13256-32-1

Basic information

• Product Name: N,N'-dimethylnitrosourea
• Synonyms: N,N'-dimethylnitrosourea;1,3-DIMETHYL-N-NITROSOUREA;NITROSODIMETHYLUREA;1,3-Dimethyl-1-nitrosourea;YT03500000;Urea, N,N'-diMethyl-N-nitroso-;1,3-Dimethyl-1-nitrourea
• CAS NO: 13256-32-1
• Molecular Formula: C₃H₇N₃O₂
• Molecular Weight: 117.13
• Mol File: 13256-32-1.mol
• Article Data: 11

Chemical Properties

• Boiling Point: 218.88°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.4020 (rough estimate)
• Refractive Index: 1.4900 (estimate)
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Temperature Sensitive
• CAS DataBase Reference: N,N'-dimethylnitrosourea(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-dimethylnitrosourea(13256-32-1)
• EPA Substance Registry System: N,N'-dimethylnitrosourea(13256-32-1)

Safety Data

• Hazardous Substances Data: 13256-32-1(Hazardous Substances Data)

Usage

Uses

1,3-Dimethyl-3-nitrosourea is a carcinogen.

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Poison by ingestion and intravenous routes. Mutation data reported. When heated to decomposition it emits toxic fumes of NOx. See also N-NITROSO COMPOUNDS.

Upstream product

• 598-94-7 1,1-Dimethylurea 
• 96-31-1 N,N'-Dimethylurea 
• 534-13-4 N,N-dimethylthiourea 
• 7782-77-6 cis-nitrous acid 
• 598-50-5 N-Methylurea 
• 7632-00-0 sodium nitrite 
• 79645-01-5 N₁,N₃-dimethyl-N₁-nitrosothiourea 

Downstream Products

• 17696-95-6 4-methylsemicarbazide 
• 38490-47-0 1-amino-1,3-dimethylurea 
• 19873-46-2 N-Methyl-N'-(4-tolyl)harnstoff 
• 78829-13-7 N-methyl-N'-pentyl-urea 
• 2158-03-4 1-piperidinecarboxamide 
• 13482-66-1 ethyl 2-(methylcarbamoyl)hydrazine-1-carboxylate 
• 65119-31-5 4-methyl-1-phenyl semicarbazide 
• 5352-88-5 3-(4-chlorophenyl)-1-methylurea 
• 39804-96-1 1-cyclohexyl-3-methylurea 
• 38014-52-7 N-methyl-N'-propylurea 
• 1007-36-9 1-methyl-3-phenylurea 
• 64-10-8 phenyl carbamate 
• 691-60-1 N-isopropylurea 
• 39499-81-5 N,n-diethyl-N'-methylurea 

Relevant articles and documents

Kinetic Study of the Nitrosation Reaction of 1,3-Dimethylurea in Dioxane-Water Mixtures

The nitrosation of dimethylurea has been studied in dioxane-water mixtures showing that the kinetic characteristics of the reaction depend on the proportion of dioxane in the medium.Adding dioxane to pure water causes the reaction rate to decrease, and pass through a minimum as a certain concentration of dioxane is reached.The further addition of dioxane increases the reaction rate steadily.At low concentrations of dioxane the system shows the behaviour seen in water, i.e. catalysis by bases and not by nucleophiles, suggesting proton transfer as the slow step.At very high proportions of dioxane, halides and thiocyanate catalyse the process, which is interpreted in terms of the formation of the corresponding nitrosyl halides which may act as efficient nitrosating agents towards the urea.The observed order of efficiency of the catalysts is the opposite to that seen in nitrosation or diazotization processes in water.

Alternative synthetic routes to N-methyl-1,2,4-triazoline-3,5-dione (MeTAD) and other triazolinedione derivatives

N-Methyl-1,2,4-triazoline-3,5-dione (MeTAD) is a powerful electrophile and a versatile synthetic reagent. In this Letter we describe two methods for the synthesis of N-methylurazole, the direct precursor to MeTAD, on gram scales and in good yields. Both methods provide pure urazole while avoiding the necessity of large scale purification via column chromatography or recrystallization. One of the methods proved to be amenable for the synthesis of derivatives other than N-methyl.

Application of N-nitrosoureas in the synthesis of organophosphorus compounds

N-nitrosoureas which are readily accessible from the reaction of urea derivatives with sodium nitrite and aqueous H2SO4 reacted with acetylenic esters in the presence of Ph3P in ethyl acetate at ambient pressure to give stable phosphorus ylides. This methodology is introduced as a simple and inexpensive procedure for the preparation of organophosphorus compounds in excellent yields.