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

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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)

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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

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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.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 261858
Product name: 2-Cyano-6-methoxybenzothiazole
Purity: 99%
Packaging: 1g
Price: $120
Updated: 2024/03/01

TCI Chemical

Product number: C1176
Product name: 2-Cyano-6-methoxybenzothiazole
Purity: >97.0%(GC)
Packaging: 1g
Price: $102
Updated: 2024/03/01

Alfa Aesar

Product number: H51082
Product name: 6-Methoxybenzothiazole-2-carbonitrile
Purity: 99%
Packaging: 1g
Price: $108.65
Updated: 2024/03/01

Alfa Aesar

Product number: H51082
Product name: 6-Methoxybenzothiazole-2-carbonitrile
Purity: 99%
Packaging: 5g
Price: $523.65
Updated: 2024/03/01

TRC

Product number: C981840
Product name: 2-Cyano-6-methoxybenzothiazole
Packaging: 5g
Price: $150
Updated: 2021/12/16

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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

Copper(I) Cyanide Sodium thiocyanate Sodium chloride Sodium nitrite p-Anisidine Diethyl ether Hydrochloric acid Sodium bicarbonate Government regulation Dichloromethane Acetic acid Dimethyl sulfoxide Sodium hydroxide Magnesium sulfate PETROLEUM ETHER POTASSIUM CYANIDE

Preparation Products

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2-Cyano-6-methoxybenzothiazole Suppliers

Americas 1 Belgium 1 China 155 Europe 3 France 1 Germany 4 India 6 Japan 3 Russia 1 Slovakia 1 Switzerland 1 Ukraine 2 United Kingdom 14 United States 25 Global 218

Beijing Hechemist Technology CO.,LTD

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Alfa Aesar

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Energy Chemical

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View Lastest Price from 2-Cyano-6-methoxybenzothiazole manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd

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

Shaanxi Dideu Medichem Co. Ltd

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

Hebei Weibang Biotechnology Co., Ltd

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

943-03-3, 2-Cyano-6-methoxybenzothiazoleRelated Search:

2,2'-Dithiobis(benzothiazole) Benzothiazole p-Anisidine 2-Mercaptobenzothiazole p-Anisaldehyde 2-Methoxyethanol Anisole (Trifluoromethoxy)benzene 4-Methoxybenzylchloride 2-Methylbenzothiazole 2-METHYL-1,3-BENZOTHIAZOL-6-OL 6-METHOXY-2-METHYLBENZOTHIAZOLE 2-CYANO-6-HYDROXYBENZOTHIAZOLE 6-METHOXY-1,3-BENZOTHIAZOLE 2-Cyanothiazole 6-Benzothiazolol(7CI,8CI,9CI) 2-Methylthiazole 2-Cyano-6-methoxybenzothiazole

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 &gt

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