20893-30-5

Basic information

• Product Name: 2-Thiopheneacetonitrile
• Synonyms: 2-Thiopheneacetonitrile, tech., 94%;2-(2-Thienyl)acetonitrile;2-Thiopheneacetonitrile,94%,tech.;2-(Cyanomethyl)thiophene, 2-(Thien-2-yl)ethanenitrile;2-Thiopheneacetonitrile,96%;2-Thiopheneacetonitrile 97%;Thiophene-2-acetonitrile for synthesis;THIOPHENE-2-ACETONITRILE
• CAS NO: 20893-30-5
• Molecular Formula: C₆H₅NS
• Molecular Weight: 123.18
• EINECS: 244-104-6
• Product Categories: Aromatic Nitriles;Thiophenes & Benzothiophenes;Thiophene&Benzothiophene;Heterocyclic Compounds;Thiophens;Thiophenes & Benzothiophenes;Building Blocks;C4 to C6;Chemical Synthesis;Heterocyclic Building Blocks;Thiophenes
• Mol File: 20893-30-5.mol
• Article Data: 21

Chemical Properties

• Melting Point: 50-51 °C
• Boiling Point: 115-120 °C22 mm Hg(lit.)
• Flash Point: 215 °F
• Appearance: clear colourless to slightly brown liquid
• Density: 1.157 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0921mmHg at 25°C
• Refractive Index: n20/D 1.542(lit.)
• Storage Temp.: Store below +30°C.
• BRN: 106960
• CAS DataBase Reference: 2-Thiopheneacetonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Thiopheneacetonitrile(20893-30-5)
• EPA Substance Registry System: 2-Thiopheneacetonitrile(20893-30-5)

Safety Data

• Hazard Codes: Xn,Xi,T
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37-23-36
• RIDADR: UN 3276 6.1/PG 3
• WGK Germany: 3
• TSCA: T
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 20893-30-5(Hazardous Substances Data)

Usage

Uses

Used in Nanotechnology:
2-Thiopheneacetonitrile is used as a reagent in the synthesis of monodisperse Au/Au@polythiophene core/shell nanospheres. These nanospheres have potential applications in various fields, such as electronics, optics, and catalysis, due to their unique size, shape, and properties.
Used in Chemical Synthesis:
As a member of the thiophenes family, 2-Thiopheneacetonitrile can be utilized in the synthesis of various organic compounds and materials. Its unique chemical structure allows it to be a valuable building block for creating new molecules with specific properties and applications in different industries.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, 2-Thiopheneacetonitrile, due to its structural similarity to other bioactive compounds, may have potential applications in the pharmaceutical industry. It could be used as a starting material or intermediate in the synthesis of new drugs or drug candidates with potential therapeutic effects.

Synthesis Reference(s)

The Journal of Organic Chemistry, 15, p. 81, 1950 DOI: 10.1021/jo01147a014Synthesis, p. 40, 1987 DOI: 10.1055/s-1987-27834

InChI:InChI=1/C6H5NS/c7-4-3-6-2-1-5-8-6/h1-2,5H,3H2

Upstream product

• 765-50-4 2-Chloromethylthiophene 
• 143-33-9 sodium cyanide 
• 151-50-8 potassium cyanide 
• 4461-29-4 2-(thiophen-2-yl)acetamide 
• 139109-61-8 2-hydroxyimino-3-[2]thienyl-propionic acid 
• 81745-84-8 2-thienylzinc chloride 
• 590-17-0 cyanomethyl bromide 
• 30807-46-6 2-(2-nitroethyl)thiophene 
• 183657-46-7 1-Nitro-2-thiophen-2-yl-ethanone oxime 
• 89677-36-1 3-thiophen-2-yl-2-thioxo-propionic acid 
• 6319-47-7 5-(2'-thiophenemethylene)rhodamine 
• 10147-40-7 1-Dodecanesulfonyl chloride 
• 1190072-73-1 C₁₂H₈IN₂S₂⁽¹⁺⁾*Cl^(1-) 
• 15022-15-8 2-thienylacetaldehyde 

