Introduction：Basic information about 2-Cyano-6-hydroxybenzothiazole CAS 939-69-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-Cyano-6-hydroxybenzothiazole Basic information
| Product Name: | 2-Cyano-6-hydroxybenzothiazole |
| Synonyms: | 2-CYANO-6-HYDROXYBENZOTHIAZOLE;2-Benzothiazolecarbonitrile, 6-hydroxy;6-Hydroxy-2-Benzothiazolecarbonitrile;6-Hydroxy-Benzothiazole-2-Carb;2-cyano-6-hydroxybenzothiazoL;2-Benzothiazolecarbonitrile,6-hydroxy-(7CI,8CI,9CI);6-hydroxy-benzothiazole-2-carbonitrile;6-hydroxy-1,3-benzothiazole-2-carbonitrile |
| CAS: | 939-69-5 |
| MF: | C8H4N2OS |
| MW: | 176.2 |
| EINECS: | |
| Product Categories: | Sulphur Derivatives;BENZOTHIAZOLE |
| Mol File: | 939-69-5.mol |
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2-Cyano-6-hydroxybenzothiazole Chemical Properties
| Melting point | 211-213°C |
| Boiling point | 374.7±34.0 °C(Predicted) |
| density | 1.53±0.1 g/cm3(Predicted) |
| storage temp. | 2-8°C |
| solubility | Chloroform (Slightly), Methanol (Slightly) |
| form | crystalline solid |
| pka | 7.52±0.40(Predicted) |
| color | Light yellow |
| InChI | InChI=1S/C8H4N2OS/c9-4-8-10-6-2-1-5(11)3-7(6)12-8/h1-3,11H |
| InChIKey | SQAVNBZDECKYOT-UHFFFAOYSA-N |
| SMILES | S1C2=CC(O)=CC=C2N=C1C#N |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 22-36 |
| Safety Statements | 26-36/37 |
| RIDADR | UN3439 |
| WGK Germany | 3 |
| HS Code | 2934208090 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral
Eye Irrit. 2 |
2-Cyano-6-hydroxybenzothiazole Usage And Synthesis
| Description | 2-Cyano-6-hydroxybenzothiazole (CBTOH) is a critical intermediate in D-luciferin biosynthesis, also used for its chemical synthesis and as luciferin bioluminescence precursor for chemical analysis. Firefly light emission involves the enzymatic oxidation of D-luciferin to yield electronically excited oxyluciferin, which is the bioluminescent molecule. Oxyluciferin is afterwards enzymatically oxidized to thioglycolic acid and CBTOH, which regenerates luciferin by condensation with cysteine[1]. |
| Synthesis | A new synthesis of 2-cyano-6-hydroxybenzothiazole has been realized starting from the reaction of 1,4-benzoquinone with l-cysteine ethyl ester, followed by oxidation-cyclization of the intermediate ethyl (R)-2-amino-3-(2,5-dihydroxyphenylsulfanyl)propan-oate hydrochloride to 2-carbethoxy-6-hydroxybenzothiazole. A suitable protection of this intermediate and conversion to the corresponding nitrile gave, after deprotection, 2-cyano-6-hydroxybenzothiazole (32% yield from 1,4-benzoquinone)[2]. |
| References | [1] Ankita S. Jadhav . “Firefly luciferin precursor 2-cyano-6-hydroxybenzothiazole: Fluorescence à la carte controlled by solvent and acidity.” Dyes and Pigments 177 (2020): Article 108285.
[2] G. Meroni. “A new synthesis of 2-cyano-6-hydroxybenzothiazole, the key intermediate of D-luciferin, starting from 1,4-benzoquinone.” Synlett 29 1 (2009): 2682–2684. |
2-Cyano-6-hydroxybenzothiazole Preparation Products And Raw materials
| Raw materials | 4,5-Dichloro-1,2,3-dithiazolium chloride-->(5Z)-4-Chloro-N-(4-methoxyphenyl)-5H-1,2,3-dithiazol-5-imine-->2-Cyano-6-methoxybenzothiazole-->p-Anisidine |
