Chemical Properties
clear colorless to pale yellow liquid
Uses
N,N-Diethylformamide was used in the synthesis of metal-organic frameworks. It was also used as solvent in the synthesis of porous cubic-shaped ZnO particles.
Uses
N,N-Diethylformamide is used in the synthesis of metal-organic frameworks and Diethyltrifluoromethylamine. It is also used as solvent in the preparation of porous cubic-shaped zinc oxide particles. It is involved in the preparation of quinazoline-2,4(1H,3H)-dione by reacting with o-aminonitrile.
Definition
ChEBI: N,N-diethyl-Formamide is a carboxamide.
General Description
N,N-Diethylformamide undergoes condensation with aromatic
o-aminonitriles in the presence of ZnCl
2 in sealed reactor to yield quinazoline-2,4(1
H,3
H)-dione.
Toxicology
N, N-Diethylformamide (DEF) is a hepatotoxic polar solvent. The metabolism has been investigated as below. DEF was deethylated by microsomal P450-dependent oxidation, forming acetaldehyde and MEF according to Michaelis-Menten kinetic parameters. Microsomes from rats pretreated with acetone and pyrazole (selective P4502E1 inducers) or rats pretreated with dexamethasone and 200 mg/kg DEF were able to deethylate DEF in a biphasic manner, showing a low Km component with a Vmax of about 0.2 nmol/(min?mg of protein) and a Km between 70 μM and 250 μM. The low Km component was not present in control microsomes or in microsomes from rats treated with phenobarbital, a-naphthoflavone, or clofibrate, where linear kinetics were observed. The use of purified P4502E1 and 2C11 in a reconstituted system showed that 2E1, which oxidized DEF with a Vmax of 4.5 nmol/(min?nmol of P450) and a Km of 0.7 mM, can partially account for the low Km DEF deethylase, whereas 2C11, which oxidized DEF with a Vmax of 4.8 nmol/(min?- nmol of P450) and a Km of 17 mM, might be the high Km deethylase. The purified 2B1 was barely able to deethylate DEF. A confirmation of the role 2E1 in DEF metabolism was obtained by using various selective inhibitors of P450 isoforms and immunoprecipitation experiments with anti-P4502E1 IgG. The low Km component of DEF deethylation in acetoneor pyrazole-induced microsomes was strongly inhibited (～90%) by diethyldithiocarbamate, 4-methylpyrazole, and anti-2E1 IgG, but in 200 mg/kg DEF-induced microsomes the inhibition was partial, suggesting that other P450(s) may be involved. Administration of DEF 200 mg/ kg ip for 4 days induced hepatic microsomal P4502E1-dependent aniline hydroxylase, P4502B1/ 2-linked pentoxyresorufin O-depentylase, 16a-testosterone hydroxylase P4503A1/2-associated erythromycin N-demethylase, and 6a-testosterone hydroxylase. Alternatively, the same dose regimen of MEF induced only the aniline hydroxylase and depressed the 3A1/2-linked activities. Immunoblot experiments verified these data. These findings indicate that DEF, at low concentrations, is predominantly oxidized by P4502E1 and that this enzyme may be induced in rodents by repeated MEF or DEF treatment, thereby increasing their metabolism and potentially their cytotoxicity through the formation of ethyl isocyanate.
Research
The multi-component solvent systems containing N, N-diethylformamide (DEF) are interesting liquid systems for the study of molecular interactions as N, N-diethylformamide (DEF) is one of the most common solvents used in chemical reactions and in many industrial processes. In the work of Wu et al, densities of binary mixtures of {N, N-diethylformamide (DEF) +o-xylene, or +m-xylene, or +p-xylene}, have been determined under atmospheric pressure as a function of composition using a vibrating-tube densimeter. The temperatures studied were T(293.15, 303.15, 313.15, 323.15, 333.15, 343.15 and 353.15) K. The excess molar volumes, Vm E, calculated from density data, are negative over the whole mole fraction range for the temperature range studied and increase with rising temperature. These indicate the presence of specific interactions between DEF and xylenes molecules[1].
References
[1] San-Jun Peng . “A study of volumetric properties of binary mixtures of N, N-diethylformamide with aromatic hydrocarbon at different temperatures.” Journal of Molecular Liquids 139 1 (2008): Pages 98-103.
[2] Meng-Yao Chao. “Unconventional Pyridyl Ligand Inclusion within a Flexible Metal-Organic Framework Bearing an N,N′-Diethylformamide (DEF)-Solvated Cd5 Cluster Secondary Building Unit.” ChemPlusChem 85 3 (2020): 503–509.
[3] Yunxue Gao. “Measurement and Correlation of Solubilities and Solution Thermodynamics for N,N-Diethylformamide + MCl (M = Na, K, Rb, and Cs) + Water Systems in the Temperature Range 288.15–338.15 K.” Journal of Chemical & Engineering Data 61 4 (2016): 1649–1656.
