14062-19-2

Usage

Uses

Used in Chemical Synthesis:
ETHYL P-TOLYLACETATE is used as an intermediate in the synthesis of various organic compounds, such as ethyl-substituted phenylpropioloylacetates and ethyl 2-(4-bromomethylphenyl)propionate. These synthesized compounds can be further utilized in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
ETHYL P-TOLYLACETATE is used as a starting material for the preparation of incrustoporin, an antifungal agent. This application highlights its importance in the development of treatments for fungal infections, contributing to the healthcare sector.
Used in Agrochemical Industry:
In the agrochemical industry, ETHYL P-TOLYLACETATE serves as a precursor for the synthesis of various bioactive compounds that can be used as pesticides or fungicides. Its role in this industry is crucial for the development of effective solutions to protect crops and maintain agricultural productivity.

InChI:InChI=1S/C11H14O2/c1-3-13-11(12)8-10-6-4-9(2)5-7-10/h4-7H,3,8H2,1-2H3

Upstream product

• 2947-61-7 (4-methylphenyl)acetonitrile 
• 5524-56-1 ethyl 2-p-tolyl-2-oxoacetate 
• 64-17-5 ethanol 
• 622-47-9 4-tolylacetic acid 
• 201230-82-2 carbon monoxide 
• 4498-99-1 4-methylbenzylthiol 
• 106-38-7 para-bromotoluene 
• 681-94-7 ethyl 2-(tributylstannyl)acetate 
• 150-46-9 triethyl borate 
• 104-81-4 4-Methylbenzyl bromide 
• 555-75-9 aluminum ethoxide 
• 104-82-5 4-Methylbenzyl chloride 
• 314765-29-2 (E)-2-(1H-1,2,3-benzotriazol-1-yl)-1-(4-methylphenyl)ethenyl trifluoromethanesulfonate 
• 5720-05-8 4-methylphenylboronic acid 

Downstream Products

• 102559-23-9 3-methylamino-3-[2]naphthyl-2-p-tolyl-propionic acid ethyl ester 
• 6632-84-4 2,4-di-p-tolyl-acetoacetic acid ethyl ester 
• 40491-23-4 1,1-diphenyl-2-p-tolyl-ethanol 
• 699-02-5 4-Methylphenethyl alcohol 
• 622-47-9 4-tolylacetic acid 
• 714258-64-7 3-oxo-2-phenyl-4-p-tolyl-butyronitrile 
• 29148-27-4 diethyl 2-(4-methylphenyl)propane-1,3-dioate 
• 29668-59-5 4-Chloro-2-p-tolyl-pent-4-enoic acid ethyl ester 
• 112323-95-2 1,1,2-tri-p-tolyl-ethanol 
• 20430-18-6 2-methyl-2-(p-tolyl)propanoic acid 
• 92241-60-6 4,4'-[2-(p-tolyl)ethene-1,1-diyl]bis(methoxybenzene) 
• 77232-15-6 6-Hydroxy-2-phenyl-4-(p-tolyl)pyrimidin 
• 15674-78-9 (+/-)-α-bromo-p-tolylacetic acid ethyl ester 
• 7398-81-4 (4-bromomethylphenyl)acetic acid ethyl ester 

Relevant academic research and scientific papers

N-Heterocyclic Carbenes as Key Intermediates in the Synthesis of Fused, Mesoionic, Tricyclic Heterocycles

Coupling between 5-bromoimidazo[1,5-a]pyridinium salts and malonate or arylacetate esters leads to a facile and straightforward access to the new mesoionic, fused, tricyclic system of imidazo[2,1,5-cd]indolizinium-3-olate. Mechanistic studies show that the reaction pathway consists of nucleophilic aromatic substitution on the cationic, bicyclic heterocycle by an enolate-type moiety and in the nucleophilic attack of a transient free N-heterocyclic carbene (NHC) species on the ester group; the relative order of these two steps depends on the nature of the starting ester. This work highlights the valuable implementation of free NHC species as key intermediates in synthetic chemistry, beyond their classical use as stabilizing ligands or organocatalysts.

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.

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.

Preparation method of 4-bromomethyl methyl benzoate and derivative thereof

The invention provides a preparation method of methyl 4-bromomethyl benzoate and a derivative thereof, and the method comprises an esterification reaction for converting methyl benzoic acid into methyl benzoate and a bromination reaction for converting the methyl benzoate into the methyl 4-bromomethyl benzoate and the derivative thereof, the brominating agent for the bromination reaction is dibromohydantoin, and the structural formulas of the 4-bromomethyl methyl benzoate and the derivatives thereof are shown in the specification, wherein n1 is equal to 0, 1 or 2; n2 is equal to 1 or 2; according to the preparation method disclosed by the invention, the reaction time can be greatly shortened, the reaction yield is high, and the production efficiency is improved.

