25796-68-3

Basic information

• Product Name: 3-BROMOTHIOPHENE-2-CARBONYL CHLORIDE
• Synonyms: 3-BROMOTHIOPHENE-2-CARBONYL CHLORIDE;BUTTPARK 145\50-40;3-Bromothiophene-2-carbonyl chloride, 95+%;3-Bromo-2-(chlorocarbonyl)thiophene, 3-Bromo-2-thenoyl chloride;3-Bromo-2-thienylcarbonyl chloride
• CAS NO: 25796-68-3
• Molecular Formula: C₅H₂BrClOS
• Molecular Weight: 225.49
• Mol File: 25796-68-3.mol
• Article Data: 19

Chemical Properties

• Melting Point: 65-68°C
• Boiling Point: 135-136°C 13mm
• Flash Point: 109.356 °C
• Appearance: /
• Density: 1.856 g/cm³
• Vapor Pressure: 0.0147mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: 3-BROMOTHIOPHENE-2-CARBONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-BROMOTHIOPHENE-2-CARBONYL CHLORIDE(25796-68-3)
• EPA Substance Registry System: 3-BROMOTHIOPHENE-2-CARBONYL CHLORIDE(25796-68-3)

Safety Data

• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: 3261
• Hazardous Substances Data: 25796-68-3(Hazardous Substances Data)

Usage

General Description

3-Bromothiophene-2-carbonyl chloride is a chemical compound that consists of a thiophene ring with a bromine atom at the 3rd-position, a carbonyl group at the 2nd-position, and a chlorine atom replacing a hydrogen of the carbonyl group. It is commonly used as a reagent in organic synthesis for the preparation of various pharmaceuticals and agrochemicals. 3-BROMOTHIOPHENE-2-CARBONYL CHLORIDE is a versatile building block for the construction of more complex molecules and is known for its role in the synthesis of heterocyclic compounds. Due to its reactivity and functional groups, it is important to handle this chemical with care and proper safety precautions.

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

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 
• 88791-37-1 3-bromo-N-p-tolylthiophene-2-carboxamide 
• 88791-41-7 3-Bromo-thiophene-2-carboxylic acid (4-chloro-phenyl)-amide 
• 26137-08-6 methyl 3-bromothiophene-2-carboxylate 
• 816418-30-1 3-bromothiophene-2-carboxylic acid methylamide 
• 816418-31-2 3-bromothiophene-2-carboxylic acid benzylamide 
• 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 
• 1428144-09-5 1-(3-(4-(diethylamino)phenylamino)thiophen-2-yl)-3-phenylprop-2-yn-1-one 
• 1428144-10-8 4,5-diphenylthieno[3,2-b]pyridin-7(4H)-one 
• 1428144-11-9 5-Phenyl-4-p-tolylthieno[3,2-b]pyridin-7(4H)-one 

Relevant articles and documents

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.

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.

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.