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Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (CAS No. 13669-10-8): A Comprehensive Overview

Ethyl 3-oxo-3-(thiophen-2-yl)propanoate (CAS No. 13669-10-8) is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and materials science. This compound, also known as ethyl 3-thiophenylacrylate, is characterized by its unique structural features, which include a thiophene ring and a ketone functional group. These characteristics make it an attractive candidate for various applications, ranging from pharmaceuticals to advanced materials.

The chemical structure of ethyl 3-oxo-3-(thiophen-2-yl)propanoate consists of a thiophene ring attached to a ketone group, with an ethyl ester moiety at the other end. The presence of the thiophene ring imparts aromatic properties, while the ketone and ester groups contribute to its reactivity and functional versatility. This combination of structural elements allows for a wide range of chemical transformations and derivatizations, making it a valuable building block in synthetic chemistry.

In the realm of medicinal chemistry, ethyl 3-oxo-3-(thiophen-2-yl)propanoate has been explored for its potential therapeutic applications. Recent studies have highlighted its role as an intermediate in the synthesis of bioactive molecules, particularly those with anti-inflammatory and anti-cancer properties. For instance, a study published in the Journal of Medicinal Chemistry reported that derivatives of this compound exhibited significant inhibition of COX enzymes, which are key targets in the treatment of inflammatory diseases.

Furthermore, the pharmacological profile of ethyl 3-oxo-3-(thiophen-2-yl)propanoate has been investigated in several preclinical studies. These studies have demonstrated its ability to modulate various biological pathways, including those involved in cell proliferation and apoptosis. The compound's ability to interact with specific protein targets makes it a promising lead for drug discovery efforts.

In addition to its medicinal applications, ethyl 3-oxo-3-(thiophen-2-yl)propanoate has found utility in the field of materials science. Its unique electronic properties make it suitable for use in organic electronics and photovoltaic devices. Research conducted at the University of California, Berkeley, has shown that derivatives of this compound can be used to enhance the performance of organic solar cells by improving charge transport and stability.

The synthesis of ethyl 3-oxo-3-(thiophen-2-yl)propanoate can be achieved through several routes, each offering different advantages in terms of yield and purity. One common method involves the condensation of thiophene with ethyl acetoacetate in the presence of a suitable catalyst. This reaction typically proceeds via a Michael addition followed by an intramolecular cyclization, yielding the desired product with high selectivity.

The physical properties of ethyl 3-oxo-3-(thiophen-2-yl)propanoate are also noteworthy. It is a colorless liquid with a characteristic odor and is soluble in common organic solvents such as ethanol and acetone. Its melting point is around -5°C, and it has a boiling point of approximately 180°C at atmospheric pressure. These properties make it easy to handle and process in laboratory settings.

In terms of safety, while ethyl 3-oxo-3-(thiophen-2-y l)propanoate is generally considered safe when handled properly, it is important to follow standard laboratory safety protocols. Proper personal protective equipment (PPE), such as gloves and goggles, should be worn during handling to prevent skin contact and inhalation. Additionally, it should be stored in a well-ventilated area away from heat sources and incompatible materials.

The environmental impact of ethyl 3-o xo -3-(thiophen -2 - yl ) propan o ate is another important consideration. While there is limited data on its environmental fate and effects, it is advisable to dispose of this compound according to local regulations to minimize any potential ecological risks.

In conclusion, E th y l 3 - ox o - 3 -(t hi o phen -2 - y l ) p ro pan o ate strong > (CAS No . 1 3669 -10 -8 ) i s a n i n t er e st ing c omp o und w i th w ide r an g ing ap p lic at io n s i n m e dic i na l c he m i str y an d m at er i al s sc ie nc e . I t s u ni q ue s tr uc tu r al fe at ur es , c he m ic al pr op e rt ie s , an d ph ar ma col og ic al pr o fi le m ak e i t a va lu ab le c on t ri bu t or t o v ar io u s r es ea r ch f ie ld s . A s re se ar ch co nt i nu es , t h e fu ll p ot en ti al o f t hi s co mp ou nd i s li ke ly t o b e u ni fo ld ed , op en i ng n ew ho ri zo ns f or sc ie nt if ic d is co ve ry an d te ch no lo gi ca l ad va nc em en ts . p >

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• 139608-65-4(Butanoic acid, 2-methyl-3-[5-(1-oxobutyl)-2-thienyl]propyl ester, (S)- (9CI))
• 59086-25-8(ethyl 4-oxo-4-(thiophen-2-yl)butanoate)
• 134568-16-4(Methyl 3-oxo-3-(thiophen-2-yl)propanoate)
• 13892-51-8(Ethyl 3-oxo-2-(thiophene-2-carbonyl)butanoate)
• 88696-86-0(2(3H)-Furanone, dihydro-4-(2-thienylcarbonyl)-)
• 170115-17-0(Tert-Butyl 3-oxo-3-(thiophen-2-yl)propanoate)
• 18760-47-9(Methyl 5-oxo-5-(thiophen-2-yl)pentanoate)
• 166180-39-8(ethyl 2-methyl-3-oxo-3-(thiophen-2-yl)propanoate)
• 139608-64-3(1-Propanone, 1-[5-[2-methyl-3-(1-oxopropoxy)propyl]-2-thienyl]-, (S)-)