915712-34-4

Usage

Uses

Used in Pharmaceutical Industry:
(E)-ethyl 2-(4-bromophenylimino)acetate is utilized as an intermediate in the production of pharmaceuticals, playing a crucial role in the synthesis of various medicinal compounds. Its unique structure allows it to be a key component in developing new drugs and improving existing ones.
Used in Agrochemical Industry:
In the agrochemical sector, (E)-ethyl 2-(4-bromophenylimino)acetate serves as an intermediate, contributing to the development of pesticides, herbicides, and other agricultural chemicals. Its incorporation aids in enhancing the effectiveness and selectivity of these products.
Used in Dye Industry:
(E)-ethyl 2-(4-bromophenylimino)acetate is also employed in the dye industry, where it acts as an intermediate for the synthesis of various dyes. Its chemical properties enable the creation of dyes with specific characteristics, such as colorfastness and stability.
Used in Organic Synthesis:
As a reagent in organic synthesis, (E)-ethyl 2-(4-bromophenylimino)acetate is used to facilitate a range of chemical reactions, leading to the formation of diverse organic compounds. Its versatility in this context is highly valued in the field of organic chemistry.
Used in Medicinal Research:
Due to its potential biological activity, (E)-ethyl 2-(4-bromophenylimino)acetate is of interest in medicinal research. Researchers explore its properties to understand its possible applications in the development of new therapeutic agents and treatments.
Used as a Building Block:
(E)-ethyl 2-(4-bromophenylimino)acetate is also used as a building block for the preparation of various other compounds. Its unique structure makes it a valuable component in the synthesis of complex organic molecules for a wide range of applications.

Upstream product

• 924-44-7 glyoxylic acid ethyl ester 
• 106-40-1 4-bromo-aniline 
• 2521-92-8 ethyl 2-((4-bromophenyl)amino)acetate 
• 6911-87-1 4-bromo-N-methylaniline 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 1134156-24-3 C₃₃H₃₆BrNO₄ 
• 1134156-39-0 C₃₃H₃₆BrNO₄ 
• 1097223-10-3 ethyl 1,3-bis(4-bromophenyl)-4-((4-bromophenyl)amino)-5-oxoimidazolidine-2-carboxylate 
• 1097223-11-4 C₂₆H₂₆Br₃N₃O₄ 
• 22289-05-0 3-methyleneheptane-2,6-dione 
• 1158957-80-2 ethyl 6'-bromo-4',4'-diphenyl-2',4'-dihydro-1'H-spiro[cyclopropane-1,3'-quinoline]-2'-carboxylate 
• 1158957-83-5 ethyl 6'-bromo-4',4'-bis(4-methoxyphenyl)-2',4'-dihydro-1'H-spiro[cyclopropane-1,3'-quinoline]-2'-carboxylate 
• 1169412-43-4 ethyl 6'-bromo-4',4'-bis(4-chlorophenyl)-2',4'-dihydro-1'H-spiro[cyclopropane-1,3'-quinoline]-2'-carboxylate 
• 1158957-81-3 ethyl 6'-bromo-4',4'-di-p-tolyl-2',4'-dihydro-1'H-spiro[cyclopropane-1,3'-quinoline]-2'-carboxylate 
• 1158957-84-6 ethyl 6'-bromo-4'-(4-methoxyphenyl)-4'-phenyl-2',4'-dihydro-1'H-spiro[cyclopropane-1,3'-quinoline]-2'-carboxylate 
• 1169412-44-5 ethyl 6'-bromo-4'-(4-chlorophenyl)-4'-phenyl-2',4'-dihydro-1'H-spiro[cyclopropane-1,3'-quinoline]-2'-carboxylate 
• 1158957-82-4 ethyl 6'-bromo-4',4'-bis(4-fluorophenyl)-2',4'-dihydro-1'H-spiro[cyclopropane-1,3'-quinoline]-2'-carboxylate 
• 1186321-38-9 ethyl 1,3-bis(4-bromophenyl)-4-methyl-5-oxoimidazolidine-2-carboxylate 
• 1400897-66-6 (S)-ethyl 2-(4-bromophenylamino)-2-phenylacetate 

Relevant academic research and scientific papers

Multicomponent Approach to Hydantoins and Thiohydantoins Involving a Deep Eutectic Solvent

We report an efficient synthetic strategy to diverse hydantoins and thiohydantoins involving a three-component reaction with the aid of deep eutectic solvent. Here, N,N′-dimethyl urea and N,N′-dimethyl thiourea play a dual role as reactant and reaction medium along with l-(+)-tartaric acid. The three-component reaction provides an easy access to 5-amino-1,3-dialkyl-substituted hydantoins and thiohydantoins in good yields.

