2,2'-Bithiazole

2,2'-Bithiazole

Identifiers
CAS Number	13816-21-2
3D model (JSmol)	Interactive image
ChemSpider	715653
PubChem CID	819109
CompTox Dashboard (EPA)	DTXSID40902751
InChI InChI=1S/C6H4N2S2/c1-3-9-5(7-1)6-8-2-4-10-6/h1-4H Key: SMSLWFZHCONMGQ-UHFFFAOYSA-N
SMILES C1=CSC(=N1)C2=NC=CS2
Properties
Chemical formula	C6H4N2S2
Molar mass	168.23 g·mol^−1
Appearance	white solid
Density	1.82 g/cm^3
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 [77 °F], 100 kPa). Infobox references

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.^[1]

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

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.^[3]

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

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.