98-03-3

Usage

Uses

Used in Organic Synthesis:
2-Thenaldehyde is used as a versatile building block in the synthesis of various organic compounds, particularly in the introduction of thenyl groups into target molecules. Its reactivity allows for the formation of diverse chemical structures, making it a valuable intermediate in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Thenaldehyde is used as a key intermediate in the synthesis of β-aryl-β-amino acids and urea derivatives. These compounds are important for the development of new drugs with potential therapeutic applications.
Used as an Arylation Reagent:
2-Thenaldehyde serves as an effective arylation reagent in chemical reactions, facilitating the introduction of aryl groups into various organic substrates. This property is particularly useful in the synthesis of complex organic molecules and pharmaceutical agents.
Used in Antiviral and Cytotoxic Agent Synthesis:
2-Thenaldehyde is also utilized in the synthesis of unsaturated ketones, which have demonstrated antiviral and cytotoxic properties. These agents have potential applications in the development of new antiviral drugs and cancer therapies.

Synthesis Reference(s)

Synthesis, p. 757, 1976 DOI: 10.1055/s-1976-24193Tetrahedron Letters, 36, p. 455, 1995 DOI: 10.1016/0040-4039(94)02284-I

Purification Methods

Wash it with 50% HCl and distil it under reduced pressure just before use. It has UV: 234nm (hexane). The Z-oxime has m 144o, 136-138o and 142o (H2O). [Beilstein

InChI:InChI=1/C5H4OS/c6-4-5-2-1-3-7-5/h1-4H

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 186581-53-3 diazomethane 
• 3437-95-4 2-Iodothiophene 
• 201230-82-2 carbon monoxide 
• 77735-41-2 4-O-acetyl-2,5-episeleno-3-S-ethyl-3-thio-D-arabinose diethyl dithioacetal 
• 188290-36-0 thiophene 
• 50-00-0 formaldehyd 
• 68-12-2 N,N-dimethyl-formamide 
• 93-61-8 N-methyl-N-phenylformamide 
• 1003-09-4 2-bromothiophene 
• 109-94-4 formic acid ethyl ester 
• 5271-67-0 2-Thiophenecarbonyl chloride 
• 13959-97-2 2-thiophenealdehyde diethyl acetal 
• 765-50-4 2-Chloromethylthiophene 

Downstream Products

• 140-19-2 2-<(2-thienylmethyl)amino>pyridine 
• 102241-69-0 3,3'-(thiophen-2-ylmethylene)bis(indole) 
• 81020-64-6 (Z)-3-(thiophen-2-yl)-2-(p-tolyl)acrylonitrile 
• 3783-65-1 (E)-2-(2-phenylethenyl)thiophene 
• 26440-92-6 (E)-2-phenyl-3-(2-thienyl)-2-propenoic acid 
• 10569-35-4 Z-3-(2-thienyl)-2-phenylacrylic acid 
• 37758-41-1 1-Nitro-1-phenyl-2-(2-thienyl)ethen 
• 89939-28-6 5-thiophen-2-ylmethylene-imidazolidine-2,4-dione 
• 139336-31-5 5-thiophen-2-ylmethylenethiazolidine-2,4-dione 
• 636-72-6 2-thiophenemethanol 
• 37629-59-7 (E)-2-(2-nitroprop-1-en-1-yl)thiophene 
• 24760-36-9 2-(thiophen-2-ylmethylene)indan-1,3-dione 
• 1022259-64-8 3-phenyl-4-[2]thienylmethylene-4H-isoxazol-5-one 
• 843638-98-2 2-((9H-fluorene-9-ylidene)methyl)thiophene 

Relevant academic research and scientific papers

Aerobic oxidation of alcohols enabled by nitrogen-doped copper nanoparticle catalysts

Heterogeneous nitrogen-doped carbon-incarcerated copper nanoparticle catalysts have been developed. The catalysts promoted the oxidation of alcohols to the corresponding aldehydes, including aliphatic substrates, in high yield in the presence of an N-oxyl

A “universal” catalyst for aerobic oxidations to synthesize (hetero)aromatic aldehydes, ketones, esters, acids, nitriles, and amides

Functionalized (hetero)aromatic compounds are indispensable chemicals widely used in basic and applied sciences. Among these, especially aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides represent valuable fine and bulk chemicals, which are used in chemical, pharmaceutical, agrochemical, and material industries. For their synthesis, catalytic aerobic oxidation of alcohols constitutes a green, sustainable, and cost-effective process, which should ideally make use of active and selective 3D metals. Here, we report the preparation of graphitic layers encapsulated in Co-nanoparticles by pyrolysis of cobalt-piperazine-tartaric acid complex on carbon as a most general oxidation catalyst. This unique material allows for the synthesis of simple, functionalized, and structurally diverse (hetero)aromatic aldehydes, ketones, carboxylic acids, esters, nitriles, and amides from alcohols in excellent yields in the presence of air.

Highly atom efficient synthesis of 2,2,4,5-tetrasubstituted 3(2H)-furanones having both hydroxyl and amino substituents

We have developed a highly atom efficient synthesis of tetrasubstituted 3(2H)-furanones from easily accessible starting materials such as C,N-diarylaldonitrones and dibenzoylacetylene. Control experiments revealed that reaction of aldonitrones having electron-withdrawing groups on the C-aryl substituent in polar aprotic solvents exhibited high product selectivity while reaction temperature has only a negligible effect on product yield and selectivity.

Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal

The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r

Samarium-based Grignard-type addition of organohalides to carbonyl compounds under catalysis of CuI

Grignard-type additions were readily achieved under the mediation of CuI (10 mol%) and samarium (2 equiv.) by employing various organohalides,e.g.benzyl, aryl, heterocyclic and aliphatic halides (Cl, Br or I), and diverse carbonyl compounds (e.g.carbonic esters, carboxylic esters, acid anhydrides, acyl chlorides, ketones, aldehydes, propylene epoxides and formamides) to afford alcohols, ketones and aldehydes, respectively, with high efficiency and chemoselectivity, in which the organosamarium intermediate might be involved.

New synthesis method of 2-thiophenecarboxaldehyde

The invention relates to a new synthesis method of 2-thiophenecarboxaldehyde. The method comprises the following steps: putting thionyl chloride into a container with the temperature of about 20-30 DEG C, and carrying out low-temperature treatment for 1 hour for later use; slowly dropwise adding the treated thionyl chloride into a container containing N, Ndimethylformamide and thiophene; raising the temperature to 75-80 DEG C, carrying out heat preservation reaction for 3-5 hours, and absorbing tail gas generated in the reaction process by using water mist; after the reaction is finished, cooling, slowly dripping reaction liquid into water, and controlling the temperature to be 20-30 DEG C; after dropwise adding is finished, extracting for three times by using an organic solvent, recovering dimethylamine hydrochloride from a water layer, combining organic phases, washing by using alkali liquor, and desolventizing the organic phases to obtain a crude product of 2-thiophenecarboxaldehyde; briefly speaking, according to the technical scheme, an excellent optimization scheme is utilized, and the problems existing in 2-thiophenecarboxaldehyde preparation are solved.

Merging N-Hydroxyphthalimide into Metal-Organic Frameworks for Highly Efficient and Environmentally Benign Aerobic Oxidation

Two highly efficient metal-organic framework catalysts TJU-68-NHPI and TJU-68-NDHPI have been successfully synthesized through solvothermal reactions of which the frameworks are merged with N-hydroxyphthalimide (NHPI) units, resulting in the decoration of pore surfaces with highly active nitroxyl catalytic sites. When t-butyl nitrite (TBN) is used as co-catalyst, the as-synthesized MOFs are demonstrated to be highly efficient and recyclable catalysts for a novel three-phase heterogeneous oxidation of activated C?H bond of primary and secondary alcohols, and benzyl compounds under mild conditions. Based on the high efficiency and selectivity, an environmentally benign system with good sustainability, mild conditions, simple work-up procedure has been established for practical oxidation of a wide range of substrates.

A Synergistic Magnetically Retrievable Inorganic-Organic Hybrid Metal Oxide Catalyst for Scalable Selective Oxidation of Alcohols to Aldehydes and Ketones

Herein, we report a synergistic silica coated magnetic Fe3O4 catalyst functionalized with nitrogen rich organic moieties and immobilized with cobalt metal ion (FNP-5) for selective oxidation of alcohols to aldehydes and ketones using tert-butyl hydroperoxide (TBHP) as oxidant. The catalyst was rigorously characterized via several techniques which delineate its core-shell structure, magnetic behavior, phase and crystal structure. The Co(III) acts as the active catalytic center for selective oxidation reaction. The control reactions revealed radical mechanistic pathway assisted by the synergism induced by the inorganic-organic hybrid nature of FNP-5. The other features of current protocol involve neat reaction conditions, high TOF values, scalability of product and low E-factor value (1.92). Moreover, FNP-5 could be effortlessly separated via an external magnet, displays recyclability over eight catalytic cycles and exhibits structural integrity even after rigorous use. Overall, these results manifest the understanding of synergistic architectures as sustainable surrogates for selective oxidation reactions.

Chemoselective and ligand-free aerobic oxidation of benzylic alcohols to carbonyl compounds using alumina-supported mesoporous nickel nanoparticle as an efficient recyclable heterogeneous catalyst

An economically efficient and operationally simple ligand-free protocol for the chemoselective oxidation of benzylic alcohols to carbonyl compounds has been developed using alumina-supported nickel nanoparticles as a stable recyclable heterogeneous catalyst along with potassium tert-butoxide in the presence of aerial oxygen as an eco-friendly oxidant. The aliphatic alcohols remained unaffected under the present condition. Excellent chemoselectivity has also been demonstrated through intermolecular and intramolecular competition experiments. This protocol accommodates a diverse range of substituents with the tolerance of various sensitive moieties during the reaction. The catalyst could be recovered by filtration and reused consecutively without any significant loss in the catalytic activity. Moreover, the heterogeneity of the catalyst has also been established by the “hot filtration method (Sheldon's test)”.

One-Pot Direct Oxidation of Primary Amines to Carboxylic Acids through Tandem ortho-Naphthoquinone-Catalyzed and TBHP-Promoted Oxidation Sequence

Biomimetic oxidation of primary amines to carboxylic acids has been developed where the copper-containing amine oxidase (CuAO)-like o-NQ-catalyzed aerobic oxidation was combined with the aldehyde dehydrogenase (ALDH)-like TBHP-mediated imine oxidation protocol. Notably, the current tandem oxidation strategy provides a new mechanistic insight into the imine intermediate and the seemingly simple TBHP-mediated oxidation pathways of imines. The developed metal-free amine oxidation protocol allows the use of molecular oxygen and TBHP, safe forms of oxidant that may appeal to the industrial application.