14062-18-1

Basic information

• Product Name: ETHYL 4-METHOXYPHENYLACETATE
• Synonyms: 4-Methoxybenzeneacetic acid ethyl ester;Ethyl 4-methoxyphenylacetate,97%;4-Methoxyphenylacetic Acid Ethyl Ester Homoanisic Acid Ethyl Ester;Ethyl 2-(4-Methoxyphenyl)acetate;AURORA KA-6002;ETHYL 4-METHOXYBENZENEACETATE;ETHYL 4-METHOXYPHENYLACETATE;HOMOANISIC ACID ETHYL ESTER
• CAS NO: 14062-18-1
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• EINECS: 237-903-6
• Product Categories: Aromatic Esters
• Mol File: 14062-18-1.mol

Chemical Properties

• Melting Point: 85 °C
• Boiling Point: 108-111 °C (3 mmHg)
• Flash Point: 46 °C
• Appearance: clear colorless to yellow liquid
• Density: 1.097
• Vapor Pressure: 0.00623mmHg at 25°C
• Refractive Index: 1.5065-1.5085
• Storage Temp.: Flammables area
• CAS DataBase Reference: ETHYL 4-METHOXYPHENYLACETATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL 4-METHOXYPHENYLACETATE(14062-18-1)
• EPA Substance Registry System: ETHYL 4-METHOXYPHENYLACETATE(14062-18-1)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG III
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 14062-18-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4-METHOXYPHENYLACETATE is used as a 15-lipoxygenase inhibitor for its ability to inhibit the enzyme 15-lipoxygenase, which plays a role in various physiological and pathological processes. This inhibition can be beneficial in the development of treatments for conditions where 15-lipoxygenase activity is a contributing factor.
Used in Chemical Research:
ETHYL 4-METHOXYPHENYLACETATE is used as a research compound for its unique chemical properties, allowing scientists to study its interactions with other molecules and its potential applications in various chemical and pharmaceutical processes.
Used in Flavor and Fragrance Industry:
Due to its distinct chemical structure, ETHYL 4-METHOXYPHENYLACETATE can be used as a component in the development of new fragrances and flavors, adding unique scents and enhancing the sensory experience of various products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 4385, 1978 DOI: 10.1021/jo00416a035Tetrahedron Letters, 21, p. 2675, 1980 DOI: 10.1016/S0040-4039(00)92837-5

InChI:InChI=1/C11H14O3/c1-3-14-11(12)8-9-4-6-10(13-2)7-5-9/h4-7H,3,8H2,1-2H3

Upstream product

• 104-01-8 4-Methoxyphenylacetic acid 
• 64-17-5 ethanol 
• 34006-60-5 ethyl 2-chloro-2-ethoxyacetate 
• 100-66-3 methoxybenzene 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 681-94-7 ethyl 2-(tributylstannyl)acetate 
• 23786-14-3 4-methoxy-phenyl acetic acid methyl ester 
• 73031-42-2 1-(1-pyrrolidinyl)-1-(4-methoxyphenyl)ethene 
• 201230-82-2 carbon monoxide 
• 6258-60-2 p-methoxybenzylmercaptan 
• 141-52-6 sodium ethanolate 
• 824-94-2 p-methoxybenzyl chloride 
• 80336-73-8 2-chloro-1,1-diethoxy-1-(4-methoxyphenyl)ethane 
• 67500-33-8 1-Ethoxy-2-(4-methoxyphenyl)acetylene 

Downstream Products

• 29903-09-1 1,3-bis(4-methoxyphenyl)acetone 
• 102586-43-6 ethyl 3-oxo-2,4-bis(4-methoxyphenyl)butanoate 
• 19838-89-2 2-(4-methoxyphenyl)-1,1-diphenylethan-1-ol 
• 104-01-8 4-Methoxyphenylacetic acid 
• 702-23-8 2-(4-Methoxyphenyl)ethanol 
• 125575-31-7 meso-2,3-bis-(4-methoxy-phenyl)-succinic acid diethyl ester 
• 95540-82-2 racem.-2,3-bis-(4-methoxy-phenyl)-succinic acid 
• 210168-09-5 1-(4-methoxyphenyl)pentane-2,4-dione 
• 62234-94-0 4-(4-methoxy-phenyl)-2-phenyl-acetoacetonitrile 
• 409324-10-3 2-(4-methoxy-benzyl)-chromen-4-one 
• 23197-67-3 diethyl 2-(4-methoxyphenyl)malonate 
• 1817-87-4 1,1,2-tris-(4-methoxy-phenyl)-ethanol 
• 20341-24-6 (4-methoxy-phenyl)-acetic acid-(3-methoxy-phenethylamide) 
• 35144-39-9 1-(4-methoxyphenyl)-2-methylpropan-2-ol 

Relevant articles and documents

CuI-catalyzed domino process to 2,3-disubstituted benzofurans from 1-bromo-2-iodobenzenes and β-keto esters

(Chemical Equation Presented) CuI-catalyzed coupling of 1-bromo-2-iodobenzenes with β-keto esters in THF at 100°C leads to 2,3-disubstituted benzofurans. This domino transformation involves an intermolecular C-C bond formation and a subsequent intramolecular C-O bond formation process. Benzofurans with different substituents at the 5- and 6-position are accessible by employing the corresponding 1-bromo-2-iodobenzenes.

