Uses
ChemicalBook > CAS DataBase List > 2-Cyano-6-methoxybenzothiazole

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

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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