822-84-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Nitrothiophene is utilized as a key intermediate in the synthesis of pharmaceutical compounds. Its chemical properties allow it to be transformed into a variety of derivative molecules that can be used in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 3-Nitrothiophene serves as an essential building block for the creation of various agrochemical products. Its ability to participate in chemical reactions enables the production of compounds that can be applied in agriculture to improve crop protection and yield.
Used in Synthesis of Fine Chemicals:
3-Nitrothiophene is also employed in the synthesis of fine chemicals, which are high-purity chemicals used in various industries, including fragrances, dyes, and specialty chemicals. Its versatility in chemical reactions facilitates the production of a wide array of fine chemicals for diverse applications.

InChI:InChI=1/C4H3NO2S/c6-5(7)4-1-2-8-3-4/h1-3H

Upstream product

• 188290-36-0 thiophene 
• 81975-00-0 2-bromo-4-nitro-thiophene 
• 2161-96-8 2-bromo-3-nitrothiophene 
• 89283-24-9 5-bromo-4-nitro-thiophene-2-carboxylic acid 
• 40358-04-1 4-nitrothiophene-2-sulphonyl chloride 
• 89283-80-7 3-nitrothiophene-2-carboxylic acid 
• 38611-19-7 3-nitro-2-trimethylsilylthiophene 
• 1192-06-9 3-thienyl lithium 
• 91-22-5 quinoline 
• 13138-70-0 4-nitro-2-thiophenecarboxylic acid 
• 6165-69-1 Thien-3-ylboronic acid 

Downstream Products

• 42602-67-5 N-(thiophen-3-yl)acetamide 
• 79128-75-9 N-Thiophen-3-yl-benzamide 
• 2160-51-2 2,5-dibromo-3-nitro-thiophene 
• 5347-12-6 2,4-dinitrothiophene 
• 17721-06-1 3-aminothiophene 
• 175731-00-7 2-dichloromethyl-3-nitrothiophene 
• 193144-25-1 (Z,Z)-1-cyclohexylamino-4-methylthio-2-nitro-1,3-butadiene 
• 193144-26-2 (Z,Z)-1-(S)-α-methylbenzylamino-4-methylthio-2-nitro-1,3-butadiene 
• 80313-09-3 2-amino-3-nitrothiophene 

Relevant academic research and scientific papers

N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids

Photocatalytic and metal-free protocols to access various aromatic and heteroaromatic nitro compounds through ipso-nitration of readily available boronic acid derivatives were developed using non-metal-based, bench-stable, and recyclable nitrating reagents. These methods are operationally simple, mild, regioselective, and possess excellent functional group compatibility, delivering desired products in up to 99% yield.

A one-pot synthesis of 3-nitrothiophene and 3-nitro-2-substituted thiophenes

A one-pot approach to the synthesis of 3-nitrothiophene and 3-nitro-2-substituted thiophenes has been developed. Exposure of 1,4-dithane-2,5-diol to nitroacetates or nitroalkenes in the presence of 25% triethylamine and subsequent treatment with molecular sieves and combinations of silica gel or acidic alumina with DDQ or chloranil formed 3-nitrothiophene or a number of 3-nitro-2-substituted thiophenes with complete regiocontrol. A simple work-up procedure removes the requirement for purification by chromatography for most post-synthetic applications.

Ipso-nitration of arylboronic acids with bismuth nitrate and perdisulfate

An efficient and one pot synthetic method of ipso-nitration of arylboronic acids has been developed. The high efficiency, general applicability, and broader substrate scope including heterocycles and functional groups make this method advantageous. Due to its simplicity, we expect to find application of this method in synthesis.

Convenient and mild synthesis of nitroarenes by metal-free nitration of arylboronic acids

A novel methodology for the direct nitration of arylboronic acids has been developed. By using inexpensive tert-butyl nitrite various aromatic nitro compounds are produced in moderate to good yields (45-87%) without the need of any catalyst.

