5326-57-8

Usage

InChI:InChI=1/C12H18N2O/c1-4-14(5-2)12-8-6-11(7-9-12)13-10(3)15/h6-9H,4-5H2,1-3H3,(H,13,15)

Upstream product

• 108-24-7 acetic anhydride 
• 93-05-0 N,N-diethylaniline 
• 104-04-1 N-(4-Nitrophenyl)acetamide 
• 75-05-8 acetonitrile 
• 2198-58-5 N,N-diethyl-p-phenylenediamine hydrochloride 
• 75-36-5 acetyl chloride 
• 122-80-5 N-acetyl-p-phenylenediamine 

Downstream Products

• 1056157-48-2 C₂₀H₃₂N₂O₂ 
• 1338496-47-1 2-acetamido-3-(4-(5-acetamido-2-(diethylamino)phenoxy)phenyl)-N-(4-hydroxybutyl)propanamide 
• 1338496-48-2 2-acetamido-3-(5'-acetamido-2'-(diethylamino)-6-hydroxy-[1,1'-biphenyl]-3-yl)-N-(4-hydroxybutyl)propanamide 
• 1338496-45-9 2-acetamido-3-(2-(N-(4-(diethylamino)phenyl)acetamido)-1H-indol-3-yl)-N-(4-hydroxybutyl)propanamide 
• 1352427-51-0 N-(4-(N-ethyl-N-nitrosoamino)phenyl)acetamide 
• 26886-71-5 N⁴,N⁴-diethylbenzene-1,2,4-triamine 

Relevant academic research and scientific papers

Modification of aniline containing proteins using an oxidative coupling strategy

A new bioconjugation reaction has been developed based on the chemoselective modification of anilines through an oxidative coupling pathway. Aryl amines were installed on the surface of protein substrates through lysine acylation reactions or through the

Ligand-directed selective protein modification based on local single-electron-transfer catalysis

A photocatalyst ([Ru(bpy)3]2+) bound to a protein ligand was essential for the title method. Local single-electron transfer from the catalyst resulted in the formation of tyrosyl radicals. N′-Acetyl-N,N- dimethyl-1,4-phenylenediamine was used as the tyrosyl radical trapping agent and used in a radical addition to afford selective modification of the target protein. Copyright

Selective N-alkylation of amines using nitriles under hydrogenation conditions: Facile synthesis of secondary and tertiary amines

Nitriles were found to be highly effective alkylating reagents for the selective N-alkylation of amines under catalytic hydrogenation conditions. For the aromatic primary amines, the corresponding secondary amines were selectively obtained under Pd/C-catalyzed hydrogenation conditions. Although the use of electron poor aromatic amines or bulky nitriles showed a lower reactivity toward the reductive alkylation, the addition of NH4OAc enhanced the reactivity to give secondary aromatic amines in good to excellent yields. Under the same reaction conditions, aromatic nitro compounds instead of the aromatic primary amines could be directly transformed into secondary amines via a domino reaction involving the one-pot hydrogenation of the nitro group and the reductive alkylation of the amines. While aliphatic amines were effectively converted to the corresponding tertiary amines under Pd/C-catalyzed conditions, Rh/C was a highly effective catalyst for the N-monoalkylation of aliphatic primary amines without over-alkylation to the tertiary amines. Furthermore, the combination of the Rh/C-catalyzed N-monoalkylation of the aliphatic primary amines and additional Pd/C-catalyzed alkylation of the resulting secondary aliphatic amines could selectively prepare aliphatic tertiary amines possessing three different alkyl groups. According to the mechanistic studies, it seems reasonable to conclude that nitriles were reduced to aldimines before the nucleophilic attack of the amine during the first step of the reaction.

Reductive and catalytic monoalkylation of primary amines using nitriles as an alkylating reagent

(Chemical Equation Presented) A selective and catalytic mono-N-alkylation method of both aromatic and aliphatic amines using nitriles as an alkylating agent with Pd/C or Rh/C as a catalyst is described. This method is particularly attractive to provide an environmentally benign and applicable alkylation method of amines without using toxic and corrosive alkylating agents such as alkyl halides and carbonyl compounds.

Retention behavior of compounds with active hydrogen atoms and their acetylated derivatives in reversed-phase HPLC

In view of poor interlaboratory reproducibility of retention indices I in reversed-phase high-performance liquid chromatography, not the indices themselves but their differences for reactants and products of interaction with various reagents can be used to identify compounds with active hydrogen atoms. For acetylated derivatives of phenols and aromatic amines, the quantity ?I = I(ArXH) -I(ArXCOCH3), where X = O or NH. has statistically significant distinguishable values of 126 ± 15 and 70 ± 20, respectively. The additivity of the parameters ?I is first revealed for the polyfunctional compounds of these classes that are incapable of intramolecular hydrogen bonding. Abnormal ?I values and deviations from the additivity rule are observed only for substances with intramolecular hydrogen bonding. This finding can be used to confirm the presence of relevant structural units in molecules.

Thermal imaging methods and materials

Leuco dyes are provided which comprise the coupling product of a N-acyl substituted aromatic amino color developer and a dye-forming coupler moiety substituted at the coupling carbon with a thermally removable leaving group. Thermal imaging systems employing these leuco dyes have the advantage of reduced bubble formation relative to thermal imaging systems employing prior art leuco dyes containing a group which thermally fragments into one or more gases.