1003-31-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Thiophenecarbonitrile is used as an intermediate in the synthesis of thiaplatinacycles, which are a class of compounds with potential applications in the pharmaceutical industry. These thiaplatinacycles have shown promise in the development of new drugs, particularly for the treatment of cancer, due to their unique chemical properties and ability to interact with biological targets.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-Thiophenecarbonitrile is used as a key building block for the preparation of 2,2′-thienylpyrroles. These heterocyclic compounds have a wide range of applications, including their use as synthetic receptors, ligands, and catalysts. They also exhibit interesting electronic, optical, and magnetic properties, making them attractive candidates for the development of new materials and technologies.
Used in Material Science:
The unique properties of 2-Thiophenecarbonitrile make it a valuable component in the development of new materials for various applications. Its ability to form stable complexes with other molecules and its compatibility with a wide range of synthetic methods make it a versatile building block for the creation of novel materials with tailored properties. These materials can be used in various industries, such as electronics, energy storage, and environmental protection.

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 26, p. 2838, 1978 DOI: 10.1248/cpb.26.2838

InChI:InChI=1/C5H3NS/c6-4-5-2-1-3-7-5/h1-3H

Upstream product

• 188290-36-0 thiophene 
• 506-68-3 bromocyane 
• 460-19-5 ethanedinitrile 
• 554-14-3 2-Methylthiophene 
• 96-43-5 2-thienyl chloride 
• 74-90-8 hydrogen cyanide 
• 60-29-7 diethyl ether 
• 57784-57-3 (Z)-thiophene-2-carbaldehyde oxime 
• 38266-87-4 thiophene-2-carbaldehyde oxime 
• 506-77-4 cyanogen chloride 
• 544-92-3 copper(I) cyanide 
• 93-61-8 N-methyl-N-phenylformamide 
• 151-50-8 potassium cyanide 
• 1003-09-4 2-bromothiophene 

Downstream Products

• 61586-98-9 2,4-di-thiophen-2-yl-5,6,7,8-tetrahydro-pyrido[2,3-d]pyrimidine 
• 49595-52-0 4,5-dimethyl-2-phenyl-7-thiophen-2-yl-2,3-dihydro-1H-[1,2]azaphosphepine 2-oxide 
• 59541-58-1 5-(thiophen-2-yl)-1H-tetrazole 
• 56382-53-7 2,4,6-tri(thiophen-2-yl)-(1,3,5)-triazine 
• 51770-35-5 3,5-bis(4-methylthiophenyl)-4-amino-1,2,4-triazole 
• 54610-49-0 methyl thiophene-2-carbimidate hydrochloride 
• 94631-60-4 5-{[1-(2-Hydroxy-5-methoxy-phenyl)-meth-(E)-ylidene]-amino}-thiophene-2-carbonitrile 
• 84197-73-9 5,7-Diphenyl-2-thiophen-2-yl-[1,2,4]triazolo[1,5-a]pyridine 
• 54610-47-8 ethyl thiophene-2-carboximidate 
• 149065-76-9 (S)-4-isopropyl-2-(thiophen-2-yl)-4,5-dihydrooxazole 
• 149065-75-8 (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline 
• 130524-42-4 1-(benzyloxy)-5-methoxy-3-(thien-2-ylcarbonyl)naphthalene 
• 130524-60-6 2-iodo-1-(benzyloxy)-5-methoxy-3-(thien-2-ylcarbonyl)naphthalene 
• 121910-37-0 4-Phenyl-2-thiophen-2-yl-6,7,8,8a-tetrahydro-pyrrolo[1,2-a]pyrimidine 

Relevant academic research and scientific papers

DMF-catalysed thermal dehydration of aldoximes: A convenient access to functionalized aliphatic and aromatic nitriles

N,N-Dimethylformamide was found to act as solvent and catalyst in the dehydration of aldoximes to nitriles. The reaction required heating at 135°C and yields of nitriles were moderate to good. (Benzylideneaminooxy)formaldehyde was detected as an intermediate in one of the reactions. Georg Thieme Verlag Stuttgart.

