2-Aminooxazole
{{short description|Chemical compound}}
{{chembox
| Name = 2-Aminooxazole
| ImageFile = 2-Aminooxazole.svg
| OtherNames = {{ubl | 2-Oxazolamine | imino oxazole | Oxazole-2-amine | oxazolyl amine}}
| IUPACName = 1,3-oxazol-2-amine
| Section1 = {{Chembox Identifiers
| 3DMet =
| CASNo = 4570-45-0
| ChEBI =
| ChemSpiderID = 485518
| EINECS =
| EC_number = 610-269-1{{cite web | title=Substance Information | website=ECHA | date=2023-05-19 | url=https://echa.europa.eu/substance-information/-/substanceinfo/100.128.287 | access-date=2024-04-28}}
| EC_number_Comment=
| Gmelin =
| InChI = InChI=1S/C3H4N2O/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)
InChIKey = ACTKAGSPIFDCMF-UHFFFAOYSA-N
| MeSHName = 2-aminooxazole
| PubChem = 558521
| RTECS =
| SMILES = C1=COC(=N1)N
}}
| Section2 = {{Chembox Properties
| Appearance = White solid (at 97% purity)
| BoilingPt = 186.7±23.0 °C
| BoilingPtC =
| Density = 1.2±0.1 g/cm3
| Formula = C3H4N2O
| MolarMass = 84.08 g/mol
| MeltingPt = 90-95 °C
| MeltingPtC =
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| Solubility =
| SolubleOther =
| Solvent =
| VaporPressure = 0.7±0.4 mmHg
}}
| Section7 = {{Chembox Hazards
| AutoignitionPt =
| ExploLimits =
| FlashPt = 66.7±22.6 °C
| LD50 =
| LC50 =
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-I =
| NFPA-S =
| PEL =
| REL =
| ExternalSDS =
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{HPhrases|H315|H319|H335}}
| PPhrases = {{PPhrases|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}}
}}
}}
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.{{Cite book |last1=Katritzky |first1=Alan R. |url=https://books.google.com/books?id=7RglQV5yxKcC&q=aminooxazole&pg=PP1 |title=Handbook of Heterocyclic Chemistry |last2=Ramsden |first2=Christopher A. |last3=Joule |first3=John A. |last4=Zhdankin |first4=Viktor V. |date=2010-08-24 |publisher=Elsevier |isbn=978-0-08-095844-6 |language=en}} 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.{{cite journal | last1=Juhás | first1=Martin | last2=Bachtíková | first2=Andrea | last3=Nawrot | first3=Daria Elżbieta | last4=Hatoková | first4=Paulína | last5=Pallabothula | first5=Vinod Sukanth Kumar | last6=Diepoltová | first6=Adéla | last7=Janďourek | first7=Ondřej | last8=Bárta | first8=Pavel | last9=Konečná | first9=Klára | last10=Paterová | first10=Pavla | last11=Šesták | first11=Vít | last12=Zitko | first12=Jan | title=Improving Antimicrobial Activity and Physico-Chemical Properties by Isosteric Replacement of 2-Aminothiazole with 2-Aminooxazole | journal=Pharmaceuticals | publisher=MDPI AG | volume=15 | issue=5 | date=2022-05-06 | issn=1424-8247 | doi=10.3390/ph15050580 | doi-access=free | page=580| pmid=35631406 | pmc=9143880 }}
The amine group of 2-Aminooxazole can potentially link with different molecules, making it a potential candidate for drug synthesis in antitubercular medicinal chemistry.{{Cite journal |last1=Azzali |first1=Elisa |last2=Girardini |first2=Miriam |last3=Annunziato |first3=Giannamaria |last4=Pavone |first4=Marialaura |last5=Vacondio |first5=Federica |last6=Mori |first6=Giorgia |last7=Pasca |first7=Maria Rosalia |last8=Costantino |first8=Gabriele |last9=Pieroni |first9=Marco |date=2020-07-09 |title=2-Aminooxazole as a Novel Privileged Scaffold in Antitubercular Medicinal Chemistry |journal=ACS Medicinal Chemistry Letters |language=en |volume=11 |issue=7 |pages=1435–1441 |doi=10.1021/acsmedchemlett.0c00173 |issn=1948-5875 |pmc=7357219 |pmid=32676151}}
2-Aminooxazole has also been hypothesised to have played a role in chemical evolution as a precursor of RNA nucleotides.{{Cite journal |last1=Szabla |first1=Rafał |last2=Tuna |first2=Deniz |last3=Góra |first3=Robert W. |last4=Šponer |first4=Jiří |last5=Sobolewski |first5=Andrzej L. |last6=Domcke |first6=Wolfgang |date=2013-08-15 |title=Photochemistry of 2-Aminooxazole, a Hypothetical Prebiotic Precursor of RNA Nucleotides |url=https://pubs.acs.org/doi/10.1021/jz401315e |journal=The Journal of Physical Chemistry Letters |language=en |volume=4 |issue=16 |pages=2785–2788 |doi=10.1021/jz401315e |issn=1948-7185|url-access=subscription }}