Imidazolidine

Imidazolidine

Structural formula of imidazolidine Ball-and-stick model of imidazolidine
Names
IUPAC name Imidazolidine
Other names Tetrahydroimidazole 1,3-diazolidine
Identifiers
CAS Number	504-74-5 Y
ChemSpider	396007 N
Jmol 3D model	Interactive image
PubChem	449488
InChI InChI=1S/C3H8N2/c1-2-5-3-4-1/h4-5H,1-3H2 N Key: WRYCSMQKUKOKBP-UHFFFAOYSA-N N InChI=1/C3H8N2/c1-2-5-3-4-1/h4-5H,1-3H2 Key: WRYCSMQKUKOKBP-UHFFFAOYAC
SMILES N1CCNC1
Properties
Chemical formula	C3H8N2
Molar mass	72.109
Vapor pressure	{{{value}}}
Supplementary data page
Structure and properties	Refractive index (n), Dielectric constant (εr), etc.
Thermodynamic data	Phase behaviour solid–liquid–gas
Spectral data	UV, IR, NMR, MS
N verify (what is YN ?)
Infobox references

Imidazolidine is a heterocyclic compound (CH₂)₂(NH)₂CH₂. The parent imidazolidine is lightly studied, but related compounds substituted on one or both nitrogen centers are more common. Generally, they are colorless, polar, basic compounds. Imidazolidines are cyclic 5-membered examples of the general class of aminals.

Preparation

Imidazolidines are traditionally prepared by condensation reaction of 1,2-diamines and aldehydes. Most commonly, one or both nitrogen center is substituted with an alkyl or benzyl (Bn) group:

(CH₂NBn)₂ + PhCHO → (CH₂NBn)₂C(H)Ph + H₂O

The first unsubstituted imidazolidine synthesis was reported in 1952.

Reactions

Unsubstituted imidazolidines are often labile. The rings are susceptible to hydrolysis back to the diamine and the aldehyde.

Formally, removal of the two hydrogens at carbon 2 (between the two nitrogens) would yield the carbene dihydroimidazol-2-ylidene. Derivatives of the latter comprise an important class of persistent carbenes.

Related imidazole-derived heterocycles

Classified as a diamine, it is formally derived by the addition of four hydrogen atoms to imidazole. The intermediate, resulting from the addition of only two hydrogen atoms is called imidazoline (dihydroimidazole). The connection of imidazolidine to related compounds is indicated in the Figure.

Structure relationship of imidazole and its reduced derivatives.