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(E)-Methyl 3-(pyridin-3-yl)acrylate, also known as 3-(pyridin-3-yl)-2-propenoic acid methyl ester, is a chemical compound with the molecular formula C9H9NO2. It is a clear, colorless to light yellow liquid with a fruity odor and is recognized for its unique chemical properties, including the presence of a pyridine ring. (E)-Methyl 3-(pyridin-3-yl)acrylate is stable under normal conditions and is used in various synthetic applications, making it a valuable intermediate in organic synthesis.

81124-48-3

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81124-48-3 Usage

Uses

Used in Pharmaceutical Industry:
(E)-Methyl 3-(pyridin-3-yl)acrylate is used as an intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical structure, which includes a pyridine ring, allows for the creation of a wide range of medicinal products.
Used in Agrochemical Industry:
In the agrochemical industry, (E)-Methyl 3-(pyridin-3-yl)acrylate is utilized as a building block for the development of new agrochemicals. Its properties make it suitable for the synthesis of compounds with potential applications in pest control and crop protection.
Used in Flavor and Fragrance Industry:
(E)-Methyl 3-(pyridin-3-yl)acrylate is used as a component in the creation of various flavors and fragrances. Its fruity odor and chemical versatility contribute to the development of unique scents and tastes for the consumer market.
Used in Research and Development:
Due to its unique chemical properties, (E)-Methyl 3-(pyridin-3-yl)acrylate is also employed in research and development for exploring new synthetic pathways and creating novel compounds with potential applications in various industries.

Check Digit Verification of cas no

The CAS Registry Mumber 81124-48-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,1,1,2 and 4 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 81124-48:
(7*8)+(6*1)+(5*1)+(4*2)+(3*4)+(2*4)+(1*8)=103
103 % 10 = 3
So 81124-48-3 is a valid CAS Registry Number.

81124-48-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 3-pyridin-3-ylprop-2-enoate

1.2 Other means of identification

Product number -
Other names 3-(3'-pyridinyl)-(E)-propenoic acid methyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:81124-48-3 SDS

81124-48-3Relevant academic research and scientific papers

Photoinduced Regioselective Olefination of Arenes at Proximal and Distal Sites

Ali, Wajid,Anjana, S. S.,Bhattacharya, Trisha,Chandrashekar, Hediyala B.,Goswami, Nupur,Guin, Srimanta,Maiti, Debabrata,Panda, Sanjib,Prakash, Gaurav,Saha, Argha,Sasmal, Sheuli,Sinha, Soumya Kumar

supporting information, p. 1929 - 1940 (2022/02/01)

The Fujiwara-Moritani reaction has had a profound contribution in the emergence of contemporary C-H activation protocols. Despite the applicability of the traditional approach in different fields, the associated reactivity and regioselectivity issues had

(E)-3-heteroaromatic propyl-2-enoic acid derivative as well as preparation and application thereof

-

Paragraph 0051-0053, (2020/09/10)

The invention relates to a (E)-3-heteroaromatic propyl-2-enoic acid derivative, and also relates to a preparation method and pharmaceutical application thereof. The compound is a novel Nrf2 activatorand has the effects of resisting oxidative stress, resisting neuritis and enhancing mitochondrial functions and biogenesis by effectively activating an Nrf2 signal path, so that nerve cells are protected, and the compound can be used for treating neurodegenerative diseases and cerebral apoplexy. In addition, the novel Nrf2 activator can also be used to treat autoimmune diseases, diabetes and nephropathy, and other chronic diseases.

Palladium-Based Catalysts Supported by Unsymmetrical XYC–1 Type Pincer Ligands: C5 Arylation of Imidazoles and Synthesis of Octinoxate Utilizing the Mizoroki–Heck Reaction

Maji, Ankur,Singh, Ovender,Singh, Sain,Mohanty, Aurobinda,Maji, Pradip K.,Ghosh, Kaushik

, p. 1596 - 1611 (2020/04/29)

A series of new unsymmetrical (XYC–1 type) palladacycles (C1–C4) were designed and synthesized with simple anchoring ligands L1–4H (L1H = 2-((2-(4-methoxybenzylidene)-1-phenylhydrazinyl)methyl)pyridine, L2H = N,N-dimethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono)methyl)aniline, L3H = N,N-diethyl-4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono)methyl) aniline and L4H = 4-(4-((2-phenyl-2-(pyridin-2-ylmethyl)hydrazono) methyl)phenyl)morpholine H = dissociable proton). Molecular structure of catalysts (C1–C4) were further established by single X-ray crystallographic studies. The catalytic performance of palladacycles (C1–C4) was explored with the direct Csp2–H arylation of imidazoles with aryl halide derivatives. These palladacycles were also applied for investigating of Mizoroki–Heck reactions with aryl halides and acrylate derivatives. During catalytic cycle in situ generated Pd(0) nanoparticles were characterized by XPS, SEM and TEM analysis and possible reaction pathways were proposed. The catalyst was employed as a pre-catalyst for the gram-scale synthesis of octinoxate, which is utilized as a UV-B sunscreen agent.

