1123-98-4

Usage

Chemical Properties

clear colorless to light yellow liquid

InChI:InChI=1/C7H4FNS/c8-7-9-5-3-1-2-4-6(5)10-7/h1-4H

Upstream product

• 136-95-8 2-amino-benzthiazole 
• 615-20-3 2-chlorobenzo[d][1,3]thiazole 
• 16495-77-5 [(4-chlorophenyl)thio]pentafluorobenzene 
• 2516-40-7 2-bromo-1,3-benzothiazole 

Downstream Products

• 1194-02-1 4-fluorobenzonitrile 
• 4846-47-3 1-(2-benzothiazolyl)benzothiazolone 
• 1083092-53-8 C₃₄H₄₀F₃N₅O₆S₂ 
• 117482-84-5 3-chloro-4-fluorobenzonitrile 
• 345-83-5 4-fluorobenzophenone 
• 62850-13-9 2-fluoro-5-phenylpyrimidine 
• 2712-12-1 2-fluoroquinoxaline 
• 56595-09-6 4-fluoroquinazoline 
• 934-34-9 2-hydroxybenzothiazole 
• 372136-54-4 (1,1-dimethyl ethyl) N-(2-benzothiazolyl)-L-tyrosinate 
• 120-75-2 2-Methylbenzothiazole 
• 1131-75-5 2-fluoro-6-nitro-benzothiazole 

Relevant academic research and scientific papers

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.]

Method for pipeline continuous fluorination with fluorine salt as fluorine source

The method comprises the following steps: dissolving a fluorine salt in an aqueous polar aprotic solvent as reaction liquid A, dissolving an aryl (heterocyclic) chloride in a polar aprotic solvent as reaction liquid B, and reacting a polar aprotic solvent in the reaction liquid A with a polar aprotic solvent of the reaction liquid B. The reaction medium consisting of the preheated reaction liquid A and the preheated reaction liquid B enters the reaction coil for a fluorination reaction, and the resulting product from the reaction coil is subjected to post-treatment to obtain the product. The method has the characteristics of no need of adding a phase transfer catalyst, continuous production, low production cost and the like.

Nucleophilic Fluorination of Heteroaryl Chlorides and Aryl Triflates Enabled by Cooperative Catalysis

Aryl and heteroaryl fluorides are growing to be dominant motifs in pharmaceuticals and agrochemicals, yet they are rare in both nature and commodity chemicals. As a consequence, there is an increasingly urgent need to develop mild, cost-effective, and scalable methods for fluorination. The most straightforward route to synthesize aryl fluorides is through the halide exchange "halex"reaction, but conditions, cost, and atom economy preclude most available methods from large-scale manufacturing processes. We report a new approach that leverages the cooperative action of 18-crown-6 ether and tetramethylammonium chloride to catalytically access the reactivity of tetramethylammonium fluoride and achieve halex fluorinations under mild conditions with operational ease. The described methodology readily converts both heteroaryl chlorides and aryl triflates to their corresponding (hetero)aryl fluorides in high yields and purities.

Rhodium-catalyzed synthesis of unsymmetric di(heteroaryl) compounds via heteroaryl exchange reactions

Unsymmetric di(heteroaryl) HetAr–X–HetAr′ compounds have flexible and rigid groups, and are expected to exhibit various biological activities by interacting with proteins and nucleic acids. Then, synthesis of such compounds is critical for the development of drugs. Unsymmetric HetAr-X-HetAr′ compounds were efficiently synthesized by rhodium-catalyzed heteroaryl exchange reactions, which involved equilibrium control by judicious design of organic heteroaryl reagents. This method allows synthesis of unsymmetric HetAr–O–HetAr′, HetAr–S–HetAr′, and HetAr–CH2–HetAr′ compounds as well as HetAr–F compounds from heteroaryl aryl ethers and heteroaryl reagents. The rhodium-catalyzed heteroaryl exchange reaction was also applied to the synthesis of C–N-linked di(heteroaryl) compounds from N-benzoyl heteroarenes and heteroaryl aryl ethers. The synthesis has a broad applicability, which gives a diversity of novel unsymmetric HetAr–X–HetAr′ and C–N-linked di(heteroaryl)s compounds containing five- and six-membered heteroarenes.

Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides

A rhodium complex catalyzed the conversion of the C-O bond of heteroaryl aryl ethers to the C-F bond. The reaction of (4-chlorophenylthio)pentafluorobenzene with heteroaryl aryl ethers provided heteroaryl fluorides and heteroaryl (4-chlorophenylthio)tetrafluorophenyl ethers; this involved the cleavage of a single heteroaryl C-O bond under equilibrium conditions. The reaction of heteroaryl aryl ethers with 2-fluorobenzothiazole in which two heteroaryl and aryl C-O bonds were cleaved provided heteroaryl fluorides and aryl fluorides. The reactions were applicable to five-membered and six-membered heteroaryl aryl ethers and also to diaryl ethers possessing one or two electron-withdrawing groups.

The [18F]2-fluoro-1,3-thiazolyl moiety - An easily-accessible structural motif for prospective molecular imaging radiotracers

2-Fluoro-1,3-thiazoles were rapidly and efficiently labeled with no-carrier-added fluorine-18 (t1/2 = 109.7 min) by treatment of readily prepared 2-halo precursors with cyclotron-produced [18F] fluoride ion. The [18F]2-fluoro-1,3-thiazolyl moiety constitutes a new and easily-labeled structural motif for prospective molecular imaging radiotracers.

Facile preparation of aromatic fluorides by deaminative fluorination of aminoarenes using hydrogen fluoride combined with bases

One-pot deaminative fluorination of aminoarenes including heteroaromatics, namely, diazotization of aminoarenes followed by in situ fluoro-dediazoniation of the corresponding diazonium ions, was successfully accomplished to produce fluoroarenes in high yields by using hydrogen fluoride combined with base solutions. The diazotization stage has been found to play the most important part in yielding fluoroarenes effectively. It was greatly influenced by the composition of the HF solution and enhanced by employing appropriate amounts of bases such as pyridine under carefully controlled conditions. The fluoro-dediazoniation stage was effectively accelerated photochemically to afford fluoroarenes having polar substituents such as hydroxyl, nitro and so on in high yields.