5407-51-2

Basic information

• Product Name: benzothiazole-2,6-diamine
• Synonyms: Benzothiazole, 2,6-diamino-;2,6-Benzothiazolediamine(9CI);(2-amino-1,3-benzothiazol-6-yl)amine;2,6-Diamine-benzo[d]thiazole;1,3-benzothiazole-2,6-diamine(SALTDATA: FREE);Benzo[d]thiazole-2,6-diaMine;2,6-Diaminobenzothiazole;6-Amino-2-aminobenzothiazole
• CAS NO: 5407-51-2
• Molecular Formula: C₇H₇N₃S
• Molecular Weight: 165.22
• Product Categories: BENZOTHIAZOLE
• Mol File: 5407-51-2.mol

Chemical Properties

• Melting Point: 207 °C
• Boiling Point: 404.4°Cat760mmHg
• Flash Point: 198.4°C
• Appearance: /
• Density: 1.49g/cm³
• Vapor Pressure: 9.49E-07mmHg at 25°C
• Refractive Index: 1.838
• Storage Temp.: 2-8°C(protect from light)
• PKA: 5.78±0.10(Predicted)
• CAS DataBase Reference: benzothiazole-2,6-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: benzothiazole-2,6-diamine(5407-51-2)
• EPA Substance Registry System: benzothiazole-2,6-diamine(5407-51-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5407-51-2(Hazardous Substances Data)

Usage

Uses

Used in Dye Industry:
Benzothiazole-2,6-diamine is used as a dye intermediate for its ability to contribute to the formation of color in dyes, enhancing the colorfastness and quality of the final product.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, benzothiazole-2,6-diamine is utilized as a building block in the synthesis of various drugs, playing a crucial role in the development of new medicinal compounds.
Used in Rubber Chemicals:
Benzothiazole-2,6-diamine is employed as a component in the production of rubber chemicals, where it helps improve the performance characteristics of rubber, such as its resistance to wear and aging.
Used in Corrosion Inhibitors:
As a corrosion inhibitor, benzothiazole-2,6-diamine is used to protect metal surfaces from corrosion, extending the service life of materials and structures in various industries.
Used in Polymer Production:
Benzothiazole-2,6-diamine is used in the manufacture of different types of polymers, where it contributes to the polymer's properties, such as stability, durability, and resistance to environmental factors.
Used as a Precursor in Organic Synthesis:
Benzothiazole-2,6-diamine serves as a precursor for the synthesis of other organic compounds, enabling the creation of a wide range of chemical products with diverse applications across various industries.

InChI:InChI=1/C7H7N3S/c8-4-1-2-5-6(3-4)11-7(9)10-5/h1-3H,8H2,(H2,9,10)

Upstream product

• 22307-44-4 6-acetylamino-2-aminobenzothiazole 
• 6285-57-0 2-amino-6-nitrobenzothiazole 
• 7440-02-0 nickel 
• 3394-08-9 (4-amino-phenyl)-thiourea 
• 7440-44-0 pyrographite 

Downstream Products

• 95-24-9 6-chloro-2-aminobenzothiazole 
• 24984-19-8 1-(2-amino-benzothiazol-6-yl)-3-(4-isobutoxy-phenyl)-thiourea 
• 138962-07-9 2-(2-Amino-benzothiazol-6-ylamino)-benzoic acid 
• 659742-86-6 1-(2-aminobenzothiazol-6-yl)-3-benzoylthiourea 
• 895533-26-3 1-[6-(6-Chloro-pyrimidin-4-ylamino)-benzothiazol-2-yl]-3-(2-methoxy-5-methyl-phenyl)-urea 
• 947403-51-2 C₂₁H₁₈ClN₅O₂S 
• 1609248-77-2 C₂₀H₁₃N₅O₂S₂ 
• 1819-51-8 N-phenyl-N'-(6-chloro)benzothiazolylthiocarbamide 
• 659742-87-7 1-(2-aminobenzothiazol-6-yl)thiourea 

Relevant articles and documents

Dual Escherichia coli DNA Gyrase A and B Inhibitors with Antibacterial Activity

The emergence of multidrug-resistant bacteria is a global health threat necessitating the discovery of new antibacterials and novel strategies for fighting bacterial infections. We report first-in-class DNA gyrase B (GyrB) inhibitor/ciprofloxacin hybrids that display antibacterial activity against Escherichia coli. Whereas DNA gyrase ATPase inhibition experiments, DNA gyrase supercoiling assays, and in vitro antibacterial assays suggest binding of the hybrids to the E. coli GyrA and GyrB subunits, an interaction with the GyrA fluoroquinolone-binding site seems to be solely responsible for their antibacterial activity. Our results provide a foundation for a new concept of facilitating entry of nonpermeating GyrB inhibitors into bacteria by conjugation with ciprofloxacin, a highly permeable GyrA inhibitor. A hybrid molecule containing GyrA and GyrB inhibitor parts entering the bacterial cell would then elicit a strong antibacterial effect by inhibition of both the GyrA and GyrB subunits of DNA gyrase and potentially slow bacterial resistance development.

