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

• 77735-41-2 4-O-acetyl-2,5-episeleno-3-S-ethyl-3-thio-D-arabinose diethyl dithioacetal 
• 1003-09-4 2-bromothiophene 
• 109-94-4 formic acid ethyl ester 
• 765-50-4 2-Chloromethylthiophene 
• 100-97-0 hexamethylenetetramine 
• 201230-82-2 carbon monoxide 
• 68-12-2 N,N-dimethyl-formamide 
• 73927-54-5 2-ethanol 
• 13679-77-1 (thiophen-2-yl)methyl acetate 
• 85455-66-9 thiophen-2-yl-methyl benzoate 
• 38266-87-4 thiophene-2-carbaldehyde oxime 
• 29683-84-9 thiophene-2-carbaldehyde oxime 
• 5780-34-7 tetrahydro[1,3]oxazolo[2,3-b][1,3]oxazole 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 

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

A Magnetically Recyclable Palladium-Catalyzed Formylation of Aryl Iodides with Formic Acid as CO Source: A Practical Access to Aromatic Aldehydes

A magnetically recyclable palladium-catalyzed formylation of aryl iodides under CO gas-free conditions has been developed by using a bidentate phosphine ligand-modified magnetic nanoparticles-anchored- palladium(II) complex [2P-Fe 3O 4@SiO 2-Pd(OAc) 2] as catalyst, yielding a wide variety of aromatic aldehydes in moderate to excellent yields. Here, formic acid was employed as both the CO source and the hydrogen donor with iodine and PPh 3as the activators. This immobilized palladium catalyst can be obtained via a simple preparative procedure and can be facilely recovered simply by using an external magnetic field, and reused at least 9 times without any apparent loss of catalytic activity.

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.

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.

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)”.

Method for preparing aldehyde compounds by oxidative cleavage of carbon-carbon bonds of terminal alkene compounds

The invention discloses a method for preparing aldehyde compounds by oxidizing and breaking carbon-carbon bonds of terminal alkene compounds. The method comprises the following steps: adding an alkene-terminated compound, an additive and a nitrogen-doped mesoporous carbon-loaded monatomic catalyst into a fatty primary alcohol solvent, putting into a pressure container, sealing, introducing oxygen source gas with a certain pressure, controlling the pressure of the oxygen source gas to be 0.1-1MPa and the reaction temperature to be 80-150 DEG C, and obtaining a reaction product, namely the aldehyde compound. The nitrogen-doped mesoporous carbon-loaded monatomic catalyst adopted by the invention is high in activity, the highest separation yield of the aldehyde compound as a reaction product reaches 99%, the method is wide in application range, the reaction conditions are easy to control, the catalyst can be recycled, the post-treatment is simple, and the method is suitable for industrial production.