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Merck

481408

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
NACRES:
NA.22
PubChem Substance ID:
24871756
UNSPSC Code:
12352101
MDL number:
MFCD00014294

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InChI

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

SMILES string

ClP(C1CCCCC1)C2CCCCC2

InChI key

AKJFBIZAEPTXIL-UHFFFAOYSA-N

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

Quality Level

100

Related Categories

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

signalword

Danger

hcodes

H314

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKDB1343
MKCX6958
MKCZ0424
MKCX8691
MKCX0471

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Intramolecular alkyl phosphine dehydrogenation in cationic rhodium complexes of tris (cyclopentylphosphine)
Douglas TM, et al.
Chemistry?A European Journal , 14(3), 1004-1022 (2008)
Latexin deletion protects against radiation-induced hematopoietic damages via selective activation of Bcl-2 prosurvival pathway.
Zhang, et al.
Haematologica (2023)
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)
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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