615-20-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Chlorobenzothiazole is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows it to be incorporated into a wide range of drug molecules, enhancing their therapeutic properties and effectiveness.
Used in Bioluminescent Compounds Synthesis:
2-Chlorobenzothiazole is used as a building block for the synthesis of chemiluminescent building blocks (CBTs), which are essential for the development of bioluminescent compounds used in imaging applications. These compounds play a crucial role in various research and diagnostic techniques, enabling the visualization and tracking of biological processes at the molecular level.
Used in Lubeluzole Synthesis:
2-Chlorobenzothiazole is used in the synthesis of (RS)and (S)-Lubeluzole, which are 1,3-benzothiazol-2-yl) amino-9-(10H)-acridinone derivatives. Lubeluzole is a neuroprotective agent that has been studied for its potential use in treating neurological disorders such as amyotrophic lateral sclerosis (ALS) and multiple sclerosis.
2-Chlorobenzothiazole is also used in the synthesis of 4H-thieno[2′,3′:4,5]pyrimido[2,1-b]benzothiazole derivatives. These compounds have potential applications in various fields, including pharmaceuticals, materials science, and agrochemicals, due to their unique chemical properties and potential biological activities.

Purification Methods

It is purified by fractional distillation in vacuo. The 2-chloro-3-methylbenzothiazolinium 2,4-dinitrobenzenesulfonate crystallises from Ac2O, m 162-163o(dec). [Young & Amstutz J Am Chem Soc 73 4773 1951, Brower et al. J Org Chem 19 1830 1954, Hunter & Jones J Chem Soc 2190 1930, Beilstein 27 H 44, 27 II 18, 27 III/IV 1072.]

InChI:InChI=1/C7H4ClNS/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H

Upstream product

• 95-16-9 1,3-Benzothiazole 
• 136-95-8 2-amino-benzthiazole 
• 934-34-9 2(3H)-Benzothiazolone 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 103-72-0 phenyl isothiocyanate 
• 149-30-4 2-Mercaptobenzothiazole 
• 75-15-0 carbon disulfide 
• 62-53-3 aniline 
• 67-66-3 chloroform 
• 1986-08-9 S-chloro-N-phenylisothiocarbamoyl chloride 
• 76-02-8 trifluoroacetyl chloride 
• 126507-54-8 benzothiazole-2-ylmagnesium chloride 
• 515-84-4 Ethyl trichloroacetate 

Downstream Products

• 2851-08-3 2-(piperidin-1-yl)benzo[d]thiazole 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 31837-04-4 (4-benzothiazol-2-ylamino-phenyl)-arsonic acid 
• 101092-33-5 N-methyl-N-(p-tolyl)benzo[d]thiazol-2-amine 
• 93476-68-7 N-[4-(benzothiazole-2-sulfonyl)-phenyl]-acetamide 
• 70292-64-7 2-ethoxy-1,3-benzothiazole 
• 23019-08-1 phenyl 2-benzothiazolyl ether 
• 64345-00-2 2-(phenylsulfonyl)benzo[d]thiazole 
• 19387-54-3 2-((4-nitrophenyl) thio)-1,3-benzothiazole 
• 130161-43-2 2-(benzo[d]thiazol-2-yl)-2-phenylacetonitrile 
• 19993-97-6 3-(4-methoxyphenyl)[1,2,4]triazolo[3,4-b][1,3]benzothiazole 
• 99840-80-9 2-(2-Dimethylamino-ethoxy)-benzothiazol 
• 6276-78-4 N-(4-chlorophenyl)benzo[d]thiazol-2-amine 
• 19993-96-5 3-phenylbenzo[4,5]thiazolo[2,3-c][1,2,4]triazole 

Relevant academic research and scientific papers

Novel usage of 2-BTSO2CF2H for metal-free electrophilic difluoroalkanethiolation of indoles

The electrophilic difluoromethylthiolation of indoles with 2-BTSO2CF2H is developed. In the presence of (EtO)2P(O)H and TMSCl, the reaction proceeded under mild conditions to give products in modest to high yields. This is a new application of 2-BTSO2CF2H for electrophilic difluoromethylthiolation.

Ionic Reactivity of 2-Isocyanoaryl Thioethers: Access to 2-Halo and 2-Aminobenzothia/Selenazoles

An ionic cascade insertion/cyclization reaction of thia-/selena-functionalized arylisocyanides has been successfully developed for the efficient and practical synthesis of 2-halobenzothiazole/benzoselenazole derivatives. This synthetic protocol, incorporating a halogen atom when forming the five-membered ring of benzothia/selenazoles, is different from the existing ones, where halogenation of the preformed benzothia/selenazole precursors happens. Additionally, a facile access to 2-aminobenzothiazoles is also achieved by the one-pot cascade reaction of 2-isocyanoaryl thioethers, iodine, and amines.

