20174-69-0

Basic information

• Product Name: 2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE
• Synonyms: (6-METHYLBENZOTHIAZOL-2-YL)-HYDRAZINE;6-METHYL-2-BENZOTHIAZOLEHYDRAZINE;1-(6-METHYLBENZO[D]THIAZOL-2-YL)HYDRAZINE;2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE;IFLAB-BB F1908-0010;SALOR-INT L482102-1EA;6-METHYL-2(3H)-BENZOTHIAZOLONE YDRAZONE;(6-Methylbenzo[d]thiazol-2-yl)-hydrazine
• CAS NO: 20174-69-0
• Molecular Formula: C₈H₉N₃S
• Molecular Weight: 179.24
• Product Categories: BENZOTHIAZOLE
• Mol File: 20174-69-0.mol
• Article Data: 21

Chemical Properties

• Melting Point: 220
• Boiling Point: 340.3 °C at 760 mmHg
• Flash Point: 159.6 °C
• Appearance: /
• Density: 1.387 g/cm³
• Vapor Pressure: 8.68E-05mmHg at 25°C
• Refractive Index: 1.774
• PKA: 2.79±0.20(Predicted)
• CAS DataBase Reference: 2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE(20174-69-0)
• EPA Substance Registry System: 2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE(20174-69-0)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 20174-69-0(Hazardous Substances Data)

Usage

Description

2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is a chemical compound with the molecular formula C8H8N4S. It is a benzothiazole derivative that features a hydrazine functional group, which makes it a potential precursor for the synthesis of other organic compounds. 2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE has garnered attention in the fields of medicinal chemistry and organic synthesis due to its unique structure and its wide range of potential applications, including pharmaceuticals, agrochemicals, dyes, and as a corrosion inhibitor.

Uses

Used in Pharmaceutical Industry:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is used as a pharmaceutical precursor for the development of new drugs, leveraging its antimicrobial and anticancer properties. Its potential in drug development is being evaluated for the treatment of various diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical sector, 2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is used as a chemical intermediate for the synthesis of agrochemicals, contributing to the development of new pesticides and other agricultural products.
Used in Dye Industry:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is utilized as a building block in the synthesis of dyes, where its unique structure can contribute to the creation of novel dyes with specific properties.
Used as a Corrosion Inhibitor:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is employed as a corrosion inhibitor in various industrial applications, where its chemical properties help to prevent the corrosion of metals, thereby extending the lifespan of equipment and structures.
Used in Antimicrobial Applications:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is used as an antimicrobial agent, which can be incorporated into products to prevent the growth of bacteria and other microorganisms, offering potential benefits in healthcare and other industries where microbial control is essential.
Used in Anticancer Applications:
2-HYDRAZINO-6-METHYL-1,3-BENZOTHIAZOLE is also being studied for its potential use as an anticancer agent, where it may contribute to the development of new therapeutic strategies against cancer.

InChI:InChI=1/C8H9N3S/c1-5-2-3-6-7(4-5)12-8(10-6)11-9/h2-4H,9H2,1H3,(H,10,11)

Upstream product

• 622-52-6 p-tolyl thiocarbamide 
• 106-49-0 p-toluidine 
• 540-23-8 p-toluidine hydrochloride 
• 622-52-6 p-methylphenylthiourea 
• 2536-91-6 6-methylbenzothiazol-2-ylamine 
• 3507-26-4 2-chloro-6-methylbenzo[d]thiazole 

Downstream Products

• 1268376-09-5 3-(3-pyridyl)-5-(4-methoxyphenyl)-4-(N-6-methyl-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole 
• 1246493-42-4 3-(3-pyridyl)-5-(4-methylphenyl)-4-(N-(6-methyl-1,3-benzothiazol-2-yl)amino)-4H-1,2,4-triazole 
• 1111097-31-4 C₁₅H₁₃BrN₄S₂ 
• 1111097-28-9 C₁₅H₁₃FN₄S₂ 
• 1111097-34-7 C₁₅H₁₃ClN₄S₂ 
• 112518-02-2 6-(4-Methoxy-phenyl)-2-(6-methyl-benzothiazol-2-yl)-4,5-dihydro-2H-pyridazin-3-one 
• 106515-46-2 1-(2'-benzothiazolyl)-3-methylpyrazol-5-ol 
• 3507-26-4 2-chloro-6-methylbenzo[d]thiazole 

