2-Cyano-6-hydroxybenzothiazole
- CAS No.
- 939-69-5
- Chemical Name:
- 2-Cyano-6-hydroxybenzothiazole
- 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%
- CBNumber:
- CB6466639
- Molecular Formula:
- C8H4N2OS
- Molecular Weight:
- 176.2
- MOL File:
- 939-69-5.mol
- MSDS File:
- SDS
- Modify Date:
- 2025/2/23 21:28:46
| 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 |
| InChIKey | SQAVNBZDECKYOT-UHFFFAOYSA-N |
2-Cyano-6-hydroxybenzothiazole Chemical Properties,Uses,Production
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
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| GLR Innovations | +91 9891111994 | New Delhi, India | 4535 | 58 | Inquiry |
| SURVIVAL TECHNOLOGIES LIMITED | +91 8108285261 | Gujarat, India | 294 | 58 | Inquiry |
| Neugen Labs | +91-8133254502 +91-8133254502 | Karnataka, India | 195 | 58 | Inquiry |
| Aravali Pharma And Lifesciences | +91-9350857917 +91-9810502945 | New Delhi, India | 119 | 58 | Inquiry |
| Santo Righello Pvt. Ltd | 91-9885571757 | Hyderabad, India | 918 | 58 | Inquiry |
| Neugen Labs | 1--8133254502 | Karnataka, India | 99 | 58 | Inquiry |
| Aravali Pharma & Lifesciences | 91--9810502945 | Delhi, India | 71 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6100 | 58 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6905 | 58 | Inquiry |
| ARCTIC EXPORTS INC | +1-3026880818 +1-3026880818 | Canada | 66 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| GLR Innovations | 58 |
| SURVIVAL TECHNOLOGIES LIMITED | 58 |
| Neugen Labs | 58 |
| Aravali Pharma And Lifesciences | 58 |
| Santo Righello Pvt. Ltd | 58 |
| Neugen Labs | 58 |
| Aravali Pharma & Lifesciences | 58 |
| A.J Chemicals | 58 |
| Alfa Aesar | 58 |
| ARCTIC EXPORTS INC | 58 |