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
• Description: Methylnitrosourea (MNU) is a methylated nitrosourea compound with alkylating,mutagenic, teratogenic, carcinogenic, and cytotoxic properties. The toxic effects of MNU are caused by the transfer of its methyl group to nucleobases in nucleic acids.
• Uses: Precursor of Diazomethane. It has a cytotoxicity effect. This product contains an undetermined amount of water MNU is the starting material for diazomethane generation. Diazomethane provides methyl derivatives with carboxylic acids and phenols in a very smooth and gentle reaction. Phenols are slower in their reactivity compared to carboxylic acids and should be converted at temperatures greater than 0
  C. However, since MNU is unstable at temperatures greater than 20
  C and is shock sensitive to a degree, other (N-methyl) nitrosamides have replaced MNU for use in diazomethane generation, and most chemical supply houses no longer carry MNU. MNU has been studied as a chemotherapeutic agent as it is an effective therapy for mice that are intraperitoneally or intracerebrally implanted with L1210 leukemia cells. MNU is currently used as a research chemical to develop animal models for human diseases.

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'-cyclohexylurea

p-tolylurea

N,N-diethylurea

1-butyl-urea

Refernces

• 1、 Ferraz, Caline G.,Ribeiro, Paulo R.,Marques, édson J.,Mendon?a, Renata,Guedes, Maria Lenise S.,Silveira, Edilberto R.,El-Bachá, Ramon,Cruz, Frederico G.. "Polyprenylated benzophenone derivatives with a novel tetracyclo[8.3.1.03,11.05,10]tetradecane core skeleton from Clusia burle-marxii exhibited cytotoxicity against GL-15 glioblastoma-derived human cell line". . . Retrieved 2019.
• 2、 Ferraz, Caline G.,Ribeiro, Paulo R.,Mendon?a, Renata,Silveira, Edilberto R.,Cruz, Frederico G.. "Novel polyprenylated benzophenone derivatives from Clusia burle-marxii". . . Retrieved 2021.
• 3、 Clusius,Endtinger. "". . p. 1823,1829. Retrieved 1958.
• 4、 Inami, Keiko,Shiino, Junko,Hagiwara, Shin,Takeda, Kei,Mochizuki, Masataka. "Transnitrosation of non-mutagenic N-nitrosoproline forms mutagenic N-nitroso-N-methylurea". . p. 3297 - 3302. Retrieved 2015.
• 5、 -. "Method for synthesizing chiral 4-(N-carbobenzoxy) pyrrolidone". Paragraph 0025; 0030. . Retrieved 2019/10/01.