95-16-9

Usage

Chemical Description

Benzothiazole is a heterocyclic compound containing a benzene ring fused to a thiophene ring and a nitrogen atom.

InChI:InChI=1/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H

Upstream product

• 290-87-9 1,3,5-Triazine 
• 137-07-5 2-amino-benzenethiol 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 64-18-6 formic acid 
• 3292-42-0 2-aminobenzenethiol hydrochloride 
• 615-22-5 2-methylmercaptobenzothiazole 
• 73042-64-5 2H-1,4-benzothiazine-2,3⁽⁴⁾-dione 
• 64-19-7 acetic acid 
• 855465-40-6 1-benzothiazol-2-yl-heptan-1-ol 
• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 151-50-8 potassium cyanide 
• 121-69-7 N,N-dimethyl-aniline 
• 1123-99-5 2-iodobenzothiazole 

Downstream Products

• 99867-06-8 4-Benzothiazolyl-(2)-pyrimidin 
• 411210-33-8 N-(2-mercapto-phenyl)-N-picryl-formamide 
• 883-93-2 2-Phenylbenzothiazole 
• 1047-61-6 1-thiobenzoyloxy-2-(N-benzoylamino)benzene 
• 3119-94-6 3-ethylbenzothiazolinium iodide 
• 5284-73-1 3-methylbenzothiazolinium methyl sulfate 
• 2786-31-4 3-methylbenzothiazolium iodide 
• 136-95-8 2-amino-benzthiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 149-30-4 2-thioxo-3H-1,3-benzothiazole 
• 3622-04-6 2-carboxybenzothiazole 
• 18821-77-7 benzothiazol-2-yl-triphenyl-silane 
• 137-07-5 2-amino-benzenethiol 
• 64-18-6 formic acid 

Relevant academic research and scientific papers

Mechanistic Investigations with the Aid of Isotopic Labeling, IX. Mechanism of the Ring Contraction Reaction of 1,4-Benzthiazin-2,3-4H-dione

By 14C-labeling it is shown that the ring contraction reaction of 1,4-benzothiazin-2,3-4H-dione (1), leading via benzthiazol-2-carbonic acid (2) finally to benzthiazole (3), proceeds via hydrolytic opening of the thiolactone-bond in 1, irrespectively of H(+) or OH(-) catalysis. - (Keywords: 14C-Labeling; Ring contraction reaction; 1,4-Benzothiazin-2,3-4H-dione; Benzthiazole)

Iron-catalyzed tandem oxidative coupling and acetal hydrolysis reaction to prepare formylated benzothiazoles and isoquinolines

The aldehyde group is one of the most versatile intermediates in synthetic chemistry, and the introduction of an aldehyde group into heteroarenes is important for the transformation of molecular structure. Herein, we achieved the direct formylation of benzothiazo/les and isoquinolines. The reaction features a novel iron-catalyzed Minisci-type oxidative coupling process using commercially available 1,3-dioxolane as a formylated reagent followed by acetal hydrolysis without a separation process. The reaction can be performed under exceedingly mild reaction conditions and exhibits broad functional group tolerance.

Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds

A photoelectrochemical strategy for the cross-dehydrogenative coupling of unactivated aliphatic hydrogen donors (e.g.alkanes) with benzothiazoles is reported. We used tetrabutylammonium decatungstate as the photocatalyst to activate strong C(sp3)-H bonds in the chosen substrates, while electrochemistry scavenged the extra electrons.

A Mild, General, Metal-Free Method for Desulfurization of Thiols and Disulfides Induced by Visible-Light

A visible-light-induced metal-free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.

Unified Approach to Benzo[ d]thiazol-2-yl-Sulfonamides

In this paper, we report a unified approach to N-substituted and N,N-disubstituted benzothiazole (BT) sulfonamides. Our approach to BT-sulfonamides starts from simple commercially available building blocks (benzo[d]thiazole-2-thiol and primary and secondary amines) that are connected via (a) a S oxidation/S-N coupling approach, (b) a S-N coupling/S-oxidation sequence, or via (c) a S-oxidation/S-F bond formation/SuFEx approach. The labile N-H bond in N-monoalkylated BT-sulfonamides (pKa (BTSO2N(H)Bn) = 3.34 ± 0.05) further allowed us to develop a simple weak base-promoted N-alkylation method and a stereoselective microwave-promoted Fukuyama-Mitsunobu reaction. N-Alkyl-N-aryl BT-sulfonamides were accessed with the help of the Chan-Lam coupling reaction. Developed methods were further used in stereo and chemoselective transformations of podophyllotoxin and several amino alcohols.

