15864-32-1

Basic information

• Product Name: 2-Amino-6-bromobenzothiazole
• Synonyms: 6-Bromobenzothiazole-2-ylamine;2-BenzothiazolaMine, 6-broMo-;6-BroMo-2-AMino Benzo Thiazole;6-BroMobenzo thiazole-2-aMine;2-Amino-6-bromobenzothiazole,98%;2-Amino-6-bromobenzothiazole 97%;Benzothiazole, 2-amino-6-bromo-;6-bromo-1,3-benzothiazol-2-amine hydrochloride
• CAS NO: 15864-32-1
• Molecular Formula: C₇H₅BrN₂S
• Molecular Weight: 229.1
• Product Categories: Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Thiazoles;ThiazolesHeterocyclic Building Blocks
• Mol File: 15864-32-1.mol

Chemical Properties

• Melting Point: 213-217 °C(lit.)
• Boiling Point: 366.8 °C at 760 mmHg
• Flash Point: 175.7 °C
• Appearance: White/Powder
• Density: 1.836 g/cm³
• Vapor Pressure: 1.42E-05mmHg at 25°C
• Refractive Index: 1.783
• Storage Temp.: Room temperature.
• Solubility: soluble in Methanol
• PKA: 3.30±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-6-bromobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-6-bromobenzothiazole(15864-32-1)
• EPA Substance Registry System: 2-Amino-6-bromobenzothiazole(15864-32-1)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-36-43
• Safety Statements: 26-36/37
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 15864-32-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Chemical Industries:
2-Amino-6-bromobenzothiazole is used as a synthetic intermediate for the production of various 2-amino-6-arylbenzothiazole compounds, which have potential applications in the pharmaceutical and chemical industries. These compounds include:
6-p-tolylbenzo[d]thiazole-2-amine
6-(4chlorophenyl)benzo[d]thiazole-2-amine
6-(4-methoxyphenyl)benzo[d]thiazole-2-amine
6-(3,5-bis(triflouromethyl)phenyl)benzo[d]thiazole-2-amine
6-phenylbenzo[d]thiazole-2-amine
These synthesized compounds can be utilized in the development of new drugs, agrochemicals, and other specialty chemicals.
Used in Organometallic Chemistry:
2-Amino-6-bromobenzothiazole may also be employed as a ligand (L) in the synthesis of organometallic derivatives of Rh(I) [Rh(CO)2(L)(Cl)]. This application is particularly relevant in the field of organometallic chemistry, where such derivatives can be used as catalysts in various chemical reactions, contributing to the advancement of material science and chemical processes.

InChI:InChI=1/C7H5BrN2S/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,(H2,9,10)

Upstream product

• 136-95-8 2-aminobenzothiazole 
• 136-95-8 2-amino-benzthiazole 
• 2646-30-2 1-(4-bromophenyl)thiourea 
• 1147550-11-5 ammonium thiocyanate 
• 106-40-1 4-bromo-aniline 
• 103-85-5 monophenylthiourea 
• 540-72-7 sodium thiocyanide 
• 1111-67-7 copper(I) thiocyanate 
• 333-20-0 potassium thioacyanate 
• 3674-54-2 tetrabutylammonium thiocyanate 
• 21327-14-0 1-(3-bromophenyl)thiourea 
• 63450-94-2 6-bromo-benzothiazol-2-ylamine; hydrobromide 
• 624-19-1 4-bromoaniline hydrochloride 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 16628-26-5 N-(6-bromo-1,3-benzothiazol-2-yl)acetamide 
• 15864-16-1 N-(6-bromobenzo[d]thiazol-2-yl)benzamide 
• 1819-43-8 1-(6-bromo-benzothiazol-2-yl)-3-phenyl-thiourea 
• 91805-51-5 6-bromo-N-phenylbenzo[d]thiazol-2-amine 
• 75104-92-6 6-bromo-N-methyl-1,3-benzothiazol-2-amine 
• 73901-11-8 6-bromo-3-methyl-3H-benzothiazol-2-ylideneamine 
• 16582-60-8 2-amino-4,6-dibromobenzo[d]thiazole 
• 63205-31-2 3-benzyl-2-(6-bromo-benzothiazol-2-ylimino)-5-methyl-thiazolidin-4-one 
• 38956-39-7 7-bromo-2-(4-nitro-phenyl)-benzo[d]imidazo[2,1-b]thiazole 
• 3427-31-4 N-(6-bromobenzo[d]thiazol-2-yl)-2-chloroacetamide 
• 38956-37-5 7-Bromo-2-phenylimidazo<2,1-b>benzothiazole 
• 3566-95-8 1-(6-Bromo-benzothiazol-2-ylazo)-<2>naphthol 
• 38956-38-6 7-bromo-2-(4-methoxy-phenyl)-benzo[d]imidazo[2,1-b]thiazole 
• 36140-73-5 1-(6-bromo-benzothiazol-2-yl)-3,5-diphenyl-formazan 

Relevant articles and documents

Synthesis of Indane-Based 1,5-Benzothiazepines Derived from 3-Phenyl-2,3-dihydro-1H-inden-1-one and Antimicrobial Studies Thereof

In the present study, a series of 20 indane-based 1,5-benzothiazepines (5a–t) has been prepared derived from 3-phenyl-2,3-dihydro-1H-inden-1-one (1). All the synthesized 1,5-benzothiazepines (5a–t) were screened for their in vitro antimicrobial activities against four bacteria [Bacillus subtilis (MTCC 441), Staphylococcus epidermidis (MTCC 6880), Escherichia coli (MTCC 1652), and Pseudomonas aeruginosa (MTCC 424)] and two fungi [Candida albicans (MTCC 227) and Aspergillus niger (MTCC 8189)]. Among all the tested derivatives, 5n and 5o against E.?coli displayed more inhibitory activity than that of the reference drug, ciprofloxacin, while the derivatives 5c, 5m–o, 5s, and 5t against C.?albicans, and 5d, 5e, 5n, 5o, 5s, and 5t against A.?niger were found to be more potent than the standard drug, that is, fluconazole.

