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2-imidazoline

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2-imidazoline

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Also known as 4,5-Dihydro-1H-imidazole, I2, I2-imidazoline

2-Imidazoline (Preferred IUPAC name: '4,5-dihydro-1H-imidazole') is one of three isomers of the nitrogen-containing heterocycle imidazoline, with the formula C3H6N2. The 2-imidazolines are the most common imidazolines commercially, as the ring exists in some natural products and some pharmaceuticals. They also have been examined in the context of organic synthesis, coordination chemistry, and homogeneous catalysis.

Chemical data

Formula
C3H6N2
Molecular weight
70.09 g/mol
IUPAC name
4,5-dihydro-1H-imidazole
SMILES
C1CN=CN1
InChIKey
MTNDZQHUAFNZQY-UHFFFAOYSA-N
XLogP
-0.8
Polar surface area
24.4 Ų
H-bond donors
1
H-bond acceptors
1
Formal charge
0

via PubChem

Wikidata facts

Subclass of
amidines
Mass
70.053
Show 3 more facts
canonical SMILES
C1CN=CN1
chemical formula
C₃H₆N₂
Commons category
Imidazoline
Sources (3)

via Wikidata · CC0

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Encyclopedic overview

11 sections
Contents
  • Synthesis
  • As natural products
  • Biological role
  • Applications
  • Pharmaceutical
  • As p53 activators
  • Surfactants
  • As precursors of imidazoles
  • Homogeneous catalysis
  • See also
  • References

2-Imidazoline (Preferred IUPAC name: '4,5-dihydro-1H-imidazole') is one of three isomers of the nitrogen-containing heterocycle imidazoline, with the formula C3H6N2. The 2-imidazolines are the most common imidazolines commercially, as the ring exists in some natural products and some pharmaceuticals. They also have been examined in the context of organic synthesis, coordination chemistry, and homogeneous catalysis.

== Synthesis == thumb|left|400px|Synthesis of imidazolines from nitrile and from ester precursors. A variety of routes exist for the synthesis of imidazolines, with the most common methods involving the condensation of 1,2-diamines (e.g. ethylenediamine) with nitriles or esters. The nitrile based route is essentially a cyclic Pinner reaction; it requires high temperatures and acid catalysis and is effective for both alkyl and aryl nitriles.

Excerpted from Wikipedia’s “2-imidazoline” article, available under the CC BY-SA 4.0 licence.

Gallery (3)