Discovery of Benzothiazole Scaffold-Based DNA Gyrase B Inhibitors

Bacterial DNA gyrase and topoisomerase IV control the topological state of DNA during replication and are validated targets for antibacterial drug discovery. Starting from our recently reported 4,5,6,7-tetrahydrobenzo[1,2-d]thiazole-based DNA gyrase B inhibitors, we replaced their central core with benzothiazole-2,6-diamine scaffold and interchanged substituents in positions 2 and 6. This resulted in equipotent nanomolar inhibitors of DNA gyrase from Escherichia coli displaying improved inhibition of Staphylococcus aureus DNA gyrase and topoisomerase IV from both bacteria. Compound 27 was the most balanced inhibitor of DNA gyrase and topoisomerase IV from both E. coli and S. aureus. The crystal structure of the 2-((2-(4,5-dibromo-1H-pyrrole-2-carboxamido)benzothiazol-6-yl)amino)-2-oxoacetic acid (24) in complex with E. coli DNA gyrase B revealed the binding mode of the inhibitor in the ATP-binding pocket. Only some compounds possessed weak antibacterial activity against Gram-positive bacteria. These results provide a basis for structure-based optimization toward dual DNA gyrase and topoisomerase IV inhibitors with antibacterial activity.

Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications

Transition metal catalysis that utilizes N-heterocyclic carbenes as noninnocent ligands in promoting transformations has not been well studied. We report here a cyclic (alkyl)(amino)carbene (CAAC) ligand-promoted nitro deoxygenative hydroboration with cost-effective chromium catalysis. Using 1 mol % of CAAC-Cr precatalyst, the addition of HBpin to nitro scaffolds leads to deoxygenation, allowing for the retention of various reducible functionalities and the compatibility of sensitive groups toward hydroboration, thereby providing a mild, chemoselective, and facile strategy to form anilines, as well as heteroaryl and aliphatic amine derivatives, with broad scope and particularly high turnover numbers (up to 1.8 × 106). Mechanistic studies, based on theoretical calculations, indicate that the CAAC ligand plays an important role in promoting polarity reversal of hydride of HBpin; it serves as an H-shuttle to facilitate deoxygenative hydroboration. The preparation of several commercially available pharmaceuticals by means of this strategy highlights its potential application in medicinal chemistry.

Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines

Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.

Trinuclear {Co2+-M3+-Co2+} complexes catalyze reduction of nitro compounds

This work presents synthesis and characterization of trinuclear {Co2+-Co3+-Co2+} and {Co2+-Fe3+-Co2+} complexes with accessible peripheral Co(ii) ions. Both trinuclear complexes function as efficient reusable heterogeneous catalysts for the selective reduction of assorted nitro compounds to the corresponding amines. The mechanistic investigations suggest the involvement of a Co(ii)-Co(i) cycle in the catalysis.

INHIBITORS OF CYTOMEGALOVIRUS

Compounds of Formula (I) wherein n, R1, R1A, R2, R4 and Z are defined herein, are useful for the treatment of cytomegalovirus disease and/or infection.

Nanoscale Fe2O3-based catalysts for selective hydrogenation of nitroarenes to anilines

Production of anilines - key intermediates for the fine chemical, agrochemical, and pharmaceutical industries - relies on precious metal catalysts that selectively hydrogenate aryl nitro groups in the presence of other easily reducible functionalities. Herein, we report convenient and stable iron oxide (Fe2O3) - based catalysts as a more earth-abundant alternative for this transformation. Pyrolysis of iron-phenanthroline complexes on carbon furnishes a unique structure in which the active Fe2O 3 particles are surrounded by a nitrogen-doped carbon layer. Highly selective hydrogenation of numerous structurally diverse nitroarenes (more than 80 examples) proceeded in good to excellent yield under industrially viable conditions.

Design, synthesis and antitumor activity of 6,7-disubstituted-4-(heteroarylamino)quinoline-3-carbonitrile derivatives

A series of new 6,7-disubstituted-4-(benzothiazol-6-ylamino)quinoline-3-carbonitrile derivatives (12a-l) were synthesized. The cytotoxicity of 12 new compounds was evaluated in AGS, HepG2 and HT-29 cell lines. The results showed that compounds 12g, 12h, 12i, 12k and 12l displayed more potent cytotoxic activities than Bosutinib, compound 12l exhibited the most potent antitumor activity among the tested compounds.

ISOSERINE DERIVATIVES FOR USE AS COAGULATION FACTOR IXA INHIBITORS

The invention relates to the compounds of formula (I) having antithrombotic activity which especially inhibit blood clotting factor IXa, to methods for producing the same and to the use thereof as drugs.

Cermide Kinase Modulation

A compound of formula (I) wherein R1 is a straight chain, branched or cyclic aliphatic, aromatic or heterocyclyl group comprising at least 8 carbon atoms, e.g. 8 to 22, R2 is a straight chain, branched or cyclic aliphatic, aromatic o