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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
Pricing and availability is not currently available.

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.[1]
  • Ni-catalyzed cross-coupling reaction of aryl fluorides and primary amines.[2]

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR2457
MKCS6675
MKCP8443
MKCM4179
MKCJ6462

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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

Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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