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HomeProduct name list2-Cyano-6-methoxybenzothiazole

2-Cyano-6-methoxybenzothiazole

Synonym(s):6-Methoxy-2-benzothiazolecarbonitrile

  • CAS NO.:943-03-3
  • Empirical Formula: C9H6N2OS
  • Molecular Weight: 190.22
  • MDL number: MFCD00010537
  • EINECS: 231-439-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-08-29 17:54:30
2-Cyano-6-methoxybenzothiazole Structural

What is 2-Cyano-6-methoxybenzothiazole?

Chemical properties

off-white to light yellow crystalline powder

The Uses of 2-Cyano-6-methoxybenzothiazole

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

The Uses of 2-Cyano-6-methoxybenzothiazole

Luciferin intermediate.

What are the applications of Application

2-Cyano-6-methoxybenzothiazole is an intermediate of the luciferase substrate luciferin

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.

Properties of 2-Cyano-6-methoxybenzothiazole

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
CAS DataBase Reference 943-03-3(CAS DataBase Reference)

Safety information for 2-Cyano-6-methoxybenzothiazole

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for 2-Cyano-6-methoxybenzothiazole

InChIKey DEWDWBYQOFXKIH-UHFFFAOYSA-N
SMILES S1C2=CC(OC)=CC=C2N=C1C#N

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