924-99-2

Basic information

• Product Name: Ethyl 3-(N,N-dimethylamino)acrylate
• Synonyms: DMAE;ETHYL 3-(DIMETHYLAMINO)ACRYLATE;ETHYL 3,3-DIMETHYLAMINOACRYLATE;3-(DIMETHYLAMINO)ACRYLIC ACID ETHYL ESTER;3-DAASE;RARECHEM AL BI 0671;Ethyl 3-(N,N-dimethylamino)acrylate, 99+%;ethyl 3-(dimethylamino)propenoate
• CAS NO: 924-99-2
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18
• EINECS: 402-650-4
• Product Categories: Acids and Derivatives;Amines and Anilines;Small molecule;API intermediates
• Mol File: 924-99-2.mol

Chemical Properties

• Melting Point: 17-18 °C
• Boiling Point: 118-121 °C (7.501 mmHg)
• Flash Point: 105 °C
• Appearance: Clear yellow to light orange/Liquid
• Density: 1
• Vapor Pressure: 0.683mmHg at 25°C
• Refractive Index: 1.5105-1.5125
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 6.67±0.70(Predicted)
• Water Solubility: 90 g/L (25 ºC)
• CAS DataBase Reference: Ethyl 3-(N,N-dimethylamino)acrylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 3-(N,N-dimethylamino)acrylate(924-99-2)
• EPA Substance Registry System: Ethyl 3-(N,N-dimethylamino)acrylate(924-99-2)

Safety Data

• Hazard Codes: Xi
• Statements: 43-36/37/38
• Safety Statements: 37-24-36/37-26
• Hazardous Substances Data: 924-99-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Ethyl 3-(N,N-dimethylamino)acrylate is used as a key intermediate in organic synthesis for the production of various chemical compounds. Its reactivity allows for the formation of a diverse array of products, making it an essential component in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, Ethyl 3-(N,N-dimethylamino)acrylate is utilized as a building block for the development of new drugs. Its unique chemical properties enable the creation of innovative pharmaceutical agents with potential therapeutic applications.
Used in Agrochemicals:
Ethyl 3-(N,N-dimethylamino)acrylate is employed as a vital component in the formulation of agrochemicals, such as pesticides and herbicides. Its incorporation into these products contributes to their effectiveness in controlling pests and promoting crop health.
Used in Dye Industry:
In the dyestuff field, Ethyl 3-(N,N-dimethylamino)acrylate is used as a precursor for the synthesis of various dyes and pigments. Its ability to form a wide range of derivatives makes it a valuable asset in the production of colorants for textiles, plastics, and other materials.

InChI:InChI=1/C7H13NO2/c1-4-10-7(9)5-6-8(2)3/h5-6H,4H2,1-3H3/b6-5+

Upstream product

• 64-17-5 ethanol 
• 34780-29-5 3-oxo-propionic acid ethyl ester 
• 506-59-2 N,N-dimethylammonium chloride 
• 5815-08-7 tert-Butoxybis(dimethylamino)methane 
• 141-78-6 ethyl acetate 
• 124-40-3 dimethyl amine 
• 623-47-2 propynoic acid ethyl ester 
• 68-12-2 N,N-dimethyl-formamide 
• 927-80-0 1-ethoxyacetylene 
• 34433-91-5 N-formyl-β-alanine ethyl ester 
• 4071-88-9 trimethylsilanyl-acetic acid ethyl ester 
• 74119-34-9 3-Dimethylamino-2-(formylaminomethyl)acrylsaeure-ethylester 
• 201230-82-2 carbon monoxide 
• 64-18-6 formic acid 