Downstream Products

• 853920-96-4 cyclohex-2-enyl-[2]thienyl-acetonitrile 
• 99856-75-4 1-(thiophen-2-yl)cyclohexanecarbonitrile 
• 1002342-12-2 3c-benzo[1,3]dioxol-5-yl-2-[2]thienyl-acrylonitrile 
• 57382-97-5 ethyl thiophen-2-ylacetate 
• 57870-96-9 -essigsaeure-aethylester-imin 
• 347-52-4 (E)-3-(4-fluorophenyl)-2-(thiophen-2-yl)acrylonitrile 
• 89986-24-3 (E)-3-phenyl-2-(thiophen-2-yl)acrylonitrile 
• 89986-25-4 3c-(4-methoxy-phenyl)-2-[2]thienyl-acrylonitrile 
• 37034-01-8 3c-(2,4-dichloro-phenyl)-2-[2]thienyl-acrylonitrile 
• 288851-81-0 3c-(2-methoxy-phenyl)-2-[2]thienyl-acrylonitrile 
• 142518-79-4 (E)-3-(4-(dimethylamino)phenyl)-2-(thiophen-2-yl)acrylonitrile 
• 37034-00-7 3c-(3,4-dichloro-phenyl)-2-[2]thienyl-acrylonitrile 
• 853920-75-9 cyano-cyclohex-2-enyl-[2]thienyl-acetic acid ethyl ester 
• 30433-91-1 [2-(2-thyenyl)ethyl]amine 

Relevant articles and documents

From Stoichiometric Reagents to Catalytic Partners: Selenonium Salts as Alkylating Agents for Nucleophilic Displacement Reactions in Water

The ability of chalcogenium salts to transfer an electrophilic moiety to a given nucleophile is well known. However, up to date, these reagents have been used in stoichiometric quantities, producing a substantial amount of waste as byproducts of the reaction. In this report, we disclose further investigation of selenonium salts as S-adenosyl-L-methionine (SAM) surrogates for the alkylation of nucleophiles in aqueous solutions. Most importantly, we were able to convert the stoichiometric process to a catalytic system employing as little as 10 mol % of selenides to accelerate the reaction between benzyl bromide and other alkylating agents with sodium cyanide in water. Probe experiments including 77Se NMR and HRMS of the reaction mixture have unequivocally shown the presence of the selenonium salt in the reaction mixture. (Figure presented.).

One-pot method for the synthesis of 1-aryl-2-aminoalkanol derivatives from the corresponding amides or nitriles

We have identified a novel one-pot method for the synthesis of β-amino alcohols, which is based on C-H bond hydroxylation at the benzylic α-carbon atom with a subsequent nitrile or amide functional group reduction. This cascade process uses molecular oxygen as an oxidant and sodium bis(2-methoxyethoxy)aluminum hydride as a reductant. The substrate scope was examined on 30 entries and, although the respective products were provided in moderate yields only, the above simple protocol may serve as a direct and powerful entry to the sterically congested 1,2-amino alcohols that are difficult to prepare by other routes. The plausible mechanistic rationale for the observed results is given and the reaction was applied to a synthesis of a potentially bioactive target. This journal is

NHC-catalyzed silylative dehydration of primary amides to nitriles at room temperature

Herein we report an abnormal N-heterocyclic carbene catalyzed dehydration of primary amides in the presence of a silane. This process bypasses the energy demanding 1,2-siloxane elimination step usually required for metal/silane catalyzed reactions. A detailed mechanistic cycle of this process has been proposed based on experimental evidence along with computational study.

Corresponding amine nitrile and method of manufacturing thereof

The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.

