943-03-3

Usage

Uses

Used in Bioluminescence Applications:
2-Cyano-6-methoxybenzothiazole is used as a key intermediate in the synthesis of firefly luciferin, the light-emitting chemical responsible for the bioluminescent properties of fireflies. 2-Cyano-6-methoxybenzothiazole plays a crucial role in the development of bioluminescent systems for various applications, such as bioimaging, diagnostics, and research.
Used in Enzyme Assays:
2-Cyano-6-methoxybenzothiazole is used in the synthesis of substrates for novel ultrasensitive enzyme assays. These assays are designed to detect and measure enzyme activity with high sensitivity and specificity, which is essential for various research and diagnostic applications.
Used in Pharmaceutical Industry:
2-Cyano-6-methoxybenzothiazole is used as a reactant in the preparation of 1,2,4-Oxadiazole EthR inhibitors. These inhibitors are being developed to improve the sensitivity of the human pathogen Mycobacterium tuberculosis, which is responsible for tuberculosis, a significant global health concern.

InChI:InChI=1/C9H6N2OS/c1-12-6-2-3-7-8(4-6)13-9(5-10)11-7/h2-4H,1H3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 75318-43-3 4,5-dichloro-1,2,3-dithiazolium chloride 
• 75318-49-9 N-(4-chloro-5H-1,2,3-dithiazol-5-ylidene)-4-methoxyaniline 
• 71369-81-8 2-(4-methoxyphenylamino)-2-thioxoacetamide 

Downstream Products

• 3022-11-5 luciferin 6'-methyl ether 
• 55318-95-1 2-Carbamoyl-6-hydroxybenzothiazin 
• 939-69-5 2-cyano-6-hydroxybenzothiazole 
• 71368-35-9 6-methoxybenzo[d]thiazole-2-carbothioamide 
• 20115-09-7 2-(6’-hydroxy-2'-benzothiazolyl)-thiazole-4-carboxylic acid 
• 20240-21-5 D-luciferin 
• 34500-31-7 (R)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid 
• 946-13-4 6-methoxybenzo[d]thiazol-2-carboxylic acid 
• 129058-56-6 methyl 6-hydroxybenzo[d]thiazole-2-carboxylate 
• 1421277-81-7 (4-(((2-cyanobenzo[d]thiazol-6-yl)oxy)methyl)phenyl)boronic acid 
• 1344979-77-6 6-((4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)oxy)benzo-[d]thiazole-2-carbonitrile 
• 1392498-16-6 C₁₇H₁₄N₂O₄S₂ 
• 697784-33-1 C₉H₉N₃O₂S 
• 2591-17-5 D-luciferin 

Relevant academic research and scientific papers

Rapid and scalable assembly of firefly luciferase substrates

Bioluminescence imaging with luciferase-luciferin pairs is a popular method for visualizing biological processes in vivo. Unfortunately, most luciferins are difficult to access and remain prohibitively expensive for some imaging applications. Here we report cost-effective and efficient syntheses of d-luciferin and 6′-aminoluciferin, two widely used bioluminescent substrates. Our approach employs inexpensive anilines and Appel's salt to generate the luciferin cores in a single pot. Additionally, the syntheses are scalable and can provide multi-gram quantities of both substrates. The streamlined production and improved accessibility of luciferin reagents will bolster in vivo imaging efforts. This journal is

A new application of the mild thiolation concept for an efficient three-step synthesis of 2-cyanobenzothiazoles: A new approach to Firefly-luciferin precursors

An easy, low cost and upscalable three-step synthesis of Firefly luciferin precursors is presented. The 6-alkoxy-2-cyano-benzothiazoles (1) were synthesized starting from easily available O-alkylated 4-aminophenoles (2) via a mild thiolation, Jacobsen cyclization and dehydratization sequence.

Eco-Friendly Microwave-Assisted Scaleable Synthesis of 2-Cyanobenzothiazoles via N-Arylimino-1,2,3-dithiazoles

The cyclization procedure of N-aryl iminodithiazoles into 2-cyanobenzothiazoles was re-investigated with the aim to develop original and environmentally friendly procedures. In this article, the benefits associated with the microwave methodology are reported and the opportunity to use solvent-free procedures in order to scale up organic synthesis is studied. The result obtained show that the strong thermal effects due to graphite/microwaves interaction can be efficiently used for the synthesis of heterocyclic molecules for which traditional methods failed or are less attractive.