615-53-2

Usage

Uses

Used in Pharmaceutical Industry:
N-NITROSO-N-METHYLURETHANE is used as a research chemical for its ability to cause chromosomal damage in HeLa cells. This property makes it valuable in the study of cancer cell behavior and the development of potential cancer treatments.
Used in Chemical Synthesis:
N-NITROSO-N-METHYLURETHANE is used as a synthetic compound in the production of antifungal agents, such as azoxybacillin. Its role in the synthesis process contributes to the development of new antifungal medications to combat various fungal infections.

Reactivity Profile

N-NITROSO-N-METHYLURETHANE is a N-nitrosated carbamate ester. Incompatible with strong acids and bases. Especially incompatible with strong reducing agents such as hydrides. Flammable gaseous hydrogen may be produced by the combination with active metals or nitrides Incompatible with oxidizing acids, peroxides, and hydroperoxides.

Health Hazard

TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.

Fire Hazard

Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes. Some are oxidizers and may ignite combustibles (wood, paper, oil, clothing, etc.). Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, tumorigenic, and teratogenic data. Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Moderately toxic by inhalation. Experimental reproductive effects. Mutation data reported. Has been implicated as a transplacental brain carcinogen. Combustible when exposed to heat, sparks, open flame, and powerful oxidizers. Explodes when heated. A storage hazard. When heated to decomposition it emits toxic fumes of NOx.

InChI:InChI=1/C4H8N2O3/c1-3-9-4(7)6(2)5-8/h3H2,1-2H3

Upstream product

• 105-40-8 Ethyl N-methylcarbamate 
• 541-41-3 chloroformic acid ethyl ester 
• 3058-37-5 (Z)-potassium methanediazotate 
• 74-88-4 methyl iodide 

Downstream Products

• 22072-22-6 thiepan-4-one 
• 185-73-9 1-oxa-6-thiaspiro<2.5>octane 
• 3350-30-9 cyclononanone 
• 1502-06-3 cyclodecanone 
• 1208-75-9 1-benzylazepan-4-one 
• 131459-19-3 4-cyclohexyl-cycloheptanone 
• 100971-69-5 4-p-tolyl-1-oxa-spiro[2.5]octane 
• 108011-64-9 3-(p-tolyl)cycloheptanone 
• 100713-65-3 4-(4-chloro-phenyl)-1-oxa-spiro[2.5]octane 
• 107774-06-1 3-(4-chloro-phenyl)-cycloheptanone 
• 108062-64-2 2-(4-methoxyphenyl)cycloheptan-1-one 
• 101869-70-9 Opt_.-inakt. 1-Hydroxy-2-methyl-1-hydroxymethyl-cyclohexan 
• 101869-71-0 optically inactive 3-methyl-1-hydroxymethyl-cyclohexanol-⁽¹⁾ 
• 186581-53-3 diazomethane 

Relevant academic research and scientific papers

IMPROVEMENTS IN OR RELATING TO ORGANIC COMPOUNDS

A process of converting a carbon-carbon multiple bond to a cyclopropane ring, comprising the addition of a N-alkyl-N-nitroso compound to a mixture of alkene precursor, aqueous base and Pd(II)-catalyst, with the N-alkyl-N-nitroso compound obtained directly from an alkyl amine derivative, NaNO2 and an acid via phase separation of the N-alkyl-N-nitroso compound from the aqueous phase.

Ambident ethyl N-nitrosocarbamate anion: Experimental and computational studies of alkylation and thermal stability

Alkylation of N-nitrosourethane tetrabutylammonium salt (2-Bu4N) with four electrophiles (Mel, Etl, i-Prl, and PhCH2Br) was studied by 1H NMR in CD2Cl2 and CD3CN solutions. The ratio of the three regioisomers N-alkyl-N-nitrosourethane 3, azoxy 4, and O-alkyldiazotate 5 was practically independent of solvent but dependent on the nature of the electrophile. The anion 2 and O-alkyl derivative 5 are thermally unstable and decompose to ethyl carbonates 9 and 10, respectively, with a first-order rate constant (2-Bu4N: k = 18.5 ± 0.1 × 10-5 S-1; 5b (R = Et): k = 1.77 ± 0.02 × 10-5 s-1; 5d (R = PhCH2): k = 4.78 ± 0.08 × 10-5 s-1 at 35 °C in CD2Cl2). Further kinetic measurements gave activation parameters for the decomposition of 2 (Ea = 24.2 ± 0.3 kcal/mol and In A = 30.9 ± 0.1). Gas-phase calculations at the MP2(fc)/6-31+G(d)//MP2(fc)/6-31G(d) level showed that the alkylation of 2 involves the lone electron pairs of the N-N-O atoms, and the calculated activation energies correspond well to the observed ratio of regioisomers 3-5. The theoretical analysis of the decomposition processes supports a concerted mechanism with a four-center transition state in the first step for all four compounds. The calculated activation energy order (2 5 3 4) is consistent with the observed order of stability. Decomposition of 2 and 5 is a unimolecular process, giving carbonates 9 and 10 in a single step. In contrast, rearrangement of 3 and 4 leads to alkyl diazonium ions. A detailed theoretical analysis indicates that the rate-determining step for thermal decomposition of 2 is the loss of molecular nitrogen, while in 5 it is the trans-cis isomerization process. The nonconcerted process involving homolytic cleavage of the O-N bond in 5 was found to be significantly less favorable.

A screening procedure for the formation of nitroso derivatives and mutagens by drug-nitrite interaction

A general procedure for screening for the formation of nitroso derivatives and/or mutagens by drug-nitrite interaction was established. A test drug (50 mM) was reacted with nitrite (500 mM) at pH 3.0-3.5 and 37°C for 4 h. The residual nitrite in the reaction mixture was decomposed with ammonium sulfamate. The nitrite-free reaction mixture was assayed for both nitroso derivatives and mutagens by colorimetry of Griess reagent-positive substances formed by treatment with hydrogen bromide and by mutagenesis assay using Salmonella typhimurium TA98 and TA100 as tester strains, respectively.