197370-13-1

Usage

Uses

Used in Organic Synthesis:
2-Bromothiophene-3-carbonyl chloride is used as a building block for the preparation of various organic molecules, contributing to the development of pharmaceuticals, agrochemicals, and materials with specific properties and applications.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Bromothiophene-3-carbonyl chloride is used as a key intermediate for the synthesis of therapeutic agents. Its unique structure allows for the creation of molecules with potential medicinal properties, targeting a range of diseases and conditions.
Used in Agrochemical Industry:
2-Bromothiophene-3-carbonyl chloride is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its reactivity enables the development of compounds that can effectively control pests and weeds, thereby enhancing crop protection and yield.
Used in Material Science:
In the field of material science, 2-Bromothiophene-3-carbonyl chloride is employed in the synthesis of advanced materials with specific properties. These materials can be used in various applications, such as electronics, coatings, and polymers, where their unique characteristics provide enhanced performance.
Safety Precautions:
Due to its corrosive nature, 2-Bromothiophene-3-carbonyl chloride can cause severe irritation to the skin, eyes, and respiratory system. It is crucial to handle 2-Bromothiophene-3-carbonyl chloride with caution and use appropriate safety measures and protective equipment to minimize risks and ensure safe handling.

InChI:InChI=1/C5H2BrClOS/c6-4-3(5(7)8)1-2-9-4/h1-2H

Upstream product

• 24287-95-4 2-bromothiophene-3-carboxylic acid 

Downstream Products

• 76360-43-5 methyl 2-bromothiophene-3-carboxylate 
• 1204601-56-8 1-(2-bromothiophen-3-yl)-3-phenylprop-2-yn-1-one 
• 1379820-80-0 2-bromo-N-phenylthiphene-3-carboxamide 

Relevant academic research and scientific papers

Synthesis and Study of Head-to-Tail Regioregular Poly(alkyl thiophene-3-carboxylates)

Regioregular head-to-tail poly(alkyl thiophene-3-carboxylates) have been prepared by very careful formation of the mono-Grignard reagent from alkyl 2,5-dibromothiophene-3-carboxylates (-40°C, 1 h) followed by nickel-catalyzed polymerization. The spectral properties are reported along with the molecular weights.

A Convergent Synthesis of Functionalized Alkenyl Halides through Cobalt(III)-Catalyzed Three-Component C?H Bond Addition

A CoIII-catalyzed three-component coupling of C(sp2)?H bonds, alkynes, and halogenating agents to give alkenyl halides is reported. This transformation proceeds with high regio- and diastereoselectivity, and is effective for a broad

An insight into the pharmacophores of phosphodiesterase-5 inhibitors from synthetic and crystal structural studies

Selective inhibitors of cyclic nucleotide phosphodiesterase-5 (PDE5) have been used as drugs for treatment of male erectile dysfunction and pulmonary hypertension. An insight into the pharmacophores of PDE5 inhibitors is essential for development of second generation of PDE5 inhibitors, but has not been completely illustrated. Here we report the synthesis of a new class of the sildenafil derivatives and a crystal structure of the PDE5 catalytic domain in complex with 5-(2-ethoxy-5-(sulfamoyl)-3-thienyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (12). Inhibitor 12 induces conformational change of the H-loop (residues 660-683), which is different from any of the known PDE5 structures. The pyrazolopyrimidinone groups of 12 and sildenafil are well superimposed, but their sulfonamide groups show a positional difference of as much as 1.5 A. The structure-activity analysis suggests that a small hydrophobic pocket and the H-loop of PDE5 are important for the inhibitor affinity, in addition to two common elements for binding of almost all the PDE inhibitors: the stack against the phenylalanine and the hydrogen bond with the invariant glutamine. However, the PDE5-12 structure does not provide a full explanation to affinity changes of the inhibitors. Thus alternatives such as conformational change of the M-loop are open and further structural study is required.

