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2-Cyano-6-methoxybenzothiazole

Basic information Uses Safety Supplier Related

2-Cyano-6-methoxybenzothiazole Basic information

Product Name:
2-Cyano-6-methoxybenzothiazole
Synonyms:
  • 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
CAS:
943-03-3
MF:
C9H6N2OS
MW:
190.22
EINECS:
231-439-8
Product Categories:
  • Furans
  • Building Blocks
  • C8 to C9
  • Chemical Synthesis
  • Heterocyclic Building Blocks
  • Thiazoles
  • BENZOTHIAZOLE
  • Sulphur Derivatives
  • pharmacetical
Mol File:
943-03-3.mol
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2-Cyano-6-methoxybenzothiazole Chemical 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
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 Information

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

MSDS

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2-Cyano-6-methoxybenzothiazole Usage And Synthesis

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.

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