22868-34-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-Nitro-phenyl)-benzothiazole is used as a key intermediate for the synthesis of 2-substituted benzoxazoles and other benzothiazoles derivatives. These synthesized compounds exhibit anti-fungal activity, making them important in the development of new anti-fungal drugs and treatments.
Used in Chemical Industry:
In the chemical industry, 2-(4-Nitro-phenyl)-benzothiazole is utilized as a building block for the creation of various chemical compounds with diverse applications. Its unique structure allows for the development of new materials and products that can be used in different sectors, such as agriculture, textiles, and coatings.

Synthesis Reference(s)

Synthetic Communications, 18, p. 1537, 1988 DOI: 10.1080/00397918808081311Synthesis, p. 128, 1974

Upstream product

• 6244-77-5 4-nitro-N-phenylthiobenzamide 
• 31366-04-8 4-nitro-benzaldehyde-[N-(4-dimethylamino-phenyl)-oxime ] 
• 137-07-5 2-amino-benzenethiol 
• 3460-11-5 4-nitrobenzanilide 
• 39549-05-8 bis(4-nitrobenzyl)disulfide 
• 62-23-7 4-nitro-benzoic acid 
• 106098-23-1 (Z)-3-chloro-3-(4-nitrophenyl)acrylaldehyde 
• 132603-48-6 E-1-phenyl-3-methyl-4-<(4-nitrophenyl)methylene>-5-pyrazolone 
• 555-16-8 4-nitrobenzaldehdye 
• 1141-88-4 2-Aminophenyl disulfide 
• 619-73-8 4-nitrobenzyl chloride 
• 615-43-0 2-iodophenylamine 
• 1129-37-9 4-nitrobenzaldehyde oxime 
• 619-72-7 4-nitrobenzonitrile 

Downstream Products

• 6265-57-2 N-[4-(1,3-benzothiazol-2-yl)phenyl]acetamide 
• 6278-73-5 2-(4-aminophenyl)benzothiazole 
• 1388658-04-5 N-(4-benzothiazol-2-yl-phenyl)-2-(3-methoxyphenoxy)acetamide 
• 1388657-72-4 N-(4-benzothiazol-2-yl-phenyl)-2-(3-cyanophenoxy)acetamide 
• 1388658-07-8 N-(4-benzothiazol-2-ylphenyl)-2-[3-(methoxyphenyl)sulfanyl]acetamide 

Relevant academic research and scientific papers

A lipophilic thioflavin-T derivative for positron emission tomography (PET) imaging of amyloid in brain

The synthesis of a new lipophilic thioflavin-T analogue (2-[4′-(methylamino)phenyl]benzothiazole, 6) with high affinity for amyloid is reported. Intravenous injection of [11C]-labeled 6 in control mice resulted in high brain uptake. Amyloid dep

Facile one-pot synthesis of 4-aryl-3-methyl-1-phenylpyrazolo[3,4-b]-[1,5] benzothiazepine derivatives via a regioselective nucleophilic addition

4-Arylidene-3-methyl-1-phenylpyrazole-5-one reacts with 2-aminobenzenethiol in ethanol-acetic acid solution to produce a mixture of 4-aryl-3-methyl-1-phenylpyrazolo[3,4-b][1,5]benzothiazepines, 2-arylbenzothiazoles and 3-methyl-1-phenylpyrazole-5-one.

Iodine-catalyzed, one-pot, solid-phase synthesis of benzothiazole derivatives

Molecular iodine was utilized in a one-pot, solid-phase, solvent-free reaction between 2-aminothiophenol and benzoic acid derivatives to obtain highly economical and excellent yield of benzothiazole derivatives in comparison to polyphosphoric acid- and [pmIm]-Br-catalyzed microwave synthesis reactions. The results of the studies revealed that the new method reduces cost by approximately 17-fold in comparison to polyphosphoric acid and has a significant cost reduction in comparison to [pmIm]-Br. Moreover, it becomes even more economical because no additional chemicals and solvents are necessary for the reaction. Copyright Taylor & Francis Group, LLC.

An efficient conversion of phenolic esters to benzothiazoles under mild and virtually neutral conditions

Phenolic esters are efficiently converted to 2-substituted benzothiazoles in a one-pot reaction by treatment with 2-aminothiophenol in the presence of a catalytic amount of K2CO3 in N-methyl-2-pyrrolidone (NMP) at 100°C.