Application of the Suzuki-Miyaura Reaction for the Postfunctionalization of the Benzo[4,5]thiazolo[3,2- c][1,3,5,2]oxadiazaborinine Core: An Approach toward Fluorescent Dyes

A fluorescent dye based on the 8-brominated benzo[4,5]thiazolo[3,2-c][1,3,5,2]oxadiazaborinine core was synthesized from benzo[d]thiazol-2-amine. The new boron complex can be effectively modified by a palladium-catalyzed Suzuki-Miyaura cross-coupling reac

Design, synthesis and QSAR studies of 2-amino benzo[d]thiazolyl substituted pyrazol-5-ones: novel class of promising antibacterial agents

Abstract: Novel analogs of 3-(4-substituted benzylideneamino)-N-(6-substituted-1,3-benzo[d]thiazol-2-yl)-4,5-dihydro-5-oxo-pyrazole-1-carboxamide (5a–s) were designed and synthesized by reacting 3-amino-N-(6-substituted-1,3-benzo[d]thiazol-2-yl)-4,5-dihydro-5-oxo-pyrazole-1-carboxamide (4a–d) with p-substituted benzaldehydes. The Infrared Spectroscopy, 1H-Nuclear Magnetic Resonance, 13C-Nuclear Magnetic Resonance, and High Resolution Mass Spectra spectral data confirmed the structures of all the novel synthesized compounds. Among the series tested, two compounds 5k and 5o displayed promising antibacterial activity especially against Staphylococcus aureus (MIC = 3.14 and 1.57 μg/mL) and Bacillus subtilis (MIC = 3.12 and 1.84 μg/mL) respectively. Further, these title compounds were also assessed for their cytotoxic activity (IC50) against mammalian Vero cell line using 3-(4,5-dimethylthiazo-2-yl)-2,5-diphenyl-tetrazolium bromide assay, indicating that the compounds exhibit antibacterial activity at non-cytotoxic concentrations. Field based three-dimensional quantitative structure–activity relationships were also discussed based on the antimicrobial screening data. Graphical Abstract: Synthesis, spectral studies, antibacterial evaluation and QSAR studies of nineteen novel Schiff bases of pyrazol-5-one derivatives derived from 2-aminobenzothiazole nucleus are described.

Iodine-catalyzed amination of benzothiazoles with KSeCN in water to access primary 2-aminobenzothiazoles

A facile and sustainable approach for the amination of benzothiazoles with KSeCN using iodine as the catalyst in water has been disclosed under transition-metal free conditions. The reaction proceeded smoothly to afford various primary 2-amino benzothiazoles in up to 96% yield. A series of control experiments were performed, suggesting a ring-opening mechanism was involved via a radical process. This protocol provides efficient synthesis of primary 2-aminobenzothiazoles

Condensation of 2-Amino-1,3-thiazole Salts and Benzo Analogs with Trifluoroacetylacetone

Abstract: The condensation of 2-amino-1,3-thiazolium perchlorates and their benzo analogs with trifluoro-acetyl-acetone in acetic acid afforded the corresponding [1,3]thiazolo[3,2-a]pyrimidinium, pyrimido[2,1-b][1,3]benzothiazolium, and naphtho[2′,1′:4,5][1,3]thiazolo[3,2-a]pyrimidinium salts as a single isomer in which the trifluoromethyl group is located in the γ-position with respect to the bridgehead nitrogen atom. The structure of the synthesized compounds was confirmed by 1H NMR spectra and elemental analyses.

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.

Synthesis, Type II diabetes inhibitory activity, antimicrobial evaluation and docking studies of indeno[1,2-c]pyrazol-4(1H)-ones

We report a convenient and efficient synthesis of indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) by the reaction of a variety of 2-acyl-(1H)-indene-1,3(2H)-diones (1) and 2-hydrazinylbenzo[d]thiazole/2-hydrazinyl-6-substitutedbenzo[d]thiazoles (2) in the presence of glacial acetic acid in good yields. The structure of the compounds thus prepared were confirmed by analytical and spectral (FT-IR, 1H NMR, 13C NMR, and HRMS) techniques. All the synthesized indeno[1,2-c]pyrazol-4(1H)-ones (4a?o) were assayed for their in vitro Type II diabetes inhibitory activity by using Acarbose as standard drug and in vitro antimicrobial activity utilizing Streptomycin and Fluconazole as reference drugs. Among the synthesized derivatives, 4e (IC50 = 6.71 μg/mL) was found to be more potent against α-glucosidase enzyme as compared with the standard Acarbose (IC50 = 9.35 μg/mL) and 4i (IC50 = 11.90 μg/mL) exhibited good inhibitory activity against α-amylase enzyme as compared with the standard Acarbose (IC50 = 22.87 μg/mL). Also, all the titled compounds showed good antimicrobial activity. In addition, in vitro α-glucosidase and α-amylase inhibition were supported by docking studies performed on the derivatives 4e and 4o, respectively. [Figure not available: see fulltext.].

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.

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.

NOVEL APOPTOSIS SIGNAL-REGULATING KINASE 1 INHIBITORS

The present invention relates to inhibitors of apoptosis signal-regulating kinase 1 ("ASK1"), a process for synthesis of the compounds of the present invention, composition comprising the compounds and use of the compounds for inhibition of ASK1.