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656577

Sigma-Aldrich

1,3-Diisopropylimidazolium chloride

greener alternative

97%

Synonym(s):

N,N′-(Isopropyl)imidazolium chloride

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About This Item

Empirical Formula (Hill Notation):
C9H17ClN2
CAS Number:
139143-09-2
Molecular Weight:
188.70
MDL number:
MFCD03840577
UNSPSC Code:
12352005
PubChem Substance ID:
24884209
NACRES:
NA.22

Assay

97%

form

solid

reaction suitability

reagent type: catalyst

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

mp

182-186 °C

greener alternative category

Aligned,

SMILES string

[Cl-].CC(C)n1cc[n+](c1)C(C)C

InChI

1S/C9H17N2.ClH/c1-8(2)10-5-6-11(7-10)9(3)4;/h5-9H,1-4H3;1H/q+1;/p-1

InChI key

DOFXKPAOJLLPII-UHFFFAOYSA-M

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

1,3-Diisopropylimidazolium chloride may be used to prepare:
  • 1,3-Diisopropylimidazole-2-thione by reacting with sulfur in the presence of potassium carbonate.
  • (C9H7)NiCl(1,3-diisopropylimidazol-2- ylidene) by reacting with bis-indenyl nickel-(II).
  • Ruthenium N-heterocyclic carbene complexes, which are efficient catalysts for the amidation of primary alcohols and amines.
Ligand for ruthenium-catalyzed greener amide bond formation by dehydrogenative coupling of amines and alcohols.

Amide Synthesis from Alcohols and Amines by the Extrusion of Dihydrogen

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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A dinuclear Bi (III) complex of a 1, 3-disubstituted imidazole-2-thione and its use as a transmetallation agent toward Pd (II).
Jagenbrein M, et al.
Journal of Organometallic Chemistry, 796, 11-16 (2015)
Chen C and Hong SH.
Organic & Biomolecular Chemistry, 9(1), 20-26 (2011)
Amide Synthesis from Alcohols and Amines Catalyzed by Ruthenium N-Heterocyclic Carbene Complexes.
Dam JH, et al.
Chemistry?A European Journal , 16(23), 6820-6827 (2010)
Indenylnickel (II) N-heterocyclic carbene complexes: Synthesis via indene elimination and catalytic activity for ethylene dimerization.
Sun HM, et al.
Organometallics, 24(2), 331-334 (2005)

Protocols

Bestmann-Ohira Reagent: Synthesis of Alkynes from Aldehydes Protocol

Acetylene chemistry has been and remains an important constituent element of molecular sciences. Its potential and widespread applications extend from organic synthesis through materials science to bioorganic chemistry. Some examples are enediynes (DNA-cleaving agents), ‘click chemistry’ tools and building blocks. Consequently, it triggers a demand for efficient syntheses of alkynes.

Catalytic Amide Bond Formation Protocol

Information on the Amide bond and the Catalytic Amide Bond Formation Protocol. Amidation of amines and alcohols. The amide bond, an important linkage in organic chemistry, is a key functional group in peptides, polymers, and many natural products and pharmaceuticals.

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