1477-42-5

Basic information

• Product Name: 2-Amino-4-methylbenzothiazole
• Synonyms: 2-Amino-4-methylbenz;2-amino-4-methyl-benzothiazol;4-Methyl-2-aminobenzothiazole;4-methyl-2-benzothiazolamin;4-Methyl-2-benzothiazolamine;Benzothiazole, 2-amino-4-methyl-;AURORA 18742;LABOTEST-BB LT00080789
• CAS NO: 1477-42-5
• Molecular Formula: C8H8N2S
• Molecular Weight: 164.23
• EINECS: 216-028-3
• Product Categories: melting point: 137°C-139°C;BENZOTHIAZOLE;Thiazoles;Building Blocks;Heterocyclic Building Blocks
• Mol File: 1477-42-5.mol

Chemical Properties

• Melting Point: 137-139 °C(lit.)
• Boiling Point: 322 °C at 760 mmHg
• Flash Point: 148.6 °C
• Appearance: White powder
• Density: 1.1724 (rough estimate)
• Vapor Pressure: 0.000287mmHg at 25°C
• Refractive Index: 1.5700 (estimate)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: pK1: 4.7(+1) (25°C)
• Water Solubility: <0.1 g/100 mL at 24℃
• Sensitive: Moisture Sensitive
• BRN: 129346
• CAS DataBase Reference: 2-Amino-4-methylbenzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-4-methylbenzothiazole(1477-42-5)
• EPA Substance Registry System: 2-Amino-4-methylbenzothiazole(1477-42-5)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-28-36/37/39-24/25
• WGK Germany: 3
• RTECS: DL2275000
• TSCA: Yes
• Hazardous Substances Data: 1477-42-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-Amino-4-methylbenzothiazole is used as a key intermediate in the synthesis of various organic compounds. It is particularly utilized in the synthesis of N-(4-methyl-1,3-benzothiazol-yl)-N-[(1,4,5,8-tetramethoxy-2-napthyl)methylidene]amine and Schiff's base via condensation with 2-acetonaphthone. This application is crucial in the development of new chemical entities with potential applications in various fields, such as pharmaceuticals, materials science, and agrochemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Amino-4-methylbenzothiazole is used as a building block for the development of novel therapeutic agents. Its unique chemical structure allows for the creation of new drugs with potential applications in treating various diseases and medical conditions.
Used in Materials Science:
2-Amino-4-methylbenzothiazole can also be employed in the field of materials science, where it can be used to develop new materials with specific properties. Its incorporation into polymers or other materials can lead to the creation of materials with enhanced performance characteristics, such as improved stability, reactivity, or conductivity.
Used in Agrochemicals:
In the agrochemical industry, 2-Amino-4-methylbenzothiazole can be used as a starting material for the synthesis of various agrochemicals, such as pesticides, herbicides, and fungicides. Its unique chemical properties make it a valuable component in the development of new and effective products for agricultural applications.

Air & Water Reactions

2-Amino-4-methylbenzothiazole is sensitive to moisture. 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-4-methylbenzothiazole emits very toxic fumes of SOx and NOx.

Fire Hazard

Flash point data for 2-Amino-4-methylbenzothiazole are not available. 2-Amino-4-methylbenzothiazole is probably combustible.

InChI:InChI=1/C8H8N2S/c1-5-3-2-4-6-7(5)10-8(9)11-6/h2-4H,1H3,(H2,9,10)

Upstream product

• 2268-77-1 4-methylbenzo[d]thiazole-2(3H)-thione 
• 614-78-8 o-tolylthiourea 
• 7791-25-5 sulfuryl dichloride 
• 108-90-7 chlorobenzene 
• 79-01-6 Trichloroethylene 
• 636-21-5 o-toluidine hydrochloride 
• 7440-44-0 pyrographite 
• 95-53-4 o-toluidine 
• 1147550-11-5 ammonium thiocyanate 
• 333-20-0 potassium thioacyanate 
• 583-60-8 2-Methylcyclohexanone 
• 17356-08-0 thiourea 