Downstream Products

• 148926-94-7 ethyl ester of 3-dimethylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid 
• 173315-57-6 ethyl 2-(2-chloro-4-fluoro-3-methyl-5-nitrobenzoyl)-3-(dimethylamino)acrylate 
• 184680-78-2 ethyl 2-chloro-α-[(dimethylamino)methylene]-4-fluoro-3-methyl-β-oxo-benzenepropanoate 
• 258345-86-7 ethyl 2-(2,4-dichloro-3-fluoro-5-nitrobenzoyl)-3-(dimethylamino)acrylate 
• 258345-84-5 ethyl 2-(2,4-dichloro-3-ethyl-5-nitrobenzoyl)-3-(dimethylamino)acrylate 
• 138998-63-7 ethyl 2-[(2,4-dichloro-5-fluoro-3-nitrophenyl)carbonyl]-3-(dimethylamino)prop-2-enoate 
• 697762-43-9 ethyl 3-(dimethylamino)-2-[(2-fluoro-5-iodophenyl)carbonyl]-2-propenoate 
• 882535-05-9 1-((2S)-1-tert-buthyldimethylsilyloxy-3-methylbutan-2-yl)-6-(3-chloro-2-fluorobenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester 
• 111453-56-6 ethyl 3-(N-cyclopropylamino)-2-(2,4-dichloro-5-fluoro-3-nitrobenzoyl) acrylate 
• 173315-66-7 7-Fluoro-1-(4-fluoro-phenyl)-8-methyl-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 173315-67-8 7-Fluoro-1-(4-methoxy-phenyl)-8-methyl-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 1026741-19-4 6-Amino-1-(4-fluoro-phenyl)-8-methyl-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 1026536-30-0 6-Amino-1-(4-methoxy-phenyl)-8-methyl-7-(4-methyl-piperazin-1-yl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 1027145-27-2 1-(4-Fluoro-phenyl)-8-methyl-7-(4-methyl-piperazin-1-yl)-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 

Relevant articles and documents

Preparation method of ethyl 3-(N,N-dimethylamino)acrylate

The invention relates to a preparation method of ethyl 3-(N,N-dimethylamino)acrylate, which comprises the following steps: carrying out heating reaction on formic acid, ethyl acetate and dimethylamineto obtain ethyl 3-(N,N-dimethylamino)acrylate and water. The preparation method of the ethyl 3-(N,N-dimethylamino)acrylate is short in reaction route, high in yield and purity and low in safety risk.

Biaryl and atropisomeric biaryl aldehyde synthesis by one-step, metal-free benzannulation of aryl enals and propiolates

A new method involving the benzannulation of aromatic enals and two alkyl propiolate molecules has been developed as a powerful route to biaryl aldehydes simply via the promotion of dimethyl amine. The benzannulation process in the absence of an oxidant additive tolerates successfully the formyl group in the enal component, leading to a straightforward one-step synthesis of biaryl and atropisomeric aldehydes. An enamine activation based on the aza-Michael addition of dimethyl amine to the propiolate and the amine elimination-based generation of cyclohexadiene intermediate constitute the major factors enabling the titled reactions. This journal is

Ethyl N,N-dimethylaminoacrylate synthesis method

The invention relates to the technical field of synthesis of fine chemical intermediates, particularly to an ethyl N,N-dimethylaminoacrylate synthesis method, which comprises that ethyl acetate, carbon monoxide and dimethylamine are used as starting raw materials, and are subjected to a reaction under the action of a solid alkali catalyst to form the target product ethyl N,N-dimethylaminoacrylate,wherein the solid alkali catalyst is preferably a supported solid alkali catalyst. According to the present invention, the problems that the raw material source is difficult, the price is expensive,the process condition is harsh, the three-waste amount is high, the yield is low, the cost is high, the method is not suitable for industrial production and the like in the prior art are solved; and the synthesis method of the present invention has characteristics of convenient raw material source, low cost, environmentally-friendly reaction condition, substantially-reduced side-product, high total yield, high raw material utilization rate, low production cost and high product purity, and is suitable for large-scale industrial continuous production.

Synthesis method for N,N-dimethylaminoethyl acrylate

The invention discloses a synthesis method for N,N-dimethylaminoethyl acrylate. The method includes the following steps that 1, raw material preparation is carried out, wherein ethyl acetate, carbon monoxide, dimethylamine carbonate and sodium ethoxide serve as raw material; 2, material blending is carried out, wherein the molar ratio of ethyl acetate to carbon monoxide to dimethylamine carbonate to sodium ethoxide is (3-4):(0.9-1.1):(1.0-1.30):(1.2-1.4); 3, ethyl acetate, dimethylamine carbonate and sodium ethoxide are added into a vessel, carbon monoxide is introduced into the vessel, the temperature in the kettle is controlled to be 45-50 DEG C at the pressure of 0.2-0.8 MPa, and a heat-preserved reaction is carried out for 10 h; 4, after the reaction is finished, reduced pressure distillation is carried out to distill off a solvent, and the distilled solvent is recycled; 5, water is added into the vessel, standing is carried out for layering, an oil phase enters a rectification system, and N,N-dimethylaminoethyl acrylate is obtained through rectification. The product synthesized with the method contains few impurities, the amount of wastewater is small, the water resource is saved, the yield is high and reaches 5%, and the content is increased to 99.5% or above from 98%.