Nickel-Catalyzed Cyanation of Benzylic and Allylic Pivalate Esters

A nickel-catalyzed cyanation reaction of benzylic and allylic pivalate esters is reported using an air-stable Ni(II) precatalyst and substoichiometric quantities of Zn(CN)2. Alkene additives were found to inhibit catalysis, suggesting that avoiding β-hydride elimination side reactions is essential for productive catalysis. An enantioenriched allylic ester undergoes enantiospecific cross-coupling to produce an enantioenriched allylic nitrile. This method was applied to an efficient synthesis of (±)-naproxen from commercially available starting materials.

Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium Complex Featuring Pyrazole Functionality

A ruthenium(II) complex bearing a naphthyridine-functionalized pyrazole ligand catalyzes oxidant-free and acceptorless selective double dehydrogenation of primary amines to nitriles at moderate temperature. The role of the proton-responsive entity on the ligand scaffold is demonstrated by control experiments, including the use of a N-methylated pyrazole analogue. DFT calculations reveal intricate hydride and proton transfers to achieve the overall elimination of 2 equiv of H2.

Preparation method of non-steroidal anti-inflammatory drug tiaprofenic acid

The invention relates to a preparation method of non-steroidal anti-inflammatory drug tiaprofenic acid. The preparation method includes: taking 2-chloromethyl thiophene as a starting raw material; synthesizing thiophene-2-acetonitrile by allowing 2-chloromethyl thiophene to react with trimethylsilyl cyanide; allowing thiophene-2-acetonitrile to react with dimethyl carbonate for methylation prior to cyan-hydrolysis; finally, performing benzoyl chloroformylation reaction to obtain tiaprofenic acid. The preparation method has the advantages that rare, valuable and dangerous materials are replacedwith common, cheap and safe raw materials, serious pollution problems are avoided, and production cost is greatly reduced; in addition, the process adopted in the method is short in route, short in reaction period, stable in reaction condition and high in yield which can be up to 90%, the product obtained is high in purity which can reach above 99%, and the preparation method is applicable to industrial production.

Synthetic process of tiaprofenic acid

The invention relates to a synthetic process of tiaprofenic acid. The synthetic process comprises the following steps: adopting 2-thiotolene as a starting raw material, enabling 2-thiotolene to reactwith trimethylsilyl cyanide to synthesize 2-thiopheneacetonitrile by virtue of bromation, then enabling the 2-thiopheneacetonitrile to react with dimethyl carbonate to be methylated, hydrolyzing cyanogroups, and finally performing F-K reaction with benzoyl chloride, and preparing tiaprofenic acid. The synthetic process has the advantages that the conventional safe raw materials low in price are used for substituting the rare expensive and dangerous raw materials, so that the severe pollution problem is avoided, and the production cost is greatly decreased; and in addition, the process route adopted by the invention is simple, the reaction period is short, the reaction condition is stable, the yield is high and can reach more than 90 percent, the produce obtained after the reaction is highin purity, and the purity can reach more than 99 percent, so that the synthetic process is suitable for the industrialized production.

Green preparation technology of 2-thiopheneacetic acid

The invention discloses a synthesis technology of 2-thiopheneacetic acid. The technology comprises the steps that 2-chloromethyl thiophene is taken as a raw material and reacts with acetone cyanohydrin in the presence of an organic solvent under the condition of a catalyst triethylamine to generate 2-thiopheneacetonitrile; 2-thiopheneacetonitrile is subjected to a series of reactions to generate 2-thiopheneacetic acid. The synthesis technology has the advantages that by selecting acetone cyanohydrin as a cyaniding reagent, usage of an extremely toxic substance sodium cyanide is avoided, the reaction yield is increased, the product quality is improved, the safety performance is relatively high, and industrialized production is promoted; the reaction conditions are mild, a little quantity of the catalyst is needed, and the processes are simple. Compared with an existing synthesis technology, the synthesis technology achieves the obvious economic benefits and environmental benefits.

Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source

A novel protocol for the synthesis of α-aryl nitriles has been successfully achieved via a copper-catalyzed cyanation of N-tosylhydrazones employing thiocyanate as the source of cyanide. The features of this method include a convenient operation, readily available substrates, low-toxicity thiocyanate salts, and a broad substrate scope.