| Identification | Back Directory | [Name]
2-CYANO-6-HYDROXYBENZOTHIAZOLE | [CAS]
939-69-5 | [Synonyms]
D-OH
2-cyano-6-hydroxybenzothiazoL
2-CYANO-6-HYDROXYBENZOTHIAZOLE
6-Hydroxy-Benzothiazole-2-Carb
2-Cyano-6-hydroxy-1,3-benzothiazole
2-Cyano-6-hydroxybenzothiazole, >=95%
6-Hydroxy-2-Benzothiazolecarbonitrile
2-Benzothiazolecarbonitrile, 6-hydroxy
6-hydroxy-benzothiazole-2-carbonitrile
6-Hydroxybenzothiazole-2-carbonitrile 96%
6-hydroxy-1,3-benzothiazole-2-carbonitrile
6-hydroxy-2-Benzothiazolecarbonitrile USP/EP/BP
2-Benzothiazolecarbonitrile, 6-hydroxy- USP/EP/BP
2-Benzothiazolecarbonitrile,6-hydroxy-(7CI,8CI,9CI) | [Molecular Formula]
C8H4N2OS | [MDL Number]
MFCD00296905 | [MOL File]
939-69-5.mol | [Molecular Weight]
176.2 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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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