29927-08-0

Basic information

• Product Name: 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE
• Synonyms: ART-CHEM-BB B014634;LABOTEST-BB LT00080718;AKOS B014634;2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE;TIMTEC-BB SBB003762;5,6-dimethylbenzothiazol-2-ylamine;2-Benzothiazolamine,5,6-dimethyl-(9CI);2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE 98%
• CAS NO: 29927-08-0
• Molecular Formula: C₉H₁₀N₂S
• Molecular Weight: 178.25
• EINECS: 249-960-4
• Product Categories: BENZOTHIAZOLE;Building Blocks;Heterocyclic Building Blocks;Thiazoles;Building Blocks;C8 to C9;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 29927-08-0.mol

Chemical Properties

• Melting Point: 185-189 °C(lit.)
• Boiling Point: 342.1°C at 760 mmHg
• Flash Point: 160.7°C
• Appearance: /
• Density: 1.1355 (rough estimate)
• Vapor Pressure: 7.68E-05mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• PKA: 4.79±0.10(Predicted)
• CAS DataBase Reference: 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE(29927-08-0)
• EPA Substance Registry System: 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE(29927-08-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 29927-08-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE is used as a therapeutic agent for its anti-inflammatory properties, which can help in reducing inflammation and associated discomfort in various medical conditions. Its neuroprotective properties also make it a valuable candidate for the development of treatments aimed at protecting the nervous system and preventing neurodegenerative diseases.
Used in Chemical Industry:
In the chemical industry, 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE can be utilized as a key intermediate in the synthesis of various compounds, taking advantage of its unique chemical structure and properties. This can lead to the development of new materials and products with specific applications in different sectors.
Used in Research and Development:
Due to its unique properties, 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE can be employed in research and development for exploring its potential in various fields, such as drug discovery, material science, and chemical engineering. This can lead to the identification of new applications and the development of innovative products and technologies.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

An amine, organosulfide. Organosulfides are incompatible with acids, diazo and azo compounds, halocarbons, isocyanates, aldehydes, alkali metals, nitrides, hydrides, and other strong reducing agents. Reactions with these materials generate heat and in many cases hydrogen gas. Many of these compounds may liberate hydrogen sulfide upon decomposition or reaction with an acid. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides.

Health Hazard

ACUTE/CHRONIC HAZARDS: When heated to decomposition, 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE may emit toxic fumes of NOx and SOx.

Fire Hazard

Flash point data for 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE are not available. 2-AMINO-5,6-DIMETHYLBENZOTHIAZOLE is probably combustible.

InChI:InChI=1/C9H10N2S/c1-5-3-7-8(4-6(5)2)12-9(10)11-7/h3-4H,1-2H3,(H2,10,11)

Upstream product

• 16738-18-4 N-(3,4-dimethylphenyl)thiourea 
• 95-64-7 4-amino-o-xylene 
• 333-20-0 potassium thioacyanate 
• 7356-54-9 3,4-dimethylaniline hydrochloride 

Downstream Products

• 5683-41-0 2,5,6-trimethyl-benzothiazole 
• 57478-55-4 1-acetylamino-2-acetylsulfanyl-5,4-dimethyl-benzene 
• 113508-93-3 ethyl 6,7-dimethylimidazo<2,1-b>benzothiazole-2-carboxylate 
• 61984-83-6 ethyl-6,7-dimethylimidazo<2,1-b>benzothiazole-2-acetate 
• 123199-79-1 N-(5,6-dimethylbenzothiazol-2-yl)salicylamide 
• 77414-57-4 Cyclopropanecarboxylic acid (5,6-dimethyl-benzothiazol-2-yl)-amide 
• 100601-29-4 2-amino-4,5-dimethylbenzenethiol 

Relevant articles and documents

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.

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 and biological activities of new 1,4-benzothiazine derivatives

New 2H-1,4-benzothiazin-3(4H)-one derivatives possessing (4-phenyl-1-piperazinyl)alkyl moieties at the 2-position were synthesized and tested for calcium antagonistic and calmodulin antagonistic activities. Antihypertensive effects in spontaneously hypertensive rats were also evaluated. In general, these compounds were rather weak calcium channel blockers, although, in contrast, many of them had moderate to potent calmodulin antagonistic activity, and 2-[3-(4-(4-fluorophenyl)-1-piperazinyl]propyl]-2H-1,4-benzothiazin-3(4H )-one derivatives 45, 74 and 75 showed potent antihypertensive effects.