943-03-3

Basic information

• Product Name: 2-Cyano-6-methoxybenzothiazole
• Synonyms: NSC 377382;6-METHOXY-2-BENZOTHIAZOLE-CARBONITRILE;6-METHOXY-1,3-BENZOTHIAZOLE-2-CARBONITRILE;6-METHOXY-BENZOTHIAZOLE-2-CARBONITRILE;2-CYANO-6-METHOXYBENZOTHIAZOLE;2-CYANO-6-METHOXYBENZOTIAZOLE;2-BENZOTHIAZOLECARBONITRILE, 6-METHOXY-;6-Methoxy-2-cyanobenzothiazole
• CAS NO: 943-03-3
• Molecular Formula: C₉H₆N₂OS
• Molecular Weight: 190.22
• Product Categories: BENZOTHIAZOLE;Sulphur Derivatives;pharmacetical;Building Blocks;C8 to C9;Chemical Synthesis;Heterocyclic Building Blocks;Thiazoles;Furans
• Mol File: 943-03-3.mol
• Article Data: 3

Chemical Properties

• Melting Point: 129-131 °C(lit.)
• Boiling Point: 334.918 °C at 760 mmHg
• Flash Point: 156.353 °C
• Appearance: Off-white to light yellow/Crystalline Powder
• Density: 1.2938 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• 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)
• CAS DataBase Reference: 2-Cyano-6-methoxybenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyano-6-methoxybenzothiazole(943-03-3)
• EPA Substance Registry System: 2-Cyano-6-methoxybenzothiazole(943-03-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-36/37
• RIDADR: 3439
• WGK Germany: 3
• Hazardous Substances Data: 943-03-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 943-03-3 differently. You can refer to the following data:
1. 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.
2. Luciferin intermediate.
3. 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

Chemical Properties

off-white to light yellow crystalline powder

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

Upstream product

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

Downstream Products

• 946-13-4 6-methoxybenzo[d]thiazol-2-carboxylic acid 
• 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 
• 3022-11-5 luciferin 6'-methyl ether 
• 34500-31-7 (R)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid 
• 20240-21-5 D-luciferin 
• 20115-09-7 2-(6’-hydroxy-2'-benzothiazolyl)-thiazole-4-carboxylic acid 
• 2591-17-5 D-luciferin 
• 884-22-0 6-methoxy-benzothiazole-2-carboxylic acid methyl ester 
• 131474-36-7 methyl 6-methoxybenzothioazole-2-carboximidate 
• 71368-35-9 6-methoxybenzo[d]thiazole-2-carbothioamide 
• 939-69-5 2-cyano-6-hydroxybenzothiazole 

Relevant articles and documents

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

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.