7209-11-2

Basic information

• Product Name: 1-(4-BROMO-2-THIENYL)ETHAN-1-ONE
• Synonyms: AKOS B020506;1-(4-BROMO-2-THIENYL)-1-ETHANONE;1-(4-BROMO-2-THIENYL)ETHAN-1-ONE;2-ACETYL-4-BROMOTHIOPHENE;BUTTPARK 95\04-34;ART-CHEM-BB B020506;1-(4-Bromo-2-thienyl)ethan-1-one, tech;1-(4-Bromo-2-thienyl)ethan-1-one ,97%
• CAS NO: 7209-11-2
• Molecular Formula: C₆H₅BrOS
• Molecular Weight: 205.07
• Mol File: 7209-11-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 66-67°C 0,2mm
• Flash Point: 125.8 °C
• Appearance: /
• Density: 1.619 g/cm³
• Vapor Pressure: 0.00299mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: 2-8°C(protect from light)
• CAS DataBase Reference: 1-(4-BROMO-2-THIENYL)ETHAN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-BROMO-2-THIENYL)ETHAN-1-ONE(7209-11-2)
• EPA Substance Registry System: 1-(4-BROMO-2-THIENYL)ETHAN-1-ONE(7209-11-2)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36-22
• Safety Statements: 26-36/37/39
• HazardClass: IRRITANT
• Hazardous Substances Data: 7209-11-2(Hazardous Substances Data)

Usage

Chemical Properties

Yellow liquid

InChI:InChI=1/C6H5BrOS/c1-4(8)6-2-5(7)3-9-6/h2-3H,1H3

Upstream product

• 872-31-1 3-Bromothiophene 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 34878-46-1 2-(1-Hydroxyethyl)-4-bromothiophene 
• 80775-47-9 3-Acetyl-2,4,5-tribromothiophene 
• 7209-12-3 1-(4,5-dibromothiophen-2-yl)ethanone 
• 88-15-3 2-Acetylthiophene 

Downstream Products

• 887910-07-8 C₁₇H₁₆N₄OS 
• 1416368-10-9 (S)-3-(5-(2-imino-1,4-dimethyl-6-oxohexahydropyrimidin-4-yl)thiophen-3-yl)benzonitrile hydrochloride 
• 1310877-42-9 C₁₆H₁₅BrN₂O₂S 
• 1310877-41-8 C₁₆H₁₇BrN₂O₂S₂ 
• 1366233-28-4 ethyl 3-(1-(4-hydroxyphenyl)-5-(4-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-1H-pyrrol-2-yl)propanoate 
• 1366233-27-3 ethyl 3-(5-(4-bromothiophen-2-yl)-1-(4-hydroxyphenyl)-1H-pyrrol-2-yl)propanoate 
• 1208317-88-7 3-(5-(4-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-1-(4-(methylsulfonamido)phenyl)-1H-pyrrol-2-yl)propanoic acid 
• 1208317-91-2 3-(1-(4-acetamidophenyl)-5-(4-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-1H-pyrrol-2-yl)propanoic acid 
• 1208317-76-3 3-(1-(4-hydroxyphenyl)-5-(4-(2-methyl-1H-imidazol-1-yl)thiophen-2-yl)-1H-pyrrol-2-yl)propanoic acid 

Relevant articles and documents

Combining structure- and property-based optimization to identify selective FLT3-ITD inhibitors with good antitumor efficacy in AML cell inoculated mouse xenograft model

FLT3 mutation is among the most common genetic mutations in acute myeloid leukemia (AML), which is also related with poor overall survival and refractory in AML patients. Recently, FLT3 inhibitors have been approved for AML therapy. Herein, a series of new compounds with pyrazole amine scaffold was discovered, which showed potent inhibitory activity against FLT3-ITD and significant selectivity against both FLT3-ITD and AML cells expressing FLT3-ITD. Compound 46, possessing the most promising cellular activity, blocked the autophosphorylation of FLT3 pathway in MV4-11 cell line. Furthermore, the apoptosis and downregulation of P-STAT5 were also observed in tumor cells extracted from the MV4-11 cell xenografts model upon compound 46 treatment. Compound 46 was also metabolically stable in vitro and suppressed tumor growth significantly in MV4-11 xenografts model in vivo. Compound 46 showed no toxicity to the viscera of mice and caused no decrease in body weight of mice. In conclusion, the results of this study could provide valuable insights into discovery of new FLT3 inhibitors, and compound 46 was worthy of further development as potential drug candidate to treat AML.

Direction of 3-bromothiophene acylation with succinyl chloride

In the reaction of 3-bromothiophene with succinyl chloride in the presence of AlCl3, a mixture of three isomeric dibromo-substituted 1,4-di(2-thienyl)butane-1,4-diones was formed. The main component was the unsymmetrical 1-(3-bromo-2-thienyl)-4-(4-bromo-2-thienyl)butane-1,4-dione rather than 1,4-di-(3-bromo-2-thienyl)butane-1,4-dione expected according to the orientation rules.

Structure-activity relationship of pyrrole based S-nitrosoglutathione reductase inhibitors: Carboxamide modification

The enzyme S-nitrosoglutathione reductase (GSNOR) is a member of the alcohol dehydrogenase family (ADH) that regulates the levels of S-nitrosothiols (SNOs) through catabolism of S-nitrosoglutathione (GSNO). GSNO and SNOs are implicated in the pathogenesis of many diseases including those in respiratory, gastrointestinal, and cardiovascular systems. The pyrrole based N6022 was recently identified as a potent, selective, reversible, and efficacious GSNOR inhibitor which is currently in clinical development for acute asthma. We describe here the synthesis and structure-activity relationships (SAR) of novel pyrrole based analogs of N6022 focusing on carboxamide modifications on the pendant N-phenyl moiety. We have identified potent and novel GSNOR inhibitors that demonstrate efficacy in an ovalbumin (OVA) induced asthma model in mice.