2-Cyano-6-methoxybenzothiazole
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- CAS-Nr.
- 943-03-3
- Englisch Name:
- 2-Cyano-6-methoxybenzothiazole
- Synonyma:
- 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
- Summenformel:
- C9H6N2OS
- Molgewicht:
- 190.22
- MOL-Datei:
- 943-03-3.mol
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2-Cyano-6-methoxybenzothiazole Eigenschaften
- Schmelzpunkt:
- 129-131 °C (lit.)
- Siedepunkt:
- 334.9±34.0 °C(Predicted)
- Dichte
- 1.2938 (rough estimate)
- Brechungsindex
- 1.6800 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- L?slichkeit
- chloroform: soluble5%, clear, colorless to faintly yellow
- Aggregatzustand
- Crystalline Powder
- pka
- -1.49±0.10(Predicted)
- Farbe
- 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 Datenbank
- 943-03-3(CAS DataBase Reference)
2-Cyano-6-methoxybenzothiazole Chemische Eigenschaften,Einsatz,Produktion Methoden
R-S?tze Betriebsanweisung:
R20/21/22:Gesundheitssch?dlich beim Einatmen,Verschlucken und Berührung mit der Haut.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-S?tze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
Chemische Eigenschaften
off-white to light yellow crystalline powder
Verwenden
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
Synthese
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].
Einzelnachweise
[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 Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
2-Cyano-6-methoxybenzothiazole Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.
Global( 217)Lieferanten
943-03-3()Verwandte Suche:
- NSC 377382
- 6-METHOXY-2-BENZOTHIAZOLE-CARBONITRILE
- 6-METHOXY-1,3-BENZOTHIAZOLE-2-CARBONITRILE
- 6-METHOXY-BENZOTHIAZOLE-2-CARBONITRILE
- 6-methoxy-1H-benzo[d]imidazole-2-carbonitrile
- 2-Cyano-6-methaxybenzothiazole
- 2-CYANO-6-METHOXYBENZOTHIAZOLE
- 2-CYANO-6-METHOXYBENZOTIAZOLE
- 2-BENZOTHIAZOLECARBONITRILE, 6-METHOXY-
- 6-Methoxy-2-cyanobenzothiazole
- 2-Benzothiazolecarbonitrile,6-methoxy-(7CI,8CI,9CI)
- 2-cyano-6-methoxy benzothiozale
- 2-CYANO-6-METHOXY BENZOTHIAZOLE 98%
- 2-Cyano-6-Methoxybenzothiazole, 99% 1GR
- 6-Methoxy-benzo[d]thiazole-2-carbonitrile
- 2-Cyano-6-methoxybenzothiazole ,98%
- 2-Cyano-6-methoxybenzothiazole,99%
- 2-Cyano-6-methoxybenzothiazole >
- 6-Methoxybenzodthiazol-2-carbonitrile
- 943-03-3
- 943-03-0
- C9H6N2OS
- Building Blocks
- Heterocyclic Building Blocks
- Thiazoles
- Furans
- Building Blocks
- C8 to C9
- Chemical Synthesis
- Heterocyclic Building Blocks
- Thiazoles
- BENZOTHIAZOLE
- Sulphur Derivatives
- pharmacetical
