7170-77-6

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-6-THIOCYANOBENZOTHIAZOLE is used as a key intermediate in the synthesis of pharmaceutical compounds, specifically for the development of potent and selective MET Kinase Inhibitors. These inhibitors play a crucial role in targeting and managing various diseases, including cancer, by modulating the activity of the MET Kinase enzyme.
In the synthesis process, 2-AMINO-6-THIOCYANOBENZOTHIAZOLE serves as a building block, contributing to the formation of the final drug molecule with desired therapeutic properties. Its presence in the molecular structure of MET Kinase Inhibitors is essential for achieving the necessary selectivity and potency required for effective treatment.

InChI:InChI=1/C8H5N3S2/c9-4-12-5-1-2-6-7(3-5)13-8(10)11-6/h1-3H,(H2,10,11)

Upstream product

• 333-20-0 potassium thioacyanate 
• 540-37-4 p-aminoiodobenzene 
• 2987-46-4 4-thiocyanatoaniline 
• 62-53-3 aniline 
• 1147550-11-5 ammonium thiocyanate 

Downstream Products

• 1196130-16-1 Nα-tert-butyloxycarbonyl-Nγ-(6-thiocyanatobenzothiazol-2-yl)asparagine benzyl ester 
• 63493-81-2 2-aminobenzo[d]thiazole-6-thiol 
• 1116743-46-4 1-(6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)-3-(2-morpholin-4-ylethyl)urea 
• 1430236-05-7 C₂₄H₁₆N₆O₂S₄ 
• 1205125-03-6 phenyl [6-(imidazo[1,2-a]pyrimidin-3-ylsulphanyl)-1,3-benzothiazol-2-yl]carbamate 
• 1205125-38-7 N-(6-{[6-(3-fluorophenyl)imidazo[1,2-a]pyrimidin-3-yl]sulphanyl}-1,3-benzothiazol-2-yl)cyclopropanecarboxamide 
• 1116743-36-2 6-{[6-(4-fluorophenyl)[1,2,4]triazolo[4,3-b]pyridazin-3-yl]sulphanyl}-1,3-benzothiazol-2-amine 
• 1116743-49-7 (6-thiocyanato-1,3-benzothiazol-2-yl)carbamate phenyl ester 

Relevant academic research and scientific papers

Visible-light photoredox catalytic approach for the direct synthesis of 2-aminobenzothiazoles from anilines

A novel, highly efficient and convenient approach for the visible-light-promoted direct synthesis of 2-aminobenzothiazoles from anilines and ammonium thiocyanate is presented. The reaction involves addition/cyclization cascade of SCN radical and anilines under photoredox catalysis with Ru(bpy)3Cl2. The salient features of the protocol include the utilization of atmospheric oxygen and visible light as clean, inexpensive and sustainable resources at room temperature.

Copper-Catalyzed Aerobic Oxidative Regioselective Thiocyanation of Aromatics and Heteroaromatics

A copper-catalyzed aerobic oxidative reaction between aromatics or heteroaromatics with KSCN is developed by using O2 as the oxidant. The combination of Cu(OTf)2, N,N,N′,N′-tetramethylethylenediamine (TMEDA) and BF3·Et2O provides an efficient catalytic system, affording substituted thiocyanation products and 2-aminobenzothiazoles in excellent yields. The reaction also possesses a good functional group tolerance for both strong electron-withdrawing and electron-donating groups.

Synthesis of some new 2-amino-6-thiocyanato benzothiazole derivatives bearing 2,4-thiazolidinediones and screening of their in vitro antimicrobial, antitubercular and antiviral activities

A series of new (E)-2-(5-substituted benzylidene-2,4-dioxothiazolidin-3-yl)-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamides have been synthesized. The structures of title compounds have been confirmed by elemental analyses, IR, 1H NMR and 13C NMR spectral data. All the synthesized compounds were tested for antimicrobial and antitubercular activity and also were evaluated for anti-HIV activity. Several compounds exhibited good antibacterial activity (9, 15, 27 and 31 against E. coli; 8 and 28 against S. aureus); some displayed good antifungal activity (4, 7, 13, 19, 23, 24, 25 and 31 against C. albicans). Compounds 14, 20 and 22 showed good antitubercular activity. Unfortunately, none of the compounds were found to be active against anti-HIV-1. However, one of the intermediates, the 2-chloro-N-(6-thiocyanatobenzo[d]thiazol-2-yl)acetamide, showed significant cytotoxicity for MT-4 cells (CC50 = 8.0 μM).

Monoazo dyestuffs derived from benzothiazole

A disperse dye of the formula, STR1 wherein R1 is an alkyl group having 5 to 6 carbon atoms, R2 is an alkyl group having 5 to 6 carbon atoms, a cyano-ethyl group, R3 is a hydrogen atom or a lower alkyl, amino or phenyl group, and Y1 and Y2 represent independently a hydrogen atom, a lower alkyl group, a lower alkoxy group, a halogen atom, a nitro group, a cyano group, a thiocyanate group or an alkylsulfonyl group, provided that both Y1 and Y2 are not hydrogen at the same time and Y1 is located at the 4- or 5-position, which is useful for dyeing hydrophobic fibers in brilliant red to violet shade with good fastnesses.