2,2'-Bithiazole
Chemical compound
From Wikipedia, the free encyclopedia
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]
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| Names | |
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| Preferred IUPAC name
2,2′-Bi-1,3-thiazole | |
| Identifiers | |
3D model (JSmol) |
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CompTox Dashboard (EPA) |
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| Properties | |
| 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 [77 °F], 100 kPa).
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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]