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479500

Sigma-Aldrich

1,2-Bis(dicyclohexylphosphino)ethane

Synonym(s):

Ethylenebis(dicyclohexylphosphine), 1,2-Ethanediylbis[dicyclohexyl]phosphine

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About This Item

Linear Formula:
(C6H11)2PCH2CH2P(C6H11)2
CAS Number:
23743-26-2
Molecular Weight:
422.61
MDL number:
MFCD00015521
UNSPSC Code:
12352001
PubChem Substance ID:
24871622
NACRES:
NA.22

form

solid

Quality Level

100

reaction suitability

reagent type: ligand
reaction type: Decarboxylations
reagent type: ligand
reaction type: Negishi Coupling
reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

mp

92.5-96.5 °C (lit.)

functional group

phosphine

SMILES string

C1CCC(CC1)P(CCP(C2CCCCC2)C3CCCCC3)C4CCCCC4

InChI

1S/C26H48P2/c1-5-13-23(14-6-1)27(24-15-7-2-8-16-24)21-22-28(25-17-9-3-10-18-25)26-19-11-4-12-20-26/h23-26H,1-22H2

InChI key

BOUYBUIVMHNXQB-UHFFFAOYSA-N

Application

1,2-Bis(dicyclohexylphosphino)ethane can be used as a ligand for:
  • Pd-catalyzed decarbonylative C-H coupling of azoles and aromatic esters.
  • Ni-catalyzed cross-coupling reaction of aryl fluorides and primary amines.

Reactant involved in:
  • Investigations of the role of ligand-based steric effects during the polymerization
  • Synthesis of molybdenum nitrosyl complexes for use as Imine hydrogenation catalysts
  • Irreversible thermal linkage isomerization of switchable C-N-bound isomers
  • Chelating for conversion of trans complexes to cis complexes

Precursor for Iridium trisboryl complexes and the substituent effect on borylation reactions

Ligand for palladium(II) complex catalyzed hydrogenation reactions

Pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Aquatic Chronic 4 - Eye Dam. 1 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

>230.0 °F - closed cup

flash_point_c

> 110 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Nickel-catalyzed amination of aryl fluorides with primary amines.
Harada T, et al.
Chemical Communications (Cambridge, England), 54(14), 1718-1721 (2018)
Pd-Catalyzed Decarbonylative C- H Coupling of Azoles and Aromatic Esters.
Matsushita K, et al.
Chemistry - An Asian Journal (2018)
Helen Larson et al.
The Journal of organic chemistry, 84(20), 13092-13103 (2019-09-25)
This manuscript details the development of the nickel-catalyzed arylation of oxazoles and benzoxazoles with aryl halides. A series of aryl, heteroaryl, and druglike electrophiles relevant to pharmaceutical applications were surveyed. The desired arylated products were obtained in synthetically useful yields

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