2644-21-5

Usage

Uses

Used in Organic Synthesis:
ETHYL N,N-DIETHYLAMINOACETATE is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions, contributing to the formation of desired products in the synthesis of complex organic molecules.
Used in Chemical Reactions as a Solvent:
In the chemical industry, ETHYL N,N-DIETHYLAMINOACETATE serves as a solvent, leveraging its solubility properties to dissolve a wide range of substances and support the progress of chemical reactions.
Used as a Catalyst in Esterification and Transesterification Reactions:
ETHYL N,N-DIETHYLAMINOACETATE is utilized as a catalyst to accelerate esterification and transesterification reactions, enhancing the efficiency and speed of these processes in the production of esters.
Used in Pharmaceutical Development:
ETHYL N,N-DIETHYLAMINOACETATE is studied for its potential applications in pharmaceuticals, suggesting its use in the development of new drugs or medicinal compounds, possibly due to its interaction with biological systems.
Used in Polymer Production:
ETHYL N,N-DIETHYLAMINOACETATE is considered for use in the production of polymers, indicating its role in the creation of new polymeric materials with specific properties for various applications.
Used in Surface Coating Formulations:
In the coatings industry, this chemical is examined for its potential use in surface coatings, which could be attributed to its ability to improve the performance or characteristics of the coatings, such as adhesion, durability, or aesthetic qualities.

InChI:InChI=1/C8H17NO2/c1-4-9(5-2)7-8(10)11-6-3/h4-7H2,1-3H3

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 121-44-8 triethylamine 
• 25079-99-6 Triethylammoniumessigsaeure-betain 
• 103628-13-3 triethyl-carboxymethyl-ammonium; hydroxide 
• 36701-37-8 silver(I) glycinate 
• 75-03-6 ethyl iodide 
• 105-39-5 chloroacetic acid ethyl ester 
• 109-89-7 diethylamine 
• 105-36-2 ethyl bromoacetate 
• 5411-58-5 ethyl N,N-diethyloxamate 
• 90524-33-7 C₁₂H₃₀NOSi⁽¹⁺⁾*CF₃O₃S^(1-) 
• 130384-02-0 meso-2,3-Di(diethylamino)bernsteinsaeurediethylester 
• 623-48-3 ethyl iodoacetae 
• 201230-82-2 carbon monoxide 

Downstream Products

• 617-83-4 Diethylcyanamide 
• 105-36-2 ethyl bromoacetate 
• 6245-02-9 5-[(N,N-diethyl-glycyl)-amino]-2-hydroxy-benzoic acid methyl ester 
• 2644-33-9 2-(diethylamino)acetylhydrazide 
• 1606-01-5 2-(diethylamino)acetic acid 
• 92789-17-8 5-diethylaminomethyl-4-phenyl-2,4-dihydro-[1,2,4]triazole-3-thione 
• 113830-78-7 trans-1-methyl-3-(N,N-diethylamino)-4-phenyl-2-azetidinone 
• 66532-86-3 2-(4-acetamidophenoxy)-N,N-diethyl-2-oxaethan-1-aminium chloride 
• 66532-85-2 Prodafalgan 
• 24376-01-0 N,N-diethylaminoacetic acid hydrochloride 
• 137-58-6 2-diethylamino-N-(2,6-dimethylphenyl)-acetamide 
• 113791-18-7 1-methyl-3-(diethylamino)-4-phenyl-2-azetidinone 
• 28744-17-4 4-Phenyl-1-diaethylaminoacetyl-semicarbazid 

Relevant academic research and scientific papers

Direct Amidation of Esters by Ball Milling**

The direct mechanochemical amidation of esters by ball milling is described. The operationally simple procedure requires an ester, an amine, and substoichiometric KOtBu and was used to prepare a large and diverse library of 78 amide structures with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochemical protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochemicals as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent.

Carbene insertion into N-H bonds with size-selectivity induced by a microporous ruthenium-porphyrin metal-organic framework

A stable and porous porphyrinic metal-organic framework, Ru-PMOF-1(Hf), has been prepared through the self-assembly of [5,10,15,20-tetrakis(4-carboxyphenyl)porphyrinato](monocarbonyl)ruthenium (Ru(TCPP)(CO)) and HfCl4. Single-crystal X-ray diff

Dual role of Cu2O nanocubes as templates and networking catalysts for hollow and microporous Fe-porphyrin networks

Cu2O nanocubes were used for the synthesis of hollow and microporous Fe porphyrin networks (H-MFePN). In this synthesis, Cu2O nanocubes performed not only as networking catalysts but also as shape controlling templates. MFePN were formed on the surface of the Cu2O nanocubes through azide-alkyne cycloaddition of tetrakis(4-ethynylphenyl) Fe-porphyrin with 1,4-diazidobenzene. H-MFePN showed excellent catalytic activities in carbene insertion into N-H bonds, maintaining their activities during five recycle tests.

Synthesis of carbamoylacetates from α-iodoacetate, CO, and amines under Pd/light combined conditions

We developed a novel synthetic method of carbamoylacetates from -iodoacetate, carbon monoxide, and amines under photoirradiation conditions in the presence of a Pd catalyst. This reaction likely proceeds via interplay of radical and organopalladium species. Georg Thieme Verlag Stuttgart · New York.

