4919-03-3

Basic information

• Product Name: 4-Aminoimidazole
• Synonyms: 3H-imidazol-4-amine;5-Aminoimidazole;5-AMINOIMIDAZOLE: AMINOIMIDAZOLE: 4-AMINOIMIDAZOLE;4-aminoimidazole;1H-imidazol-5-ylamine;1H-iMidazol-4-aMine;4(5)-AMinoiMidazole;5-AMino-1H-iMidazole
• CAS NO: 4919-03-3
• Molecular Formula: C₃H₅N₃
• Molecular Weight: 83.09
• Mol File: 4919-03-3.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 415.5 °C at 760 mmHg
• Flash Point: 234.4 °C
• Appearance: /
• Density: 1.313 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 16.92±0.10(Predicted)
• CAS DataBase Reference: 4-Aminoimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Aminoimidazole(4919-03-3)
• EPA Substance Registry System: 4-Aminoimidazole(4919-03-3)

Safety Data

• Hazardous Substances Data: 4919-03-3(Hazardous Substances Data)

Usage

Chemical Properties

Off-White to Beige Solid

Uses

4-Aminoimidazole is used as a building block for the synthesis vitamin B12-analogs via Eubacterium limosu.

Definition

ChEBI: An aminoimidazole that is 1H-imidazole substituted by an amino group at position 4.

InChI:InChI=1/C3H5N3/c4-3-1-5-2-6-3/h1-2H,4H2,(H,5,6)

Upstream product

• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 7647-01-0 hydrogenchloride 
• 34665-48-0 tert-butyl (1H-imidazol-4-yl)carbamate 
• 76055-00-0 2-formylamino-N-(2-pyridyl)acetamide 

Downstream Products

• 795310-08-6 2-methoxy-6-amino-5,8-diaza-7,9-dicarbapurine 
• 795310-11-1 4-(imidazol-4'-yl)allophanic acid phenyl ester 
• 274-67-9 imidazo[1,5-a]pyrimidine 
• 30086-17-0 4-fluoro-1H-imidazole 
• 3034-38-6 1H-4⁽⁵⁾-nitroimidazole 
• 145799-22-0 N-Imidazol-4-yl-N-phenylthiourea 
• 145799-21-9 N-Imidazol-4-yl-N-phenylurea 
• 145837-41-8 ethyl N-<(1H-imidazol-4-yl)aminomethylene>carbamate 

Relevant articles and documents

Convenient synthesis of imidazo[1,5-a]pyrimidine derivatives and their unusual recyclization into 3H-imidazo[4,5-b]pyridine derivatives

[Figure not available: see fulltext.] New derivatives of imidazo[1,5-a]pyrimidine have been synthesized by cyclization of in situ generated 1H-imidazol-4(5)-amine with 1,3-diketones or malondialdehyde derivatives. Utilization of asymmetrical 1,3-diketones leads to the formation of a mixture of regioisomers. The discovered conversion of imidazo[1,5-a]pyrimidine core into 3H-imidazo[4,5-b]pyridine that takes place only under acidic conditions can be considered as a new version of Dimroth rearrangement involving cleavage of C–N bond and formation of C–C bond.

Determination of inter-ionic and intra-ionic interactions in a monofluorinated imidazolium ionic liquid by a combination of X-ray crystallography and NOE NMR spectroscopy

We report the very first application of a Transient 1D 1H{19F} NOE NMR experiment in neat ionic liquids. In comparison with classical 2D HOESY NMR spectroscopy, a substantial reduction in measurement time is gained with comparable quality and information content of the spectra. In combination with classical X-ray crystallography, we have applied this technique for the determination of inter-ionic distances (i.e. probabilities of presence) utilizing an ionic liquid containing a monofluorinated imidazolium cation. Copyright

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

(Chemical Equation Presented) C-Nucleosidation with cyclic iminium salts occurring under mild reaction conditions and affording C-nucleosides that are isosteric with N-nucleosides of natural purines is shown to be a consistent property of the entire family of 2,6-(oxo or amino)-disubstituted 5,8-diaza-7,9-dicarba-purines.