1747-46-2

Usage

Uses

Used in Pharmaceutical Industry:
BENZOTHIAZOLE, 2-(2-FLUOROPHENYL)is utilized as a building block in the synthesis of pharmaceuticals for its potential medicinal properties. The presence of the fluorine atom can impart specific characteristics to the compound, such as increased lipophilicity or metabolic stability, which are advantageous in drug development.
Used in Agrochemical Industry:
In the agrochemical sector, BENZOTHIAZOLE, 2-(2-FLUOROPHENYL)serves as a key intermediate in the production of pesticides. Its chemical structure can be tailored to target specific pests or to enhance the effectiveness and selectivity of the agrochemicals.
Used in Organic Synthesis:
BENZOTHIAZOLE, 2-(2-FLUOROPHENYL)is employed as a versatile intermediate in organic synthesis, allowing for the creation of a wide range of organic compounds. Its unique structure and the presence of the fluorine atom make it a valuable component in the synthesis of various specialty chemicals and materials.
Used in Research and Development:
BENZOTHIAZOLE, 2-(2-FLUOROPHENYL)is also used in research and development settings to explore new chemical reactions and to understand the effects of fluorine substitution on the properties and reactivity of benzothiazole derivatives. This can lead to the discovery of new applications and improvements in existing ones.

InChI:InChI=1/C13H8FNS/c14-10-6-2-1-5-9(10)13-15-11-7-3-4-8-12(11)16-13/h1-8H

Upstream product

• 2027-54-5 2-fluoro-N-phenyl-thiobenzamide 
• 1629-20-5 2-Chlor-N-(2-fluor-thiobenzoyl)-anilin 
• 394-47-8 2-fluorobenzonitrile 
• 137-07-5 2-amino-benzenethiol 
• 446-52-6 2-Fluorobenzaldehyde 
• 1391062-84-2 C₁₃H₁₀FNS 
• 95-16-9 1,3-Benzothiazole 
• 79477-86-4 2-fluorophenylglyoxylic acid 
• 89-99-6 2-fluorobenzylamine 
• 376605-69-5 C₁₃H₁₁FIN 
• 1034926-54-9 bis(2-fluorophenyl)iodonium tetrafluoroborate 
• 445-29-4 o-fluoro-benzoic acid 
• 95-52-3 2-Fluorotoluene 
• 615-36-1 2-bromoaniline 

Downstream Products

• 1440999-80-3 2-(benzo[d]thiazol-2-yl)-3-fluorophenyl acetate 
• 1454287-69-4 (2-(benzo[d]thiazol-2-yl)-3-fluorophenyl)(phenyl)methanone 
• 152993-87-8 2-(2,6-difluorophenyl)-1,3-benzothiazole 

Relevant academic research and scientific papers

The Construction of C-N, C-O, and C(sp2)-C(sp3) Bonds from Fluorine-Substituted 2-Aryl Benzazoles for Direct Synthesis of N-, O-, C-Functionalized 2-Aryl Benzazole Derivatives

Herein, a general and practical route to 2-(2-aminophenyl)- and 2-(2-alkoxyphenyl)-substituted benzazoles by nucleophilic aromatic substitution (SNAr) is described. Upon treatment with Cs2CO3, the formation of C-N, C-O bonds occur between fluorine-substituted 2-aryl benzazoles and a diverse range of nitrogen, oxygen nucleophiles to provide the targets in good to excellent yields. Commercially available nucleophiles and high atom economy are notable features of the protocol. Meanwhile, the construction of C(sp2)-C(sp3) bond was also furnished in the presence of palladium catalyst.

Photocatalyst- And Transition-Metal-Free Visible-Light-Promoted Intramolecular C(sp2)-S Formation

A photocatalyst- and transition-metal-free visible-light-induced cyclization of ortho-halothiobenzanilides has been developed. Upon irradiation with visible light, substrates undergo dehalogenative cyclization to 2-aryl benzothiazoles with high efficiency and selectivity. This photocyclization exhibits a high tolerance to various functional groups, is applicable for the synthesis of 2-alkyl benzothiazoles, and is easy to set up for gram-scale reaction.

