2-Aminothiazole

2-Aminothiazole is a heterocyclic amine featuring a thiazole core. It can also be considered a cyclic isothiourea. It possesses an odor similar to pyridine and is soluble in water, alcohols and diethyl ether. It is commonly used as a starting point for the synthesis of many compounds including sulfur drugs, biocides, fungicides, dyes and chemical reaction accelerators. 2-Aminothiazole can be used as a thyroid inhibitor in the treatment of hyperthyroidism and has antibacterial activity. Alternatively, its acid tartrate salt can be used. Recent studies using prion-infected neuroblastoma cell lines have suggested that aminothiazole may be used as a therapeutic drug for prion diseases.[2]

2-Aminothiazole
Skeletal formula of aminothiazole
Space-filling model of the aminothiazole molecule
Names
Preferred IUPAC name
1,3-Thiazol-2-amine
Other names
2-Thiazolamine, Aminothiazole, 2-Thiazylamine, Basedol, 2-Thiazolylamine, 4-Thiazolin-2-onimine, 2-Amino-1,3-thiazole, Abadole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.284
EC Number
  • 202-511-6
KEGG
UNII
  • InChI=1S/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5) checkY
    Key: RAIPHJJURHTUIC-UHFFFAOYSA-N checkY
  • InChI=1/C3H4N2S/c4-3-5-1-2-6-3/h1-2H,(H2,4,5)
    Key: RAIPHJJURHTUIC-UHFFFAOYAZ
  • c1csc(n1)N
Properties
C3H4N2S
Molar mass 100.14 g·mol−1
Appearance Light yellow crystals
Melting point 86 to 89 °C (187 to 192 °F; 359 to 362 K)
Boiling point 117 °C (243 °F; 390 K) (20 hPa)
100 g/L (20 °C)
-56.0·10−6 cm3/mol
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H302, H319
P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamond
2
0
0
600 °C (1,112 °F; 873 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Many 2-aminothiazoles and 2-amidothiazoles are drugs: avatrombopag, amthamine, amiphenazole, abafungin, acotiamide, pramipexole.

References
  1. "2-Aminothiazole". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2022.
  2. Gallardo-Godoy A; Gever J; Fife KL; Silber BM; Prusiner SB; Renslo AR. (Feb 24, 2011). "2-Aminothiazoles as therapeutic leads for prion diseases". J Med Chem. 54 (4): 1010–21. doi:10.1021/jm101250y. PMC 3041857. PMID 21247166.
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