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)

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

• Language:English Provider:2-Cyano-6-methoxybenzothiazole
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

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.

2-Cyano-6-methoxybenzothiazole(943-03-3)Related Product Information

• 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