67827-53-6

Basic information

• Product Name: 2,4,6-TRIMETHOXYCINNAMIC ACID ETHYL ESTER
• Synonyms: 3-(2,4,6-trimethoxyphenyl)-2-propenoicaciethylester;Ethyl (2E)-3-(2,4,6-trimethoxyphenyl)-2-propenoate;2,4,6-TRIMETHOXYCINNAMIC ACID ETHYL ESTER;ETHYL 2,4,6-TRIMETHOXYCINNAMATE;3-(2,4,6-Trimethoxyphenyl)acrylic acid ethyl ester;3-(2,4,6-Trimethoxyphenyl)propenoic acid ethyl ester;2-Propenoic acid, 3-(2,4,6-trimethoxyphenyl)-, ethyl ester
• CAS NO: 67827-53-6
• Molecular Formula: C₁₄H₁₈O₅
• Molecular Weight: 266.29
• Product Categories: Aromatic Cinnamic Acids, Esters and Derivatives
• Mol File: 67827-53-6.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 407.2ºC
• Flash Point: 180.4 ºC
• Appearance: /
• Density: 1.114 g/cm³
• Vapor Pressure: 7.66E-07mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 2,4,6-TRIMETHOXYCINNAMIC ACID ETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-TRIMETHOXYCINNAMIC ACID ETHYL ESTER(67827-53-6)
• EPA Substance Registry System: 2,4,6-TRIMETHOXYCINNAMIC ACID ETHYL ESTER(67827-53-6)

Safety Data

• Hazardous Substances Data: 67827-53-6(Hazardous Substances Data)

Usage

General Description

2,4,6-Trimethoxycinnamic acid ethyl ester is a chemical compound that belongs to the class of cinnamic acid derivatives. It is a yellowish crystalline substance with a molecular formula of C13H16O5, and a molecular weight of 252.26 g/mol. 2,4,6-TRIMETHOXYCINNAMIC ACID ETHYL ESTER is mainly used in the pharmaceutical and cosmetic industries for its antioxidant and UV-absorbing properties. It is also used in the synthesis of various other organic compounds due to its ability to undergo reactions such as esterification, hydrolysis, and hydrogenation. Additionally, 2,4,6-Trimethoxycinnamic acid ethyl ester has potential applications in the field of organic electronics and as a building block in the creation of new materials with specific properties.

InChI:InChI=1/C14H18O5/c1-5-19-14(15)7-6-11-12(17-3)8-10(16-2)9-13(11)18-4/h6-9H,5H2,1-4H3/b7-6+

Upstream product

• 621-23-8 1,2,3-trimethoxybenzene 
• 623-47-2 propynoic acid ethyl ester 
• 140-88-5 ethyl acrylate 
• 623-73-4 diazoacetic acid ethyl ester 
• 830-79-5 2,4,6-trimethoxybenzaldehyde 
• 1071-46-1 hydrogen ethyl malonate 

Downstream Products

• 80161-74-6 2,2,6,6-tetramethyl-5-(2,4,6-trimethoxyphenyl)heptan-3-one 
• 80152-78-9 ethyl 4,4-dimethyl-3-(2,4,6-trimethoxyphenyl)pentanoate 
• 80152-79-0 ethyl 3,3-dimethyl-2-(2,4,6-trimethoxyphenylmethyl)butanoate 
• 100257-91-8 (E)-3-(2,4,6-trimethoxyphenyl)prop-2-en-1-ol 
• 591228-81-8 2,4-diformyl 1,3,5-trimethoxy benzene 
• 621-23-8 1,2,3-trimethoxybenzene 

Relevant articles and documents

Ligand-accelerated non-directed C-H functionalization of arenes

The directed activation of carbon-hydrogen bonds (C-H) is important in the development of synthetically useful reactions, owing to the proximity-induced reactivity and selectivity that is enabled by coordinating functional groups. Palladium-catalysed non-directed C-H activation could potentially enable further useful reactions, because it can reach more distant sites and be applied to substrates that do not contain appropriate directing groups; however, its development has faced substantial challenges associated with the lack of sufficiently active palladium catalysts. Currently used palladium catalysts are reactive only with electron-rich arenes, unless an excess of arene is used, which limits synthetic applications. Here we report a 2-pyridone ligand that binds to palladium and accelerates non-directed C-H functionalization with arene as the limiting reagent. This protocol is compatible with a broad range of aromatic substrates and we demonstrate direct functionalization of advanced synthetic intermediates, drug molecules and natural products that cannot be used in excessive quantities. We also developed C-H olefination and carboxylation protocols, demonstrating the applicability of our methodology to other transformations. The site selectivity in these transformations is governed by a combination of steric and electronic effects, with the pyridone ligand enhancing the influence of sterics on the selectivity, thus providing complementary selectivity to directed C-H functionalization.

Synthesis, structure and catalytic activity of a gold(i) complex containing 1,2-bis(diphenylphosphino)benzene monoxide

The gold(i) complex [Au(dppbO)Cl] was synthesized by reaction of Na[AuCl4]·2H2O with 1,2-bis(diphenylphosphino)benzene (dppb) in the presence of water. This is a new method for the synthesis of a bisphosphine monoxide gold(i) complex. The new gold(i) complex was characterized by NMR spectroscopy and X-ray crystal structure analysis. In the solid state structure a relatively short contact between the oxygen atom of the phosphine oxide group and the gold center was observed. The catalytic activity of [Au(dppbO)Cl] was tested for three different intermolecular alkyne hydrofunctionalization reactions. Silver tetrafluoroborate was used as co-catalyst for halide abstraction. While the bisphosphine monoxide gold(i) complex showed moderate activity for the hydration of various alkynes and the hydroamination of phenyl acetylene, high activity was observed for the hydroarylation of ethylpropiolate. Electron-rich arenes add very fast to the C-C triple bond but with relatively low selectivity.

A catalyst-free one-pot construction of skeletons of 5-methoxyseselin and alloxanthoxyletin in water

In refluxing water and without an additional catalyst, electron-rich phenols could react with alkynoic acids or alkynoates to provide coumarin structures. The skeletons of two natural pyranocoumarins, 5-methoxyseselin and alloxanthoxyletin, could be constructed (total yield up to 76%) in an aqueous multicomponent reaction in which isoprenyl acetate, propiolic acid, and phloroglucinol were simply mixed and refluxed in water.