81124-45-0

Basic information

• Product Name: (E)-Methyl 3-(pyridin-2-yl)acrylate
• Synonyms: (E)-Methyl 3-(pyridin-2-yl)acrylate
• CAS NO: 81124-45-0
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17326
• EINECS: -0
• Mol File: 81124-45-0.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (E)-Methyl 3-(pyridin-2-yl)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-Methyl 3-(pyridin-2-yl)acrylate(81124-45-0)
• EPA Substance Registry System: (E)-Methyl 3-(pyridin-2-yl)acrylate(81124-45-0)

Safety Data

• Hazardous Substances Data: 81124-45-0(Hazardous Substances Data)

Usage

Description

(E)-Methyl 3-(pyridin-2-yl)acrylate, with the molecular formula C9H9NO2, is a chemical compound derived from the ester form of acrylic acid. It is a colorless to pale yellow liquid with a fruity odor and is soluble in organic solvents like ethanol and acetone. This versatile compound is commonly used as a building block or intermediate in the synthesis of pharmaceuticals and agrochemicals. However, it is also known to be a potential sensitizer and irritant to the skin, eyes, and respiratory tract, necessitating proper handling and protective measures in laboratory or industrial settings.

Uses

Used in Pharmaceutical Industry:
(E)-Methyl 3-(pyridin-2-yl)acrylate is used as a building block for the synthesis of various pharmaceutical compounds. Its unique structure and reactivity make it a valuable intermediate in the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
In the agrochemical industry, (E)-Methyl 3-(pyridin-2-yl)acrylate is utilized as an intermediate in the production of various agrochemicals, such as pesticides and herbicides. Its chemical properties allow for the creation of effective compounds that can protect crops and enhance agricultural productivity.
Used in Chemical Research:
(E)-Methyl 3-(pyridin-2-yl)acrylate is also used in chemical research as a model compound for studying various reaction mechanisms and exploring new synthetic routes. Its reactivity and structural features make it an interesting subject for scientific investigation and the development of novel chemical methodologies.

Upstream product

• 67-56-1 methanol 
• 54495-51-1 (E)-3-(2-pyridyl)acrylic acid 
• 2916-76-9 methyl (trimethylsilyl)acetate 
• 38010-70-7 (R,E)-N-(1-phenylethyl)-1-(pyridin-2-yl)methanimine 
• 79-20-9 acetic acid methyl ester 
• 109-04-6 2-bromo-pyridine 
• 292638-85-8 acrylic acid methyl ester 
• 1121-60-4 pyridine-2-carbaldehyde 
• 5927-18-4 trimethyl phosphonoacetate 
• 1529-78-8 [(methoxycarbonyl)methyl]triphenylarsonium bromide 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 16695-14-0 Malonic acid monomethyl ester 
• 6832-16-2 methyl diazoacetate 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 

Downstream Products

• 1224606-00-1 methyl (S)-2-(diphenylarsanyl)-3-(pyridin-2-yl)propanoate 
• 28819-26-3 methyl 3-(pyridin-2-yl)propanoate 
• 119522-93-9 3-Hydroxy-5-(2-pyridyl)isoxazole 

Relevant articles and documents

Efficient synthesis of acrylates bearing an aryl or heteroaryl moiety: One-pot method from aromatics and heteroaromatics using formylation and the horner-wadsworth-emmons reaction

Acrylates bearing an aryl or heteroaryl moiety were efficiently prepared by a one-pot process employing a sequence of lithiation, formylation and the Horner-Wadsworth-Emmons reaction starting from aromatic and heteroaromatic compounds. This method can efficiently introduce an acrylate moiety into aromatic and heteroaromatic compounds.

Radical Chain Reduction via Carbon Dioxide Radical Anion (CO2?-)

We developed an effective method for reductive radical formation that utilizes the radical anion of carbon dioxide (CO2?-) as a powerful single electron reductant. Through a polarity matched hydrogen atom transfer (HAT) between an electrophilic radical and a formate salt, CO2?- formation occurs as a key element in a new radical chain reaction. Here, radical chain initiation can be performed through photochemical or thermal means, and we illustrate the ability of this approach to accomplish reductive activation of a range of substrate classes. Specifically, we employed this strategy in the intermolecular hydroarylation of unactivated alkenes with (hetero)aryl chlorides/bromides, radical deamination of arylammonium salts, aliphatic ketyl radical formation, and sulfonamide cleavage. We show that the reactivity of CO2?- with electron-poor olefins results in either single electron reduction or alkene hydrocarboxylation, where substrate reduction potentials can be utilized to predict reaction outcome.

Stereodivergent Synthesis of Alkenylpyridines via Pd/Cu Catalyzed C-H Alkenylation of Pyridinium Salts with Alkynes

The first Pd/Cu catalyzed selective C2-alkenylation of pyridines with internal alkynes has been developed via the pyridinium salt activation strategy. Importantly, the configuration of the product alkenylpyridines could be tuned by the choice of the proper N-alkyl group of the pyridinium salts, thus allowing for both the Z- and E-alkenylpyridines synthesized with good regio- and stereoselectivity. A plausible mechanism was proposed based on the Hammett study and KIE experiment.