34772-98-0

Basic information

• Product Name: (E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE
• Synonyms: (E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE;3-(diMethylaMino)-1-(thiophen-2-yl)prop-2-en-1-one;1-(2-Thienyl)-3-(dimethylamino)-2-propen-1-one;3-(Dimethylamino)-1-thien-2-ylprop-2-en-1-one
• CAS NO: 34772-98-0
• Molecular Formula: C₉H₁₁NOS
• Molecular Weight: 181.25474
• Mol File: 34772-98-0.mol
• Article Data: 78

Chemical Properties

• Melting Point: 197-198℃ (1,4-dioxane )
• Boiling Point: 265.8 °C at 760 mmHg
• Flash Point: 114.6 °C
• Appearance: /
• Density: 1.126 g/cm³
• Vapor Pressure: 0.00895mmHg at 25°C
• Refractive Index: 1.564
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE(34772-98-0)
• EPA Substance Registry System: (E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE(34772-98-0)

Safety Data

• Hazardous Substances Data: 34772-98-0(Hazardous Substances Data)

Usage

Description

(E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE, an organosulfur compound with the molecular formula C9H11NOS, features a thiophene ring and a propenone moiety. This unique structure and reactivity make it a valuable building block in the synthesis of pharmaceuticals and agrochemicals, as well as a key intermediate in the production of certain drugs and a reagent in organic chemistry reactions.

Uses

Used in Pharmaceutical Industry:
(E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE is used as a building block for the synthesis of various pharmaceuticals due to its unique structure and reactivity, contributing to the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
(E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE is used as a building block in the synthesis of agrochemicals, playing a crucial role in the development of new pesticides and other agricultural chemicals to improve crop protection and yield.
Used in Organic Chemistry:
(E)-3-DIMETHYLAMINO-1-THIOPHEN-2-YL-PROPENONE is used as a reagent in organic chemistry reactions, facilitating the synthesis of new compounds and materials, and contributing to advancements in chemical research and development.

InChI:InChI=1/C9H11NOS/c1-10(2)6-5-8(11)9-4-3-7-12-9/h3-7H,1-2H3

Upstream product

• 893739-40-7 1-(2-(thiophen-2-yl)phenyl)ethan-1-one 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 88-15-3 2-Acetylthiophene 
• 1188-33-6 N,N-dimethylformamide diethyl diacetal 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 187749-78-6 3-benzamido-6-(2-thienyl)-pyran-2-one 
• 190579-92-1 6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 
• 313380-32-4 2-(cyanomethylthio)-6-(2-thienyl)pyridine-3-carbonitrile 
• 175202-75-2 4-(thiophen-2-yl)-pyrimidine-2-thiol 

Relevant articles and documents

Metal-free synthesis of gem-difluorinated heterocycles from enaminones and difluorocarbene precursors

A cascade strategy to synthesise gem-difluorinated 2H-furans from reactions of BrCF2CO2Et with enaminones has been described. The reactions tolerate a wide variety of functional groups under metal-free conditions. An active aminocyclopropane is proposed to be a key intermediate through the cyclopropanation of difluorocarbene with enaminones, which further triggers a regioselective C-C bond cleavage in situ to afford the corresponding gem-difluorinated 2H-furans.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

Herein we report a microscale parallel synthetic approach allowing for rapid access to libraries of N-acylated aminotriazoles and screening of their inhibitory activity against factor XIIa (FXIIa) and thrombin, which are targets for antithrombotic drugs. This approach, in combination with post-screening structure optimization, yielded a potent 7 nM inhibitor of FXIIa and a 25 nM thrombin inhibitor; both compounds showed no inhibition of the other tested serine proteases. Selected N-acylated aminotriazoles exhibited anticoagulant properties in vitro influencing the intrinsic blood coagulation pathway, but not extrinsic coagulation. Mechanistic studies of FXIIa inhibition suggested that synthesized N-acylated aminotriazoles are covalent inhibitors of FXIIa. These synthesized compounds may serve as a promising starting point for the development of novel antithrombotic drugs.

An expedient synthesis of highly functionalized 1,3-dienes by employing cyclopropenes asC4units

An efficient method has been described to synthesize dicarbonyl functionalized 1,3-dienes by cleaving the CC bond of enaminones with cyclopropenes in the presence of a rhodium catalyst. The acetate-substituted cyclopropenes are judiciously chosen as standardC4units of 1,3-diene precursors. The reactions are believed to undergo a unique cutting and insertion process, involving a CC bond cleavage of the enaminone and insertion of a newC(sp2) source with the formation of two C-C single bonds. A broad range of substrates can be used to synthesize the corresponding 1,3-dienes under very mild reaction conditions, including low catalyst-loading, ambient temperature, and a neutral reaction solvent.