Uranyl-Organic Coordination Compounds Incorporating Photoactive Vinylpyridine Moieties: Synthesis, Structural Characterization, and Light-Induced Fluorescence Attenuation

Wu, Si,Mei, Lei,Li, Fei-Ze,An, Shu-Wen,Hu, Kong-Qiu,Nie, Chang-Ming,Chai, Zhi-Fang,Shi, Wei-Qun

supporting information, p. 14772 - 14785 (2018/11/23)

The fluorescence of uranyl originated from electronic transitions (S11-S00 and S10-S0v, v = 0-4) of the ligand-to-metal charge transfer (LMCT) process is an intrinsic property of many uranyl coordination compounds. However, light-induced regulation on fluorescence features of uranyl hybrid materials through photoactive functional groups is less investigated. In this work, the photoactive vinyl group-containing ligands, (E)-methyl 3-(pyridin-4-yl)acrylate and (E)-methyl 3-(pyridin-3-yl)acrylate, have been used in the construction of uranyl coordination polymers in the presence of 1,10-phenanthroline (phen). Five compounds (UO2)3(μ3-O)(μ2-OH)2(L1)2(phen)2(1), (UO2)3(μ3-O)(μ2-OH)3(L1)(phen)2 (2), (UO2)3(μ3-O)(μ2-OH)3(L2)(phen)2 (3), [(UO2)2(μ2-OH)2(L2)2(phen)2]·2H2O (4), and (UO2)Zn(SO4)(phen)(H2O)(OH)2(5) were obtained under hydrothermal conditions. Compounds 1-4 are polynuclear uranyl structures with abundant π-π interactions and hydrogen bonds contributed to the 3D crystal packing of them. As model compounds, 1 and 3 are selected for exploring photoresponsive behaviors. The emission intensities of these two compounds are found to decrease gradually over the exposure time of UV irradiation. X-ray single crystal structural analysis suggests that the fluorescence attenuation can be explained by the slight rotation of pyridinyl groups around the carbon-carbon double bond during UV irradiation, which is accompanied by the change of weak interactions, i.e., π-π interactions and hydrogen bonds in strength and density. This feature of light-induced fluorescence attenuation may enable these two compounds to act as potential photoresponsive sensor materials.

BIARYL PYRAZOLES AS NRF2 REGULATORS

-

Page/Page column 260, (2017/08/01)

The present invention relates to biaryl pyrazole compounds, methods of making them, pharmaceutical compositions containing them and their use as NRF2 regulators.

Efficient nickel(II) naringenin-oxime complex catalyzed Mizoroki-Heck cross-coupling reaction in the presence of hydrazine hydrate

Song, Jin-Yi,Liu, Yang,Zhao, Hong-Yan,Han, Hua-Tao,Li, Zhuo-Fei,Guo, Wei-Hao,Chu, Wen-Yi,Sun, Zhi-Zhong

, p. 12288 - 12292 (2017/10/16)

A novel nickel(ii) naringenin-oxime complex was designed, synthesized and characterized. Therein, the nickel(ii) naringenin oxime complex as an efficient catalyst was used in Mizoroki-Heck coupling reactions of aryl halides containing electron-rich and electron-deficient substituents with styrene, methyl acrylate and divinylbenzene (DVB), respectively. The reaction proceeded efficiently under alkaline conditions in the presence of 0.30 mol% of the Ni(ii) naringenin oxime complexand N2H4·H2O as the reductant in EtOH at 80 °C, and 32 alkene products were afforded in moderate to excellent yields, containing four new olefins. The new catalytic system not only provided an inexpensive and efficient process with greener conditions, but also broadened the reaction scope.

A practical, chemoselective approach to O-methylation of carboxylic acids with dimethyl malonate

Mao, Jincheng,Liu, Defu,Li, Yongming,Zhao, Jinzhou,Rong, Guangwei,Yan, Hong,Zhang, Guoqi

, p. 9067 - 9072 (2015/11/09)

A practical and chemoselective method is described for the O-methylation of carboxylic acids. Dimethyl malonate, a low toxic and commercially available compound was found to be an effective methylating reagent for a variety of carboxylic acids affording methyl ester products in good to high yields and with excellent chemoselectivity, without the use of strong bases as additives. A mechanism involving the utilization of potassium bromide is tentatively proposed.

A biocompatible alkene hydrogenation merges organic synthesis with microbial metabolism

Sirasani, Gopal,Tong, Liuchuan,Balskus, Emily P.

supporting information, p. 7785 - 7788 (2014/08/05)

Organic chemists and metabolic engineers use orthogonal technologies to construct essential small molecules such as pharmaceuticals and commodity chemicals. While chemists have leveraged the unique capabilities of biological catalysts for small-molecule production, metabolic engineers have not likewise integrated reactions from organic synthesis with the metabolism of living organisms. Reported herein is a method for alkene hydrogenation which utilizes a palladium catalyst and hydrogen gas generated directly by a living microorganism. This biocompatible transformation, which requires both catalyst and microbe, and can be used on a preparative scale, represents a new strategy for chemical synthesis that combines organic chemistry and metabolic engineering. Reduction to practice: A hydrogenation reaction has been developed that employs hydrogen generated in situ by a microorganism and a biocompatible palladium catalyst to reduce alkenes on a synthetically useful scale. This type of transformation, which directly combines tools from organic chemistry with the metabolism of a living organism for small-molecule production, represents a new strategy for chemical synthesis.

A robust first-pass protocol for the heck-mizoroki reaction

Murray, Paul M.,Bower, John F,Cox, David K,Galbraith, Ewan K,Parker, Jeremy S,Sweeney, Joseph B.

, p. 397 - 405 (2013/04/24)

The Heck-Mizoroki (HM) reaction is one of the most widely used C-C bond-forming methods of contemporary synthesis. Notwithstanding this, these reactions frequently require significant optimization before efficient transformations can be obtained. We describe here the results of a study that aimed to establish a generic experimental protocol for HM reactions which enables acceptable yields from first-pass experiments. The methodology utilizes readily available stable catalysts and can be applied to a broad range of coupling partners.

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