20358-03-6

Basic information

• Product Name: 2-Amino-5-bromobenzothiazole
• Synonyms: 5-BROMO-BENZOTHIAZOL-2-YLAMINE;2-Amino-5-bromobenzothiazole;2-Amino-5-bromobenzothiazole.HBr;2-Amino-5-bromobenzothiazole hydrobromide;5-bromobenzo[d]thiazol-2-amine;2-Amino-5-bromo-1,3-benzothiazole;2-BenzothiazolaMine, 5-broMo-;5-broMo-2-BenzothiazolaMine
• CAS NO: 20358-03-6
• Molecular Formula: C₇H₅BrN₂S
• Molecular Weight: 229.1
• EINECS: 1308068-626-2
• Product Categories: Thiazoles;API;Thiazole;Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;ThiazolesHeterocyclic Building Blocks;Building Blocks;C3 to C7;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks
• Mol File: 20358-03-6.mol

Chemical Properties

• Melting Point: 194-198 °C
• Boiling Point: 366.848 °C at 760 mmHg
• Flash Point: 175.664 °C
• Appearance: White to brown/Solid
• Density: 1.837 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.783
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 3.43±0.10(Predicted)
• Water Solubility: Soluble in water.
• CAS DataBase Reference: 2-Amino-5-bromobenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-5-bromobenzothiazole(20358-03-6)
• EPA Substance Registry System: 2-Amino-5-bromobenzothiazole(20358-03-6)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 20358-03-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-bromobenzothiazole is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique chemical structure allows it to serve as a building block in the development of new pharmaceutical compounds, contributing to the advancement of medical treatments.
As a Chemical Intermediate:
2-Amino-5-bromobenzothiazole is utilized as a chemical intermediate in the synthesis of a wide range of organic compounds. Its reactivity and functional groups enable it to participate in various chemical reactions, facilitating the production of different molecules with specific properties and applications.

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

Upstream product

• 854890-84-9 (2,5-dibromo-phenyl)-thiourea 
• 333-20-0 potassium thioacyanate 
• 591-19-5 m-Bromoaniline 
• 1147550-11-5 ammonium thiocyanate 
• 824403-26-1 5-bromo-2-chlorobenzo[d]thiazole 
• 199475-45-1 5-bromo-1,3-benzothiazol-2(3H)-one 
• 93933-49-4 2-amino-4-bromobenzenethiol 
• 768-11-6 5-bromo-benzthiazole 
• 3425-46-5 potassium selenocyanate 
• 21327-14-0 1-(3-bromophenyl)thiourea 
• 56967-17-0 m-bromoaniline hydrochloride 
• 875-51-4 4-Bromo-2-nitroaniline 
• 157645-54-0 4-bromo-2-nitro-1-thiocyanato-benzene 

Downstream Products

• 1309261-76-4 C₂₁H₁₃BrN₄OS 
• 1309261-61-7 3-(5-bromo-1,3-benzothiazol-2-yl)-2-phenylquinazolin-4(3H)-one 
• 1453813-80-3 2-(4-methoxylphenylthio)-5-bromophenylcyanamide 
• 1453813-79-0 2-(4-methylphenylthio)-5-bromophenylcyanamide 
• 1453813-85-8 ({4-bromo-2-[(5-chloro-2-methoxyphenyl)sulfanyl]phenyl}amino)carbonitrile 
• 1453813-84-7 2-(4-fluorophenylthio)-5-bromophenylcyanamide 
• 1453813-83-6 2-(2-bromophenylthio)-5-bromophenylcyanamide 
• 1453813-82-5 2-(4-chlorophenylthio)-5-bromophenylcyanamide 
• 1453813-81-4 2-(3-methylphenylthio)-5-bromophenylcyanamide 
• 1135869-10-1 2-chloro-5-(5-(1-(2-(5-bromobenzothiazol-2-yl)hydrazono)ethyl)furan-2-yl)benzoic acid 
• 66820-95-9 2-bromo-10H-phenothiazine 
• 1415695-83-8 C₁₄H₉F₃N₂OS 
• 1415695-82-7 C₁₆H₁₄N₂O₂S 
• 23451-95-8 2-amino-5-bromobenzenethiol 

Relevant articles and documents

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

PIPERIDIN-1- YL-N-PYRYDI NE-3-YL-2-OXOACET AM IDE DERIVATIVES USEFUL FOR THE TREATMENT OF MTAP-DEFICIENT AND/OR MT A-ACCUMULATING CANCERS

Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, R4, R6, R7, R8 and n are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Optimization of Benzothiazole and Thiazole Hydrazones as Inhibitors of Schistosome BCL-2

Limited therapeutic options are available for the treatment of human schistosomiasis caused by the parasitic Schistosoma flatworm. The B cell lymphoma-2 (BCL-2)-regulated apoptotic cell death pathway in schistosomes was recently characterized and shown to share similarities with the intrinsic apoptosis pathway in humans. Here, we exploit structural differences in the human and schistosome BCL-2 (sBCL-2) pro-survival proteins toward a novel treatment strategy for schistosomiasis. The benzothiazole hydrazone scaffold previously employed to target human BCL-XL was repurposed as a starting point to target sBCL-2. We utilized X-ray structural data to inform optimization and then applied a scaffold-hop strategy to identify the 5-carboxamide thiazole hydrazone scaffold (43) with potent sBCL-2 activity (IC50 30 nM). Human BCL-XL potency (IC50 13 nM) was inadvertently preserved during the optimization process. The lead analogues from this study exhibit on-target activity in model fibroblast cell lines dependent on either sBCL-2 or human BCL-XL for survival. Further optimization of the thiazole hydrazone class is required to exhibit activity in schistosomes and enhance the potential of this strategy for treating schistosomiasis.