Downstream Products

• 1819-99-4 1-(4-methyl-benzothiazol-2-yl)-3-phenyl-thiourea 
• 3622-32-0 2-chloro-4-methyl-benzothiazole 
• 1819-96-1 1-(4-methyl-benzothiazol-2-yl)-3-p-tolyl-thiourea 
• 5923-69-3 1-benzyl-3-(4-methyl-benzothiazol-2-yl)-thiourea 
• 108719-45-5 1-(4-methyl-benzothiazol-2-yl)-3-phenyl-urea 
• 1819-95-0 1-(4-chloro-phenyl)-3-(4-methyl-benzothiazol-2-yl)-thiourea 
• 3323-85-1 2-chloro-N-(4-methylbenzothiazol-2-yl)acetamide 
• 1819-92-7 1-(4-methoxy-phenyl)-3-(4-methyl-benzothiazol-2-yl)-thiourea 
• 1819-91-6 1-(4-ethoxy-phenyl)-3-(4-methyl-benzothiazol-2-yl)-thiourea 
• 1819-98-3 1-(4-methyl-benzothiazol-2-yl)-3-o-tolyl-thiourea 
• 1819-97-2 1-(4-methyl-benzothiazol-2-yl)-3-m-tolyl-thiourea 
• 1819-94-9 1-(4-bromo-phenyl)-3-(4-methyl-benzothiazol-2-yl)-thiourea 
• 1457-46-1 3-phenylrhodanine 
• 117844-38-9 N,N'-Bis-(6-methyl-benzothiazol-2-yl)-hydrazine; hydrobromide 

Relevant articles and documents

ETUDE DE LA FRAGMENTATION PAR IMPACT ELECTRONIQUE DE DERIVES DU BENZOTHIAZOLE

The mass spectra of eighteen substituted benzothiazoles are reported and discussed.All these compounds are thermodynamically stable and give an intense molecular ion, which undergoes different types of fragmentation depending on the nature of the substituent which is rarely eliminated directly. β-Cleavage with respect to the heterocyclic double bond is often obseved.Specific 2H-, 13C-, 15N- and 34S-labelling have been used in order to confirm the fragmentation patterns.

Method for synthesizing 4-methyl-2-benzothiazolehydrazine

The invention discloses a method for synthesizing 4-methyl-2-benzothiazolehydrazine. The method comprises the following steps: carrying out synthesis reaction on o-toluidine and thiocyanate in acid toobtain o-tolylthiourea; carrying out a synthesis reaction on the o-tolylthiourea and a catalyst in water to obtain 2-amino-4-methylbenzothiazole; and carrying out a synthesis reaction on the 2-amino-4-methylbenzothiazole in hydrazine hydrate, so as to obtain the 4-methyl-2-benzothiazolehydrazine. The method for synthesizing the 4-methyl-2-benzothiazolehydrazine, provided by the invention, is simple to operate, less in three wastes, capable of repeatedly applying wastewater, high in product content, good in quality and suitable for industrial mass production.

Scalable synthesis and antibacterial evaluation of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles

A new series of 2-(3-(N-(substituted phenyl)sulfamoyl)ureido)benzothiazoles was synthesized via a one-pot efficient and scalable method, involving the condensation of 2-aminobenzothiazoles derivatives, substituted anilines, and chlorosulfonyl isocyanate. The products were obtained in good yield with a simple workup, and their structures were confirmed from their spectral analyses. The synthesized compounds were further screened for their antibacterial activity against Gram-positive and Gram-negative pathogenic strains. The molecules show promising activity in the MIC value range of 2–0.25 μg/ml against selected bacterial strains, especially against nonfermentative carbapenem-resistant bacteria (Pseudo VIM-2 and Acinetobacter baumanni).

SN-Donor methylthioanilines and copper(II) complexes: Synthesis, spectral properties, and in vitro antimicrobial activity

Methylthioanilines, a series of sulfur-nitrogen donor ligands substituted with OCH3, CH3, Cl, and Br, and their copper(II) complexes have been synthesized and characterized by 1H and 13C NMR, elemental analysis, FTIR, UV-Vis and EPR spectra, molar conductance, and magnetic susceptibility measurements. The NMR spectra of the ligands revealed that the para/ortho protons and para carbon were sensitive to the electronic effect of substituents. The CHNS analysis presented CuLCl2 (L = OCH3, CH3, Cl) and CuL2Cl2 (L = Br) stoichiometries for the copper complexes. FTIR spectra showed that the bidentate ligands were coordinated to the copper ion through their nitrogen and sulfur atoms. The electronic spectra have suggested square planar and octahedral geometries for these complexes. The EPR spectra demonstrated that the solid state copper(II) complexes possess dx2-y2 orbital ground state and g= > g > 2.0023 in a tetragonal environment. The compounds were evaluated for in vitro antimicrobial activity against S. aureus, B. subtilis, E. coli, and C. albicans. The copper complexes showed higher activity than the parent ligands against S. aureus and B. subtilis; the electron-donating OCH3 and CH3 derivatives were more active than the withdrawing Br- A nd Cl-substituted compounds.

