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Methyl (E)-2-Cyano-3-phenylacrylate, a chemical compound with the molecular formula C11H9NO2, is a light yellow liquid possessing a molecular weight of 191.2 g/mol. It serves as a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals, and is also utilized as a reagent in organic chemical reactions, particularly for the formation of carbon-carbon and carbon-nitrogen bonds. Due to its potentially hazardous nature, it should be handled with care in a controlled laboratory setting.

14533-86-9

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14533-86-9 Usage

Uses

Used in Pharmaceutical Industry:
Methyl (E)-2-Cyano-3-phenylacrylate is used as a key building block for the synthesis of various pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its ability to form carbon-carbon and carbon-nitrogen bonds makes it a valuable component in the creation of complex molecular structures.
Used in Agrochemical Industry:
In the agrochemical industry, Methyl (E)-2-Cyano-3-phenylacrylate is employed as a precursor in the synthesis of agrochemicals, such as pesticides and herbicides. Its reactivity in forming essential chemical bonds aids in the development of effective and targeted agricultural products.
Used in Fine Chemicals Industry:
Methyl (E)-2-Cyano-3-phenylacrylate is utilized as a building block in the synthesis of fine chemicals, which are high-purity chemicals used in various applications, including fragrances, dyes, and specialty chemicals. Its versatility in forming chemical bonds allows for the creation of a wide range of high-quality products.
Used as a Reagent in Organic Chemical Reactions:
Methyl (E)-2-Cyano-3-phenylacrylate is used as a reagent in organic chemical reactions, particularly for the formation of carbon-carbon and carbon-nitrogen bonds. Its reactivity and stability make it a valuable tool in the synthesis of complex organic compounds and contribute to the advancement of organic chemistry research.

Check Digit Verification of cas no

The CAS Registry Mumber 14533-86-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,5,3 and 3 respectively; the second part has 2 digits, 8 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 14533-86:
(7*1)+(6*4)+(5*5)+(4*3)+(3*3)+(2*8)+(1*6)=99
99 % 10 = 9
So 14533-86-9 is a valid CAS Registry Number.

14533-86-9SDS

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 (E)-Methyl 2-Cyano-3-phenyl-2-propenoate

1.2 Other means of identification

Product number -
Other names Methyl (E)-2-Cyano-3-phenylacrylate

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:14533-86-9 SDS

14533-86-9Relevant academic research and scientific papers

Knoevenagel condensation catalyzed by K2NiP2O 7. Synthesis of (E)-methyl-α-cyanocinnamates in high yields

El Maadi, Aicha,Matthiesen, Chance L.,Ershadi, Philip,Baker, Jennifer,Herron, Derrick M.,Holt, Elizabeth M.

, p. 757 - 763 (2003)

The Knoevenagel reaction of benzaldehyde and several chloroderivatives with methyl cyanoacetate catalyzed by K2NiP2O7 leads to methyl (E)-α-cyanocinnamate derivatives in 40 min with yields of 71.65-83.45%. Pure products ar

Phosphate Naturel et Phosphate Trisodique : Nouveaux Catalyseurs Solides de la Condensation de Knoevenagel en Milieu Heterogene

Sebti, Said,Saber, Ahmed,Rhihil, Abdallah

, p. 9399 - 9400 (1994)

The Knoevenagel condensation of aldehydes with active methylene compounds was carried out at room temperature, on a heterogenous media, in the absence of solvent or in the methanol, using phosphate ore or sodium phosphate as new catalysts.

Synthesis, characterization and application of α-Ca3 (PO4)2 as a heterogeneous catalyst for the synthesis of 2.3-diphenylquinoxaline derivatives and knoevenagel condensation under green conditions

Anahmadi, Haddou,Benzekri, Zakaria,Boukhris, Said,El hajri, Fatima,El youbi, Mohamed Salahdine,Fathi, Majda,Idrissi, Brahim Chafik El,Sibous, Sarra,Souizi, Abdelaziz

, (2021/09/20)

Green chemistry is now paramount in modern life and industrial sector. It has become a research priority and a scientific challenge. In this study, alpha-tricalcic phosphate was prepared as a green catalytic medium. This medium has been characterized by v

Highly Active Copper(I)-Chalcogenone Catalyzed Knoevenagel Condensation Reaction Using Various Aldehydes and Active Methylene Compounds

Mannarsamy, Maruthupandi,Prabusankar, Ganesan

, (2021/10/05)

First copper(I) chalcogenones catalysed Knoevenagel Condensation reactions have been reported. No illustration of the utilization of this copper-chalcogenone complex class in Knoevenagel Condensation catalysis can be found. Thus, copper(I) bis(benzimidazole-2-chalcogenone) catalysts [Cu(L1)4]+BF4? (1) and [Cu(L2)4]+BF4? (2) (L1 = bis(1-isopropyl-benzimidazole-2-selone)-3-ethyl; L2 = bis(1-isopropyl-benzimidazole-2-thione)-3-ethyl) have been utilized as catalysts in the Knoevenagel Condensation reactions. These copper(I) chalcogenone catalysts have shown high efficiency for the catalytic Knoevenagel Condensation of aryl aldehydes and active methylene compounds. In particular, complex 2, exhibit the best catalytic activities. The scope of the catalytic reactions has been investigated with 22 different molecules. The excellent catalytic activity has been depicted for various types of substrates with either electron-rich or deficient aryl aldehydes. The present investigation features relatively mild reaction conditions with good functional group tolerance and excellent yields. Graphic Abstract: The first copper(I)-chalcogenone complexes catalysed Knoevenagel Condensation reactions?have also been investigated, and revealed the best catalytic activities. [Figure not available: see fulltext.]

