481408

Sigma-Aldrich

Chlorodicyclohexylphosphine

97%

Synonym(s):
Dicyclohexylchlorophosphine, Dicyclohexylphosphine chloride, Dicyclohexylphosphinous chloride
Linear Formula:
(C6H11)2PCl
CAS Number:
Molecular Weight:
232.73
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

97%

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: ligand

refractive index

n20/D 1.533 (lit.)

bp

165 °C/12 mmHg (lit.)

density

1.054 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

ClP(C1CCCCC1)C2CCCCC2

InChI

1S/C12H22ClP/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h11-12H,1-10H2

InChI key

AKJFBIZAEPTXIL-UHFFFAOYSA-N

Application

Chlorodicyclohexylphosphine can be used as a reactant in the synthesis of:
  • 1,2-Bis(dicyclohexylphosphinoxy)ethane ligand by reacting with ethylene glycol in the presence of triethylamine via Michaelis−Arbuzov type rearrangements.
  • 1,1,2,2-tetracyclohexyldiphosphine monosulfide ligand by treating with LiS.

It can be also used as a starting material for the preparation of some other ligands such as dicyclohexylphosphine oxide , phosphino substituted N-aryl pyrroles , di-tert-butyl((dicyclohexylphosphino)methyl)phosphine , dicyclohexylcyclopentylphosphine. These ligands are used in Pd-catalyzed cross-coupling reactions.

Packaging

1, 5 g in glass bottle

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Supp Hazards

EUH014

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3265 8 / PGII

WGK Germany

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

A sulfur mimic of 1, 1-bis (diphenylphosphino) methane: a new ligand opens up
Sues PE, et al.
Chemical Communications (Cambridge, England), 50(36), 4707-4710 (2014)
Characterization of secondary phosphine oxide ligands on the surface of iridium nanoparticles
Cano I, et al.
Physical Chemistry Chemical Physics, 19(32), 21655-21662 (2017)
Practical synthesis of new and highly efficient ligands for the Suzuki reaction of aryl chlorides
Zapf A, et al.
Chemical Communications (Cambridge, England), 19(1), 38-39 (2004)
Synthesis of 1, 2-bis [(diorgano) phosphino] ethanes via Michaelis-Arbuzov type rearrangements
Baldwin LC and Fink MJ
Journal of Organometallic Chemistry, 646(1-2), 230-238 (2002)
Intramolecular alkyl phosphine dehydrogenation in cationic rhodium complexes of tris (cyclopentylphosphine)
Douglas TM, et al.
Chemistry?A European Journal , 14(3), 1004-1022 (2008)

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