[...] aromatic amines acetylcholine esterase inhibitor synthesis and use (by machine translation)

The present invention provides a formula for the (I) or (II) [...] aromatic amines of the acetylcholine esterase inhibitor and its pharmaceutically acceptable salt or a stereoisomer thereof, a process for their preparation and its in the preparation of acetylcholine esterase inhibitors and treatment of Alzheimer's disease and/or myasthenic application of the medicament, type definition of each group in the specification. The invention of aromatic amine derivatives as [...] of acetylcholine esterase inhibitors with micromolar level to nanomolar inhibiting activity, has further developed into an anti-Alzheimer's disease possibility of drug. (by machine translation)

Preparation method of 2-amino-4-methylbenzothiazole

The invention relates to a preparation method of 2-amino-4-methylbenzothiazole. The preparation method comprises the steps of cyclization reaction, filtering and washing, recycling and the like. By the method, operation risks are reduced, the utilization rate of sulfuric acid is increased, zero emission of gas is realized basically, the emission amount of waste water is reduced effectively, and thus, the yield of synthesis is stable.

Preparation method of tricyclazole intermediate

The invention relates to a preparation method of a tricyclazole intermediate. According to the preparation method, 2-methyl-cyclohexan-1-one and thiourea are taken as reaction raw materials, environment-friendly, and safe and economic air is taken as an oxidant, so that the tricyclazole intermediate is prepared under an alkali catalyst system.

Discovery of 18β-glycyrrhetinic acid conjugated aminobenzothiazole derivatives as Hsp90-Cdc37 interaction disruptors that inhibit cell migration and reverse drug resistance

A series of 18β-glycyrrhetinic acid (GA) conjugated aminobenzothiazole derivatives were designed, synthesized and evaluated for disruption activity of Hsp90-Cdc37 as well as the effects of in vitro cell migration. These compounds exhibited relatively good disruption activity against Hsp90-Cdc37 with IC50 values in low micromolar range. A docking study of the most active compound 11g revealed key interactions between 11g and Hsp90-Cdc37 complex in which the benzothiazole moiety and the amine chain group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU and showed potent suppression activity against drug-resistant cancer cells. In particular, compound 11 g appeared to be the most potent compound against the A549 cell line, at least partly, by inhibition of the activity of Hsp90 and apoptosis induction. The treatment of A549 cells with compound 11g resulted in inhibition of in vitro cell migration through wound healing assay and S phase of cell cycle arrested. In addition, 11g-induced apoptosis was significantly facilitated in A549 cells. Thus, we conclude that GA aminobenzothiazole derivatives may be the potential Hsp90-Cdc37 disruptors with the ability to suppress cells migration and reversed drug-resistant.

Novel Piperine Derivatives with Antidiabetic Effect as PPAR-γ Agonists

Piperine is an alkaloid responsible for the pungency of black pepper. In this study, piperine isolated from Piper nigrum L. was hydrolyzed under basic condition to obtain piperic acid and was used as precursor to carry out the synthesis of twenty piperine derivatives containing benzothiazole moiety. All the benzothiazole derivatives were evaluated for their antidiabetic potential by OGT test followed by assessment of active derivatives on STZ-induced diabetic model. It was observed that nine of twenty novel piperine analogues (5b, 6a-h), showed significantly higher antidiabetic activity in comparison with rosiglitazone (standard). Furthermore, these active derivatives were evaluated for their action as PPAR-γ agonists demonstrating their mechanism of action. The effects on body weight, lipid peroxidation, and hepatotoxicity after administration with active derivatives were also studied to further establish these derivatives as lead molecules for treatment of diabetes with lesser side-effects.

Efficient and facile protocol for one-pot synthesis of 2-amino-substituted benzothiazoles catalyzed by nano-BF3/SiO2 under mild conditions

Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles through the reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described. In this method, all of the 2-amino-substituted benzothiazoles were obtained in high to excellent yields and short reaction times under mild conditions. The structures of the resulting products were characterized and confirmed by melting point, FT-IR, 1H NMR and 13C NMR techniques. Graphical Abstract: A highly efficient and simple protocol for the preparation of 2-aminobenzothiazoles by reaction of potassium thiocyanate and substituted anilines in the presence of nano-BF3/SiO2 as a reusable heterogeneous catalyst is described.[Figure not available: see fulltext.]