Bis [hydrazinium (1+)] hexafluoridosilicate:(N2H5)2SiF6 novel hybrid crystal as an efficient, reusable and environmentally friendly heterogeneous catalyst for Knoevenagel condensation and synthesis of biscoumari

El hajri, Fatima,Benzekri, Zakaria,Sibous, Sarra,Ouasri, Ali,Boukhris, Said,Hassikou, Amina,Rhandour, Ali,Souizi, Abdelaziz

, (2021/02/03)

A simple, effective, green and nontoxic protocol was used for the Knoevenagel condensation and the biscoumarin derivatives synthesis. It have demonstrated that the use of a new hybrid crystal as a heterogeneous catalyst makes it possible to obtain several

Reductive Knoevenagel Condensation with the Zn-AcOH System

Ivanov, Konstantin L.,Melnikov, Mikhail Ya.,Budynina, Ekaterina M.

, p. 1285 - 1291 (2020/11/13)

An efficient gram-scale one-pot approach to 2-substituted malonates and related structures is developed, starting from commercially available aldehydes and active methylene compounds. The technique combines Knoevenagel condensation with the reduction of the C=C bond in the resulting activated alkenes with the Zn-AcOH system. The relative ease with which the C=C bond reduction occurs can be traced to the accepting abilities of the substituents in the intermediate arylidene malonates.

Direct Cyclopropanation of α-Cyano β-Aryl Alkanes by Light-Mediated Single Electron Transfer Between Donor–Acceptor Pairs

Li, Jing,Lear, Martin J.,Hayashi, Yujiro

supporting information, p. 5901 - 5905 (2021/03/09)

Cyclopropanes are traditionally prepared by the formal [2+1] addition of carbene or radical based C1 units to alkenes. In contrast, the one-pot intermolecular cyclopropanation of alkanes by redox active C1 units has remained unrealised. Herein, we achieve

A Tailored Heptazine-Based Porous Polymeric Network as a Versatile Heterogeneous (Photo)catalyst

Sharma, Neha,Kumar, Sunil,Battula, Venugopala R.,Kumari, Anu,Giri, Arkaprabha,Patra, Abhijit,Kailasam, Kamalakannan

supporting information, p. 10649 - 10656 (2021/06/16)

A heptazine-based microporous polymeric network, HMP-TAPA was synthesised by direct coupling of trichloroheptazine and tris(4-aminophenyl)amine (TAPA). A high surface area of 424 m2/g was achieved, which is the highest surface area among heptaz

trans-Selective hydrocyanation of ynoates, ynones and ynoic acids catalyzed by nucleophilic phosphines

Meyer, Maximilian,Peri?, Milica,Sch?mberg, Fritz,Vilotijevi?, Ivan

supporting information, (2021/10/04)

trans-Selective hydrocyanation of ynoates and ynones in the presence of TMSCN and an alcohol additive are catalyzed by nucleophilic phosphines. The trisubstituted E-olefin products of anti-addition of hydrogen cyanide to the alkyne are produced with high regio- and stereoselectivity. The alcohol additive reacts with TMSCN to produce hydrogen cyanide in situ. Ynoic acids undergo the phosphine catalyzed hydrocyanation in the presence of TMSCN under aprotic conditions only. In these reactions, TMSCN reacts with the acid to generate hydrogen cyanide and the silyl ester which, unlike the acid, undergoes phosphine catalyzed hydrocyanation and gives the stereo-defined E-2-cyano-acrylic acids after work up.

Engineering cellulose into water soluble poly(protic ionic liquid) electrolytes in the DBU/CO2/DMSO solvent system as an organocatalyst for the Knoevenagel condensation reaction

Shen, Yuqing,Yuan, Chaoping,Zhu, Xianyi,Chen, Qin,Lu, Shenjun,Xie, Haibo

, p. 9922 - 9934 (2021/12/24)

The facile design and preparation of polyelectrolytes is a frontier topic in the fields of polymer science, energy storage devices and catalysis. Herein, linear water soluble cellulosic poly(protic ionic liquid) (CPIL) electrolytes were facilely and atom economically prepared after the dissolution of cellulose in the newly developed DBU/CO2/DMSO solvent system, followed by the simple addition of succinic anhydride under mild conditions. The DBU not only participated in the dissolution of cellulose as a solvent component, but also acted as an organocatalyst for the acylation reaction of cellulose with succinic anhydride, as well as a cation component in the targeted CPIL electrolytes. The reaction was optimized, and the effect of the reaction conditions on the chemical and physical properties of the CPILs was investigated. And then, as a proof of concept, the CPIL electrolyte aqueous solution was successfully used as the catalytic reaction media for the Knoevenagel condensation reaction. It was found that the reaction was homogeneous at the beginning, and the products could precipitate out from the media with the proceeding of the reaction, thus affording satisfactory filtration yields ranging from 56.7% to 93.8%. The solution properties of the CPIL aqueous solution were primarily investigated towards an in-depth understanding of the catalytic mechanism, by which a synergetic catalytic mechanism of the CPILs was proposed, and the reaction started with a nucleophilic addition reaction, and was then followed by a fast dehydration reaction. Finally, the direct reusability potential of the CPIL aqueous solution after the product filtration was also primarily investigated for the Knoevenagel condensation reaction.

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