4-Aminoimidazole

Base Information

• Chemical Name: 4-Aminoimidazole
• CAS No.: 4919-03-3
• Molecular Formula: C3H5N3
• Molecular Weight: 83.0928
• Hs Code.: 2933290090
• UNII: 7854BCQ2PS
• DSSTox Substance ID: DTXSID00197702
• Nikkaji Number: J507.002C
• Wikidata: Q27101994
• Metabolomics Workbench ID: 38413
• Mol file: 4919-03-3.mol

Synonyms:4-aminoimidazole;5-aminoimidazole

Chemical Property of 4-Aminoimidazole

Chemical Property:

• Boiling Point: 415.5 °C at 760 mmHg
• PKA: 16.92±0.10(Predicted)
• Flash Point: 234.4 °C
• PSA: 54.70000
• Density: 1.313 g/cm³
• LogP: 0.57310
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 83.048347172
• Heavy Atom Count: 6
• Complexity: 45.3

Purity/Quality:

97% ^*data from raw suppliers

4-AminoimidazoleDiHCl ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(NC=N1)N
• General Description: 4-Aminoimidazole is a key intermediate in the synthesis of purine analogues, such as those explored in the study of Mannich-type C-nucleosidation reactions. It serves as a precursor for the preparation of isoguanine and xanthine analogues, demonstrating its versatility in the construction of modified nucleobases. These derivatives are valuable for investigating nucleic acid structure and have potential applications in medicinal chemistry and chemical biology.

Technology Process of 4-Aminoimidazole

There total 4 articles about 4-Aminoimidazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1H-4(5)-nitroimidazole (3034-38-6) → 4-amino-1H-imidazole (4919-03-3)

Guidance literature:

With hydrogenchloride; tin(ll) chloride;

Reference yield:

tert-butyl (1H-imidazol-4-yl)carbamate (34665-48-0) → 4-amino-1H-imidazole (4919-03-3)

Guidance literature:

With trifluoroacetic acid; at 10 - 25 ℃; for 0.2h;

DOI:10.1007/s10593-021-02942-2

Reference yield:

2-formylamino-N-(2-pyridyl)acetamide (76055-00-0) → 3H-imidazol-4-ylamine (4919-03-3)

Guidance literature:

With ammonium chloride; ammonia; palladium on activated charcoal; at 100 ℃; for 0.5h;

DOI:10.1039/P19800002316

upstream raw materials:

1H-4⁽⁵⁾-nitroimidazole

hydrogenchloride

tert-butyl (1H-imidazol-4-yl)carbamate

2-formylamino-N-(2-pyridyl)acetamide

Downstream raw materials:

ethyl N-<(1H-imidazol-4-yl)aminomethylene>carbamate

N-Imidazol-4-yl-N-phenylurea

N-Imidazol-4-yl-N-phenylthiourea

2-methoxy-6-amino-5,8-diaza-7,9-dicarbapurine

Refernces

Synthesis of fluorinated purine and 1-deazapurine glycosides as potential inhibitors of adenosine deaminase

10.1021/jo102579g

This research focuses on the synthesis of fluorinated purine and 1-deazapurine glycosides as potential inhibitors of adenosine deaminase (ADA) and inosine monophosphate dehydrogenase (IMPDH) enzymes. The study explores two synthetic strategies: a de novo approach involving the electrophilic annulation of pyridine and pyrimidine rings using fluorine-containing dielectrophiles, and a salvage approach starting with 5-aminoimidazole. The synthesis involves multiple steps, including glycosylation, deprotection, and the formation of stable hydrates. The resulting compounds are characterized using NMR and X-ray crystallography, providing a foundation for the design of enzyme inhibitors with potential therapeutic applications in treating diseases like cancer and genetic disorders.

Mannich-type C-nucleosidations in the 5,8-diaza-7,9-dicarba-purine family

10.1021/ol048649m

The study investigates the Mannich-type C-nucleosidation reactions of 2,6-(oxo or amino)-disubstituted 5,8-diaza-7,9-dicarba-purines, a family of nucleobase analogues that are isomeric to natural purine nucleobases like adenine and guanine. The researchers synthesized various purinoids (1-4) and their adenine analogue using different chemical methods. For instance, the guanine analogue (2) was synthesized from N-formyl-glycyl-guanidine and trichloroacetonitrile through a series of reactions including hydrolysis and cyclization. The isoguanine analogue (3) and xanthine analogue (4) were prepared from 5-aminoimidazole using different reagents and reaction conditions. The study found that all these purinoids can undergo Mannich-type C-nucleosidation reactions with cyclic iminium salts, such as pyrroline derivatives (12 and 15), under mild conditions to form C-nucleosides. These C-nucleosides are isosteric with conventional N-nucleosides of natural purines. The reactivity of the purinoids in these C-nucleosidation reactions varies, with the 2,6-diamino derivative (1) being the most reactive and the 2-deamino derivative (adenine analogue) being the least reactive. The study also explored the stability and configuration of the resulting nucleosides, as well as the potential tautomerism in the isoguanine analogue (3). The findings suggest that these purinoids could be useful in studying the chemical etiology of nucleic acid structure and have potential applications in informational chemistry, medicinal chemistry, and chemical biology.