

mp

164-166 °C (lit.), 165.5 °C

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

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.

Legal Information

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

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This Item
PMC2007932191675784
description

95%

description

≥98%, ISOM8

description

-

description

-

reaction suitability

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

reaction suitability

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

reaction suitability

reagent type: catalyst
reaction type: Cross Couplings

reaction suitability

reagent type: ligand
reaction type: Arylations, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling, reagent type: ligand
reaction type: Buchwald-Hartwig Cross Coupling Reaction, reagent type: ligand
reaction type: Sonogashira Coupling

assay

95%

assay

≥98%, (HPLC)

assay

-

assay

-

functional group

phosphine

functional group

phosphine

functional group

-

functional group

phosphine

form

powder or crystals

form

solid

form

solid

form

-

mp

164-166 °C (lit.), 165.5 °C

mp

164-166 °C (lit.), 164-166 °C °C (Lit.)

mp

-

mp

211-219 °C

sustainability

Greener Alternative Product

sustainability

Greener Alternative Product

sustainability

Greener Alternative Product

sustainability

-


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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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