Facile synthesis of 3-nitro-2-substituted thiophenes

A new approach to 3-nitro-2-substituted thiophenes has been developed. Exposure of commercially available 1,4-dithane-2,5-diol to nitroalkenes in the presence of 20% triethylamine results in a tandem Michael?intramolecular Henry reaction to form the corresponding tetrahydrothiophene. Subsequent microwave irradiation on acidic alumina in the presence of chloranil effects the solvent free dehydration and aromatization to form 3-nitro-2-substituted thiophenes cleanly and rapidly. A simple workup procedure removes the requirement for purification by chromatography in most cases.

Studies on the biological activity of some nitrothiophenes

The biological activity of nineteen substituted thiophenes (3) have been assessed by evaluating the minimum inhibitory concentration required to inhibit the growth of E. coli, M. luteus and A. niger. The series displays a wide range of activities with 2-chloro-3,5-dinitrothiophene (3a) or 2-bromo-3,5- dinitrothiophene (3c) showing the highest activity against all three organisms, while the simplest compound of the series, 2-nitrothiophene (3s) shows the smallest activity in each case. The mode of action of 3a and 3c is thought to involve nucleophilic attack by intracellular thiols at the 2-position of the heterocyclic ring leading to displacement of halogen, but other active derivatives, such as 2,4-dinitrothiophene (3h) and 5-nitrothiophene-2- carbaldehyde (3d) which have no displaceable halogen or leaving group are thought to act by forming Meisenheimer complexes. The Royal Society of Chemistry 2006.

A mild and efficient method for the mononitration of aromatic compounds by cerium (III) ammonium nitrate in acetic anhydride

A mild and efficient method for the mononitration of aromatic and olefinic compounds is described. This method is especially useful for active substrates.

A novel method for the nitration of simple aromatic compounds

Simple aromatic compounds such as benzene, alkylbenzenes, halogenobenzenes, and some disubstituted benzenes are nitrated in excellent yields with high regioselectivity under mild conditions using zeolite β as a catalyst and a stoichiometric quantity of nitric acid and acetic anhydride. The zeolite can be recycled, and the only byproduct is acetic acid, which can be separated easily from the nitration product by distillation; the process is inexpensive and represents an attractive method for the clean synthesis of a range of nitroaromatic compounds. For example, nitration of toluene gives a quantitative yield of mononitrotoluenes, of which 79% is 4-nitrotoluene; fluorobenzene gives a quantitative yield of mononitro compounds, of which 94% is 4-nitrofluorobenzene; and 2-fluorotoluene gives a 96% yield of mononitro products, of which 90% is the 5-nitro isomer and 10% is the 4-nitro isomer.

Five membered ring analogues of nifedipine - Part 1: 2-Nitro-3-furanecarbaldehyde and 2-nitro-3-thiophenecarbaldehyde in the Hantzsch pyridine synthesis

The heterocyclic aldehydes 4 in the Hantzsch pyridine synthesis afforded dependent on the choosen variation, either the 1,4-dihydropyridines (DHP) 5, the 1,2-DHP 6 or the 1,2,3,4-tetrahydropyrimidines (THPM) 7 as main products. 5-7 were dehydrogenated to the corresponding heteroaromatics 8-10 by cerium(IV). The lactames 11 and 12 were isolated by appropiate reduction of the nitro group from 8 and 9 by neighbour group participation of an ester function. The synthesis of 12 represents for the second time the evidence of an 2-aminofurane compound. 11 and 12 were converted with phosphorous oxychloride to form the annulated chloronaphthyridines 13 and 14 which were cyclized with sodium azide to yield the tetrazoles 15 and 16. The half wave potentials E1/2 of the DHP and THPM 5-7 were determined by anodic oxidation with the rotating platinum electrode using difference pulse voltammetry (DPV). These are comparable with those of the 2-nitrophenyl analogues.