2-Cyano-6-methoxybenzothiazole

Base Information

• Chemical Name: 2-Cyano-6-methoxybenzothiazole
• CAS No.: 943-03-3
• Molecular Formula: C9H6N2OS
• Molecular Weight: 190.225
• Hs Code.: 29341000
• Mol file: 943-03-3.mol

Synonyms:2-Benzothiazolecarbonitrile,6-methoxy-;6-Methoxy-2-benzothiazolecarbonitrile;NSC 377382;

Chemical Property of 2-Cyano-6-methoxybenzothiazole

Chemical Property:

• Appearance/Colour: off-white to light yellow crystalline powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 129-131 °C(lit.)
• Refractive Index: 1.654
• Boiling Point: 334.918 °C at 760 mmHg
• PKA: -1.49±0.10(Predicted)
• Flash Point: 156.353 °C
• PSA: 74.15000
• Density: 1.36 g/cm³
• LogP: 2.17658
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: chloroform: soluble5%, clear, colorless to faintly yellow

Purity/Quality:

98% ^*data from raw suppliers

2-Cyano-6-methoxybenzothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

• 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. Luciferin intermediate. 2-Cyano-6-methoxybenzothiazole has been used in the synthesis of:firefly luciferin via condensation with cysteineluciferin β-glycosides, substrates for novel ultrasensitive enzyme assays

Technology Process of 2-Cyano-6-methoxybenzothiazole

There total 4 articles about 2-Cyano-6-methoxybenzothiazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 61.0%

N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methoxyaniline (75318-49-9) → 2-cyano-6-hydroxybenzothiazole (939-69-5) + 2-cyano-6-methoxybenzothiazole (943-03-3)

Guidance literature:

With pyridine hydrochloride; In sulfolane; at 180 ℃; for 1h;

DOI:10.1039/c4ob02529f

Reference yield: 51.0%

4-methoxy-aniline (104-94-9) + 4,5-dichloro-1,2,3-dithiazolium chloride (75318-43-3) → 2-cyano-6-hydroxybenzothiazole (939-69-5) + 2-cyano-6-methoxybenzothiazole (943-03-3)

Guidance literature:

4-methoxy-aniline; 4,5-dichloro-1,2,3-dithiazolium chloride; In sulfolane; at 40 - 180 ℃; for 3.33333h; Sealed tube; Inert atmosphere;

With pyridine hydrochloride; In sulfolane; at 180 ℃; for 1h; Sealed tube; Inert atmosphere;

DOI:10.1039/c4ob02529f

Reference yield: 50.0%

5-(p-Anisylimino)-4-chloro-5H-1,2,3-dithiazole → N-(p-Anisyl)cyanoimidoyl chloride + 2-cyano-6-methoxybenzothiazole (943-03-3)

Guidance literature:

With pyrographite; at 150 ℃; for 0.0833333h; microwave irradiation;

DOI:10.1081/SCC-120025190

upstream raw materials:

2-(4-methoxyphenylamino)-2-thioxoacetamide

4-methoxy-aniline

4,5-dichloro-1,2,3-dithiazolium chloride

N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methoxyaniline

Downstream raw materials:

D-luciferin

(4-(((2-cyanobenzo[d]thiazol-6-yl)oxy)methyl)phenyl)boronic acid

methyl 6-hydroxybenzo[d]thiazole-2-carboxylate

6-methoxybenzo[d]thiazol-2-carboxylic acid

Refernces

• 1、 Wuerfel, Hendryk,Weiss, Dieter,Beckert, Rainer,Guether, Angelika. "A new application of the mild thiolation concept for an efficient three-step synthesis of 2-cyanobenzothiazoles: A new approach to Firefly-luciferin precursors". . p. 9 - 16. Retrieved 2012/07/01.