105337-18-6

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 3,5-DIMETHYLPHENYLACETATE is used as a reagent in the selective cross-coupling reaction of halogenated quinolines. This reaction is crucial for the synthesis of various pharmaceutical compounds, as quinolines are a common structural motif in many drugs. The use of this intermediate allows for the efficient and selective formation of desired products, which can then be further modified or used as active pharmaceutical ingredients.
Used in Chemical Synthesis:
ETHYL 3,5-DIMETHYLPHENYLACETATE is used as a key intermediate in the synthesis of styrene and stilbene compounds. Styrene and stilbenes are important classes of organic compounds with a wide range of applications, including as monomers for polymer production, precursors for pharmaceuticals, and as components in various chemical processes. The use of this intermediate facilitates the formation of these valuable compounds, contributing to the advancement of the chemical industry.

InChI:InChI=1/C12H16O2/c1-4-14-12(13)8-11-6-9(2)5-10(3)7-11/h5-7H,4,8H2,1-3H3

Upstream product

• 27129-87-9 3,5-dimethylbenzyl alcohol 
• 64-17-5 ethanol 
• 42288-46-0 (3,5-dimethylphenyl)acetic acid 
• 556-96-7 5-bromo-1,3-xylene 
• 105-53-3 diethyl malonate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 172975-69-8 3,5-dimethylphenyl boronic acid 
• 201230-82-2 carbon monoxide 
• 108-67-8 1,3,5-trimethyl-benzene 
• 108-69-0 3,5-dimethylaminoaniline 
• 2745-54-2 3,5-dimethylbenzyl chloride 
• 39101-54-7 3,5-dimethylphenylacetonitrile 

Downstream Products

• 62343-67-3 β-(3,5-Dimethylphenyl)ethyl alcohol 
• 200215-42-5 3-oxo-2-(3,5-dimethylphenyl)propionic acid ethyl ester 
• 42288-46-0 (3,5-dimethylphenyl)acetic acid 
• 34577-33-8 1-(3,5-dimethyl-phenyl)-2-methyl-propanol-2-ol 
• 94204-41-8 1,3-diethyl 2-(3,5-dimethylphenyl)propane-1,3-dioate 

Relevant academic research and scientific papers

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.

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.

Synthesis and anti-inflammatory activity of hydrazones bearing biphenyl moiety and vanillin based hybrids

The intense research work in the field of medicinal chemistry has enhanced the significance of Biphenyl moiety as pharmacologically important compound. Some of the compounds bearing Biphenyl moiety possess important medicinal properties like antihypertensive and calcium channel blocker, anti-inflammatory, diuretic, anti-diabetic activity, antipsychotic and anxiolytic activity. The present article describes the synthesis of novel benzohydrazides and 2-phenylacetohydrazides bearing Biphenyl moiety and vanillin hybrid. The synthesized compounds (31-40) were characterized by 1H NMR, Mass and IR spectroscopic techniques and were evaluated for anti-inflammatory activity by carrageenan paw edema method. The results of the study revealed that compounds 39 and 40 (bearing 2-(4-nitrophenyl)acetohydrazide and 2-(2,3-dihydrobenzofuran-5-yl)acetohydrazide) showed maximum anti-inflammatory activity while the compounds 31, 32, 33, 34 and 38 bearing benzohydrazides displayed moderate anti-inflammatory activity.

Synthesis and anti-inflammatory activity of hydrazide-hydrazones bearing anacardic acid and 1,2,3-triazole ring based hybrids

A novel series of hydrazide-hydrazone derivatives 39-50, linked with anacardic acid motif and 1,2,3-triazole ring were synthesized by reacting 4-(1-(2-methoxy-6-pentadecylbenzyl)-1H-1, 2, 3-triazol-4-yl)benzaldehyde with 2-phenyl-acetohydrazides and benzohydrazides. The structures of the newly synthesized hydrazide-hydrazone derivatives 39-50 were confirmed by 1H NMR, MS and IR spectroscopic tools. These compounds were also evaluated for their anti-inflammatory activity by carrageenan paw edema method.

Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.

PROCESS FOR SYNTHESIZING PHENYLACETIC ACID BY CARBONYLATION OF TOLUENE

A production process for substituted phenylacetic acids or ester analogues thereof is disclosed. In this process toluene or toluene substituted with various substituents, an alcohol, an oxidant and carbon monoxide are used as raw materials to obtain compounds comprising structure of phenylacetic acid ester or analogues thereof by catalysis of the complex catalyst formed from transition metal and ligand, and such compounds are hydrolyzed to obtain various substituted phenylacetic acid based compounds. This type of compounds and their derivatives serve as important fine chemicals used widely in the industries of pharmaceuticals, pesticides, perfume and the like.

Palladium-catalyzed oxidative carbonylation of benzylic C-H bonds via nondirected C(sp3)-H activation

A new strategy for generating benzylpalladium reactive species from toluenes via nondirected C(sp3)-H activation has been developed. This led to construction of an efficient Pd-catalyzed reaction protocol for the oxidative carboxylation of benzylic C-H bonds to form substituted 2-phenylacetic acid esters and derivatives from inexpensive, commercially available starting materials.

1,2-disubstituted-6-oxo-3-phenyl-piperidine-3-carboxamides and combinatorial libraries thereof

The invention relates to combinatorial libraries containing two or more novel piperidine-3-carboxamide derivative compounds, methods of preparing the piperidine-3-carboxamide derivative compounds and piperidine-3-carboxamide derivative compounds bound to a resin