42791-51-5

Usage

Uses

Used in Pharmaceutical Research:
2-Acetyl-4-nitrothiophene is used as a building block in pharmaceutical research for the production of various drugs and other bioactive molecules. Its unique chemical structure makes it a valuable component in the synthesis of new compounds with potential therapeutic applications.
Used in Organic Synthesis:
In the field of organic synthesis, 2-Acetyl-4-nitrothiophene is employed as a key intermediate for the creation of a wide range of chemical compounds. Its versatility in reactions allows for the development of new molecules with diverse properties and potential uses.

InChI:InChI=1/C6H5NO3S/c1-4(8)6-2-5(3-11-6)7(9)10/h2-3H,1H3

Upstream product

• 88-15-3 2-Acetylthiophene 
• 108-24-7 acetic anhydride 
• 13138-70-0 4-nitro-2-thiophenecarboxylic acid 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 4565-29-1 5-acetylthiophene-2-carbaldehyde 
• 24647-78-7 methyl 4-nitrothiophene-2-carboxylate 

Downstream Products

• 92576-84-6 1-(4-nitro-[2]thienyl)-ethanone-(4-bromo-phenylhydrazone) 
• 692889-40-0 2-acetyl-4-amino-thiophene 

Relevant academic research and scientific papers

Ethylammonium nitrate (EAN)/Tf2O and EAN/TFAA: Ionic liquid based systems for aromatic nitration

Acting as in situ sources of triflyl nitrate (TfONO2) and trifluoroacetyl nitrate (CF3COONO2), the EAN/Tf 2O and EAN/TFAA systems, generated via metathesis in the readily available ethylammonium nitrate (EAN) ionic liquid as solvent, are powerful electrophilic nitrating reagents for a wide variety of aromatic and heteroaromatic compounds. Comparative nitration experiments indicate that EAN/Tf2O is superior to EAN/TFAA for nitration of strongly deactivated systems. Both systems exhibit low substrate selectivity (K T/KB = 5-10) in (Figure presented) between values reported for covalent nitrates and preformed nitronium salts.

COMPOSITIONS USEFUL AS INHIBITORS OF ROCK AND OTHER PROTEIN KINASES

The present invention relates to substitute thiazole and thiophene derivatives useful as inhibitors of rock and other protein kinaeses. The invention also provides pharmaceutically acceptable compositions comprising said compounds and methods of using the compositions in the treatment of various disease, conditions, or disorders, including proliferative, cardiac and neurodegenerative diseases.

Synthesis and antibacterial activity of 4,7-dihydro-4-ethyl-7-oxothieno(3,2-b)pyridine-6-carboxylic acids

The synthesis of some new 4,7-dihydro-4-ethyl-7-oxothieno(3,2-b)pyridine-6-carboxylic acids with various substituents on position 2 is described. The evaluation of the anti-bacterial activity of some compounds shows an activity different to those of the thieno(2,3-b)pyridine series.

Meisenheimer-type Adducts from Thiophene Derivates. Part 6. A Kinetic and Thermodynamic Study of Substituent Effects on the Formation of Some non-gem Adducts

The rate and equilibrium constants for the formation of the Meisenheimer-type adducts from some 4-nitro-2-X- (5) or some 2-nitro-4-X-thiophenes (7) and sodium methoxide have been measured at 25 deg C in methanol or methanol-dimethyl sulphoxide mixtures.The observed stability and reactivity patterns have been interpreted in the light of the hyper-ortho relation in the thiophene ring and the special ability of the nitro group to stabilize effectively the adducts from a para-like position also.

The Synthesis of 2-Heteroarylimidazopyridin-3-ols and Related Compounds

A reaction between pyridin-2-amine 1-oxides and phenalcyl bromides has been extended to some bromoacetyl heteroaromatic compounds to form the title compounds.The reaction of some 2-aminodiazine 1-oxides with phenacyl bromides has also been studied.The imidazopyrimidne and imidazophthalazine systems have been prepared but reaction of pyrazin-2-amine 1-oxide did not give the desired cyclization.

NITRO DERIVATIVES OF THE THIOPHENE SERIES. 4. NITRATION OF THIOPHENE DERIVATIVES WITH METAL NITRATES IN ACETIC ANHYDRIDE

The nitration of 2-formylthiophene, 2-acetothienone, and unsaturated ketones of the thiophene series with copper and aluminum nitrates in acetic anhydride at various temperatures was studied.At low temperatures 2-acetothienone gives a mixture of 4- and 5-nitro isomers, while 2-formylthiphene gives only a 5-nitro-substituted compound in the diacetate form; α,β-unsaturated ketones are not nitrated under these conditions.When the reaction is carried out at 70-90 degC, one can obtain mixtures of nitro ketones in the case of unsaturated ketones; 2-formylthiophene is oxidized to thiophene-2-carboxylic acid, while 2-acetothienone gives a substance, the structure of which could not be established.The reaction of copper and aluminum nitrates with acetic anhydride was investigated by means of thermal and X-ray diffraction analysis.It is shown that the reaction is accompanied by the formation of free nitric acid, and the nitrating agent in these mixtures is consequently the nitronium cation.