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| | 2-Cyano-6-methoxybenzothiazole Basic information | | Uses |
| | 2-Cyano-6-methoxybenzothiazole Chemical Properties |
| 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) |
| | 2-Cyano-6-methoxybenzothiazole Usage And Synthesis |
| Uses | 2-Cyano-6-methoxybenzothiazole is a key intermediate in the synthesis of fireflys’ luciferol, the light emitting chemical. Also a reactant in the preparation of 1,2,4-Oxadiazole EthR inhibitors used in the effort to improve the sensitivity of the human pathogen mycobacterium tuberculosis. | | 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
| | Uses | Luciferin intermediate. | | 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 |
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