Tin powder-promoted oxidation/allylation of glycine esters: Synthesis of γ,δ-unsaturated α-amino acid esters

An efficient tin powder-promoted oxidation/allylation reaction of glycine esters with allyl bromides is developed, which affords γ,δ-unsaturated α-amino acid esters under mild conditions without any other transition metal catalysts. This method avoids the use of unstable imine as starting material, and provides an efficient method for synthesis of γ,δ-unsaturated α-amino acid esters and α-methylene-γ-lactam derivatives. Additional supporting information may be found in the online version of this article at the publisher's web site.

Polarity-Reversed Addition of Enol Ethers to Imines under Visible Light: Redox-Neutral Access to Azide-Containing Amino Acids

A three-component and polarity-reversed addition cascade with a glyoxylate-based imine, an enol ether, and TMSN3 was established for the construction of γ-azido amino acids under visible light. This transformation features mild and redox-neutra

Asymmetric Organocatalytic Synthesis of Bisindoles – Scope and Derivatizations

Starting from 3-vinylindoles and glyoxolate imines, we created a library of diverse 4,6-bis(1H-indole-3-yl)piperidine 2-carboxylates by using 10 mol-% of a chiral phosphoric acid. Utilising electron-withdrawing groups on the starting material during the r

Synthesis of Dihydrophenanthridines and Oxoimidazolidines from Anilines and Ethylglyoxylate via Aza Diels-Alder Reaction of Arynes and KF-Induced Annulation

The transition-metal-free multicomponent coupling of arynes, anilines, and ethylglyoxylate, proceeding via an inverse electron-demand aza Diels-Alder cycloaddition and N-arylation, has been demonstrated. This protocol allows rapid access to N-aryl dihydrophenanthridine derivatives in moderate to high yields at room temperature from readily available starting materials. In addition, an unprecedented fluoride induced annulation of ethyl(arylimino)acetates led to the formation of highly functionalized oxoimidazolidine derivatives in good yields under mild conditions.

Asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine- 2 carboxylates

We developed an asymmetric organocatalytic synthesis of 4,6-bis(1H-indole-3-yl)-piperidine-2-carboxylates using 10 mol% of a chiral phosphoric acid. The products, which are novel bisindole-piperidine-amino acid hybrids, can be obtained in one step from 3-

Indium-assisted aluminium-based stereoselective allylation of prostereogenic α,α-disubstituted cycloalkanones and imines

The use of a catalytic amount of InCl3in combination with Al0for the allylation of a variety of prostereogenic α,α-disubstituted (hindered) cycloalkanones, 1,2-dione-based systems and various imino systems (CN functional groups) is reported. The stereoselective InCl3-catalyzed Al-based allylation of various 2-substituted-2-carbethoxycycloalkanones gave the corresponding products with moderate to excellent diastereoselectivity. The allylation and propargylation of imines including α-imino esters using a catalytic amount of InCl3in combination with Al0gave the corresponding allylated and propargylated compounds in moderate to good yields. If γ-substituted allylic halides were added to imino compounds, low to very good diastereoselectivity was obtained. The allylation of chiral N-tert-butylsulfinyl imine systems gave the corresponding products in moderate yields with good to excellent diastereoselectivity. This journal is

Synthesis and biological evaluation of urea derivatives as highly potent and selective rho kinase inhibitors

RhoA and its downstream effector ROCK mediate stress fiber formation and cell contraction through their effects on the phosphorylation of myosin light chain (MLC). Inhibition of the RhoA/ROCK pathway has proven to be a promising strategy for several indications such as cardiovascular disease, glaucoma, and inflammatory disease. In 2010, our group reported urea-based ROCK inhibitors as potential antiglaucoma agents. These compounds showed potent IC50 values in enzymatic and cell-based assays and significant intraocular pressure (IOP)-lowering effects in rats (～7 mmHg).(22) To develop more advanced ROCK inhibitors targeting various potential applications (such as myocardial infarction, erectile dysfunction, multiple sclerosis, etc.) in addition to glaucoma, a thorough SAR for this urea-based scaffold was studied. The detailed optimization process, counter-screening, and in vitro and in vivo DMPK studies are discussed. Potent and selective ROCK inhibitors with various in vivo pharmacokinetic properties were discovered.

Ruthenium(II)-catalyzed regioselective reductive coupling of α-imino esters with dienes

A method for the highly regioselective reductive coupling reaction of N-aryl-α-imino esters with dienes is described. The method utilizes the RuHCl(CO)(PPh3)3/iPrOH catalytic system under an Ar atmosphere and provides α-branched allylic α-amino acid derivatives. Application of this transformation to the concise synthesis of a natural plant growth regulator is demonstrated.

Palladium(II)-catalyzed enantioselective arylation of α-imino esters

A protocol for Pd(II)-catalyzed asymmetric arylation of N-aryl imino esters has been developed. The method affords a practical and direct access to chiral arylglycine derivatives in good yields and with high enantioselectivities.