N-Nitroso-N-methylurea

Base Information

• Chemical Name: N-Nitroso-N-methylurea
• CAS No.: 684-93-5
• Deprecated CAS: 126742-50-5,820-60-0,820-60-0
• Molecular Formula: C2H5N3O2
• Molecular Weight: 103.081
• Hs Code.: 29241990
• European Community (EC) Number: 211-678-4
• NSC Number: 23909
• UN Number: 2811,3077
• UNII: W8KW4E3XSU
• DSSTox Substance ID: DTXSID4021006
• Nikkaji Number: J3.020A
• Wikipedia: N-Nitroso-N-methylurea
• Wikidata: Q3023727
• NCI Thesaurus Code: C645
• Metabolomics Workbench ID: 52534
• ChEMBL ID: CHEMBL288958
• Mol file: 684-93-5.mol

Synonyms:Methylnitrosourea;N Methyl N nitrosourea;N-Methyl-N-nitrosourea;Nitrosomethylurea;NSC 23909;NSC-23909;NSC23909

Chemical Property of N-Nitroso-N-methylurea

Chemical Property:

• Appearance/Colour: Off-white to pale yellow solid
• Vapor Pressure: 0.605mmHg at 25°C
• Melting Point: 119-124°C
• Refractive Index: 1.574
• Boiling Point: 164.3 °C at 760 mmHg
• PKA: 12.36±0.50(Predicted)
• Flash Point: 53.1 °C
• PSA: 75.76000
• Density: 1.46 g/cm³
• LogP: 0.37860
• Storage Temp.: 2-8°C
• Water Solubility.: Soluble. <0.1 g/100 mL at 18 C
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 103.038176411
• Heavy Atom Count: 7
• Complexity: 90.9
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

N-Methyl-N-nitrosoUrea(ContainsWater) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F; T
• Hazard Codes: F,T
• Statements: 45-46-61-11-25
• Safety Statements: 53-45-24/25-22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrosamines
• Canonical SMILES: CN(C(=O)N)N=O
• General Description: 1-Methyl-1-nitrosourea (MNU) is a nitrosated derivative of methylurea, formed through a proton transfer mechanism during nitrosation reactions. The kinetics of its formation are influenced by the solvent, catalytic anions (e.g., acetate), and the hydrophobic nature of the alkyl group, with methylurea exhibiting higher reactivity compared to longer-chain or allyl-substituted ureas. The rate-determining step involves proton transfer from the protonated intermediate to the solvent or anionic catalysts, supported by kinetic isotope effects and Bronsted parameters. This reactivity trend aligns with the ability of the protonated intermediate to form hydrogen bonds, hindered by steric and hydrophobic effects of the alkyl substituent.

Technology Process of N-Nitroso-N-methylurea

There total 11 articles about N-Nitroso-N-methylurea which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

N-Methylurea (598-50-5) → 1-methyl-1-nitrosourea (684-93-5)

Guidance literature:

With dinitrogen tetroxide impregnated on activated charcoal; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1081/SCC-200057999

Reference yield: 70.0%

urea (57-13-6) + methylamine (74-89-5) → 1-methyl-1-nitrosourea (684-93-5)

Guidance literature:

urea; methylamine; With hydrogenchloride; In water; for 3h; Reflux;

With sodium nitrite; at 0 - 20 ℃;

DOI:10.1002/ejoc.201701610

Reference yield: 51.0%

1-methylurea nitrite → 1-methyl-1-nitrosourea (684-93-5)

Guidance literature:

With sulfuric acid; water; at 0 ℃;

DOI:10.1021/jm201150j

upstream raw materials:

N-acetyl-N'-methylurea

potassium cyanate

methylamine hydrochloride

urea

Downstream raw materials:

n-propylurea

ethyl allophanate

1-hexylurea

1-[2]naphthylazo-[2]naphthylamine