Per-6-amino-β-cyclodextrin/CuI catalysed cyanation of aryl halides with K4[Fe(CN)6]

Efficient cyanation of aryl halides is achieved using less toxic K 4[Fe(CN)6] as the reagent and amino-β-cyclodextrins as supramolecular ligands for CuI. Four different amino cyclodextrins viz. per-6-amino-β-CD, per-6-methylamino-β-CD, per-6-butyl-amino-β-CD and mono-6-amino-β-CD are prepared and studied. Aryl and heteroaryl nitriles are obtained in good to excellent yield for even bromo derivatives of flavone and 2-aminopyrans. This system uses catalytic amounts (10 mol%) of both copper iodide and per-6-amino-β-cyclodextrin. Easy separation, the absence of nitrogen atmosphere and excellent yield are the other significant outcomes of this protocol. The Royal Society of Chemistry and the Centre National de la Recherche Scientifique.

Palladium nanoparticles stabilized by a copolymer of N-vinylimidazole with N-vinylcaprolactam as efficient recyclable catalyst of aromatic cyanation

A new recyclable catalytic system was developed based on palladium nanoparticles and a copolymer of N-vinylimidazole and N-vinylcaprolactam for cyanation of aromatic bromides. The source of the cyanide ion was a nontoxic potassium hexacyanoferrate.

SYNTHESIS OF 3-THIENYL-SUBSTITUTED ISOTHIAZOLINES-2- AND 1,2,4-THIADIAZOLES BASED ON NITRILE SULFIDES OF THE THIOPHENE SERIES

The reaction of substituted α- and β-thienylcarboxamides with chlorocarbonylsulfenyl chloride gave 5-thienyl-substituted 1,3,4-oxathiazol-2-ones.Decarboxylation of the latter by heating in o-dichlorobenzene generated in situ α- and β-thienylnitrile sulfid

Direct Conversion of Benzyl Ethers into Aryl Nitriles

A direct method was developed for the conversion of benzyl ethers into aryl nitriles by using NH 4 OAc as the nitrogen source and oxygen as the terminal oxidant with catalysis by TEMPO/HNO 3; the method is valuable for both the synthesis of aromatic nitriles and for the deprotection of ether-protected hydroxy groups to form nitrile groups in multistep organic syntheses.

Selectivity-tunable amine aerobic oxidation catalysed by metal-free N,O-doped carbons

Herein, we present a series of N,O-doped mesoporous carbons obtained at different pyrolysis temperatures as the first metal-free catalysts which successfully switch between imine and nitrile products for amine oxidation. Systematic characterization studies and control experiments revealed that the C-O group on the surface could function as a catalytically active site for nitrile synthesis and the N-doping environment was essential.

Metal-free one-pot conversion of electron-rich aromatics into aromatic nitriles

Various electron-rich aromatics could be smoothly converted into the corresponding aromatic nitriles in good to moderate yields by treatment of electron-rich aromatics with POCl3 and DMF, followed by treatment with molecular iodine in aqueous ammonia. The present reaction is a novel metal-free one-pot method for the preparation of aromatic nitriles from electron-rich aromatics.

Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate) catalyzed Suzuki, Heck, Sonogashira, and cyanation reactions

Palladium bis(2,2,6,6-tetramethyl-3,5-heptanedionate): a structurally well-defined O-containing transition metal complex is reported as an efficient catalyst for Suzuki, Heck, and Sonogashira cross-coupling reactions. The protocol was also applied successfully for cyanation of aryl halides under milder operating conditions. The system tolerated the coupling of various aryl halides with alkenes, alkynes, and organoboronic acid along with the cyanation of aryl halides providing good to excellent yields of desired products.

A clean conversion of aldehydes to nitriles using a solid-supported hydrazine

A polymer-supported hydrazine reagent has been applied to the conversion of a range of aldehydes to nitriles, providing a clean and efficient route to more diverse building blocks for combinatorial chemistry programmes.

A one-pot conversion of carboxylic acids into nitriles catalysed by PEG400 under microwave irradiation

A new efficient method for the synthesis of nitriles is reported. Carboxylic acids were converted into nitriles by a onepot reaction with hydroxylamine sulfate and zinc catalysed by PEG400 under microwave irradiation in excellent yields. The most suitable condition was 20 minutes under the microwave power of 231 W with 5 mol% PEG400.