2-Cyano-6-methoxybenzothiazole
Uses- Product Name
- 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
- Formula Weight
- 190.22
- MOL File
- 943-03-3.mol
2-Cyano-6-methoxybenzothiazole Property
- 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
- pka
- -1.49±0.10(Predicted)
- form
- Crystalline Powder
- 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
- 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
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 261858
- Product name
- 2-Cyano-6-methoxybenzothiazole
- Purity
- 99%
- Packaging
- 1g
- Price
- $120
- Updated
- 2024/03/01
- Product number
- C1176
- Product name
- 2-Cyano-6-methoxybenzothiazole
- Purity
- >97.0%(GC)
- Packaging
- 1g
- Price
- $102
- Updated
- 2024/03/01
- Product number
- H51082
- Product name
- 6-Methoxybenzothiazole-2-carbonitrile
- Purity
- 99%
- Packaging
- 1g
- Price
- $108.65
- Updated
- 2024/03/01
- Product number
- H51082
- Product name
- 6-Methoxybenzothiazole-2-carbonitrile
- Purity
- 99%
- Packaging
- 5g
- Price
- $523.65
- Updated
- 2024/03/01
- Product number
- C981840
- Product name
- 2-Cyano-6-methoxybenzothiazole
- Packaging
- 5g
- Price
- $150
- Updated
- 2021/12/16
2-Cyano-6-methoxybenzothiazole Chemical Properties,Usage,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
Luciferin intermediate.
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
Preparation Products
2-Cyano-6-methoxybenzothiazole Suppliers
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- Russia
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View Lastest Price from 2-Cyano-6-methoxybenzothiazole manufacturers
- Product
- 2-Cyano-6-methoxybenzothiazole 943-03-3
- Price
- US $10.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 20ton
- Release date
- 2024-06-06
- Product
- 2-Cyano-6-methoxybenzothiazole 943-03-3
- Price
- US $0.10/KG
- Min. Order
- 1KG
- Purity
- 99.0%
- Supply Ability
- 1000 tons
- Release date
- 2024-08-28
- Product
- 2-Cyano-6-methoxybenzothiazole 943-03-3
- Price
- US $10.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- 10 mt
- Release date
- 2023-05-23