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2-Aminooxazole

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Chemical compound
2-Aminooxazole
Names
IUPAC name 1,3-oxazol-2-amine
Other names
  • 2-Oxazolamine
  • imino oxazole
  • Oxazole-2-amine
  • oxazolyl amine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.128.287 Edit this at Wikidata
EC Number
  • 610-269-1
MeSH 2-aminooxazole
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C3H4N2O/c4-3-5-1-2-6-3/h1-2H,(H2,4,5) InChIKey = ACTKAGSPIFDCMF-UHFFFAOYSA-N
SMILES
  • C1=COC(=N1)N
Properties
Chemical formula C3H4N2O
Molar mass 84.08 g/mol
Appearance White solid (at 97% purity)
Density 1.2±0.1 g/cm3
Melting point 90-95 °C
Boiling point 186.7±23.0 °C
Vapor pressure 0.7±0.4 mmHg
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H319, H335
Precautionary statements P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Flash point 66.7±22.6 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

2-Aminooxazole is a heterocyclic organic compound, belonging to the class of oxazoles. It is a five-membered ring structure containing one oxygen and two nitrogen atoms.

Properties

2-Aminooxazole contains a primary amine group which can participate in various reactions like protonation, acylation, or alkylation. The oxazole ring can also show reactions like ring expansion, electrophilic substitution, etc. and also contributes aromatic character and stability to the molecule.

Applications

2-Aminooxazole possesses antimicrobial properties against various fungal and bacterial strains especially against Tuberculosis-causing Mycobacterium tuberculosis.

The amine group of 2-Aminooxazole can potentially link with different molecules, making it a potential candidate for drug synthesis in antitubercular medicinal chemistry.

2-Aminooxazole has also been hypothesised to have played a role in chemical evolution as a precursor of RNA nucleotides.

See also

References

  1. "Substance Information". ECHA. 2023-05-19. Retrieved 2024-04-28.
  2. Katritzky, Alan R.; Ramsden, Christopher A.; Joule, John A.; Zhdankin, Viktor V. (2010-08-24). Handbook of Heterocyclic Chemistry. Elsevier. ISBN 978-0-08-095844-6.
  3. Juhás, Martin; Bachtíková, Andrea; Nawrot, Daria Elżbieta; Hatoková, Paulína; Pallabothula, Vinod Sukanth Kumar; Diepoltová, Adéla; Janďourek, Ondřej; Bárta, Pavel; Konečná, Klára; Paterová, Pavla; Šesták, Vít; Zitko, Jan (2022-05-06). "Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole". Pharmaceuticals. 15 (5). MDPI AG: 580. doi:10.3390/ph15050580. ISSN 1424-8247. PMC 9143880. PMID 35631406.
  4. Azzali, Elisa; Girardini, Miriam; Annunziato, Giannamaria; Pavone, Marialaura; Vacondio, Federica; Mori, Giorgia; Pasca, Maria Rosalia; Costantino, Gabriele; Pieroni, Marco (2020-07-09). "2-Aminooxazole as a Novel Privileged Scaffold in Antitubercular Medicinal Chemistry". ACS Medicinal Chemistry Letters. 11 (7): 1435–1441. doi:10.1021/acsmedchemlett.0c00173. ISSN 1948-5875. PMC 7357219. PMID 32676151.
  5. Szabla, Rafał; Tuna, Deniz; Góra, Robert W.; Šponer, Jiří; Sobolewski, Andrzej L.; Domcke, Wolfgang (2013-08-15). "Photochemistry of 2-Aminooxazole, a Hypothetical Prebiotic Precursor of RNA Nucleotides". The Journal of Physical Chemistry Letters. 4 (16): 2785–2788. doi:10.1021/jz401315e. ISSN 1948-7185.
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