Synthesis method of benzothiazole compound

The invention relates to a novel process for synthesizing benzothiazole compounds, which comprises the following steps of: (1) heating and stirring orthoester, o-aminothiophenol and derivatives thereof to react, monitoring the reaction process by TLC, and obtaining crude benzothiazole compounds after the reaction is finished; and (2) distilling the crude benzothiazole compound obtained in the step (1) or recrystallizing by using a solvent, and filtering to obtain the benzothiazole compound. According to the method, no solvent is added in the reaction process, the separation and purification process is optimized, and green production of fine chemicals is effectively achieved; and no catalyst is added, the operation is simple, the reaction time is remarkably shortened, the production efficiency of the product is improved, and the yield can reach 79%-90%. The problems of environmental pollution, potential safety hazards, harm to human health, resource waste and the like caused by the solvent are fundamentally solved, and the method has extremely high green industrialization value.

Method for reducing aromatic C-N/Cl C/I bond to aromatic-H / D

A method of reducing C an aromatic-N C/Cl/I bond to an aromatic-H / D, the process being a stable aromatic quaternary ammonium salt. After addition of the base and the solvent, the aromatic compound or the deuterated aromatic compound can be efficiently prepared by irradiation with visible light or ultraviolet light. The method can efficiently convert stable aromatic-N/I chemical bonds into aromatic-H / D bonds by visible light or ultraviolet light in a cheap and easily available solvent or deuterated solvent without using a catalyst or a transition metal compound C C. The whole production process is green, environment-friendly, low in cost, wide in substrate applicability, high in yield, high in deuterated rate, simple and convenient to operate, free of explosion risk and remarkable in advantage compared with the conventional production process.

A substituent- And temperature-controllable NHC-derived zwitterionic catalyst enables CO2upgrading for high-efficiency construction of formamides and benzimidazoles

Chemocatalytic upgrading of the greenhouse gas CO2 to valuable chemicals and biofuels has attracted broad attention in recent years. Among the reported approaches, N-formylation of CO2 with an amine is of great significance due to its versatility in the construction of N-containing linear and cyclic skeletons. Herein, a stable N-heterocyclic carbene-carboxyl adduct (NHC-CO2) was facilely prepared and could be used as a recyclable zwitterionic catalyst for efficient CO2 reductive upgrading via either N-formylation or further coupling with cyclization under mild conditions (25 °C, 1 atm CO2) using hydrosilane as a hydrogen source. More than 30 different alkyl and aromatic amines could be transformed into the corresponding formamides or benzimidazoles with remarkable yields (74%-98%). The electronic effect of the introduced substituent on NHC-CO2 was found to evidently affect the thermostability and nucleophilicity of the zwitterionic catalyst, which is directly correlated with its catalytic activity. Moreover, NHC-CO2 could supply CO2 by in situ decarboxylation at a specific temperature that is dependent on the introduced substituent type. Experimental and computational studies showed that the carboxyl species on NHC-CO2 was not only a nucleophilic center, but also a C1 source which rapidly captures or substitutes ambient CO2 during hydrosilylation. In addition, a simple and green conceptual process was designed for the product purification and catalyst recycling, with a good feasibility for small-scale production.

Reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to synthesize 1H-benzoimidazole derivatives

A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH3NH3 promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramolecular nucleophilic addition-elimination for the formation of target product. In this process, BH3NH3 served multifunctional roles, acting as a reducing agent and a formylation catalyst.

Purification of high-purity 2-mercaptobenzothiazole by two-steps

High-purity 2-mercaptobenzothiazole (2-MBT) is prepared from crude 2-MBT by aniline method under high pressure by solvent crystallization and deep impurity removal. For the first step of toluene purification, the semi-finished 2-MBT with excellent purity and yield can be obtained when the temperature of toluene solution reaches 100 oC and the content of toluene is about 1.5 times of that of crude 2-MBT. For the second step of deep purification, the by-products of semi-finished 2-MBT could be further removed by Na2SO3 when the mass ratio of water, the 2-MBT and Na2SO3 is 2: 1: 0.12 and the reaction condition is under 100 oC for 0.75 h. As a result, the purity and yield of 2-MBT can reach 99.9% and 97.3%, respectively. The preparation of high-purity 2-MBT would further optimize the market demand and meet the quality standard requirements for the development of other pharmaceutical intermediates or fine chemicals. This strategy solves the current problem of purification 2-MBT, and develops a new process technology route for the production of high-purity 2-MBT.