25796-68-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromothiophene-2-carbonyl chloride is used as a reagent in the synthesis of various pharmaceuticals for its ability to form complex molecular structures that can exhibit therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Bromothiophene-2-carbonyl chloride is utilized as a precursor in the development of compounds that can be used in crop protection and pest management, leveraging its capacity to create diverse chemical entities.
Used in Organic Synthesis:
3-Bromothiophene-2-carbonyl chloride is employed as a key intermediate in organic synthesis for constructing more intricate molecules, which can be further modified for specific applications in various chemical and material sciences.
Used in Heterocyclic Compound Synthesis:
3-BROMOTHIOPHENE-2-CARBONYL CHLORIDE is used as a building block in the synthesis of heterocyclic compounds, which are important in medicinal chemistry and have a wide range of biological activities, including antimicrobial, anticancer, and antiviral properties.

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

Upstream product

• 7311-64-0 3-bromothiophene-2-carboxylic acid 
• 22288-78-4 Methyl 3-aminothiophene-2-carboxylate 
• 26137-08-6 methyl 3-bromothiophene-2-carboxylate 
• 930-96-1 3-bromo-2-thiophenecarboxaldehyde 

Downstream Products

• 153046-39-0 4-Iodo-benzo[1,3]dioxole-5-carboxylic acid 2-(3-bromo-thiophene-2-carbonyloxy)-benzyl ester 
• 78031-18-2 3-bromo-2-carboxamidothiophene 
• 88791-38-2 3-Bromo-thiophene-2-carboxylic acid (3-methoxy-phenyl)-amide 
• 816418-30-1 3-bromothiophene-2-carboxylic acid methylamide 
• 1204601-58-0 1-(3-bromothiophen-2-yl)-3-phenylprop-2-yn-1-one 
• 1338543-29-5 3-bromo-N-[4-(tert-butyldimethylsilyloxy)phenyl]thiophene-2-carboxamide 
• 1338543-30-8 tert-butyl 3-bromothiophene-2-carbonyl[4-(tert-butyldimethylsilyloxy)phenyl]carbamate 
• 189331-46-2 methyl 3-ethylthiophene-2-carboxylate 
• 74965-84-7 3-ethyl-2-thiophenecarboxylic acid 
• 1275804-56-2 3-bromo-N-(4-methoxy-2-methylphenyl)thiophene-2-carboxamide 
• 1338543-44-4 tert-butyl 3-bromothiophene-2-carbonyl(4-methoxy-2-methylphenyl)carbamate 
• 1338545-57-5 (R)-tert-butyl 1-(4-(8-methoxy-6-methyl-4-oxo-4,5-dihydrothieno[2,3-c]quinolin-9-yl)phenyl)ethylcarbamate 
• 1338543-46-6 9-bromo-8-methoxy-6-methylthieno[2,3-c]quinolin-4(5H)-one 

Relevant academic research and scientific papers

Ni-Catalyzed Reductive Arylcyanation of Alkenes

We disclose a Ni-catalyzed reductive arylcyanation of alkene using environmentally benign and nontoxic organo cyanating reagent N-cyano-N-phenyl-p-toluenesulfonamide. This reaction provides a new method for the rapid synthesis of cyano-substituted oxindoles and isoquinoline-1,3-diones and features high functional group tolerance. In addition, an enantioselective version was developed for the construction of enantiomerically enriched 3-cyanomethyl oxindole. This method has also been applied to the synthesis of natural alkaloids (+)-esermethole and (+)-physostigmine.

Photoinduced and Palladium-Catalyzed Remote Desaturation of Amide Derivatives

A photoinduced and palladium-catalyzed remote desaturation of O-acyl hydroxamides to unsaturated amides under mild conditions has been achieved. The formation of the alkyl Pd(II) intermediate by the recombination of alkyl radical and Pd(I) species is critical to achieve this efficient and selective desaturation of alkanes. This reaction features good site-selectivity, is terminal oxidant-free, and produces moderate to excellent yields for a variety of unsaturated amides. Remarkably, this approach enables late-stage desaturation of complex and biologically important molecules.

