56042-77-4

Basic information

• Product Name: 2-(DiMethylaMino)benzaMide
• Synonyms: 2-(DiMethylaMino)benzaMide
• CAS NO: 56042-77-4
• Molecular Weight: 164.20438
• Mol File: 56042-77-4.mol

Chemical Properties

• CAS DataBase Reference: 2-(DiMethylaMino)benzaMide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(DiMethylaMino)benzaMide(56042-77-4)
• EPA Substance Registry System: 2-(DiMethylaMino)benzaMide(56042-77-4)

Safety Data

• Hazardous Substances Data: 56042-77-4(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
2-(DiMethylaMino)benzaMide is used as a reagent in organic synthesis for its ability to facilitate various chemical reactions and contribute to the development of new compounds.
Used in Medicinal Chemistry and Drug Development:
2-(DiMethylaMino)benzaMide is used as a building block in the design and synthesis of pharmaceuticals, aiding in the creation of novel drug candidates.
Used as a Fluorescent Probe:
2-(DiMethylaMino)benzaMide is used as a fluorescent probe in biological and biochemical studies, allowing researchers to track and visualize specific molecules or processes within living organisms.
Used in Photodynamic Therapy Research:
2-(DiMethylaMino)benzaMide has been studied for its potential applications in photodynamic therapy, a treatment method that uses light-sensitive compounds to target and destroy cancer cells and other diseased tissues.

Upstream product

• 28144-70-9 anthranilic acid amide 
• 74-88-4 methyl iodide 
• 616-38-6 carbonic acid dimethyl ester 
• 141814-27-9 2-(2-Methoxyethoxy)ethyl methyl carbonate 

Downstream Products

• 1298023-71-8 N₁-(2-(dimethylcarbamoyl)phenyl)-N₃-octylmalonamide 
• 42863-76-3 3-(2-dimethylamino-benzyl)-5-(2-hydroxy-ethyl)-4-methyl-3H-thiazole-2-thione 

Relevant articles and documents

Reaction of functionalized anilines with dimethyl carbonate over NaY faujasite. 3. Chemoselectivity toward mono-N-methylation

In the presence of NaY faujasite, dimethyl carbonate (MeOCO2Me, DMC) is a highly chemoselective methylating agent of functionalized anilines such as aminophenols (1), aminobenzyl alcohols (2), aminobenzoic acids (3), and aminobenzamides (4). The reaction proceeds with the exclusive formation of N-methylanilines without any concurrent O-methylation or N-/O-methoxy carbonylation side processes. Particularly, only mono-N-methyl derivatives [XC6H4NHMe, X = o-, m-, and p-OH; o- and p-CH 2OH; o- and P-CO2H; o- and p-CONH2] are obtained with selectivity up to 99% and isolated yields of 74-99%. DMC, which usually promotes methylations only at T > 120 °C, is activated by the zeolite catalyst and it reacts with compounds 1, 2, and 4, at 90 °C. Aminobenzoic acids (3) require a higher reaction temperature (≥130 °C).

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.