3760-54-1

Usage

Uses

1. Used in Chemical Synthesis:
1-Formylpyrrolidine is used as a key intermediate in the synthesis of complex organic molecules. Its application in this field is due to its ability to react with other compounds to form new chemical entities with specific properties.
2. Used in the Synthesis of Silacyclopentane Derivatives:
1-Formylpyrrolidine is used as a building block for the synthesis of 1-oxa-3,4-dimethyl-5-(1-pyrrolldino)-2,2-di(tert-butyl)silacyclopentane and 1-oxa-4-isopropyl-5-(1-pyrrolidino)-2,2-di(tert-butyl)silacyclopentane. These silicyclopentane derivatives are important in the development of new materials and pharmaceuticals due to their unique structural and chemical properties.
3. Used in Gas Clathrate Inhibition:
1-Formylpyrrolidine is used as a monomer constituent in the development of gas clathrate inhibitors. Clathrate inhibitors are essential in the oil and gas industry to prevent the formation of gas hydrates, which can cause blockages in pipelines and other equipment. The use of 1-Formylpyrrolidine in this application is due to its ability to interact with other molecules and form stable clathrate structures, thus preventing the formation of unwanted gas hydrates.

InChI:InChI=1/C5H9NO/c7-4-5-2-1-3-6-5/h4-6H,1-3H2

Upstream product

• 123-75-1 pyrrolidine 
• 64-18-6 formic acid 
• 75-87-6 chloral 
• 50-00-0 formaldehyd 
• 67-66-3 chloroform 
• 18197-22-3 N-formylformamide 
• 201230-82-2 carbon monoxide 
• 77287-34-4 formamide 
• 68-12-2 N,N-dimethyl-formamide 
• 110-83-8 cyclohexene 
• 109-94-4 formic acid ethyl ester 
• 7549-99-7 1-[N-(4-chloro-phenyl)-formimidoyl]-pyrrolidine 
• 6908-73-2 (E)-1-styrylpyrrolidine 
• 4625-58-5 Bis(1-pyrrolidinyl)acetonitril 

Downstream Products

• 120-94-5 1-Methylpyrrolidine 
• 58415-03-5 C₉H₉NOS 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 86869-55-8 C₉H₁₀N₂OS 
• 119141-10-5 2,4-dichloro-3-(pyrrolidinylmethylene)-1,4-cyclohexadiene-1,5-dicarboxaldehyde 
• 1817-49-8 1,3-diphenyl-1-propyn-3-ol 
• 85377-68-0 C₈H₆ClNOS 
• 5564-73-8 1-(dimethoxymethyl)pyrrolidine 
• 7632-86-2 1-p-methoxyphenyl-3-pyrrolidino-2-propen-1-thione 
• 3760-55-2 N-nitropyrrolidine 
• 87167-61-1 9-benzyl-1-methyl-9H-carbazole-3-carbaldehyde 
• 87167-64-4 (9-benzyl-1,2,3,4-tetrahydrocarbazol-1-yl)carboxaldehyde 
• 764-93-2 1-decyne 
• 112-31-2 caprinaldehyde 

Relevant academic research and scientific papers

Chromium-catalysed efficient: N -formylation of amines with a recyclable polyoxometalate-supported green catalyst

A simple and efficient protocol for the formylation of amines with formic acid, catalyzed by a polyoxometalate-based chromium catalyst, is described. Notably, this method shows excellent activity and chemoselectivity for the formylation of primary amines; diamines have also been successfully employed. Importantly, the chromium catalyst is potentially non-toxic, environmentally benign and safer than the widely used high valence chromium catalysts such as CrO3 and K2Cr2O7. The catalyst can be recycled several times with a negligible impact on activity. Finally, a plausible mechanism is provided based on the observation of intermediate and control experiments.

Nickel-Catalyzed Amination of Aryl Chlorides with Amides

A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.

DMF·HCl as a versatile and straightforward N- and O-formylating agent

Inspired by the serendipitous isolation of N-formylpiperazines when we attempted the synthesis of a series of piperazines, we have developed a straightforward methodology for the N- and O- formylation of secondary cyclic amines, anilines and steroids, respectively. Such approach is based on the hitherto non-reported use of DMF·HCl complex, as a versatile and easily-available formylating system that can be stored without apparent loss of activity.

Olefin functionalized IPr.HCl monomer as well as preparation method and application thereof

The invention relates to an olefin functionalized IPr.HCl monomer, a preparation method thereof, a method for preparing an N-heterocyclic carbene functionalized organic polymer (PS-IPr-x) by using the olefin functionalized IPr.HCl monomer, and application of the N-heterocyclic carbene functionalized organic polymer as a heterogeneous catalyst for catalyzing reduction N-formylation of carbon dioxide and amine. A heterogeneous catalyst is prepared by using cheap and easily available DVB as a polymerization cross-linking agent through an AIBN-initiated olefin polymerization method, and has the advantages of low preparation cost and simple preparation method. Meanwhile, the catalytic activity of the catalyst is obviously higher than that of reported catalysts, and the catalyst has a wide practical application prospect.

