16689-02-4

Usage

Uses

Used in Pharmaceutical Industry:
5-Nitrothiophene-2-carbonitrile is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique chemical structure allows it to be a building block for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Nitrothiophene-2-carbonitrile is utilized as an intermediate for the production of various agrochemicals. Its incorporation into these compounds can contribute to the development of effective pesticides and other agricultural products designed to protect crops and enhance yield.
Used in Organic Synthesis:
5-Nitrothiophene-2-carbonitrile is employed as a versatile intermediate in organic synthesis. Its reactivity and functional groups make it suitable for the preparation of a wide range of organic compounds, including dyes, pigments, and other specialty chemicals.

InChI:InChI=1/C5H2N2O2S/c6-3-4-1-2-5(10-4)7(8)9/h1-2H

Upstream product

• 1003-31-2 thiophene-2-carbonitrile 
• 4521-33-9 5-nitro-2-thiophenecarboxaldehyde 
• 6277-18-5 2-iodo-5-nitrothiophene 
• 7697-37-2 nitric acid 
• 108-24-7 acetic anhydride 
• 6030-18-8 5-nitrothiophene-2-carbaldehyde oxime 
• 57784-57-3 (Z)-thiophene-2-carbaldehyde oxime 
• 14289-24-8 5-nitrothiophene-2-carboxaldehyde diacetate 
• 143-33-9 sodium cyanide 
• 87997-11-3 5-nitro-2-thienyltrimethylammonium bromide 
• 104416-19-5 5-nitrothiophene-2-aldoxime 
• 98-03-3 thiophene-2-carbaldehyde 

Downstream Products

• 5832-01-9 methyl 5-nitrothiophene-2-carboxylate 
• 5832-00-8 5-nitrothiophene-2-carboxamide 
• 6317-37-9 5-nitrothiophene-2-carboxylic acid 
• 32415-91-1 5-fluorothiophene-2-carbonitrile 
• 65089-54-5 5-Nitro-then-2-amidoxim 
• 849806-06-0 5-(3-fluorophenoxy)thiophene-2-carbonitrile 
• 849806-10-6 5-(4-fluoro-phenoxy)-thiophene-2-carbonitrile 
• 849811-48-9 5-(3-bromophenoxy)-thiophene-2-carbonitrile 
• 849811-49-0 5-(3-benzyloxy-phenoxy)-thiophene-2-carbonitrile 
• 849806-14-0 5-p-Tolyloxy-thiophene-2-carbonitrile 
• 944457-18-5 [Fe(η5-cyclopentadienyl(1,2-bis(diphenylphosphino)ethane)(5-nitrothiophene-2-carbonitrile)]PF6 
• 1187947-31-4 [Ru(η5-C5H5)(1,2-bis(diphenylphosphino)ethane)(5-nitrothiophene-2-carbonitrile)]PF6 
• 1359763-59-9 5-(3-trifluoromethylphenyloxy)-thiophen-2-carbonitrile 
• 207849-74-9 (5-fluorothiophen-2-yl)formyl chloride 

Relevant academic research and scientific papers

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.

An unexpected involvement of ethyl-2-cyano-2-(hydroxyimino) acetate cleaved product in the promotion of the synthesis of nitriles from aldoximes: A mechanistic perception

While attempting to synthesize nitriles from aldoximes using O-sulfonate esters of oxyma [ethyl 2-cyano-2-(hydroxyimino)acetate], an unexpected involvement of oxyma cleaved product in promoting the synthesis of nitriles was observed. Such involvement of the oxyma cleaved product in the reaction mechanism, together with the usual anticipated pathway improved drastically the applicability of the method by reducing the time needed for the reaction to be completed over that of the sulfonyl chlorides. Other advantages of the present protocol are excellent yields in ambient and milder conditions.

Compromise between conjugation length and charge-transfer in nonlinear optical η5-monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile ligands: Synthesis, electrochemical studies and first hyperpolarizabilities

A systematic series of η5-monocyclopentadienyliron(II) complexes with substituted oligo-thiophene nitrile ligands of general formula [FeCp(P_P)(NC{SC4H2}nNO2)][P F6] (P_P = dppe, (+)-diop;

Efficient transformation of aldoximes to nitriles using 2-chloro-1-methylpyridinium iodide under mild conditions

Various (aliphatic, aromatic, and heterocyclic aromatic) types of aldoximes were converted into the corresponding nitriles in good to excellent yields using 2-chloro-1-methylpyridinium iodide (CMPI) as a dehydrating agent under mild conditions.

One-pot synthesis of nitriles from aldehydes under microwave irradiation: Influence of the medium and mode of microwave irradiation on product formation

Chemoselective transformation of aldehyde to nitrile takes place in a one-pot reaction by treatment with H2NOHHCl in N- methyl-2-pyrrolidinone (NMP) under microwave irradiation using convection mode.

Elimination reactions of (Z)-thiophene- and (Z)-furan-2-carbaldehyde O- benzoyloximes. Effect of β-aryl group upon the nitrile-forming anti transition state

Elimination reactions of (Z)-thiophene- and (Z)-furan-2-carbaldehyde O- benzoyloximes 1 and 2 with DBU in MeCN have been investigated kinetically. The reactions are second order and exhibit substantial values of Hammett ρ and k(H)/k(D) values, and an E2 m

A Useful Method for the Conversion of Aldehyde Oximes into Nitriles Using 1,1'-Oxalyldiimidazole

Under neutral conditions, aliphatic, alicyclic, aromatic, and heteroaromatic aldehyde oximes (3) react with 1,1'-oxalyldiimidazole (2) in an appropriate solvent such as benzene, acetonitrile, chloroform, or tetrahydrofuran at 65-70 degC within 1 h to give the corresponding nitriles (4) in good yield.Keywords --- dehydration; 1,1'-carbonyldiimidazole; 1,1'-oxalyldiimidazole; oxime; nitrile

SYNTHESIS AND REACTIONS OF TRIMETHYLAMMONIUM SALTS OF 5-NITRO-2-FURAN AND 5-NITRO-2-THIOPHENE. THE PREPARATION OF 5-NITRO-2-FURYL- AND 5-NITRO-2-THIENYL AZIDE

Preparation of new water-soluble derivatives of 5-nitro-2-furan and 5-nitro-2-thiophene from 2-bromo-5-nitrofuran (Ia) or 2-bromo-5-nitrothiophene (Ib) and trimethylamine is described.The trimethylammonium derivatives IIa, IIb react with the azide or cyan