Relevant articles and documents

The synthesis of some new 7-methyl-3-substituted-1,2,4-triazolo[3,4-b]benzothiazoles

New 7-Methyl-3-substituted-1,2,4-triazolo[3,4-b]benzothiazoles were synthesized from p-methylaniline to 5 with various aromatic carbonic acids. The yielded product 6a-j was investigated with Elemental analyses, NMR, MS and IR techniques.

Microwave-assisted, solvent-free, one-pot, three-component synthesis of fused pyran derivatives containing benzothiazole nucleus catalyzed by pyrrolidine-acetic acid and their biological evaluation

Abstract: An efficient method for the synthesis of fused pyran derivatives has been developed by a one-pot, three-component, solvent-free reaction of 1H-pyrazole-4-carbaldehyde and various active methylenes and malononitriles under microwave irradiation in the presence of pyrrolidine-acetic acid as bifunctional catalyst. The salient features of this protocol are the solvent-free reaction, shorter reaction time, greater selectivity, and straightforward workup procedure. All the synthesized compounds were confirmed by analytical and spectral data. The synthesized compounds were investigated against a representative panel of pathogenic strains using the broth microdilution MIC method for their in vitro antimicrobial activity. Graphical abstract: [Figure not available: see fulltext.].

Novel Triapine Derivative Induces Copper-Dependent Cell Death in Hematopoietic Cancers

Triapine, an iron chelator that inhibits ribonucleotide reductase, has been evaluated in clinical trials for cancer treatment. Triapine in combination with other chemotherapeutic agents shows promising efficacy in certain hematologic malignancies; however, it is less effective against many advanced solid tumors, probably due to the unsatisfactory potency and pharmacokinetic properties. In this report, we developed a triapine derivative IC25 (10) with potent antitumor activity. 10 Preferentially inhibited the proliferation of hematopoietic cancers by inducing mitochondria reactive oxygen species production and mitochondrial dysfunction. Unlike triapine, 10 executed cytotoxic action in a copper-dependent manner. 10-Induced up-expression of thioredoxin-interacting protein resulted in decreased thioredoxin activity to permit c-Jun N-terminal kinase and p38 activation and ultimately led to the execution of the cell death program. Remarkedly, 10 showed good bioavailability and inhibited tumor growth in mouse xenograft models. Taken together, our study identifies compound 10 as a copper-dependent antitumor agent, which may be applied to the treatment of hematopoietic cancers.

Synthesis of 2-anilinopyridyl linked benzothiazole hydrazones as apoptosis inducing cytotoxic agents

A series of 2-anilinopyridyl linked benzothiazole-hydrazone conjugates (5a-aa) were designed, synthesized and evaluated for their in vitro cytotoxic potency against a panel of cancer cell lines like mouse skin melanoma (B16F10), lung adenocarcinoma (A549), breast adenocarcinoma (MCF-7), triple negative breast cancer (MDA-MB-231) and normal lung epithelial (L132) cell lines. Preliminary screening results revealed that some of these conjugates like 5i and 5l exhibited a significant antiproliferative effect against human breast cancer (MCF-7) with IC50 values of 1.03 and 1.69 μM respectively. Further, detailed biological studies of this promising conjugate (5i) were carried out on MCF-7 cells. The flow cytometric analysis revealed that this conjugate induces cell-cycle arrest in the G2/M phase in a dose dependent manner. Furthermore, in order to determine the effect of the conjugate on cell viability, various cell based assays such as clonogenic assay, ethidium bromide staining, Hoechst staining, detection of ROS generation and annexin V-FITC/PI assays were performed. In these studies, apoptotic features were clearly observed indicating that this conjugate inhibited cell proliferation by apoptosis.