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Merck

481408

Sigma-Aldrich

Chlorodicyclohexylphosphine

97%

Sinónimos:

Dicyclohexylchlorophosphine, Dicyclohexylphosphine chloride, Dicyclohexylphosphinous chloride

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About This Item

Fórmula lineal:
(C6H11)2PCl
Número de CAS:
Peso molecular:
232.73
MDL number:
UNSPSC Code:
12352101
PubChem Substance ID:
NACRES:
NA.22

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

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


Certificados de análisis (COA)

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Visite la Librería de documentos

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)
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)
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)
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)
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)

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