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
- MDL Number:
- MFCD00296905
- MOL File:
- 939-69-5.mol
- MSDS File:
- SDS
| 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 price More Price(29)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 776823 | 6-Hydroxybenzothiazole-2-carbonitrile 96% | 939-69-5 | 500mg | $68.4 | 2024-03-01 | Buy |
| TRC | C998385 | 2-Cyano-6-hydroxybenzothiazole | 939-69-5 | 50mg | $45 | 2021-12-16 | Buy |
| TRC | C998385 | 2-Cyano-6-hydroxybenzothiazole | 939-69-5 | 100mg | $60 | 2021-12-16 | Buy |
| SynQuest Laboratories | 8H37-1-Y2 | 6-Hydroxy-1,3-benzothiazole-2-carbonitrile 97% | 939-69-5 | 5G | $368 | 2021-12-16 | Buy |
| Biosynth Carbosynth | FC09476 | 2-Cyano-6-hydroxybenzothiazole | 939-69-5 | 10g | $370 | 2021-12-16 | Buy |
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 | |
|---|---|---|---|---|---|
| ARCTIC EXPORTS INC | +1-3026880818 +1-3026880818 | ARCTICEXPORTSINC@GMAIL.COM | Canada | 69 | 58 |
| Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | sales@capotchem.com | China | 29798 | 60 |
| Shanghai Daken Advanced Materials Co.,Ltd | +86-371-66670886 | info@dakenam.com | China | 16914 | 58 |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | info@tianfuchem.com | China | 21668 | 55 |
| career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29894 | 58 |
| Shenzhen Nexconn Pharmatechs Ltd | +86-755-89396905 +86-15013857715 | admin@nexconn.com | China | 10312 | 58 |
| Accela ChemBio Inc. | +1-858-6993322 | info@accelachem.com | United States | 19343 | 58 |
| Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | sales@chemdad.com | China | 39916 | 58 |
| Alchem Pharmtech,Inc. | 8485655694 | sales@alchempharmtech.com | United States | 63711 | 58 |
| CONIER CHEM AND PHARMA LIMITED | +8618523575427 | sales@conier.com | China | 49391 | 58 |
View Lastest Price from 2-Cyano-6-hydroxybenzothiazole manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-07-13 | 2-Cyano-6-hydroxybenzothiazole
939-69-5
|
US $1.00 / kg | 100kg | 99% | 1000000 | ARCTIC EXPORTS INC | |
 |
2022-09-08 | 2-Cyano-6-hydroxybenzothiazole
939-69-5
|
US $0.00-0.00 / KG | 1KG | 98% | 1Ton | Henan Aochuang Chemical Co.,Ltd. | |
 |
2022-02-22 | 2-Cyano-6-hydroxybenzothiazole
939-69-5
|
US $0.00 / KG | 1KG | 98.5% | 100 tons | Honest Joy Holdings Limited
|
-
- 2-Cyano-6-hydroxybenzothiazole
939-69-5
- US $1.00 / kg
- 99%
- ARCTIC EXPORTS INC
-
- 2-Cyano-6-hydroxybenzothiazole
939-69-5
- US $0.00-0.00 / KG
- 98%
- Henan Aochuang Chemical Co.,Ltd.
-
- 2-Cyano-6-hydroxybenzothiazole
939-69-5
- US $0.00 / KG
- 98.5%
- Honest Joy Holdings Limited