Method for catalyzing nitrogen heterocyclic ring aerobic dehydrogenation based on ionic liquid porous carbon material

The invention discloses a method for catalyzing nitrogen heterocycle aerobic dehydrogenation based on an ionic liquid porous carbon material, and is suitable for the field of organic synthesis. A heterogeneous catalysis system takes nitrogen heterocycle and derivatives thereof as substrates, a carbon material as a catalyst, water or ethanol as a solvent and air or oxygen spheres as an oxygen source, and a reaction is carried out at 0-80 DEG C under normal pressure, oxidative dehydrogenation of nitrogen heterocyclic compounds can be realized, and target products such as indole, quinoline, isoquinoline, quinazoline, quinoxaline, benzothiazole, Hanus ester and derivatives thereof and other medical intermediates can be synthesized. The non-metal catalyst is prepared by using the ionic liquid as the precursor, no activating agent or other additives are used in the reaction process, and the method has industrial application prospects.

A biomass-derived N-doped porous carbon catalyst for the aerobic dehydrogenation of nitrogen heterocycles

N-doped porous carbon (NC) was synthesized from sugar cane bagasse, which is a sustainable and widely available biomass waste. The preferred NC sample had a well-developed porous structure, a graphene-like surface morphology and different N species. More

Heterocyclic reaction inducted by Br?nsted–Lewis dual acidic Hf-MOF under microwave irradiation

Use of green chemistry and alternative strategies has been explored to prepare diverse organic derivatives. The combination between heterogeneous catalyst, environmentally benign reaction and high-yielding methods is gaining momentum. Herein, a defective 6-connected Hf-MOF, named Hf-BTC, was efficiently synthesized and characterized for the heterogeneous catalysis under microwave irradiation. The MOF features including structural defect, porosity, acidity, and stability was analyzed by powder X-ray diffraction, N2 sorption isotherms, acid-base titration, and thermal gravimetric analysis. In the catalytic studies, the Br?nsted-Lewis dual acidic Hf-BTC was efficiently applied for the synthesis of the heterocyclic compounds via the microwave-assisted cycloaddition and condensation reactions. The reactions proceeded smoothly in the presence of the Hf-MOF with a broad scope of substrates provided the expected products in high to excellent yields (up to 99 %) for few minutes and the catalyst could be easily recycle over many consecutive reactions without loss of its reactivity and structure.

Pyrazole-Mediated C-H Functionalization of Arene and Heteroarenes for Aryl-(Hetero)aryl Cross-Coupling Reactions

Herein we introduce a transition-metal-free protocol that involves a commercially available, inexpensive pyrazole molecule to conduct C-C cross-coupling reactions at room temperature via a radical pathway. Using this method, an aryldiazonium salt has been coupled to a wide range of arenes and heteroarenes including benzene, mesitylene, thiophene, furan, benzoxazole to result the corresponding biaryl products. The full reaction mechanism is elucidated along with the crystallographic probation of an active initiator species. A potassium-stabilized deprotonated pyrazole steers single-electron transfer to the substrate and behaves as an initiator for the reaction.

Method for catalytically synthesizing benzothiazole compound by using copper complex

The invention relates to a method for catalytically synthesizing benzothiazole compounds by using a copper complex, which is characterized in that a copper complex containing ortho-carborane Schiff base ligand is used as a catalyst to form aldehydes. 2 - Bromoaniline and sodium sulfide are used as raw materials, and the reaction is carried out at room temperature to obtain a benzothiazole compound. Compared with the prior art, the copper complex catalytic aldehyde, 2 -bromoaniline and sodium sulfide (Na) containing the ortho-carborane Schiff base ligand are utilized. 2 Multiple components of S) react to prepare benzothiazole compounds, and the catalyst is low in dosage, mild in reaction conditions, high in reaction rate, high in yield, wide in substrate range, cheap and accessible in raw materials and wide in application prospect in industry.

Fast and high-efficiency synthesis of 2-substituted benzothiazoles via combining enzyme catalysis and photoredox catalysis in one-pot

An efficient and green method, combining enzymatic and visible-light catalysis for synthesis of the widely applicable 2-substituted benzothiazoles, has been developed. This method features a relay catalysis protocol consisting of biocatalytic promiscuity