2-Aminooxazole

2-Aminooxazole

Names
IUPAC name 1,3-oxazol-2-amine
Other names 2-Oxazolamine imino oxazole Oxazole-2-amine oxazolyl amine
Identifiers
CAS Number	4570-45-0
3D model (JSmol)	Interactive image
ChemSpider	485518
ECHA InfoCard	100.128.287
EC Number	610-269-1 [1]
MeSH	2-aminooxazole
PubChem CID	558521
CompTox Dashboard (EPA)	DTXSID00339766
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
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 [77 °F], 100 kPa). Infobox references

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. ^[2] 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. ^[3]

The amine group of 2-Aminooxazole can potentially link with different molecules, making it a potential candidate for drug synthesis in antitubercular medicinal chemistry. ^[4]

2-Aminooxazole has also been hypothesised to have played a role in chemical evolution as a precursor of RNA nucleotides. ^[5]

See also

• Oxazoles
• 2-Aminothiazole

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.