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2-Aminobenzothiazole
View on Wikipediafrom Wikipedia
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| Names | |
|---|---|
| Preferred IUPAC name
1,3-Benzothiazol-2-amine | |
| Other names
2-aminobenzthiazole
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| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.004.790 |
| EC Number |
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PubChem CID
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| UNII | |
| UN number | 2811 (2-AMINOBENZOTHIAZOLE) |
CompTox Dashboard (EPA)
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| Properties | |
| C7H6N2S | |
| Molar mass | 150.20 g·mol−1 |
| Density | 1.753 g/cm3[1] |
| Melting point | 126–129 °C (259–264 °F; 399–402 K) |
| Hazards | |
| GHS labelling:[1] | |
 
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| Warning | |
| H302, H319, H400 | |
| P264, P264+P265, P270, P273, P280, P301+P317, P305+P351+P338, P330, P337+P317, P391, P501 | |
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-Aminobenzothiazole is the organic compound with the formula C6H4S(N)CNH2. It is related to the parent benzothiazole, but with an amino group at the unique methyne position on the thiazole ring. As confirmed by X-ray crystallography, it is a planar molecule, which exists as the amine tautomer.[1]
2-Aminobenzothiazoles are often prepared by cyclization of 2-bromo-substituted arylthioureas.[2]
- BrC6H4NHC(S)NH2 → C6H4SNCNH2 + HBr
Isothiocyanic acid, which can be generated in situ from sodium thiocyanate, adds to anilines to also afford 2-aminobenzothiazoles.[3] Many other methods are available.[4]
Diazotization of 2-aminobenzothiazoles gives diazonium salts. These salts undergo azo coupling with anilines. In this way some are prepared some useful dyes such as Basic Blue 54.[5]
References
[edit]- ^ a b Altaf, Muhammad; Stoeckli-Evans, Helen (2009). "1,3-Benzothiazol-2-amine". Acta Crystallographica Section E: Structure Reports Online. 65 (8): o1894. Bibcode:2009AcCrE..65o1894A. doi:10.1107/S1600536809027561. PMC 2977242. PMID 21583584.
- ^ Ding, Qiuping; He, Xiaodan; Wu, Jie (2009). "Synthesis of 2-Aminobenzothiazole via Copper(I)-Catalyzed Tandem Reaction of 2-Iodobenzenamine with Isothiocyanate". Journal of Combinatorial Chemistry. 11 (4): 587–591. doi:10.1021/cc900027c. PMID 19449803.
- ^ Allen, C. F. H.; VanAllan, J. (1942). "2-Amino-6-Methylbenzothiazole". Organic Syntheses. 22: 16. doi:10.15227/orgsyn.022.0016
{{cite journal}}: CS1 maint: multiple names: authors list (link). - ^ Prajapati, Neelam P.; Vekariya, Rajesh H.; Borad, Mayuri A.; Patel, Hitesh D. (2014). "Recent Advances in the Synthesis of 2-Substituted Benzothiazoles: A Review". RSC Adv. 4 (104): 60176–60208. Bibcode:2014RSCAd...460176P. doi:10.1039/C4RA07437H.
- ^ Berneth, Horst (2008). "Methine Dyes and Pigments". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a16_487.pub2. ISBN 978-3-527-30385-4.