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.

ANTIBIOTIC COMPOUNDS, PHARMACEUTICAL FORMULATIONS THEREOF AND METHODS AND USES THEREFOR

The present invention relates to compounds of formula (I) wherein G1 to G8 are as defined herein. The compounds are PK inhibitors and as such represent a new approach to treating pathogenic infections, including multidrug resistant pathogens. Disclosed herein are the compounds of formula (I), pharmaceutical compositions comprising the compounds of formula (I) and their use in the treatment of antimicrobial infection. (Formula (1))

Design, Synthesis, and Biological Evaluation of 4-Phenoxyquinoline Derivatives Containing Benzo[d]thiazole-2-yl Urea as c-Met Kinase Inhibitors

A series of novel 4-phenoxyquinoline derivatives containing the benzo[d]thiazole-2-yl urea moiety were synthesized and evaluated for their cytotoxicity against the HT-29, MKN-45, and H460 cell lines. The structures of the target compounds were confirmed by 1H NMR and MS spectra. Most of them showed moderate to excellent potency against the three tested cell lines. Especially, compound 23 was identified a promising agent (c-Met IC50 = 17.6 nM), showing the most potent anticancer activities with IC50 values of 0.18, 0.06, and 0.01 μM against the HT-29, MKN-45, and H460 cell lines, respectively. The docking results of 23 with the c-Met kinase model 3LQ8 showed a specific binding mode between the ligand and the target protein.

Probing the ATP-Binding Pocket of Protein Kinase DYRK1A with Benzothiazole Fragment Molecules

DYRK1A has emerged as a potential target for therapies of Alzheimer's disease using small molecules. On the basis of the observation of selective DYRK1A inhibition by firefly d-luciferin, we have explored static and dynamic structural properties of fragment sized variants of the benzothiazole scaffold with respect to DYRK1A using X-ray crystallography and NMR techniques. The compounds have excellent ligand efficiencies and show a remarkable diversity of binding modes in dynamic equilibrium. Binding geometries are determined in part by interactions often considered "weak", including "orthogonal multipolar" types represented by, for example, F-CO, sulfur-aromatic, and halogen-aromatic interactions, together with hydrogen bonds that are modulated by variation of electron withdrawing groups. These studies show how the benzothiazole scaffold is highly promising for the development of therapeutic DYRK1A inhibitors. In addition, the subtleties of the binding interactions, including dynamics, show how full structural studies are required to fully interpret the essential physical determinants of binding.

PHENYLIMIDE-CONTAINING BENZOTHIAZOLE DERIVATIVE OF ITS SALT AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

Provided is a phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt can selectively inhibit the protein-protein interaction between KRS and a laminin receptor (LR), thereby inhibiting migration of cancer cells. Therefore, the phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt may be usefully applied for preventing or treating the diseases associated with cancer cell metastasis.

PHENYLIMIDE-CONTAINING BENZOTHIAZOLE DERIVATIVE OR ITS SALT AND PHARMACEUTICAL COMPOSITION COMPRISING THE SAME

The present invention provides a phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt, a process for the preparation thereof, and a pharmaceutical composition comprising the same. The phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt can selectively inhibit the protein-protein interaction between KRS and a laminin receptor (LR), thereby inhibiting migration of cancer cells. Therefore, the phenylimide-containing benzothiazole derivative or its pharmaceutically acceptable salt may be usefully applied for preventing or treating the diseases associated with cancer cell metastasis.

QSAR modeling of synthesized 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potent antibacterial agents

Present communication elicits the designing and synthesis of 3-(1,3-benzothiazol-2-yl) 2-phenyl quinazolin-4(3H)-ones as potential antibacterial agents. A number of substituted 2-amino benzothiazoles, 2-amino-5-[(E)-phenyl diazenyl] benzoic acid, and 2-phenyl-4H benzo[d] [1,3] oxazin-4-one were synthesized as the precursor substrates. The compounds were synthesized in excellent yields and the structures were corroborated on the basis of IR, 1H NMR, Mass, and elemental analysis data. These compounds were screened in vitro for their antibacterial activity against a representative panel of Gram positive and Gram negative bacteria and models were generated through quantitative structure-activity relationship (QSAR).The activity contributions due to structural and substituent effects were determined using sequential regression procedure. The antimicrobial assay data show that the synthesized compounds are found to manifest profound antimicrobial activity. Springer Science+Business Media, LLC 2011.