16582-58-4

Basic information

• Product Name: 2-Amino-6-Iodobenzothiazole
• Synonyms: 2-Amino-6-Iodobenzothiazole;6-IODO-2-BENZOTHIAZOLAMINE;6-IODOBENZOTHIAZOL-2-YLAMINE;UKRORGSYN-BB BBV-209389;2-BenzothiazolaMine, 6-iodo-;6-Jod-benzothiazol-2-ylamin
• CAS NO: 16582-58-4
• Molecular Formula: C₇H₅IN₂S
• Molecular Weight: 276.09747
• Mol File: 16582-58-4.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 389.8±34.0 °C(Predicted)
• Appearance: /
• Density: 2.114±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 3.44±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-6-Iodobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-Iodobenzothiazole(16582-58-4)
• EPA Substance Registry System: 2-Amino-6-Iodobenzothiazole(16582-58-4)

Safety Data

• Hazardous Substances Data: 16582-58-4(Hazardous Substances Data)

Usage

General Description

2-Amino-6-Iodobenzothiazole is a chemical compound with the molecular formula C7H5IN2S. It is a derivative of benzothiazole and contains both an amino group and an iodine atom. 2-Amino-6-Iodobenzothiazole is widely used in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. Its unique structure and functional groups make it a valuable building block for the synthesis of various biologically active compounds. Additionally, it has potential applications in the field of materials science, particularly in the development of organic semiconductors and optoelectronic devices. The presence of the iodine atom also makes 2-Amino-6-Iodobenzothiazole useful in radiolabeling studies and as a precursor for the synthesis of iodinated organic compounds.

Upstream product

• 18879-80-6 1-(4-iodophenyl)thiourea 
• 15192-76-4 copper(II) thiocyanate 
• 540-37-4 p-aminoiodobenzene 
• 540-72-7 sodium thiocyanide 
• 67-66-3 chloroform 
• 7726-95-6 bromine 
• 1147550-11-5 ammonium thiocyanate 
• 333-20-0 potassium thioacyanate 

Downstream Products

• 855282-75-6 2-chloro-6-iodobenzothiazole 
• 1262983-59-4 C₆H₆INS 
• 1352149-35-9 bis(4-iodoanilin-2-yl)disulfide 

Relevant articles and documents

Chemical Genetics Reveals a Role of Squalene Synthase in TGFβ Signaling and Cardiomyogenesis

KY02111 is a widely used small molecule that boosts cardiomyogenesis of the mesoderm cells derived from pluripotent stem cells, yet its molecular mechanism of action remains elusive. The present study resolves the initially perplexing effects of KY02111 on Wnt signaling and subsequently identifies squalene synthase (SQS) as a molecular target of KY02111 and its optimized version, KY-I. By disrupting the interaction of SQS with cardiac ER-membrane protein TMEM43, KY02111 impairs TGFβ signaling, but not Wnt signaling, and thereby recapitulates the clinical mutation of TMEM43 that causes arrhythmogenic right ventricular cardiomyopathy (ARVC), an inherited heart disease that involves a substitution of myocardium with fatty tissue. These findings reveal a heretofore undescribed role of SQS in TGFβ signaling and cardiomyogenesis. KY02111 may find its use in ARVC modeling as well as serve as a chemical tool for studying TGFβ/SMAD signaling.

ARS-TiO2 photocatalyzed direct functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions under visible light

An ARS-TiO2 photocatalyst has been prepared, by a simple method through stirring a mixture of ARS and TiO2 at room temperature in the dark, to extend the photocatalytic response of titanium dioxide toward the visible light spectrum. The synergic effect of ARS and TiO2 in the photocatalyst system has catalyzed direct C-H functionalization of sp2 C-H bonds toward thiocyanation and cyclization reactions. Several aromatic and heteroaromatic scaffolds (2-phenylamino-thiazole, phenol, aniline, indole and pyrrole derivatives) were treated with the thiocyanate anion at room temperature. Herein, the first report on thiocyanation of phenol and synthesis of 2-aminobenzothiazole derivatives under visible light is presented.

Chrysin-benzothiazole conjugates as antioxidant and anticancer agents

7-(4-Bromobutoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, obtained from chrysin with 1,4-dibromobutane, was combined with a wide range of 6-substituted 2-aminobenzthiazoles, which had been prepared from the corresponding anilines with potassium thiocyanate. Free radical scavenging efficacies of newer analogues were measured using DPPH and ABTS assays, in addition to the assessment of their anticancer activity against cervical cancer cell lines (HeLa and CaSki) and ovarian cancer cell line (SK-OV-3) implementing the SRB assay. Cytotoxicity of titled compounds was checked using Madin-Darby canine kidney (MDCK) non-cancer cell line. Overall, 6a-r indicated remarkable antioxidant power as DPPH and ABTS+ scavengers; particularly the presence of halogen(s) (6g, 6h, 6j-6l) was favourable with IC50 values comparable to the control ascorbic acid. Unsubstituted benzothiazole ring favored the activity of resultant compounds (6a and 6r) against HeLa cell line, whereas presence of chlorine (6g) or a di-fluoro group (6k) was a key to exert strong action against CaSki. Moreover, a mono-fluoro (6j) and a ketonic functionality (6o) were beneficial to display anticipated anticancer effects against ovarian cancer cell line SK-OV-3. The structural assignments of the new products were done on the basis of IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.