2-Cyano-6-methoxybenzothiazole
- CAS No.
- 943-03-3
- Chemical Name:
- 2-Cyano-6-methoxybenzothiazole
- Synonyms
- NSC 377382;2-CYANO-6-METHOXYBENZOTIAZOLE;6-Methoxy-2-cyanobenzothiazole;2-CYANO-6-METHOXYBENZOTHIAZOLE;2-Cyano-6-methaxybenzothiazole;2-cyano-6-methoxy benzothiozale;2-Cyano-6-methoxybenzothiazole,99%;2-Cyano-6-methoxybenzothiazole >2-CYANO-6-METHOXY BENZOTHIAZOLE 98%;2-Cyano-6-methoxybenzothiazole ,98%
- CBNumber:
- CB8467670
- Molecular Formula:
- C9H6N2OS
- Molecular Weight:
- 190.22
- MOL File:
- 943-03-3.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/8/29 17:54:30
| Melting point | 129-131 °C (lit.) |
|---|---|
| Boiling point | 334.9±34.0 °C(Predicted) |
| Density | 1.2938 (rough estimate) |
| refractive index | 1.6800 (estimate) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | chloroform: soluble5%, clear, colorless to faintly yellow |
| form | Crystalline Powder |
| pka | -1.49±0.10(Predicted) |
| color | Off-white to light yellow |
| InChI | InChI=1S/C9H6N2OS/c1-12-6-2-3-7-8(4-6)13-9(5-10)11-7/h2-4H,1H3 |
| InChIKey | DEWDWBYQOFXKIH-UHFFFAOYSA-N |
| SMILES | S1C2=CC(OC)=CC=C2N=C1C#N |
| CAS DataBase Reference | 943-03-3(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H302+H312+H332-H315-H319-H335 | |||||||||
| Precautionary statements | P261-P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338 | |||||||||
| Hazard Codes | Xn,Xi | |||||||||
| Risk Statements | 20/21/22-36/37/38 | |||||||||
| Safety Statements | 26-36-36/37 | |||||||||
| RIDADR | 3439 | |||||||||
| WGK Germany | 3 | |||||||||
| HS Code | 29341000 | |||||||||
| NFPA 704 |
|
2-Cyano-6-methoxybenzothiazole price More Price(5)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 261858 | 2-Cyano-6-methoxybenzothiazole 99% | 943-03-3 | 1G | ₹13953.43 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 261858 | 2-Cyano-6-methoxybenzothiazole 99% | 943-03-3 | 1G | ₹13953.43 | 2022-06-14 | Buy |
| TCI Chemicals (India) | C1176 | 2-Cyano-6-methoxybenzothiazole min. 97.0 % | 943-03-3 | 1G | ₹7400 | 2022-05-26 | Buy |
| ottokemi | C 2772 | 2-Cyano-6-methoxybenzothiazole, 99% | 943-03-3 | 1gm | ₹13005 | 2022-05-26 | Buy |
| ottokemi | C 2772 | 2-Cyano-6-methoxybenzothiazole, 99% | 943-03-3 | 5gm | ₹58005 | 2022-05-26 | Buy |
2-Cyano-6-methoxybenzothiazole Chemical Properties,Uses,Production
Chemical Properties
off-white to light yellow crystalline powder
Uses
2-Cyano-6-methoxybenzothiazole has been used in the synthesis of:
- firefly luciferin via condensation with cysteine
- luciferin β-glycosides, substrates for novel ultrasensitive enzyme assays
Synthesis
Typical routes to 2-cyano-6-methoxybenzothiazole include the classical Rosenmund-von Braun and Sandmeyer reactions. These methods proceed with low atom economy and require toxic reagents such as KCN, NaCN, Zn(CN)2, or TMSCN, which are also challenging to handle in a large-scale synthesis. Shahmoradi et al. introduced a Cu-catalyzed cyanation of 2-iodo-6-methoxybenzothiazole to synthesize 2-cyano-6-methoxybenzothiazole. K4[Fe(CN)6] was applied as a source of cyanide, and CuI in the presence of N, N N′, N′-tetramethylethylenediamine (TMEDA) was used as part of the catalyst system. 2-Amino-6-methoxybenzothiazole as a starting material was synthesized from p-anisidine as shown below and subsequently converted into 2-iodo-6-methoxybenzothiazole using a simple and efficient one-pot sequential diazotization-iodination method. The one-pot cyanation of 2-iodo-6-methoxybenzothiazole to 2-cyano-6-methoxybenzothiazole was achieved using 0.25 mmol of K4[Fe(CN)6], 0.25 mmol of CuI and 3 mmol of TMEDA in acetonitrile at 160°C. In addition, 1 mmol of mystril trimethyl bromide (MTMAB) was used as a phase transfer agent. The presence of a phase-transfer catalyst is essential for a successful cyanation reaction. Under these conditions, 2-cyano-6-methoxybenzothiazole was produced in a 90% yield[1].
References
[1] Ghasem Shahmoradi, S. Amani. “Synthesis, characterization and computational studies of 2-cyano-6-methoxybenzothiazole as a firefly-luciferin precursor.” Heterocyclic Communications 24 1 (2018): 255–258.
2-Cyano-6-methoxybenzothiazole Preparation Products And Raw materials
Raw materials
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