Skip to Content
Merck
All Photos(3)

Key Documents

View All Documentation

479500

Sigma-Aldrich

1,2-Bis(dicyclohexylphosphino)ethane

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(3)

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

Signal Word

Danger

Hazard Statements

H315,H318,H335,H413

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCP8443
MKCM4179
MKCJ6462
MKCG1105
MKCD0095

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service