Deaminative chlorination of aminoheterocycles

Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]

A 2 - chlorobenzene and method of synthesizing

The invention discloses a 2 - chlorobenzene and method of synthesizing, by the benzothiazole by chlorine direct chlorination synthesis 2 - chlorobenzene and thiazole; specifically comprises the following steps: the metering the inert solvent with the benzothiazole, catalyst is added with the cooler and the tail gas absorption device, can be carried out with stirring and chlorine is introduced into the tube reactor, heating, started to access the metering of chlorine reaction; after the reaction, then after treatment to obtain the 2 - chlorobenzene and thiazole. The invention has the easy availability of raw materials, the process is simple, the operation is simple, mild reaction conditions, the solvent can be recycled, high yield, high quality, and is suitable for industrial production and the like; reduce the production cost, reduce the pollution of the environment.

Synthesis and biological evaluation of heteroarylnonanenitriles as potential antitrypanosomal agents: Serendipitous discovery of novel anticholinesterase hits

We have recently developed three antitrypanosomal leads that feature a unit of huprine or (6-chloro-)tacrine linked to a 8-cyanooctyl side chain, which, unfortunately, exhibit very potent (low nanomolar) acetylcholinesterase (AChE) inhibitory activity, which might lead to unwanted cholinergic side-effects. Because huprine and tacrine moieties impart high acetylcholinesterasic potency, we have explored their replacement by alternative heteroaromatic systems (thiazolylbenzamido, quinoxalinecarboxamido, benzimidazolecarboxamido, and benzothiazolylamino moieties), while retaining the 8- cyanooctyl side chain. These structural modifications led to the desired drop in AChE inhibitory activity (low micromolar), albeit at the expense of the antitrypanosomal potency. However, despite the lower AChE inhibitory activity of the novel compounds compared to that of the initial leads, their potency is comparable to that of some AChE inhibitors currently approved for Alzheimer’s disease (AD) treatment. They are brain permeable and less lipophilic than the leads, thereby emerging as interesting novel hits for future AChE inhibitor-based AD drug discovery programs.

Water-Promoted Chlorination of 2-Mercaptobenzothiazoles

Substituted benzothiazoles play an important role in medicinal chemistry due to their pharmacological properties. Their 2-substituted derivatives are often prepared from 2-chlorobenzothiazoles, which in turn can be synthesized from the 2-mercapto precursor using sulfuryl chloride. In practice, this seemingly straightforward and widely used reaction can be impeded by poor reproducibility and low reaction yields. In this communication, we report that the simple addition of water to the reaction leads to remarkable improvements in reaction efficiency. We attribute this effect to the formation of acid through partial hydrolysis of sulfuryl chloride. This hypothesis is supported by the observation that improved yields were also obtained in the presence of some anhydrous acidic additives. The simple combination of sulfuryl chloride and water reproducibly provides excellent yields for a range of chlorinated products.

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.

T -BuONa-mediated direct C-H halogenation of electron-deficient (hetero)arenes

An efficient halogenation of electron-deficient (hetero)arenes is described. The reaction utilizes common t-BuONa as a catalyst (for iodination) or a promoter (for bromination and chlorination), and perfluorobutyl iodide, CBr4 or CCl4 as the readily-available halogenating agents, respectively. The protocol features broad scope, high efficiency, mild conditions and gram scalability. An ionic pathway involving halogen bond formation and halophilic attack is proposed. The utility of the resulting iodinated heteroarenes is demonstrated in visible light-mediated Caryl-Caryl cross-coupling reaction.

2 - chlorobenzene and method of synthesizing (by machine translation)

The invention relates to the field of chemical industry, discloses a 2 - chlorobenzene and method of synthesizing, comprising the following steps: (1) will be 2 - mercaptobenzothiazole dispersed in water to form a paste 2 - mercapto benzothiazole; (2) to the paste 2 - mercaptobenzothiazole added in the mass fraction is 30% hydrochloric acid mixed so as to obtain a mixture; (3) the mixture is heated to 35 - 45 °C after, dropping the oxidizing agent, thermal insulation reaction to the detection to the system of 2 - mercaptobenzothiazole content of less than 0.2% stop the instillment states oxidizing agent; (4) pulling out the upper layered oily liquid is 2 - chlorobenzene and thiazole crude product. Compared with the prior art, the method reduces the waste gas output, reducing the pollution of the environment, and does not require the use of dangerous raw materials, reduces the risk of in the production process, the production cost is reduced. (by machine translation)

Efficient transposition of the sandmeyer reaction from batch to continuous process

The transposition of Sandmeyer chlorination from a batch to a safe continuous-flow process was investigated. Our initial approach was to develop a cascade method using flow chemistry which involved the generation of a diazonium salt and its quenching with copper chloride. To achieve this safe continuous process diazotation, a chemometric approach (Simplex method) was used and extrapolated to establish a fully continuous-flow method. The reaction scope was also examined via the synthesis of several (het)aryl chlorides. Validation and scale-up of the process were also performed. A higher productivity was obtained with increased safety.