2,2'-Bithiazole

Identifiers
CAS Number	13816-21-2
Properties
Chemical formula	C6H4N2S2
Molar mass	168.23 g·mol−1
Appearance	white solid
Density	1.82 g/cm3
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

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

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