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.

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.

BF3·OEt2-promoted tandem Meinwald rearrangement and nucleophilic substitution of oxiranecarbonitriles

Tandem Meinwald rearrangement and nucleophilic substitution of oxiranenitriles was realized. Arylacetic acid derivatives were readily synthesized from 3-aryloxirane-2-carbonitriles with amines, alcohols, or water in the presence of boron trifluoride under microwave irradiation, and the designed synthetic strategy includes introducing a cyano leaving group into arylepoxides and capturing the in situ generated toxic cyanide with boron trifluoride, making the reaction efficient, safe, and environmentally benign. The reaction occurs through an acid-promoted Meinwald rearrangement, producing arylacetyl cyanides, followed by an addition-elimination process with nitrogen or oxygen-containing nucleophilic amines, alcohols or water. The current method provides a new application of the tandem Meinwald rearrangement.

Computer-Assisted Discovery and Structural Optimization of a Novel Retinoid X Receptor Agonist Chemotype

As universal heterodimer partners of many nuclear receptors, the retinoid X receptors (RXRs) constitute key transcription factors. They regulate cell proliferation, differentiation, inflammation, and metabolic homeostasis and have recently been proposed as potential drug targets for neurodegenerative and inflammatory diseases. Owing to the hydrophobic nature of RXR ligand binding sites, available synthetic RXR ligands are lipophilic, and their structural diversity is limited. Here, we disclose the computer-assisted discovery of a novel RXR agonist chemotype and its systematic optimization toward potent RXR modulators. We have developed a nanomolar RXR agonist with high selectivity among nuclear receptors and superior physicochemical properties compared to classical rexinoids that appears suitable for in vivo applications and as lead for future RXR-targeting medicinal chemistry.

Mechanistic studies on gold-catalyzed direct arene c-h bond functionalization by carbene insertion: The coinage-metal effect

The catalytic functionalization of the Csp2-H bond of benzene by means of the insertion of the CHCO2Et group from ethyl diazoacetate (N2= CHCO2Et) has been studied with the series of coinage-metal complexes IPrMCl (IPr = 1,3-bis- (diisopropylphenyl)imidazol-2-ylidene) and NaBArF 4 (BArF 4 = tetrakis(3,5-bis(trifluoromethyl)phenyl)borate). For Cu and Ag, these examples constitute the first use of such metals toward this transformation, which also provides ethyl cyclohepta-2,4,6-trienecarboxylate as a byproduct from the so-called Buchner reaction. In the case of methyl-substituted benzenes, the reaction exclusively proceeds onto the aromatic ring, the Csp3-H bond remaining unreacted. A significant coinage-metal effect has been observed, since the gold catalyst favors the formation of the insertion product into the Csp2-H bond whereas copper and silver preferentially induce the formation of the cycloheptatriene derivative. Experimental studies and theoretical calculations have explained the observed selectivity in terms of the formation of a common Wheland intermediate, resembling an electrophilic aromatic substitution, from which the reaction pathway evolves into two separate routes to each product.

Iron and manganese catalysts for the selective functionalization of arene C(sp2)-H bonds by carbene insertion

The first examples of the direct functionalization of non-activated aryl sp2 C-H bonds with ethyl diazoacetate (N2CHCO2Et) catalyzed by Mn- or Fe-based complexes in a completely selective manner are reported, with no formation of the frequently observed cycloheptatriene derivatives through competing Buchner reaction. The best catalysts are FeII or MnII complexes bearing the tetradentate pytacn ligand (pytacn= 1-(2-pyridylmethyl)-4,7-dimethyl-1,4,7-triazacyclononane). When using alkylbenzenes, the alkylic C(sp3)-H bonds of the substituents remained unmodified, thus the reaction being also selective toward functionalization of sp2 C-H bonds. Exclusive catalysis: Iron- and-manganese-based catalysts selectively functionalize the C(sp2)-H bonds of benzene or alkylbenzenes through the formal insertion of the CHCO2Et group from N2CHCO2Et (see scheme). When using alkylbenzenes, the alkylic C(sp3)-H bonds of the substituents remain unmodified.