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481408

Sigma-Aldrich

Chlorodicyclohexylphosphine

97%

Synonym(s):

Dicyclohexylchlorophosphine, Dicyclohexylphosphine chloride, Dicyclohexylphosphinous chloride

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About This Item

Linear Formula:
(C6H11)2PCl
CAS Number:
16523-54-9
Molecular Weight:
232.73
MDL number:
MFCD00014294
UNSPSC Code:
12352101
PubChem Substance ID:
24871756
NACRES:
NA.22

Quality Level

100

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.

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

Supplementary Hazards

EUH014

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW2271
MKCV4442
MKCV2586
MKCM4689
MKCQ7199

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Sterically crowded diphosphinomethane ligands: molecular structures, UV-photoelectron spectroscopy and a convenient general synthesis of t Bu 2 PCH 2 P t Bu 2 and related species
Eisentrager, F, et al.
New. J. Chem., 27(3), 540-550 (2003)
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)
Simon Doherty et al.
Nature protocols, 7(10), 1870-1883 (2012-09-29)
This protocol describes the synthesis of a representative example of the electron-rich biaryl-like KITPHOS class of monophosphine, 11-dicyclohexylphosphino-12-phenyl-9,10-dihydro-9,10-ethenoanthracene (H-KITPHOS). The bicyclic architecture of H-KITPHOS is constructed via [4+2] Diels-Alder cycloaddition between 1-(dicyclohexylphosphinoylethynyl)benzene and anthracene. H-KITPHOS monophosphine is prepared via an
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