6573-15-5

Basic information

• Product Name: 2,3,5,6-tetrahydro-1H-iMidazo[1,2-a]iMidazole
• Synonyms: 2,3,5,6-tetrahydro-1H-iMidazo[1,2-a]iMidazole;1,4,6-Triazabicyclo[3.3.0]oct-4-ene
• CAS NO: 6573-15-5
• Molecular Formula: C₅H₉N₃
• Molecular Weight: 111.14506
• Mol File: 6573-15-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 158-159 °C
• Boiling Point: 179.8±23.0 °C(Predicted)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• PKA: 10.00±0.70(Predicted)
• CAS DataBase Reference: 2,3,5,6-tetrahydro-1H-iMidazo[1,2-a]iMidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,5,6-tetrahydro-1H-iMidazo[1,2-a]iMidazole(6573-15-5)
• EPA Substance Registry System: 2,3,5,6-tetrahydro-1H-iMidazo[1,2-a]iMidazole(6573-15-5)

Safety Data

• Hazardous Substances Data: 6573-15-5(Hazardous Substances Data)

Usage

General Description

2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole is a chemical compound with a molecular formula C6H8N2. It is a bicyclic heterocyclic compound with a unique structure containing two fused imidazole rings. 2,3,5,6-tetrahydro-1H-iMidazo[1,2-a]iMidazole is used in organic synthesis and medicinal chemistry, and it has been studied for its potential pharmaceutical properties, including as a potential anti-cancer drug and as an anti-inflammatory agent. Its structure gives it a high degree of rigidity, which can make it a useful scaffold for drug design. It is also used as a reaction catalyst in certain chemical reactions, and its derivatives are being investigated for a variety of potential applications in pharmaceuticals and materials science.

Upstream product

• 40778-59-4 1-(2-aminoethyl)-2-imidazolidinethione 
• 75-15-0 carbon disulfide 
• 111-40-0 3-azapentane-1,5-diamine 
• 56-18-8 bis(3-aminopropyl)amine 
• 726-42-1 di-p-tolylcarbodiimide 
• 693-13-0 diisopropyl-carbodiimide 
• 50-01-1 guanidine hydrochloride 

Downstream Products

• 109129-49-9 1-(2,4-dichloro-phenoxy)-3-(2,3,5,6-tetrahydro-imidazo[1,2-a]imidazol-1-yl)-propan-2-ol 
• 644-33-7 N,N'-ethanediyl-bis-benzamide 
• 109892-18-4 1-(4-nitro-benzenesulfonyl)-2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole 
• 109506-83-4 acetic acid-[4-(2,3,5,6-tetrahydro-imidazo[1,2-a]imidazole-1-sulfonyl)-anilide] 
• 6281-42-1 2-aminoethylimidazolidone 
• 7664-41-7 ammonia 
• 107-15-3 ethylenediamine 
• 110251-98-4 1-sulfanilyl-2,3,5,6-tetrahydro-1H-imidazo[1,2-a]imidazole 

Relevant articles and documents

High-Field NMR Spectroscopy Reveals Aromaticity-Modulated Hydrogen Bonding in Heterocycles

From DNA base pairs to drug–receptor binding, hydrogen (H-)bonding and aromaticity are common features of heterocycles. Herein, the interplay of these bonding aspects is explored. H-bond strength modulation due to enhancement or disruption of aromaticity of heterocycles is experimentally revealed by comparing homodimer H-bond energies of aromatic heterocycles with analogs that have the same H-bonding moieties but lack cyclic π-conjugation. NMR studies of dimerization in C6D6 find aromaticity-modulated H-bonding (AMHB) energy effects of approximately ±30 %, depending on whether they enhance or weaken aromatic delocalization. The attendant ring current perturbations expected from such modulation are confirmed by chemical shift changes in both observed ring C?H and calculated nucleus-independent sites. In silico modeling confirms that AMHB effects outweigh those of hybridization or dipole–dipole interaction.

Ti-amide catalyzed synthesis of cyclic guanidines from di-/triamines and carbodiimides

A titanacarborane monoamide catalyzed, one-step synthesis of mono/bicyclic guanidines from commercially available di/triamines and carbodiimides is reported. The reaction mechanism is also proposed.

Cyclic guanidine organic catalysts: What is magic about triazabicyclodecene?

(Chemical Equation Presented) The bicyclic guanidine 1,5,7- triazabicyclo[4.4.0]dec-5-ene (TBD) is an effective organocatalyst for the formation of amides from esters and primary amines. Mechanistic and kinetic investigations support a nucleophilic mechanism where TBD reacts reversibly with esters to generate an acyl-TBD intermediate that acylates amines to generate the amides. Comparative investigations of the analogous bicyclic guanidine 1,4,6-triazabicyclo[3.3.0]oct-4-ene (TBO) reveal it to be a much less active acylation catalyst than TBD. Theoretical and mechanistic studies imply that the higher reactivity of TBD is a consequence of both its higher basicity and nucleophilicity than TBO as well as the high reactivity of the acyl-TBD intermediate, which is sterically prevented from adopting a planar amide structure.