21561-99-9

Usage

Safety Profile

Suspected carcinogen with experimental carcinogenic and tumorigenic data. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C8H9N3O2/c1-11(10-13)8(12)9-7-5-3-2-4-6-7/h2-6H,1H3,(H,9,12)

Upstream product

• 62-53-3 aniline 
• 1007-36-9 1-methyl-3-phenylurea 
• 624-83-9 methyl isocyanate 

Downstream Products

• 17425-24-0 phenylthiocarbamic acid S-ethyl ester 
• 5628-90-0 phenyl-thiocarbamic acid S-(2-hydroxy-ethyl ester) 
• 102-07-8 bis(diphenyl)urea 
• 62-53-3 aniline 
• 99307-07-0 S-(2-propenyl) N-phenylmonothiocarbamate 
• 5394-12-7 N-phenylthiocarbamic acid S-cyclohexyl ester 
• 66018-75-5 phenyl-thiocarbamic acid S-4-methylphenyl ester 
• 4910-32-1 1,3-diphenylcarbamothioate 
• 62603-67-2 phenyl-thiocarbamic acid S-tert-butyl ester 
• 17425-13-7 phenyl-thiocarbamic acid S-butyl ester 
• 56741-08-3 phenyl-thiocarbamic acid S-isobutyl ester 

Relevant academic research and scientific papers

PREPARATION AND PROPERTIES OF 3-ALKYL-i-ARYLNITROSOUREAS AND RELATED COMPOUNDS

Nitrosation of 3-alkyl-1-arylureas was investigated with sodium nitrite in 99percent formic acid or with isoamyl nitrite in chloroform.The preparation of 3-alkyl-1-aryl-1-nitrosoureas was effectively performed by using isoamyl nitrite in the absence of acids, since the 1-nitrosoureas were isomerized to the 3-nitroso isomers by acids.The carbon-13 nuclear magnetic resonance and infrared spectral properties of the products were examined and their structural features are discussed.It was found that 3-alkyl-1-aryl-1-nitrosoureas decomposed to form alkyl isocyanates and 3-alkyl-1-(2-nitroaryl)ureas in carbon tetrachloride. 1,3-Rearrangement and transnitrosation also took place in this solvent.Keywords - 3-alkyl-1-arylnitrosourea; 3,3-diethyl-1-tolyl-1-nitrosourea; N-nitrosourea; nitrosation; 1,3-rearrangement; isomerization; transnitrosation; nitration

N-Nitroso Compounds. IV. Reaction of N-Nitrosourea with Thiol. A New Synthesis of Thiocarbamic S-Esters

Thirteen thiocarbamic S-esters have been prepared in good yield by the reaction of thiol with substituted N-methyl-N-nitrosourea in anhydrous acetonitrile.

Kinetics and Mechanism of Decomposition of N-Methyl-N'-aryl-N-nitrosoureas and Related Compounds in Aqueous Buffer Solution

The decomposition reactions of N-methyl-N'-aryl-N-nitrosoureas (1) and of N,N'-dimethyl-N'-aryl-N-nitrosoureas (2) were studied kinetically in phosphate buffer solution.All nitrosoureas 1 were easily hydrolyzed even under conditions and the rates of hydrolysis were found to be proportional to the hydroxide ion concentration over pH range 5.4-7.6.General base catalysis by buffer components was negligible. The reaction was subjected to the elimination mechanism in which an abstraction of the urcido proton was involved as an initial step.On the other hand, nitrosoureas 2 had no significant reactivity under the same conditions.

Conformational Preferences in Alkylnitrosoureas

The spectroscopic properties of several N-alkyl-N-nitrosoureas, N,N'-dialkyl-N-nitrosoureas, and N,N',N'-trialkyl-N-nitrosoureas have been studied in carbon disulfide and chloroform solutions.The NH stretching frequencies in the IR spectra have been observed in both concentrated and dilute solution and in the presence of added dioxane.The results indicate that there is a strong intramolecular hydrogen bond in the mono- and dialkylnitrosoureas.The chemical shifts and line widths of the NMR spectra have also been studied in these solvents.The large chemical shift differences, about 1.3 ppm, for the NH protons in the monoalkylnitrosoureas and other spectroscopic features in the monoalkyl- and dialkylnitrosoureas also indicate that an intramolecular hydrogen bond contributes to a strong conformational preference.The temperature dependence of the NMR spectra of several N,N',N'-trialkyl-N-nitrosoureas establishes that the energy barrier for rotation about the carbon dialkylamide bond is about 13 kcal mol-1.Dipolar resonance interactions are primarily responsible for this barrier.This interaction is augmented by a strong, 8-10 kcal mol-1, hydrogen bond in the mono- and dialkylnitrosoureas.