Preparation of Tetrahydrothienoazocinone Derivatives

Three regioisomeric thieno[c]azocine derivatives were prepared in six steps from bromothiophene carboxylic acids. The reaction sequence started with an esterification with isopropyl alcohol. The resulting esters were submitted to a Heck reaction with tert-butyl acrylate followed by catalytic hydrogenation. Subsequent Dieckmann condensation gave cyclopentathiophenes with a cyclic β-oxo ester motif, which were α-alkylated with phenacyl bromide to furnish 1,4-diketones. The latter were converted in the key step, a bismuth-catalyzed ring transformation with methylamine, yielding the racemic eight-membered ring lactams, that is, tetrahydrothieno[2,3-c]-, [3,2-c]-, and -[3,4-c]azocine derivatives in overall yields of 25%, 16% and 12%, respectively.

Synthesis and molecular properties of isomeric thienoisoindigo

Three isomers of thienoisoindigo (TII) are prepared by changing the ring-fusion mode or the amide arrangement of lactam units, namely, 5,10-dihexyl-5,10-dihydrodithieno[3,2-c:3′,2′-h][2,6]naphthyridine-4,9-dione (TVTDA), 4,10-dihexyldithieno[3,2-c:3′,2′-h

Organocatalyst in Direct C(sp2)-H Arylation of Unactivated Arenes: [1-(2-Hydroxyethyl)-piperazine]-Catalyzed Inter-/Intra-molecular C-H Bond Activation

This article describes the identification of 1-(2-hydroxyethyl)-piperazine as a new, cost-effective, highly efficient organocatalyst, which promotes both inter- A nd intra-molecular direct C(sp2)-H arylations of unactivated arenes in the presence of potassium tert-butoxide. While the inter-molecular C-H arylation of unactivated benzenes with aryl halides (Ar-X; X = I, Br, Cl) toward biaryl syntheses underwent smoothly in the presence of only 10 mol percent organocatalyst, the intra-molecular C-H arylation catalytic system composed of 40 mol percent each of the catalyst and the additive (4-dimethylaminopyridine (DMAP)). The novel catalyst was also able to perform both inter- A nd intra-molecular direct arylations simultaneously in a single pot. The mechanistic studies confirmed the involvement of aryl radical anions and proceeded via a single-electron-transfer (SET) mechanism. The large substrate scope, high functional group tolerance, competition experiments, gram-scale synthesis, and kinetic studies further highlight the importance and versatile nature of the methodology as well as the compatibility of the new catalyst. To the best of our knowledge, this is the first report on any organocatalyst that reported detailed investigations of both inter- A nd intra-molecular direct C(sp2)-H arylations of unactivated arenes in a single representation.

SELECTIVE INHIBITORS OF CLINICALLY IMPORTANT MUTANTS OF THE EGFR TYROSINE KINASE

The present invention provides compounds of Formula (I) or a subgeneric structure or species thereof, or a pharmaceutically acceptable salt, ester, solvate, and/or prodrug thereof, and methods and compositions for treating or ameliorating abnormal cell pr

ORGANIC MATERIAL AND PHOTOELECTRIC CONVERSION ELEMENT

PROBLEM TO BE SOLVED: To provide an organic material capable of obtaining high photoelectric conversion efficiency even in the case of weak light such as indoor light. SOLUTION: The invention provides an organic material represented by the general formula

Palladium-catalyzed intramolecular C-H arylation of 2-halo-: N -Boc- N -arylbenzamides for the synthesis of N-H phenanthridinones

A palladium catalyzed synthesis of N-H phenanthridinones was developed via C-H arylation. The protocol gives phenanthridinones regioselectively by one-pot reaction without deprotection. It exhibits broad substrate scope and affords targets in up to 95% yields. Importantly, it could be applied for the less reactive o-chlorobenzamides.

A further decrease in the catalyst loading for the palladium-catalyzed direct intramolecular arylation of amides and sulfonamides

The direct arylation of N-substituted o-bromobenzanilides and benzenesulfonamides via C-H bond functionalization has been developed using very low catalyst loadings. This novel cost-effective and more sustainable method relies on a PCN-type palladium pincer complex as a highly active palladium source, providing a general and efficient access to phenanthridinones, biaryl sultams and related heterocyclic systems. The beneficial effect of water as cosolvent has been observed in this process, which is not seriously influenced by electronic effects at the arene moieties or sterically demanding substituents at the amide or sulfonamide nitrogen. In addition, a number of experiments (kinetic plot, poisoning assays, TEM, ESI) have been performed in order to understand the role of the employed palladium complex in this reaction.