Visible-Light Carbon Nitride-Catalyzed Aerobic Cyclization of Thiobenzanilides under Ambient Air Conditions

A metal-free heterogeneous photocatalysis has been developed for the synthesis of benzothiazoles via intramolecular C-H functionalization/C-S bond formation of thiobenzanilides by inexpensive graphitic carbon nitride (g-C3N4) under visible-light irradiation. This reaction provides access to a broad range of 2-substituted benzothiazoles in high yields under an air atmosphere at room temperature without addition of a strong base or organic oxidizing reagents. In addition, the catalyst was found to be stable and reusable after five reaction cycles.

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C-S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles

An efficacious and mild KOtBu-promoted intramolecular C-S cross-coupling of ortho-iodothioanilides in conjunction with a catalytic quantity of phenanthroline as an additive has been described for the convenient synthesis of 2-substituted benzothiazoles. The methodology is suitable for attaining a wide variety of 2-alkyl- and 2-aryl-substituted benzothiazoles. Single-crystal XRD, DFT calculations, NMR, and UV studies suggest that halogen bonds between the units of ortho-iodothioanilides may assist in the electron transfer process.

Method for preparing benzothiazole compound from visible light promoted N-(2-bromophenyl) thioamide

The invention discloses a method for preparing a benzothiazole compound from N-(2-bromophenyl) thioamide under the promotion of visible light. Specifically, under the protection of inert gas, according to the molar ratio of N-(2-bromophenyl) thioamide to inorganic base being 1: 0.5, reactants are added into a reaction container provided with a stirring device, then dimethyl sulfoxide is added, and stirring reaction is carried out for 2-24 hours at room temperature under the irradiation of visible light to obtain the benzothiazole compound. Under the condition of not adding any photosensitizer or transition metal catalyst, sodium phosphate is used as alkali, and under the irradiation of a 45W household compact fluorescent lamp, a series of intramolecular cross-coupling reactions of N-(2-bromophenyl) thioamide are realized. In addition, the benzothiazole compound can be obtained with high yield. The whole process is green, efficient and easy to operate, and the method is a good method for synthesizing the benzothiazole compound.

NCS/TBHP promoted C2 arylation of benzothiazoles with aldehydes in DMSO

A N-chlorosuccinimide catalyzed oxidative synthesis of 2-aryl benzothiazole from benzothiazoles and aryl aldehydes using tert-butyl peroxybenzoate as an oxidant in dimethyl sulfoxide (DMSO) has been developed in moderate to good yields. Solvent DMSO as a strong Lewis base plays an efficient role in the reaction. Various substrates were tolerated under optimized conditions affording the arylated products in 12–94% yields for 28 examples. Additionally, acylated benzothiazoles were produced with 4 examples.

Preparation method of substituted benzothiazole C2 arylated derivative

The invention discloses a substituted benzothiazole C2 arylated derivative and a preparation method thereof. The preparation method comprises the following steps: mixing substituted benzothiazole represented by a formula (II) and substituted benzaldehyde represented by a formula (III); adding a free radical initiator N-chlorosuccinimide (NCS) and an oxidant tert-butyl hydroperoxide (TBHP), carrying out a stirring reaction for about 12 h at 120 DEG C in a nitrogen atmosphere by using DMSO as a solvent, and after the reaction is finished, separating and purifying the reaction liquid to prepare the substituted benzothiazole C2 arylated derivative represented by a formula (I). The invention provides a new method for synthesizing a benzothiazole C2 arylated derivative by taking an NCS/TBHP double component as an oxidation system through a stirring and reaction for about 12 hours at 120 DEG C in a nitrogen atmosphere under the assistance of a strong Lewis base DMSO; and according to the method, an NCS/TBHP double-component oxidation system and an aprotic solvent are selected, and the method has the advantages of being simple in catalytic system, good in product yield and wide in substrate range.

Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Synthesis of Benz-Fused Azoles via C-Heteroatom Coupling Reactions Catalyzed by Cu(I) in the Presence of Glycosyltriazole Ligands

Glycosyl triazoles are conveniently accessible and contain multiple metal-binding units that may assist in metal-mediated catalysis. Azide derivatives of d-glucose have been converted to their respective aryltriazoles and screened as ligands for the synthesis of 2-substituted benz-fused azoles and benzimidazoquinazolinones by Cu-catalyzed intramolecular Ullmann type C-heteroatom coupling. Good to excellent yields for a variety of benz-fused heterocyles were obtained for this readily accessible catalytic system.