Palladium-Catalyzed ortho-Olefination of Phenyl Acetic and Phenyl Propylacetic Esters via C-H Bond Activation

A highly regioselective palladium-catalyzed ester-directed ortho-olefination of phenyl acetic and propionic esters with olefins via C-H bond activation has been developed. A wide variety of phenyl acetic and propionic esters were tolerated in this transformation, affording the corresponding olefinated aromatic compounds. The ortho-olefination of heterocyclic acetic and propionic esters also took place smoothly giving the products in good yields, thus proving the potential utility of this protocol in synthetic chemistry.

Water and fluorinated alcohol mediated/promoted tandem insertion/aerobic oxidation/bisindolylation under metal-free conditions: Easy access to bis(indolyl)methanes

A green tandem reaction, including insertion/aerobic oxidation/bisindolylation, starting from indoles and diazo compounds has been developed. The combination of water and fluorinated alcohol plays dual roles as solvent and promoter in this chemical transformation. Molecular oxygen in the air acts as an oxidant. 3,3′-Bis(indolyl)methanes with quaternary carbon were produced under metal-free conditions. No any catalyst and additive were required. N2 and water were released as sole by-products. Absence of water and fluorinated alcohol resulted in Wolff rearrangement product.

Photoassisted Cross-Coupling Reaction of α-Chlorocarbonyl Compounds with Arylboronic Acids

A Suzuki-Miyaura cross-coupling reaction of α-chloroacetates or α-chloroacetamides with arylboronic acids is made possible by visible-light irradiation. This reaction provides a useful method for the synthesis of α-arylacetates and α-arylacetamides from chlorides under mild reaction conditions. An indole-3-acetic acid derivative that is the key intermediate of the plant hormone auxin can be synthesized from 1-Boc-indole in two steps by combining an iridium-catalyzed C-H borylation and a palladium-catalyzed cross-coupling reaction.

Coupling of Reformatsky Reagents with Aryl Chlorides Enabled by Ylide-Functionalized Phosphine Ligands

The coupling of aryl chlorides with Reformatsky reagents is a desirable strategy for the construction of α-aryl esters but has so far been substantially limited in the substrate scope due to many challenges posed by various possible side reactions. This limitation has now been overcome by the tailoring of ylide-functionalized phosphines to fit the requirements of Negishi couplings. Record-setting activities were achieved in palladium-catalyzed arylations of organozinc reagents with aryl electrophiles using a cyclohexyl-YPhos ligand bearing an ortho-tolyl-substituent in the backbone. This highly electron-rich, bulky ligand enables the use of aryl chlorides in room temperature couplings of Reformatsky reagents. The reaction scope covers diversely functionalized arylacetic and arylpropionic acid derivatives. Aryl bromides and chlorides can be converted selectively over triflate electrophiles, which permits consecutive coupling strategies.

Copper-Catalyzed Ullmann-Type Coupling and Decarboxylation Cascade of Arylhalides with Malonates to Access α-Aryl Esters

We have developed a high-efficiency and practical Cu-catalyzed cross-coupling to directly construct versatile α-aryl-esters by utilizing readily available aryl bromides (or chlorides) and malonates. These gram-scale approaches occur with turnovers of up to 1560 and are smoothly conducted by the usage of a low catalyst loading, a new available ligand, and a green solvent. A variety of functional groups are tolerated, and the application occurs with α-aryl-esters to access nonsteroidal anti-inflammatory drugs (NSAIDs) on the gram scale.

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Copper-Catalyzed Methoxylation of Aryl Bromides with 9-BBN-OMe

A Cu-catalyzed cross-coupling reaction between aryl bromides and 9-BBN-OMe to provide aryl methyl ethers under mild conditions is reported. The oxalamide ligand BHMPO plays a key role in the transformation. Various functional groups on bromobenzenes are well tolerated, providing the desired anisole products in moderate to high yields.

Photocatalytic acyl azolium-promoted alkoxycarbonylation of trifluoroborates

Despite recent advancements in the selective generation and coupling of organic radical species, the alkoxycarbonyl radical remains underexplored relative to other carbon-containing radical species. Drawing inspiration from new strategies for generating acyl radical equivalents utilizing dual N-heterocyclic carbene catalysis and photocatalysis, we have prepared dimethylimidazolium esters that can function as an alkoxycarbonyl radical surrogate under photocatalytic conditions. We demonstrate the synthetic utility of these azolium-based partners through the preparation of esters arising from the coupling of this radical surrogate with an oxidatively generated alkyl radical.

Aryl or heteroaryl methoxylation reaction method

The invention discloses an aryl or heteroaryl methoxylation reaction method. The method comprises the following steps: preparing a substrate. The coupling agent, ligand, solvent, catalyst and base are mixed homogeneously in an inert gas to give the aryl or heteroaryl methoxy compounds. Compared with a methoxylation reaction method in the prior art, the method has the advantages that the reaction system conditions are mild, the usage amount of the catalyst and the ligand is low to 5% of the amount of the substrate material, and the catalytic efficiency is improved. The method has better compatibility to different substrate expansion and discovery of aryl halides or heteroaryl halides with different functional groups. The yield of aryl or heteroaryl methoxy compounds prepared by the method disclosed by the invention is 36% - 89%.