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Identifiers | |
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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).
|
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-bromo thiazole using copper metal. [1]
2,2'-Bithiazole is planar, according to X-ray crystallography. [2]
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]
![]() | |
Identifiers | |
---|---|
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).
|
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-bromo thiazole using copper metal. [1]
2,2'-Bithiazole is planar, according to X-ray crystallography. [2]
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]