924708-78-1

Basic information

• Product Name: 6-CHLORO-2-(1,1-DIMETHYLETHYL)BENZOTHIAZOLE
• Synonyms: 6-CHLORO-2-(1,1-DIMETHYLETHYL)BENZOTHIAZOLE
• CAS NO: 924708-78-1
• Molecular Formula: C11H12ClNS
• Molecular Weight: 0
• Mol File: 924708-78-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-CHLORO-2-(1,1-DIMETHYLETHYL)BENZOTHIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-CHLORO-2-(1,1-DIMETHYLETHYL)BENZOTHIAZOLE(924708-78-1)
• EPA Substance Registry System: 6-CHLORO-2-(1,1-DIMETHYLETHYL)BENZOTHIAZOLE(924708-78-1)

Safety Data

• Hazardous Substances Data: 924708-78-1(Hazardous Substances Data)

Upstream product

• 103197-72-4 p-Chlor-pivalinsaeurethioanilid 
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• 106-47-8 4-chloro-aniline 
• 873-38-1 4-chloro-2-bromoaniline 
• 3282-30-2 pivaloyl chloride 
• 2942-10-1 6-chloro-1,3-benzothiazole 
• 75-98-9 Trimethylacetic acid 
• 23474-98-8 2-amino-5-chlorobenzenethiol 
• 59997-51-2 trimethylacetylacetonitrile 
• 195372-65-7 N-(2-bromo-4-chlorophenyl)pivalamide 

Relevant articles and documents

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.

Method for preparing alkyl benzothiazole derivative under visible light

The invention discloses a method for preparing an alkyl benzothiazole derivative under visible light, which specifically comprises the following steps: under the protection of inert gas, adding N-(2-bromophenyl) alkyl thioamide and inorganic base into a reaction container provided with a stirring device, then adding dimethyl sulfoxide, stirring and reacting for 24 hours at room temperature under the irradiation of visible light, and obtaining the alkyl benzothiazole derivative. 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) alkyl thioamide are realized. In addition, the alkylbenzothiazole derivative 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 alkylbenzothiazole derivative.

Visible Light-Induced Decarboxylative Alkylation of Heterocyclic Aromatics with Carboxylic Acids via Anthocyanin as a Photocatalyst

A visible light-induced decarboxylative alkylation of heterocyclic aromatics with aliphatic carboxylic acids was developed by using anthocyanins as a photocatalyst under mild conditions. A series of alkylated heterocyclic compounds were obtained in modera

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.

Photocatalytic Oxidative C-H Thiolation: Synthesis of Benzothiazoles and Sulfenylated Indoles

We report studies on the photocatalytic formation of C-S bonds to form benzothiazoles via an intramolecular cyclization and sulfenylated indoles via an intermolecular reaction. Cyclic voltammetry (CV) and density functional theory studies suggest that benzothiazole formation proceeds via a mechanism that involves an electrophilic sulfur radical, while the indole sulfenylation likely proceeds via a nucleophilic sulfur radical adding into a radical cationic indole. These conditions were successfully extended to several thiobenzamides and indole substrates.

External Oxidant-Free Oxidative Cross-Coupling: A Photoredox Cobalt-Catalyzed Aromatic C-H Thiolation for Constructing C-S Bonds

An external oxidant-free oxidative coupling for aromatic C-H thiolation by visible-light photoredox cobalt-catalysis has been developed. Various substrates could afford benzothiazoles in good to excellent yields, and only H2 is generated as a side product. When catalytic TBAOH was used as the base, not only 2-aryl but also 2-alkylbenzothiazoles could be obtained through this novel dehydrogenative coupling reaction. This method could be scaled up and applied to the synthesis of biologically active molecules bearing benzothiazole structural scaffolds (potent antitumor agents). Furthermore, the unexpected oxidation byproduct amides, which are often generated in oxidative cyclization of thiobenzanilides, can be completely avoided. Mechanistic studies showed that the H2 originates from the substrates. The kinetic studies indicate that the interaction between the cobalt catalyst and proton might be involved in the rate-limiting process. (Chemical Equation Presented).

Organocatalytic syntheses of benzoxazoles and benzothiazoles using aryl iodide and oxone via C-H functionalization and C-O/S bond formation

An organocatalytic protocol for the syntheses of 2-substituted benzoxazoles and benzothiazoles is described from alkyl-/arylanilides and alkyl-/arylthioanilides using 1-iodo-4-nitrobenzene as catalyst and oxone as an inexpensive and environmentally safe terminal oxidant at room temperature in air via oxidative C-H functionalization and C-O/S bond formation. The procedure is simple and general and provides an effective route for the construction of functionalized 2-alkyl-/arylbenzoxazoles and 2-alkyl-/arylbenzothiazoles with moderate to high yields. The synthetic and mechanistic aspects have been described.

Silver catalyzed decarboxylative direct C2-alkylation of benzothiazoles with carboxylic acids

A novel and efficient silver catalyzed decarboxylative direct C2-alkylation of benzothiazoles with carboxylic acids for the synthesis of 2-alkyl benzothiazoles was developed.

Microwave-assisted "green" synthesis of 2-alkyl/ arylbenzothiazoles in one pot: A facile approach to anti-tumor drugs

A series of new 2-alkyl/arylbenzothiazoles has been synthesized on the basis of the potent and selective in vitro anti-tumor properties of 2-(3,4-diethoxyphenyl)-5-fluorobenzothiazole. The synthesis of benzothiazole analogs was achieved via microwave irradiation of a 1:1 mixture of o-aminothiophenol and alkyl/aryl acylacetonitriles at temperature of 200 °C for 10 min. The yields are very good to excellent. All the products were characterized by 1H nmr, 13C nmr and elemental analysis.