57731-17-6

Basic information

• Product Name: 2-BROMO-1-(5-CHLORO-THIOPHEN-2-YL)-ETHANONE
• Synonyms: 2-BROMO-1-(5-CHLORO-THIOPHEN-2-YL)-ETHANONE;2-BROMO-1-(5-CHLORO-2-THIENYL)-1-ETHANONE;TIMTEC-BB SBB005585;2-(Bromoacetyl)-5-chlorothiophene;2-Bromo-1-(5-chloro-2-thienyl)ethan-1-one;2-Bromo-1-(5-chlorothien-2-yl)ethan-1-one;AKOS BBS-00006555;2-BROMO-1-(5-CHLOROTHIEN-2-YL)ETHANONE
• CAS NO: 57731-17-6
• Molecular Formula: C₆H₄BrClOS
• Molecular Weight: 239.52
• Mol File: 57731-17-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 73-75
• Boiling Point: 309.2 °C at 760 mmHg
• Flash Point: 140.8 °C
• Appearance: /
• Density: 1.766 g/cm³
• Vapor Pressure: 0.00065mmHg at 25°C
• Refractive Index: 1.614
• Storage Temp.: Keep Cold
• Sensitive: Lachrymatory
• CAS DataBase Reference: 2-BROMO-1-(5-CHLORO-THIOPHEN-2-YL)-ETHANONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMO-1-(5-CHLORO-THIOPHEN-2-YL)-ETHANONE(57731-17-6)
• EPA Substance Registry System: 2-BROMO-1-(5-CHLORO-THIOPHEN-2-YL)-ETHANONE(57731-17-6)

Safety Data

• Hazard Codes: C,Xn
• Statements: 22-36
• Safety Statements: 26
• HazardClass: IRRITANT
• Hazardous Substances Data: 57731-17-6(Hazardous Substances Data)

Usage

General Description

2-Bromo-1-(5-chloro-thiophen-2-yl)-ethanone is a chemical compound that consists of a 2-bromo-1-ethyl group attached to a 5-chloro-thiophen-2-yl group. It is a ketone with a molecular formula C6H5BrClOS and a molecular weight of 209.48 g/mol. 2-BROMO-1-(5-CHLORO-THIOPHEN-2-YL)-ETHANONE is commonly used in the synthesis of pharmaceuticals and agrochemicals, as well as in the production of various organic chemicals. Its properties and uses make it an important intermediate in the production of a wide range of products, making it a valuable chemical in the chemical industry.

InChI:InChI=1/C6H4BrClOS/c7-3-4(9)5-1-2-6(8)10-5/h1-2H,3H2

Upstream product

• 6310-09-4 2-acetyl-5-chlorothiophene 

Downstream Products

• 174347-68-3 6-(5-chloro-thiophen-2-yl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizine 
• 483367-55-1 3,6-dichloro-2-(5-chlorothien-2-yl)imidazo[1,2-b]pyridazine 
• 200211-82-1 [2-(5-chloro-thiophen-2-yl)-6,6-dimethyl-1-phenyl-6,7-dihydro-5H-pyrrolizin-3-yl]-acetic acid 
• 174347-69-4 ethyl [6-(5-chloro-thiophen-2-yl)-2,2-dimethyl-7-phenyl-2,3-dihydro-1H-pyrrolizin-5-yl]-2-oxoacetate 
• 736177-19-8 1-(4-chlorobenzylideneamino)-4-(5-chlorothiophen-2-yl)-1H-imidazol-2-amine 
• 374555-88-1 [4-(5-chlorothiophen-2-yl)thiazol-2-yl]-[3-(imidazol-1-yl)phenyl]amine 
• 1240348-33-7 6-chloro-2-(5-chlorothiophen-2-yl)imidazo[1,2-a]pyridine 
• 1232082-91-5 6-chloro-3-iodo-2-(5-chlorothien-2-yl)imidazo[1,2-b]pyridazine 
• 353512-04-6 (4-amino-2-phenylaminothiazol-5-yl)-(5-chlorothiophen-2-yl)methanone 

Relevant articles and documents

5-Keto-3-cyano-2,4-diaminothiophenes as selective maternal embryonic leucine zipper kinase inhibitors

Maternal embryonic leucine zipper kinase (MELK) is involved in several key cellular processes and displays increased levels of expression in numerous cancer classes (colon, breast, brain, ovary, prostate and lung). Although no selective MELK inhibitors ha

Usnic Acid Enaminone-Coupled 1,2,3-Triazoles as Antibacterial and Antitubercular Agents

(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles 10-44 as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone 8 with a terminal ethynyl moiety. It was further reacted with various azides A1-A35 under copper catalysis to give triazoles 10-44 in good yields. Among the synthesized compounds, saccharin derivative 36 proved to be the most active analogue, inhibiting Mycobacterium tuberculosis (Mtb) at an MIC value of 2.5 μM. Analogues 16 and 27, with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited Mtb at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on Bacillus subtilis, with compounds 18 [3-(trifluoromethyl)phenacyl] and 29 (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.

Synthesis and antifungal activity of novel oxazolidin-2-one-linked 1,2,3-triazole derivatives

Novel oxazolidin-2-one-linked 1,2,3-triazole derivatives (4a-k) were synthesized by straightforward and versatile azide-enolate (3 + 2) cycloaddition. The series of compounds was screened for antifungal activity against four filamentous fungi as well as six yeast species of Candida spp. According to their efficiency and breadth of scope, they can be ordered as 4k > 4d > 4h > 4a, especially in relation to the activity displayed against Candida glabrata ATCC-34138, Trichosporon cutaneum ATCC-28592 and Mucor hiemalis ATCC-8690, i.e. compounds 4d, 4h and 4k showed excellent activity against C. glabrata (MIC 0.12, 0.25 and 0.12 μg mL-1, respectively), better than that of itraconazole (MIC 1 μg ml-1). The activity of compound 4d (MIC = 2 μg mL-1) was higher than that observed for the standard antifungal drug (MIC = 8 μg mL-1) against Trichosporon cutaneum, while compound 4k displayed an excellent antimycotic activity against Mucor hiemalis (MIC = 2 μg mL-1vs. 4 μg mL-1 for itraconazole). In addition, we describe herein a novel mild and eco-friendly synthetic protocol for obtaining β-ketosulfones (adducts to afford compounds 4a-k) from α-brominated carbonyls in an aqueous nanomicellar medium at room temperature.