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2,2'-Bithiazole

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2,2'-Bithiazole
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H4N2S2/c1-3-9-5(7-1)6-8-2-4-10-6/h1-4HKey: SMSLWFZHCONMGQ-UHFFFAOYSA-N
SMILES
  • C1=CSC(=N1)C2=NC=CS2
Properties
Chemical formula C6H4N2S2
Molar mass 168.23 g·mol
Appearance white solid
Density 1.82 g/cm
Melting point 102.5 °C (216.5 °F; 375.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

2,2'-Bithiazole is an organic compound with the formula (H2C3NS)2. The molecule consists of two thiazole rings linked by a C-C bond. Diverse isomers are possible depending on the carbon atoms that are coupled, but the 2,2' isomer is common. The compound was first prepared by Ullmann coupling of 2-bromothiazole using copper metal.

2,2'-Bithiazole is planar, according to X-ray crystallography.

Occurrence

Bleomycin A2, a bithiazole-containing natural product

2,2'-Bithiazole itself is mainly of academic interest, but substituted, isomeric bithiazoles have attracted attention in medicinal chemistry. Naturally occurring bithiazoles are derived from cysteine, as are most naturally-occurring thiazoles. Well-studied derivatives are the bleomycins, which feature 2,4'-bithiazole incorporated into glycopeptides. The cystothiazoles are another family of bithiazoles, but they feature 2,5-linkage. Luciferin contains a benzothiazole subunit linked to a thiazolidine (dihydrothiazole) via a 2,2' linkage.

2,2'-Bithiazole forms a variety of coordination complexes.

References

  1. Erlenmeyer, H.; Schmid, Erich H. (1939). "Über isostere und strukturähnliche Verbindungen XI. Darstellung und Eigenschaften des 2,2′-Dithiazolyl". Helvetica Chimica Acta. 22: 698–700. doi:10.1002/hlca.19390220186.
  2. ^ Craig, DC; Goodwin, H. A.; Onggo, D.; Rae, AD (1988). "Coordination of 2,2'-Bithiazole. Spectral, Magnetic and Structural Studies of the Iron(II) and Nickel(II) Complexes". Australian Journal of Chemistry. 41 (11): 1625. doi:10.1071/CH9881625.
  3. Jin, Zhong (2011). "Muscarine, imidazole, oxazole, and thiazole alkaloids". Natural Product Reports. 28 (6): 1143–1191. doi:10.1039/C0NP00074D. PMID 21472175.
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