Ethyl 4-dimethylaminobenzoate

Base Information

• Chemical Name: Ethyl 4-dimethylaminobenzoate
• CAS No.: 10287-53-3
• Deprecated CAS: 207575-35-7,97003-31-1
• Molecular Formula: C11H15NO2
• Molecular Weight: 193.246
• Hs Code.: 29224995
• European Community (EC) Number: 233-634-3
• UNII: 829S8D3Y0X
• DSSTox Substance ID: DTXSID2044763
• Nikkaji Number: J92.469E
• Wikidata: Q27123150
• Metabolomics Workbench ID: 58073
• ChEMBL ID: CHEMBL3185245
• Mol file: 10287-53-3.mol

Synonyms:4-dimethylaminobenzoic acid ethyl ester;ethyl 4-dimethylaminobenzoate;p-dimethylaminobenzoic acid ethyl ester;parbenate

Chemical Property of Ethyl 4-dimethylaminobenzoate

Chemical Property:

• Appearance/Colour: White crystal powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 62-65 °C
• Refractive Index: 1.5080 (estimate)
• Boiling Point: 296.5 °C at 760 mmHg
• PKA: 2.56±0.12(Predicted)
• Flash Point: 115 °C
• PSA: 29.54000
• Density: 1.061 g/cm³
• LogP: 1.92930
• Storage Temp.: Store below +30°C.
• Solubility.: Chloroform, Methanol
• Water Solubility.: insoluble
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 193.110278721
• Heavy Atom Count: 14
• Complexity: 184

Purity/Quality:

99%,98%, ^*data from raw suppliers

Ethyl 4-dimethylaminobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Plastics & Rubber -> Curing Agents (Aromatic)
• Canonical SMILES: CCOC(=O)C1=CC=C(C=C1)N(C)C
• Uses: Ethyl 4-dimethylaminobenzoate is employed as a photoinititator in cell encapsulation applications. It is also useful for organic synthesis. Further, it is used in UV-curing coatings and inks for the initiation of photo polymerization of unsaturated prepolymers. In addition to this, it acts as a active pharmaceutical ingredient intermediate. Et-PABA is used as a co-initiator with camphorquinone (CQ) to form a self-adhesive composite for the fabrication of photosensitizers in dental materials.

Technology Process of Ethyl 4-dimethylaminobenzoate

There total 33 articles about Ethyl 4-dimethylaminobenzoate 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: 92.0%

ethyl 4-dimethylaminobenzoate N-oxide → ethyl p-dimethyaminolbenzoate (10287-53-3)

Guidance literature:

With phenylsilane; In acetonitrile; for 0.166667h; chemoselective reaction; Irradiation;

DOI:10.1002/cphc.202100108

Reference yield: 91.0%

formic acid (64-18-6) + ethyl 4-(methylamino)benzoate (10541-82-9) → ethyl p-dimethyaminolbenzoate (10287-53-3)

Guidance literature:

With platinum on carbon; phenylsilane; In toluene; at 80 ℃; for 15h;

DOI:10.1039/c6cy00674d

Reference yield: 88.0%

ethanol (64-17-5) + p-N,N-dimethylaminobenzoic acid (619-84-1) → ethyl p-dimethyaminolbenzoate (10287-53-3)

Guidance literature:

With chloro-trimethyl-silane; at 65 ℃; for 1h;

upstream raw materials:

ethanol

p-N,N-dimethylaminobenzoic acid

p-aminoethylbenzoate

4-(dimethylamino)benzoyl chloride

Downstream raw materials:

4-isopropenyldimethylaniline

(4-dimethylamino-phenyl)-diphenyl-methanol

1-[4-(N,N-dimethylamino)phenyl]-2-(4-pyridyl)ethanone

2-Benzotriazol-1-yl-1-(4-dimethylamino-phenyl)-2-p-tolyl-ethanone

Refernces

• 1、 Afanasyev, Oleg I.,Cherkashchenko, Ilia,Kuznetsov, Anton,Kliuev, Fedor,Semenov, Sergey,Chusova, Olga,Denisov, Gleb,Chusov, Denis. "Alkyl formates as reagents for reductive amination of carbonyl compounds". . p. 112 - 113. Retrieved 2020.
• 2、 Liu, Xiao-Fang,Li, Xiao-Ya,Qiao, Chang,Fu, Hong-Chen,He, Liang-Nian. "Betaine Catalysis for Hierarchical Reduction of CO2 with Amines and Hydrosilane To Form Formamides, Aminals, and Methylamines". . p. 7425 - 7429. Retrieved 2017.
• 3、 Han, Buxing,Ke, Zhengang,Li, Ruipeng,Liu, Zhimin,Tang, Minhao,Wang, Huan,Zeng, Wei,Zhao, Yanfei. "Alcohol promoted N -methylation of anilines with CO2/H2over a cobalt catalyst under mild conditions". . p. 9147 - 9153. Retrieved 2021/11/30.
• 4、 Sarki, Naina,Goyal, Vishakha,Tyagi, Nitin Kumar,Puttaswamy,Narani, Anand,Ray, Anjan,Natte, Kishore. "Simple RuCl3-catalyzed N-Methylation of Amines and Transfer Hydrogenation of Nitroarenes using Methanol". . p. 1722 - 1729. Retrieved 2021/04/19.