39565-00-9

Usage

Safety Profile

Mutation data reported. Aflammable liquid. When heated to decomposition it emitstoxic vapors of NOx and SOx.

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

Upstream product

• 88-15-3 2-Acetylthiophene 
• 108-24-7 acetic anhydride 

Downstream Products

• 91394-79-5 1-(5-nitro-[2]thienyl)-ethanone-(4-bromo-phenylhydrazone) 
• 6317-37-9 5-nitrothiophene-2-carboxylic acid 
• 98453-29-3 2-acetyl-5-nitrothiophene E-oxime 
• 98453-30-6 2-acetyl-5-nitrothiophene Z-oxime 
• 1020847-61-3 1-(4-nitrophenyl)-4-(5-nitrothiophen-2-yl)butane-1,4-dione 

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.

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.