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901906

Sigma-Aldrich

SPhos

95%

Synonym(s):

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

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10 MG
₩163,720
50 MG
₩647,063

₩163,720


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10 MG
₩163,720
50 MG
₩647,063

About This Item

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

₩163,720


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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

mp

164-166 °C (lit.)
165.5 °C

functional group

phosphine

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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This Item
M4074F9428Y0000284
assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

≥98% (HPLC)

assay

-

form

powder

form

powder

form

powder

form

-

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

-

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

solubility

DMSO: 5 mg/mL, clear (warmed)

solubility

DMSO: ≥20 mg/mL

solubility

DMSO: ≥10 mg/mL

solubility

-

color

white to beige

color

white to off-white

color

white

color

-

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.

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.[1]
  • Palladium catalyzed Suzuki-Miyaura cross-coupling reaction between 4-methyl-substituted piperidinylzinc reagent and different aryl or heteroaryl iodides to form various substituted piperidines.[2]
  • Intramolecular Suzuki-Miyaura coupling to form the 18-membered macrocyclic ring during the multi-step synthesis of riccardin C.[3]
Utilized in conjunction with palladium to form a highly active catalyst for C-N bond formation[4]

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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