55426-74-9

Basic information

• Product Name: Ethyl 2-dimethylaminobenzoate
• Synonyms: 2-DIMETHYLAMINO-BENZOIC ACID ETHYL ESTER;ETHYL O-DIMETHYLAMINOBENZOATE;ETHYL-2-(DIMETHYLAMINO)BENZOATE;Ethyl-2-dimethylaminobenzoate,97%;ethyl 2-(diMethylaMiNA)benzoate
• CAS NO: 55426-74-9
• Molecular Formula: C₁₁H₁₅NO₂
• Molecular Weight: 193.24
• EINECS: 259-634-3
• Mol File: 55426-74-9.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 281.2 °C at 760 mmHg
• Flash Point: 98 °C
• Appearance: clear yellow to straw yellow liquid
• Density: 1.061
• Vapor Pressure: 0.00362mmHg at 25°C
• Refractive Index: 1.537-1.539
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.83±0.18(Predicted)
• CAS DataBase Reference: Ethyl 2-dimethylaminobenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 2-dimethylaminobenzoate(55426-74-9)
• EPA Substance Registry System: Ethyl 2-dimethylaminobenzoate(55426-74-9)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• Hazardous Substances Data: 55426-74-9(Hazardous Substances Data)

Usage

Chemical Properties

clear yellow to straw yellow liquid

InChI:InChI=1/C11H15NO2/c1-4-14-11(13)9-7-5-6-8-10(9)12(2)3/h5-8H,4H2,1-3H3

Upstream product

• 141814-27-9 2-(2-Methoxyethoxy)ethyl methyl carbonate 
• 87-25-2 2-ethoxycarbonylaniline 
• 64-17-5 ethanol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 121-69-7 N,N-dimethyl-aniline 
• 74-88-4 methyl iodide 

Downstream Products

• 35472-56-1 N-methyl-anthranilic acid ethyl ester 

Relevant articles and documents

Noncovalent Interactions in Ir-Catalyzed C-H Activation: L-Shaped Ligand for Para-Selective Borylation of Aromatic Esters

An efficient strategy for the para-selective borylation of aromatic esters is described. For achieving high para-selectivity, a new catalytic system has been developed modifying the core structure of the bipyridine. It has been proposed that the L-shaped ligand is essential to recognize the functionality of the oxygen atom of the ester carbonyl group via noncovalent interaction, which provides an unprecedented controlling factor for para-selective C-H activation/borylation.

Mono-N-methylation of functionalized anilines with alkyl methyl carbonates over NaY faujasites. 4. Kinetics and selectivity

(Chemical Equation Presented) In the presence of NaY faujasite as the catalyst, the reaction of bifunctional anilines (1-4: XC6H 4-NH2; X = OH, CO2H, CH2OH, and CONH2) with methyl alkyl carbonates [MeOCO2R′: R′ = Me or MeO(CH2)2O(CH2)2] proceeds with a very high mono-N-methyl selectivity (XC6H 4NHMe up to 99%), and chemoselectivity as well, with other nucleophilic functions (OH, CO2H, CH2OH, CONH2) fully preserved from alkylation and/or transesterification reactions. Aromatic substituents, however, modify the relative reactivity of amines 1-4: good evidence suggests that, not only steric and electronic effects, but, importantly, direct acid-base interactions between substituents and the catalyst are involved. Weakly acidic groups (OH, CH2OH, CONH2, pKa ≥ 10) may help the reaction, while aminobenzoic acids (pK a of 4-5) are the least reactive substrates. The solvent polarity also affects the reaction, which is faster in xylene than in the more polar diglyme. The mono-N-methyl selectivity is explained by the adsorption pattern of reagents within the zeolite pores: a BAl2 displacement of the amine on methyl alkyl carbonate should occur aided by the geometric features of the NaY supercavities. Different factors account for the reaction chemoselectivity. Evidence proves that the polarizability of the two nucleophilic terms (NH 2 and X groups) of anilines is relevant, although adsorption and confinement phenomena of reagents promoted by the zeolite should also be considered.