2-Aminothiazole

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 Edit this at Wikidata
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 diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
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 ?)

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. 2-Aminothiazole itself is mainly of academic interest, with few exceptions. It is a precursor to a sulfathiazole ("sulfa drugs"). 2-Aminothiazole can be used as a thyroid inhibitor in the treatment of hyperthyroidism.[2]

2-Aminothiazole is prepared from paraldehyde, thiourea, and sulfuryl chloride.[3]

  1. ^ "2-Aminothiazole". pubchem.ncbi.nlm.nih.gov. Retrieved 12 December 2022.
  2. ^ Dahlmanns, Simone M.; Müller-Gärtner, Hans-Wilhelm (2000). "Thyrotherapeutic Agents". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_039. ISBN 9783527303854.
  3. ^ Erlenmeyer, H.; Herzfeld, L.; Prijs, B. (1955). "Zur Synthese von 2-Amino-thiazolderivaten". Helvetica Chimica Acta. 38 (5): 1291–1294. doi:10.1002/hlca.19550380529.