Method for preparing formamide compound by using MCOF to catalyze CO2 as carbon source at normal temperature and pressure

The invention provides a method for preparing a formamide compound by using MCOF to catalyze CO2 as a carbon source at normal temperature and pressure, and belongs to the technical field of chemistry and chemical engineering. Under the conditions of normal temperature and normal pressure, CO2 is used as a carbon source to realize N-formylation reaction of various amine substrates. The method has the advantages that the reaction system uses the metal ion-doped two-dimensional covalent organic framework MCOF as the catalyst, CO2 is reduced at normal temperature and normal pressure to provide acyl, high-pressure hydrogen and toxic CO are prevented from being used, and the reaction conditions are mild (normal temperature and normal pressure). According to the method for preparing the formamide, the greenhouse gas carbon dioxide serves as a carbon source, the cost is low, operation is easy, reaction conditions are mild (normal temperature and normal pressure), the yield of the prepared formamide product is excellent (99%), and a green synthesis method is provided for N-acylation reaction.

Mesoporous Sn(IV) Doping DFNS Supported BaMnO3 Nanoparticles for Formylation of Amines Using Carbon Dioxide

Abstract: In the present paper, Sn(IV) doping DFNS (SnD) supported nanoparticles of BaMnO3 (BaMnO3/SnD) and using as a catalyst for the N-formylation of amines by CO2 hydrogenation. In this catalyst, the SnD with the ratios of Si/Sn in the range of from 6 to 50 were obtained with method of direct hydrothermal synthesis (DHS) as well as the nanoparticles of BaMnO3 were on the surfaces of SnD in situ reduced. Scanning electron microscope (SEM), X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), X-ray energy dispersive spectroscopy (EDS), and transmission electron microscopy (TEM) were utilized for characterizing the nanostructures BaMnO3/SnD. It is found that the nanostructures of BaMnO3/SnD can be a nominate due to its effective and novel catalytic behavior in N-formylation of amines through hydrogenation of CO2. Graphic Abstract: [Figure not available: see fulltext.]

Bifunctional Ru-loaded Porous Organic Polymers with Pyridine Functionality: Recyclable Catalysts for N-Formylation of Amines with CO2 and H2

A series of pyridine functionalized porous organic polymers (POPs-Py&PPh3) have been synthesized by polymerizing tris(4-vinylphenyl)phosphane and 4-vinylpyridine. The pyridine moieties in the copolymer materials contribute to CO2 adsorption and promote the subsequent conversion of CO2. The POP supported Ru catalyst (Ru/POP3-Py&PPh3) shows a high catalytic activity (TON up to 710) in the N-formylation of various primary and secondary amines with CO2/H2, affording the corresponding formamides in good yields (55–95%) under mild reaction conditions. The heterogeneous catalyst can be easily separated from the reaction system and reused for at least eight cycles in the N-formylation of morpholine. (Figure presented.).

Highly Efficient and Selective N-Formylation of Amines with CO2 and H2 Catalyzed by Porous Organometallic Polymers

The valorization of carbon dioxide (CO2) to fine chemicals is one of the most promising approaches for CO2 capture and utilization. Herein we demonstrated a series of porous organometallic polymers could be employed as highly efficient and recyclable catalysts for this purpose. Synergetic effects of specific surface area, iridium content, and CO2 adsorption capability are crucial to achieve excellent selectivity and yields towards N-formylation of diverse amines with CO2 and H2 under mild reaction conditions even at 20 ppm catalyst loading. Density functional theory calculations revealed not only a redox-neutral catalytic pathway but also a new plausible mechanism with the incorporation of the key intermediate formic acid via a proton-relay process. Remarkably, a record turnover number (TON=1.58×106) was achieved in the synthesis of N,N-dimethylformamide (DMF), and the solid catalysts can be reused up to 12 runs, highlighting their practical potential in industry.

Design of Lewis base functionalized ionic liquids for the N-formylation of amines with CO2 and hydrosilane: The cation effects

A series of functionalized ionic liquids (ILs) were developed for the reductive functionalization of CO2 with amine and hydrosilane to afford formamides under mild conditions. It was found that 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-based IL i.e. [DBUC12]Br showed high efficiency for the N-formylation reaction of amines without using any organic solvents or additives. Furthermore, control experiments suggested the cations with active hydrogen may weaken the nucleophilicity of anions through ion pairing interactions, thereby affecting the activation of hydrosilane. The reaction mechanism was then investigated by Density Functional Theory (DFT) calculations. This protocol represents a highly efficient and environmentally friendly example for catalytic conversion of CO2 into value-added chemicals such as formamide derivatives by employing DBU functionalized ILs.

Copper-Catalyzed Formylation of Amines by using Methanol as the C1 Source

Cu/TEMPO catalyst systems are known for the selective transformation of alcohols to aldehydes, as well as for the simultaneous coupling of alcohols and amines to imines under oxidative conditions. In this study, such a Cu/TEMPO catalyst system is found to catalyze the N-formylation of a variety of amines by initial oxidative activation of methanol as the carbonyl source via formaldehyde and formation of N,O-hemiacetals and oxidation of the latter under very mild conditions. A vast range of amines, including aromatic and aliphatic, primary and secondary, and linear and cyclic amines are formylated under these conditions with good to excellent yields. Moreover, paraformaldehyde can be used instead of methanol for the N-formylation.