Ethyl 3-(N,N-dimethylamino)acrylate

Base Information

• Chemical Name: Ethyl 3-(N,N-dimethylamino)acrylate
• CAS No.: 1117-37-9
• Molecular Formula: C7H13NO2
• Molecular Weight: 143.186
• Hs Code.: 2922499990
• European Community (EC) Number: 402-650-4,627-077-9,677-349-6
• DSSTox Substance ID: DTXSID101009957
• Nikkaji Number: J1.865.998K,J355.005B
• Wikidata: Q76305507
• Mol file: 1117-37-9.mol

Synonyms:Acrylic acid, 3-(dimethylamino)-, ethylester, (E)- (8CI);2-Propenoic acid,3-(dimethylamino)-, ethyl ester, (E)-;

Chemical Property of Ethyl 3-(N,N-dimethylamino)acrylate

Chemical Property:

• Vapor Pressure: 0.683mmHg at 25°C
• Refractive Index: 1.451
• Boiling Point: 185.9 °C at 760 mmHg
• PKA: 5.60±0.70(Predicted)
• Flash Point: 68.9 °C
• PSA: 29.54000
• Density: 0.964 g/cm³
• LogP: 0.62480
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 143.094628657
• Heavy Atom Count: 10
• Complexity: 130

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 3-(N,N-dimethylamino)acrylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 24-37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C=CN(C)C
• Isomeric SMILES: CCOC(=O)/C=C/N(C)C

Technology Process of Ethyl 3-(N,N-dimethylamino)acrylate

There total 30 articles about Ethyl 3-(N,N-dimethylamino)acrylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

tert-Butoxybis(dimethylamino)methane (5815-08-7) + 3-Dimethylamino-2-(formylaminomethyl)acrylsaeure-ethylester (74119-34-9) → ethyl 3-(dimethylamino)acrylate (924-99-2,1117-37-9,114894-59-6) + dimethyl amine (124-40-3) + tert-butyl alcohol (75-65-0)

Guidance literature:

at 160 ℃; for 3h;

Reference yield: 95.5%

carbon monoxide (201230-82-2) + ethyl acetate (141-78-6) + dimethyl amine (124-40-3) → ethyl 3-(dimethylamino)acrylate (924-99-2,1117-37-9,114894-59-6)

Guidance literature:

With solid base catalyst; In 5,5-dimethyl-1,3-cyclohexadiene; at 50 ℃; for 4h; under 7500.75 Torr; Temperature; Autoclave;

Reference yield: 93.0%

2-dimethylamino-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (557087-01-1) + propynoic acid ethyl ester (623-47-2) → ethyl (E)-3-(dimethylamino)acrylate (1117-37-9)

Guidance literature:

With sodium t-butanolate; tricyclohexylphosphine; In methanol; at 70 ℃; for 17h; Inert atmosphere; Schlenk technique;

DOI:10.1002/anie.201305098

upstream raw materials:

ethanol

3-oxo-propionic acid ethyl ester

N,N-dimethylammonium chloride

tert-Butoxybis(dimethylamino)methane

Downstream raw materials:

ethyl ester of 3-dimethylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid

ethyl 2-(2-chloro-4-fluoro-3-methyl-5-nitrobenzoyl)-3-(dimethylamino)acrylate

ethyl 2-chloro-α-[(dimethylamino)methylene]-4-fluoro-3-methyl-β-oxo-benzenepropanoate

ethyl 2-(2,4-dichloro-3-fluoro-5-nitrobenzoyl)-3-(dimethylamino)acrylate

Refernces

• 1、 Robertson, Jeffrey M.,Jones, Ian W.,Kayne, Kevin M.,Contreras, Cristina G.,Witter, Daniel J.,Bates, Robert B.,Hall Jr.. "A new synthesis of alkyl (E)-(3-dimethylamino)acrylates". . p. 6080 - 6081. Retrieved 2011.
• 2、 Ke, Yi-Yin,Li, Yu-Jin,Jia, Jian-Hong,Sheng, Wei-Jian,Han, Liang,Gao, Jian-Rong. "Efficient synthesis of β-enaminoesters via highly stereoselective Reformatsky reaction with disubstituted formamides as novel electrophiles". . p. 1389 - 1391. Retrieved 2009.
• 3、 -. "Preparation method of ethyl 3-(N,N-dimethylamino)acrylate". Paragraph 0027-0044. . Retrieved 2021/02/10.
• 4、 -. "Ethyl N,N-dimethylaminoacrylate synthesis method". Paragraph 0064-0075. . Retrieved 2019/04/26.