55-18-5Relevant academic research and scientific papers
Synthesis of N,N-diethylhydrazine and its reactions with carboxylic acids and alkyl halides
Akhmedov,Tadzhimukhamedov,Akhmedov
, p. 1720 - 1722 (2005)
N,N-Diethylhydrazine was synthesized by a modified procedure via nitrosation of diethylamine, followed by reduction of the resulting N-nitrosodiethylamine with zinc amalgam in a hydrochloric acid medium. Reactions of N, N-diethylhydrazine with carboxylic acids and alkyl halides resulted in formation of the corresponding hydrazinium salts.
Formation of nitrosamines in organic solvents and aqueous systems containing organic solvents
Iitsuka,Hoshino,Kato,Kikugawa
, p. 2516 - 2521 (1985)
Formation of N-nitrosodimethylamine and N-nitrosodiethylamine in organic solvents such as chloroform, benzene, ethyl acetate, n-hexane, acetonitrile and dioxane was much faster than that in the control citrate buffer at pH 3. This effect of the organic solvents may be due to their ability to suppress ionization of nitrous acid. Formation of the nitrosamines in acetone was faster, but the yield was less than in other organic solvents, probably due to reaction of the solvent with nitrous acid. Ethyl alcohol was not useful as the control buffer, since it consumed nitrous acid to produce nitrite ester. The use of pH-controlled aqueous systems containing acetonitrile and dioxane accelerated the formation of the nitrosamines by increasing the concentration of nitrous acid; the 25% acetonitrile-containing system produced 3 times as much N-nitrosodimethylamine and 6 times as much N-nitrosodiethylamine as compared to the control citrate buffer at pH 4. Formation of the nitrosamines in citrate was accelerated or inhibited by addition of acetone and ethyl alcohol depending upon the pH conditions. It is concluded that most organic solvents suppressed the ionization of nitrous acid and accelerated the nitrosation of the secondary amines.
Visible-Light-Induced Photoaddition of N-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines
Patil, Dilip V.,Si, Tengda,Kim, Hun Young,Oh, Kyungsoo
supporting information, p. 3105 - 3109 (2021/05/05)
The generation of aminium radical cation species from N-nitrosoamines is disclosed for the first time through visible-light excitation at 453 nm. The developed visible-light-promoted photoaddition reaction of N-nitrosoamines to alkenes was combined with the o-NQ-catalyzed aerobic oxidation protocol of amines to telescope the direct handling of harmful N-nitroso compounds, where the desired α-amino oxime derivatives were obtained in a one-pot tandem N-nitrosation and photoaddition sequence.
Kinetic and Theoretical Study of the Nitrate (NO3) Radical Gas Phase Reactions with N-Nitrosodimethylamine and N-Nitrosodiethylamine
Maguta, Mihayo Musabila,Stenstr?m, Yngve,Nielsen, Claus J.
, p. 6970 - 6977 (2016/10/12)
The reaction rates of (CH3)2NNO and (CH3CH2)2NNO with NO3 radicals were determined relative to formaldehyde (CH2O) and ethene (CH2CH2) at 298 ± 2 K and 1013 ± 10 hPa in purified air by long path FTIR spectroscopy. The reactions are too slow to be of importance at atmospheric conditions: k NO3+(CH3)2NNO = (1.47 ± 0.23) × 10-16 and k NO3+(CH3CH2)2NNO = (5.1 ± 0.4) × 10-16 cm3 molecule-1 s-1 (1σ error limits). Theoretical calculations, based on CCSD(T?)-F12a/aug-cc-pVTZ//M06-2X/aug-cc-pVTZ results, predict the corresponding imines as the sole primary products in nitrosamine reactions with NO3 and OH radicals.
Facile N-nitrosation of secondary amines using poly(N,N'-dibromo-Nethylene- benzene-1,3-disulfonamide) and N,N,N′,N′-tetrabromobenzene-1,3- disulfonamide/NaNO2 under mild conditions
Ghorbani-Vaghei, Ramin,Shiri, Lotfi,Ghorbani-Choghamarani, Arash
, p. 204 - 208 (2013/07/26)
In this research project, a combination of poly(N,N′-dibromo-N- ethylene-benzene-1,3-disulfonamide) [PBBS] and/or (N,N,N′,N′- tetrabromobenzene-1,3-disulfonamide) [TBBDA] with sodium nitrite in the presence of wet SiO2 (50% w/w) was used as an efficient nitrosating agent for the conversion of secondary amines to their corresponding nitroso compounds. N-Nitrosation reaction has been performed in dichloromethane at room temperature under mild and heterogeneous conditions. The reaction is operationally simple and corresponding products were achieved in good to excellent yields.
Ionic liquid 1-(4-nitritobutyl)-3-methylimidazolium chloride as a new reagent for the efficient N-nitrosation of secondary amines under mild conditions
Valizadeh, Hassan,Gholipour, Hamid,Shomali, Ashkan
experimental part, p. 467 - 470 (2012/06/15)
1-(4-Nitritobutyl)-3-methylimidazolium chloride has been developed as a new reagent for efficient nitrosation of secondary amines at 0 °C to room temperature. A variety of N-nitrosamines were prepared in excellent yields by use of this task-specific ionic liquid under mild and heterogeneous conditions.
1-butyl-3-methylimidazolium nitrite as a reagent for the efficient n-nitrosation of secondary amines
Valizadeh,Gholipour
experimental part, p. 857 - 861 (2012/06/18)
1-Butyl-3-methylimidazolium nitrite, [bmim]NO2 was used as a new effective reagent for the preparation of N-nitrosamines from the corresponding secondary amines at 0 °C to room temperature, under mild conditions in good to excellent yields.
N-nitrosation of secondary amines using p-TSA-NaNO2 as a novel nitrosating agent under mild conditions
Borikar, Sanjay P.,Paul, Vincent
experimental part, p. 654 - 660 (2011/02/27)
A combination of p-toluenesulfonic acid (p-TSA) and sodium nitrite was used as a novel effective nitrosating agent for the N-nitrosation of secondary amines to their corresponding nitroso derivatives under mild and heterogeneous conditions in moderate to excellent yields.
Synthesis of N,N-dialkylnitramines from secondary ammonium nitrates in liquid or supercritical carbon dioxide
Kuchurov,Fomenkov,Zlotin
experimental part, p. 2058 - 2062 (2011/01/08)
An efficient explosion-proof method was developed for the preparation of N,N-dialkylnitramines by treatment of dialkylammonium nitrates with a mixture of nitric acid and acetic anhydride in the presence of ZnCl2 in liduid or supercritical carbon dioxide.
Mechanistic studies on the reaction between R2N-NONOates and aquacobalamin: evidence for direct transfer of a nitroxyl group from R 2N-NONOates to cobalt(III) centers
Hassanin, Hanaa A.,Hannibal, Luciana,Jacobsen, Donald W.,El-Shahat, Mohamed F.,Hamza, Mohamed S. A.,Brasch, Nicola E.
supporting information; experimental part, p. 8909 - 8913 (2010/03/01)
Tales of the unexpected: Transfer of a nitroxyl group from R2N-NONOates to aquacobalamin to form nitroxylcobaiamin does not proceed via H+-catalyzed R2NNONOate decomposition, but instead occurs via a probable NONOate-cobalamin intermediate (see scheme; r.
