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
- MDL Number:
- MFCD00010537
- MOL File:
- 943-03-3.mol
- MSDS File:
- SDS
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 |
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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 |
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2-Cyano-6-methoxybenzothiazole price More Price(36)
Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
---|---|---|---|---|---|---|---|
Sigma-Aldrich | 261858 | 2-Cyano-6-methoxybenzothiazole 99% | 943-03-3 | 1g | $120 | 2024-03-01 | Buy |
TCI Chemical | C1176 | 2-Cyano-6-methoxybenzothiazole >97.0%(GC) | 943-03-3 | 1g | $102 | 2024-03-01 | Buy |
Alfa Aesar | H51082 | 6-Methoxybenzothiazole-2-carbonitrile 99% | 943-03-3 | 1g | $108.65 | 2024-03-01 | Buy |
Alfa Aesar | H51082 | 6-Methoxybenzothiazole-2-carbonitrile 99% | 943-03-3 | 5g | $523.65 | 2024-03-01 | Buy |
TRC | C981840 | 2-Cyano-6-methoxybenzothiazole | 943-03-3 | 5g | $150 | 2021-12-16 | Buy |
2-Cyano-6-methoxybenzothiazole Chemical Properties,Uses,Production
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.
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2-Cyano-6-methoxybenzothiazole Preparation Products And Raw materials
Raw materials
1of4
Preparation Products
Supplier | Tel | Country | ProdList | Advantage | |
---|---|---|---|---|---|
Hongxiong | +undefined18915499068 | Suzhouhongxiong@163.com | China | 120 | 58 |
Hebei Mojin Biotechnology Co., Ltd | +8613288715578 | sales@hbmojin.com | China | 12450 | 58 |
Henan Bao Enluo International TradeCo.,LTD | +86-17331933971 +86-17331933971 | deasea125996@gmail.com | China | 2503 | 58 |
Hebei Zhuanglai Chemical Trading Co.,Ltd | +8613343047651 | admin@zlchemi.com | China | 3002 | 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 |
Nanjing ChemLin Chemical Industry Co., Ltd. | 025-83697070 | product@chemlin.com.cn | CHINA | 3012 | 60 |
career henan chemical co | +86-0371-86658258 +8613203830695 | sales@coreychem.com | China | 29894 | 58 |
Hebei Guanlang Biotechnology Co., Ltd. | +86-19930503282 | alice@crovellbio.com | China | 8822 | 58 |
Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | sales@chemdad.com | China | 39916 | 58 |
View Lastest Price from 2-Cyano-6-methoxybenzothiazole manufacturers
Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
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2024-06-06 | 2-Cyano-6-methoxybenzothiazole
943-03-3
|
US $10.00 / kg | 1kg | 99% | 20ton | Hebei Zhuanglai Chemical Trading Co.,Ltd | |
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2024-04-22 | 2-Cyano-6-methoxybenzothiazole
943-03-3
|
US $50.00 / kg | 1kg | 99.10% | 50000kg | Ouhuang Engineering Materials (Hubei) Co., Ltd | |
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2023-08-02 | 2-Cyano-6-methoxybenzothiazole
943-03-3
|
US $50.00 / kg | 1kg | 99.9% | 10000MT | Henan Bao Enluo International TradeCo.,LTD |
-
- 2-Cyano-6-methoxybenzothiazole
943-03-3
- US $10.00 / kg
- 99%
- Hebei Zhuanglai Chemical Trading Co.,Ltd
-
- 2-Cyano-6-methoxybenzothiazole
943-03-3
- US $50.00 / kg
- 99.10%
- Ouhuang Engineering Materials (Hubei) Co., Ltd
-
- 2-Cyano-6-methoxybenzothiazole
943-03-3
- US $50.00 / kg
- 99.9%
- Henan Bao Enluo International TradeCo.,LTD