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Sigma-Aldrich

1,2-Bis(dicyclohexylphosphino)ethane

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Synonym(s):
Ethylenebis(dicyclohexylphosphine), 1,2-Ethanediylbis[dicyclohexyl]phosphine
Linear Formula:
(C6H11)2PCH2CH2P(C6H11)2
CAS Number:
Molecular Weight:
422.61
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

solid

Quality Level

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

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This Item
106496261920436437
reaction suitability

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

reaction suitability

reagent type: ligand
reaction type: C-C Bond Formation, reagent type: ligand
reaction type: Carbonylations, reagent type: ligand
reaction type: Cycloadditions, reagent type: ligand
reaction type: Decarboxylations, reagent type: ligand
reaction type: Diels-Alder Reaction, reagent type: ligand
reaction type: Heck Reaction, reagent type: ligand
reaction type: Negishi Coupling, reagent type: ligand
reaction type: Suzuki-Miyaura Coupling

reaction suitability

-

reaction suitability

-

mp

92.5-96.5 °C (lit.)

mp

137-142 °C (lit.)

mp

-

mp

95-102 °C (lit.)

functional group

phosphine

functional group

phosphine

functional group

phosphine

functional group

phosphine

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

> 110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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