3445-84-9

Usage

Uses

N,N-Bis(2-cyanoethyl)formamide? as a Liquid Phase for Gas Chromatography.

Preparation

Synthesis of N,N-bis-(2-cyanoethyl)-formamide: Reactions of acrylonitrile and formamide in the presence of bases have been described. Thus, according to DRP 735,771, N,N-bis-(2-cyanoethyl)-formamide is obtained from 2 moles of acrylonitrile and 1 mole of formamide using catalytic quantities of sodium.Literature source US04923952

InChI:InChI=1/C7H9N3O/c8-3-1-5-10(7-11)6-2-4-9/h7H,1-2,5-6H2

Upstream product

• 77287-34-4 formamide 
• 107-13-1 acrylonitrile 
• 111-94-4 3,3'-Iminodipropionitrile 
• 124-38-9 carbon dioxide 

Relevant academic research and scientific papers

Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide

We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.

Synthesis of formamides containing unsaturated groups by: N -formylation of amines using CO2 with H2

Formamides have wide applications in the industry and have been synthesized using CO2 as a carbon source and H2 as a reducing agent. However, previous systems required a noble catalyst and high temperature to achieve high efficiency, and the substrate scope was mostly limited to saturated amines. The selective N-formylation of amines containing unsaturated groups using CO2 and H2 is challenging because the efficient catalysts for the N-formylation are usually very active for hydrogenation of the unsaturated groups. Herein, we achieved for the first time a selective and efficient N-formylation of amines containing unsaturated groups using CO2 and H2 with a Cu(OAc)2-4-dimethylaminopyridine (DMAP) catalytic system. The substrates were converted to the desired formamides, while the unsaturated groups, such as the carbonyl group, the CC bond, CN bond and the ester group remained. The main reason for the excellent selectivity of the Cu(OAc)2-DMAP catalytic system was that it was very active for the N-formylation reaction, but was not active for the hydrogenation of the unsaturated groups.

A Titanium Dioxide Supported Gold Nanoparticle Catalyst for the Selective N-Formylation of Functionalized Amines with Carbon Dioxide and Hydrogen

A TiO2-supported, gold nanoparticle catalyst was found to allow the N-formylation of various amines, including normally unreactive anilines, by using CO2 as the carbonyl source under a H2 atmosphere. A series of reducible functional groups, such as olefins, halogens, carbonyls, carbamates, and cyano moieties, were completely retained during the formylation, which proved the highly selective nature of the formylation reaction. The catalyst was also found to be reusable without any loss of activity or selectivity.