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

General Description

(E)-Methyl 3-(pyridin-2-yl)acrylate is a chemical compound with the molecular formula C9H9NO2. It is a derivative of the ester form of acrylic acid and is commonly used as a building block or intermediate in the synthesis of pharmaceuticals and agrochemicals. (E)-Methyl 3-(pyridin-2-yl)acrylate is a colorless to pale yellow liquid with a fruity odor and is soluble in organic solvents such as ethanol and acetone. It is also known to be a potential sensitizer and irritant to the skin, eyes, and respiratory tract, so proper handling and protective measures are necessary when working with it in a laboratory or industrial setting. Overall, (E)-Methyl 3-(pyridin-2-yl)acrylate is a versatile compound with various industrial applications, but caution is needed in its handling and use.

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 6832-16-2 methyl diazoacetate 
• 96-32-2 bromoacetic acid methyl ester 
• 21204-67-1 methyl (triphenylphosphoranylidene)acetate 
• 67-56-1 methanol 
• 109-04-6 2-bromo-pyridine 
• 292638-85-8 acrylic acid methyl ester 
• 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 
• 79-20-9 acetic acid methyl ester 
• 38010-70-7 (R,E)-N-(1-phenylethyl)-1-(pyridin-2-yl)methanimine 
• 2916-76-9 methyl (trimethylsilyl)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

Reduction of Electron-Deficient Alkenes Enabled by a Photoinduced Hydrogen Atom Transfer

Direct hydrogen atom transfer from a photoredox-generated Hantzsch ester radical cation to electron-deficient alkenes has enabled the development of an efficient formal hydrogenation under mild, operationally simple conditions. The HAT-driven mechanism is supported by experimental and computational studies. The reaction is applied to a variety of cinnamate derivatives and related structures, irrespective of the presence of electron-donating or electron-withdrawing substituents in the aromatic ring and with good functional group compatibility. (Figure presented.).

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.