3-N,N-dimethylamino ethyl acrylate preparation method

The invention relates to a 3-N,N-dimethylamino ethyl acrylate synthesis method, which comprises the following reaction process that under a medium pressure of 10-15 bar, piperidine is adopted as a catalyst, ethyl acetate reacts with sodium ethoxide and carbon monoxide to generate a formyl ethyl acetate sodium salt, and the formyl ethyl acetate sodium salt reacts with a dimethylamine hydrochloride to generate the 3-N,N-dimethylamino ethyl acrylate. According to the present invention, the piperidine is adopted as the catalyst, such that the 50 bar high pressure necessarily required in the prior art is reduced, and the complete reaction can be achieved within the medium-low pressure range of 10-15 bar so as to reduce the operation difficulty and the danger during the production.

Gold nanoparticles on OMS-2 for heterogeneously catalyzed aerobic oxidative α,β-dehydrogenation of β-heteroatom-substituted ketones

In the presence of Au nanoparticles supported on manganese oxide OMS-2 (Au/OMS-2), various kinds of β-heteroatom-substituted α,β-unsaturated ketones (heteroatom = N, O, S) can be synthesized through α,β-dehydrogenation of the corresponding saturated ketones using O2 (in air) as the oxidant. The catalysis of Au/OMS-2 is truly heterogeneous, and the catalyst can be reused.

Carbamoylcholine analogs as nicotinic acetylcholine receptor agonists-Structural modifications of 3-(dimethylamino)butyl dimethylcarbamate (DMABC)

Compounds based on the 3-(dimethylamino)butyl dimethylcarbamate (DMABC) scaffold were synthesized and pharmacologically characterized at the α4β2, α3β4, α4β4 and α7 neuronal nicotinic acetylcholine receptors (nAChRs). The carbamate functionality and a small hydrophobic substituent in the C-3 position were found to be vital for the binding affinity to the nAChRs, whereas the carbamate nitrogen substituents were important for nAChR subtype selectivity. Finally, the compounds were found to be agonists at the α3β4 nAChR.

Synthesis of 1-Aryl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic Acids and Esters

Ethyl 1-aryl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylates 2 were prepared by the condensation of arylhydrazines with ethyl 3-ethoxy-2-(trifluoroacetyl)-2-propenoate (1a) at low temperature.The corresponding acids were also synthesized.X-ray diffraction analysis of an amide derivative 4 verified the position of the trifluoromethyl group on the pyrazole ring.

REACTION OF GOLD'S REAGENT WITH ACTIVATED METHYLENE GROUPS DERIVED FROM ESTERS AND NITROARENES

A series of esters and nitrotoluenes were reacted with Gold's reagent under basic conditions and were found to produce the corresponding dimethylamino methyleneated product in both cases.

Orthoamides, XXXII. - Reactions of tert-Butoxy-N,N,N',N'-tetramethylmethanediamine with NH- and CH-acidic Compounds

tert-Butoxy-N,N,N',N'-tetramethylmethanediamine (1) reacts with N-formylglycine ethyl ester (2) and with N-formyl-β-alanine ethyl ester (9) to form the aminomethylene compounds 3 and 10, respectively.Glycine ester is aminomethylenated by 1 at the acidic NH2 group to give the amidine 6.Dimethylaminoformaldehyde dimethyl acetal (5) is also suitable for this reaction.On reaction with 1 the compounds 3 as well as 6 yield the amidine 4.N-Monosubstituted formamides are transformed by 1 into formamidines 13.Reaction of isocyanoacetate 17 and 1 affords the enamine 18, whereas reaction of benzyl isonitrile with 1 gives the amidine 19. 2-Alkyl-Δ2-oxazolines 21, carboximidates 23, 25, and amidines 27 are aminomethylenated by 1 to yield the products 22, 24, 26, and 28, respectively.The vinylogous guanidinium salt 34 is obtained by reaction of 1 with N,N,N',N'-tetramethylacetamidinium tetrafluoroborate (31a).Phosphonates 36 react with 1 to afford the enamines 37.The reaction of 1 on ethyl trimethylsilylacetate (39) gives rise to formation of ethyl 3-dimethylaminoacrylate (11).