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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
Last updated:2024-01-19 13:34:10

2-Cyano-6-methoxybenzothiazole 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)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
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
0
2 0

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
Product number Packaging Price Buy
261858 1g $120 Buy
C1176 1g $102 Buy
H51082 1g $108.65 Buy
H51082 5g $523.65 Buy
C981840 5g $150 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.

32338-02-6
75318-43-3
943-03-3
Synthesis of 2-Cyano-6-methoxybenzothiazole from 2-BROMO-4-METHOXY-PHENYLAMINE and 4,5-Dichloro-1,2,3-dithiazolium chloride
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View Lastest Price from 2-Cyano-6-methoxybenzothiazole manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
2-Cyano-6-methoxybenzothiazole pictures 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 pictures 2023-07-26 2-Cyano-6-methoxybenzothiazole
943-03-3
US $12150.00 / kg 1kg 99% 20tons Hebei Mojin Biotechnology Co., Ltd
2-Cyano-6-methoxybenzothiazole pictures 2023-05-24 2-Cyano-6-methoxybenzothiazole
943-03-3
US $10.00 / KG 1KG 99% 10 mt Hebei Guanlang Biotechnology Co., Ltd.
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