5432-28-0

Usage

Safety Profile

Poison by ingestion, intravenous,and intraperitoneal routes. Questionable carcinogen withexperimental tumorigenic data. Mutation data reported.Many N-nitroso compounds are carcinogens. Whenheated to decomposition it emits toxic fumes of NOx. Seealso

InChI:InChI=1/C7H14N2O/c1-9(8-10)7-5-3-2-4-6-7/h7H,2-6H2,1H3

Upstream product

• 100-60-7 N-methylcyclohexylamine 
• 60-29-7 diethyl ether 
• 98-94-2 N,N-dimethyl-cyclohexanamine 
• 611-75-6 bromhexine monohydrochloride 

Downstream Products

• 55984-45-7 C₂₀H₂₄N₂O₂ 
• 97379-92-5 2-Hydroxy-thiobenzoesaeure-(N²-methyl-N²-cyclohexyl-hydrazid) 
• 100-60-7 N-methylcyclohexylamine 
• 14300-39-1 N-Cyclohexyl-formamidoxim 
• 33668-52-9 1-methyl-1-cyclohexylhydrazine 

Relevant academic research and scientific papers

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

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.

N-nitrosation of secondary amines using supported perchloric acid on silica gel and stereoselectivity study of nitrosated products

N-Nitrosation of different types of secondary amines has been proceeded using supported perchloric acid on silica gel and sodiume nitrite under heterogeneous conditions. The operational system is simple and high pure products can be easily isolated with good to high yields.

Ph3P/Br2/n-Bu4NNO2 as an efficient system for the preparation of N-nitrosamines and azides

The combination PPh3/Br2/n-Bu4NNO2 was developed as a new reagent system for the efficient preparation of N-nitrosamines and azides from the corresponding amines and hydrazine derivatives, respectively, at 0 °C to room temperature, in excellent yields.

Efficient procedure for chemoselective N-nitrosation of secondary amines with trichloromelamine-NaNO2

A combination of trichloromelamine and sodium nitrite in the presence of wet silica gel was used as an effective nitrosating agent for the transformation of secondary amines into the corresponding N-nitroso derivatives under mild and heterogeneous conditions in good to excellent yields.

Molybdate sulfuric acid/NaNO2: A novel heterogeneous system for the N-nitrosation of secondary amines under mild conditions

Wet molybdate sulfuric acid (=dioxo[bis(sulfato-κO)]molybdenum; MSA), a new solid acid, can be used in combination with sodium nitrite (NaNO 2) to transform a variety of secondary amines to the corresponding N-nitroso compounds under mild, heterogeneous conditions (Table). The process has several advantages: the reagents are inexpensive and non-hazardous, the reaction is clean, fast, and high-yielding, and MSA can be readily removed by filtration and re-used (after treatment with HCl) without loss of activity. Further, only N-nitrosation was observed, but no C- or O-nitrosation.

Alumina-methanesulfonic acid (AMA)/NaNO2 as an efficient procedure for the chemoselectivite N-nitrosation of secondary amines

A combination of alumina/methanesulfonic acid (AMA) and sodium nitrite was used as an effective nitrosating agent for the nitrosation of secondary amines under mild and heterogeneous conditions in good to excellent yields. Copyright Taylor & Francis Group, LLC.

The use of Nafion-H/NaNO2 as an efficient procedure for the chemoselective N-nitrosation of secondary amines under mild and heterogeneous conditions

A combination of Nafion-H and sodium nitrite in the presence of wet SiO2 was used as an effective agent for the N-nitrosation of secondary amines under mild and heterogeneous conditions in good to excellent yields.

Trichloroisocyanuric acid/NaNo2 as a novel heterogeneous system for the N-nitrosation of N,N-dialkylamines under mild conditions

A combination of trichloroisocyanuric acid and sodium nitrite in the presence of wet SiO2 was used as an effective nitrosating agent for the nitrosation of N,N-dialkyl amines to their corresponding nitroso derivatives under mild and heterogeneous conditions in moderate to excellent yields.

Silica sulfuric acid/NaNO2 as a novel heterogeneous system for the chemoselective N-nitrosation of secondary amines under mild conditions

Neat chlorosulfonic acid reacts with silica gel to give silica sulfuric acid in which sulfuric acid is immobilized on the surface of silica gel via a covalent bond. A combination of silica sulfuric acid and sodium nitrite in the presence of wet SiO2 was used as an effective nitrosating agent for the nitrosation of secondary amines to their corresponding nitroso derivatives under mild and heterogeneous conditions in excellent yields.

Differences in the activity of neutral and ionized β-cyclodextrin on the nitrosation of amines by phenylpropyl nitrites

The influence of β-cyclodextrin (β-CD) on the base-catalyzed hydrolysis reaction of 1-phenyl-1-propyl, 2-phenyl-1propyl and 3-phenyl-1-propyl nitrites and on the nitrosation of pyrrolidine, piperidine and N-methylcyclohexylamine by the aforementioned alkyl nitrites (RONO) is studied in aqueous buffers of the amines and in an alkaline medium with [OH-] = 0.20 M. The hydrolysis reaction is catalyzed by the presence of β-CD owing to the formation of reactive 1:1 inclusion complexes between the alkyl nitrite and the ionized β-CD; the addition of potential inhibitors, such as dodecyltrimethylammonium bromide monomers, accelerates the reaction even more. The effect is quite significant in the case of 1-phenyl-1-propyl nitrite and is viewed as a case of allostery. In the presence of neutral β-CD, the nitrosation by 1-phenyl-1-propyl nitrite, either of pyrrolidine or piperidine, is inhibited by β-CD addition; however, the nitrosation reaction of piperidine by 2-phenyl-1-propyl nitrite is catalyzed (passing through a maximum) by β-CD, whereas the nitrosation of pyrrolidine promoted by 3-phenyl-1-propyl nitrite exhibits practically no change upon β-CD addition. In alkaline media (containing ionized β-CD) the nitrosation of pyrrolidine by 1-phenyl-1-propyl nitrite is inhibited by the presence of β-CD; in contrast, the nitrosation of both piperidine and N-methylcyclohexylamine is catalyzed in all cases, but the degree of catalysis depends not only on the alkyl nitrite structure, but also on the type and concentration of the amine. Kinetic results are quantitatively interpreted on the basis of the proposed reaction mechanism in each case, and the kinetic rate constants of the different steps are determined. Comparison of the results obtained in aqueous alkaline media and in aqueous buffers of the amines themselves allows us to establish important characteristics of the transition state of the reaction.