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04124

Sigma-Aldrich

1-(3-Cyanopropyl)-3-methylimidazolium chloride

Task Specific Ionic Liquid (TSIL), ≥98.5% (T)

Synonym(s):

1-Methyl-3-(3-cyanopropyl)imidazolium chloride

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About This Item

Empirical Formula (Hill Notation):
C8H12ClN3
CAS Number:
683224-96-6
Molecular Weight:
185.65
MDL number:
MFCD09265183
UNSPSC Code:
12352100
PubChem Substance ID:
329747884
NACRES:
NA.22

Quality Level

100

assay

≥98.5% (T)
≥98.5% (elemental analysis, N)

form

powder

impurities

≤0.5% water

SMILES string

[Cl-].C[n+]1ccn(CCCC#N)c1

InChI

1S/C8H12N3.ClH/c1-10-6-7-11(8-10)5-3-2-4-9;/h6-8H,2-3,5H2,1H3;1H/q+1;/p-1

InChI key

HGPSWUJKMXIBKA-UHFFFAOYSA-M

General description

Nitrile-functionalized ionic liquid showing superior characteristics in Suzuki and Stille coupling reactions[1].

Application

1-(3-Cyanopropyl)-3-methylimidazolium chloride can be used:
  • To prepare ionic polymers stabilized with palladium nanoparticle catalysts, which are applicable in the hydrogenation of alkenes and arenes.[2]
  • As a solvent in the synthesis of substituted 4-arylthio-1,2-oxazoles by reacting different aryl iodides with acetylenic oximes in the presence of Pd-NHC catalyst.[3]

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Recent advances in sulfuration chemistry enabled by bunte salts
Wang M, et al.
Aldrichimica Acta, 53(1), 19-19 (2020)
Aqueous-phase hydrogenation of alkenes and arenes: The growing role of nanoscale catalysts
Bulut S, et al.
Catalysis Today, 247, 96-103 (2015)
Dongbin Zhao et al.
Journal of the American Chemical Society, 126(48), 15876-15882 (2004-12-02)
A series of relatively low-cost ionic liquids, based on the N-butyronitrile pyridinium cation [C(3)CNpy](+), designed to improve catalyst retention, have been prepared and evaluated in Suzuki and Stille coupling reactions. Depending on the nature of the anion, these salts react

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