Design, synthesis and biological evaluation of novel 1-phenyl phenanthridin-6(5H)-one derivatives as anti-tumor agents targeting TOPK

T–lymphokine-activated killer cell–originated protein kinase (TOPK) is a serine-threonine mitogen-activated protein kinase that is highly expressed in many types of human cancer. Due to its important role in cancer progression, TOPK is becoming an attractive target in chemotherapeutic drug design. In this study, a series of 1-phenyl phenanthridin-6(5H)-one derivatives have been identified as a novel chemical class of TOPK inhibitors. Some of them displayed very potent anti-cancer activity with IC50s less than 100 nM, superior than reference compound OTS964. The most potent compound, 9g suppressed the growth of cancer cells by apoptosis and specifically inhibited the activities of TOPK. Oral administration of 9g effectively suppressed tumor growth with TGI >79.7% in colorectal cancer xenograft models, demonstrating superior efficacy compared to OTS964. Pharmacokinetic studies reveal its good oral bioavailability. Our findings therefore show that 9g is a specific inhibitor of TOPK both in vitro and in vivo that may be further developed as a potential therapeutic agent against colorectal cancer.

Design, synthesis and activity evaluation study of novel substituted N-sulfonyl homoserine lactone derivatives as bacterial quorum sensing inhibitors

A novel series of N-sulfonyl homoserine lactone derivatives 7a–7m has been designed, synthesized, and evaluated for quorum sensing inhibitory activities through the violacein inhibition in Chromobacterium violaceum CV026. Compound 7e displayed the high level of inhibitory activity among all the compounds synthesized. Studies of structure-activity relationship indicated that compounds with thiophene group in side chain showed better activity than those substituted by furan, pyrrole, pyridyl, and phenethyl group. Thiophene substituted compounds which connected electron withdrawing group exhibited better inhibitory activity relate to those connected electron donating group. Further analysis indicated that compound bearing an electron withdrawing substituent at the position 2 of their thiophene ring exhibited superior activity against violacein production to those bearing the substituent at the position 3 and 4. Compound 7e in particular, with IC50 value of 6.19 μM, were identified as promising lead compounds for further development.

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.

Exploiting the gem-Disubstitution Effect in FcPHOX and HetPHOX P,N Ligands: Synthesis and Applications in Pd-Catalyzed Intermolecular Heck Reactions

The synthesis of a range of novel gem-disubstituted and electronically varied thiophene-oxazoline (HetPHOX) ligands and ferrocene-oxazoline (FcPHOX) ligands and their application in the Pd-catalyzed intermolecular asymmetric Heck reaction (IAH) is described. These investigations show that gem-disubstitution of i-Pr-PHOX-type ligands can lead to effective and cost-efficient alternatives to the corresponding t-Bu-PHOX systems. The Pd complexes of these ligands were very effective in the IAH, providing phenylated products in up to 100% conversion with up to 97% ee.

CuI-catalyzed cycloisomerization of propargyl amides

The synthesis of substituted dihydrooxazoles by the CuI-catalyzed cycloisomerization of terminal propargyl amides is reported. The reaction has been shown to have good substrate scope and experiments to delineate the mechanism have been performed. Substrates containing a benzylic methylene were oxidized to the ketone under the reaction conditions.

Diastereoselective palladium-catalyzed arylcyanation/heteroarylcyanation of enantioenriched N -allylcarboxamides

A diastereoselective Pd-catalyzed arylcyanation/heteroarylcyanation of chiral N-allylcarboxamides using Zn(CN)2 as the cyanide source is reported. Nitrile-containing dihydroisoquinolinone products are obtained in good to excellent yields with u

Efficient synthesis of novel thieno[3,2-b]-, [2,3-c]- and [3,2-c]pyridones by Sonogashira coupling of bromothiophenes with terminal alkynes and subsequent intramolecular C-N bond-forming reaction

The coupling of bromothiophenes with terminal alkynes using triethylamine or diisopropyl amine under Sonogashira conditions (PdCl2(PPh 3)2, CuI) followed by subsequent addition of amines or ammonium to the intermediate thienyl acetylenes represents a novel access to a wide range of thieno[3,2-b]-, [2,3-c]-, and [3,2-c]pyridones under basic conditions and in excellent yields.

TRYCYCLIC COMPOUNDS AND PBK INHIBITORS CONTAINING THE SAME

Trycyclic compounds are provided. These compounds are PBK inhibitors, and are useful for the treatment of PBK related diseases, including cancer.