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| | 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 |  |
| | 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) | | pka | 7.52±0.40(Predicted) | | form | crystalline solid | | 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 |
| 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.
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| | 2-Cyano-6-hydroxybenzothiazole Preparation Products And Raw materials |
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