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
• Article Data: 76

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

Description

ETHYL 4-METHOXYPHENYLACETATE, also known as Ethyl (4-Methoxyphenyl)acetate, is a clear colorless to yellow liquid with unique chemical properties. It is a compound that has been identified for its potential applications in various industries due to its specific characteristics.

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 
• 40140-16-7 ethyl (p-methoxyphenyl)oxoacetate 
• 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 

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.

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.