A RuII-N-heterocyclic carbene (NHC) complex from metal-metal singly bonded diruthenium(I) precursor: Synthesis, structure and catalytic evaluation

A mononuclear Ru(II)-N-heterocyclic carbene (NHC) complex [Ru II(CO)2(κ2C,N-BIN)(H2O)Br] [OTf] (OTf = trifluoromethane sulphonate) (1) has been synthesized in high-yield by the oxidative cleavage of the metal-metal singly-bonded diruthenium(I) precursor [Ru2(CO)4(CH3CN)6(OTf) 2] with 1,8-naphthyridine functionalized NHC precursor 1-benzyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazolium bromide (BIN·HBr) at room temperature. Compound 1 catalyzes transfer hydrogenation of ketones to alcohols, and carbene-transfer from ethyl diazoacetate to a variety of substrates. It is shown to be an excellent catalyst for the insertion of carbene into the O-H and N-H bonds of alcohols and amines.

N,N′-Dialkylaminoalkylcarbonyl (DAAC) prodrugs and aminoalkylcarbonyl (AAC) prodrugs of 4-hydroxyacetanilide and naltrexone with improved skin permeation properties

N,N′-Dialkylaminoalkylcarbonyl (DAAC) and aminoalkylcarbonyl (AAC) prodrugs of phenolic drugs acetaminophen (APAP) and naltrexone (NTX) are reported. The effects of incorporation of a basic amine group into the promoiety of an acyl prodrug of a phenolic drug on its skin permeation properties are also presented. DAAC-APAP prodrugs were synthesized via a three-step procedure starting with haloalkylcarbonyl esters which were reacted with five different amines: dimethylamine, diethylamine, dipropylamine, morpholine, and piperidine. The spacing between the amino group and the carbonyl group of the acyl group was 1-3 CH2. After the hydrolysis of the ester, the carboxylic acid product was subsequently coupled with the parent drug via a dicyclohexyl carbodiimide (DCC) mediated coupling to yield the DAAC-APAP-HCl prodrugs in excellent yields. The AAC prodrugs were synthesized using commercially available Boc-protected amino acids using DCC or EDCI as coupling agents. The yields of the prodrugs synthesized using these two different methods have been compared. Half-lives (t1/2) of a few members of the DAAC and AAC series were measured in buffer (pH 6.0, 20 mM). The members evaluated in hydrolysis experiments exhibit a t1/2 range of 15-113 min. Among AAC-APAP prodrugs, the isopropyl group in valinate-APAP-HCl exerted a steric effect that increased the t1/2 value for this prodrug compared to alaninate-APAP-HCl or prolinate-APAP-HCl. The 2-morpholinylacetate-APAP prodrug was able to achieve twice the flux of APAP in in vitro diffusion cell experiments through hairless mouse skin.

Synthesis of new copper(i) complexes with tris(2-pyridyl) ligands. Applications to carbene and nitrene transfer reactions

New copper(i) complexes with tris(2-pyridyl)methane (TPC), tris(2-pyridyl)methoxymethane (TPM) and tris(2-pyridyl)amine (TPN) ligands have been synthesized and characterized, including structural determinations by X-ray diffraction of some examples. Their activity as catalysts in carbene and nitrene transfer reactions was studied.

Catalytic insertion of diazo compounds into N-H bonds: The copper alternative

The complexes TpXCu (TpX = homoscorpionate) catalyse the insertion of diazo compounds into nitrogen-hydrogen bonds of amines and amides, under very mild conditions, with quantitative yields being obtained with equimolar ratios of reactants.

Insertion of ethyl diazoacetate into N-H and S-H bonds catalyzed by ruthenium porphyrin complexes

Ruthenium porphyrin complexes catalyze insertion of ethyl diazoacetate into sulfur-hydrogen and nitrogen-hydrogen bonds under mild conditions and with reasonable to very good yields.

Efficient and Highly Selective Copper(II) Transport across a Bulk Liquid Chloroform Membrane Mediated by Lipophilic Dipeptides

Several structurally simple N-monoalkylated and -dialkylated dipeptides made of α-amino acids Gly, Phe, and Leu, 1-11, were synthesized and investigated as carriers for the transport of Cu(II), Zn(II), and Ni(II) from an aqueous pH = 5.6 buffer source to a 0.1 M HCl receiving phase across a bulk chloroform membrane. The proton-driven translocation was followed during the process by analyzing the metal ion concentrations in the three phases. The transport efficiency depends on the ease of formation of a neutral complex with Cu(II) (the peptide group and carboxylic acid being deprotonated) at the source-chloroform interface and on that of its disruption by protonation at the receiving phase: the carrier's lipophilicity favors the metal ion uptake and not the release. By modulating the length of the N-alkyl chains and the hydrophobicity of the dipeptide moiety, a quite remarkable transport efficiency was observed for Cu(II), in most cases superior to that of the industrial extractant Kelex 100. Moreover, using L,L- and L,D-N-octyl-PheLeu as carriers, remarkable diastereomeric effects were observed in the rate of uptake and release of Cu(II) ion although the differences mutually compensate in the overall transport rate. Under the conditions used the carriers are much less effective in the translocation of Zn(II) and Ni(II) and their transport efficiency drops dramatically in the presence of Cu(II), the latter being favored by factors of 1.2 × 103 and > 104, respectively. Such very high selectivities depend on the fact that only Cu(II) among other transition metal ions can form neutral complexes at the pH value of the source phase.