N-Nitroso-N-methylurethane

Base Information

• Chemical Name: N-Nitroso-N-methylurethane
• CAS No.: 615-53-2
• Molecular Formula: C4H8 N2 O3
• Molecular Weight: 132.119
• Hs Code.: 2928000090
• European Community (EC) Number: 210-432-3
• NSC Number: 2860
• UN Number: 2811,3082
• UNII: 741GDM4803
• DSSTox Substance ID: DTXSID4021472
• Nikkaji Number: J1.659D
• Wikidata: Q26840976
• NCI Thesaurus Code: C29829
• ChEMBL ID: CHEMBL3188414
• Mol file: 615-53-2.mol

Synonyms:Methylnitrosourethane;Nitrosomethylurethane

Chemical Property of N-Nitroso-N-methylurethane

Chemical Property:

• Vapor Pressure: 6.18mmHg at 25°C
• Refractive Index: 1.4360 to 1.4400
• Boiling Point: 66 °C / 13mmHg
• PKA: -2.73±0.70(Predicted)
• Flash Point: 38.6°C
• PSA: 58.97000
• Density: 1,14 g/cm3
• LogP: 0.75610
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Ethyl Acetate , Methanol
• Water Solubility.: 36.99g/L(24 oC)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 132.05349212
• Heavy Atom Count: 9
• Complexity: 114
• Transport DOT Label: Poison

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-Methyl-N-nitrosourethane ^*data from reagent suppliers

Safty Information:

• Statements: 5-36/37/38-40
• Safety Statements: 23-35-45-53

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitrosamines
• Canonical SMILES: CCOC(=O)N(C)N=O
• Uses: N-Methyl-N-nitrosourethane is a nitrosamide which causes chromosomal damage in HeLa cells. It is also used in the synthesis of antifungal agents such as azoxybacillin.

Technology Process of N-Nitroso-N-methylurethane

There total 3 articles about N-Nitroso-N-methylurethane 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:

Ethyl N-methylcarbamate (105-40-8) → ethyl N-methyl-N-nitrosocarbamate (615-53-2)

Guidance literature:

With sodium nitrite; In hydrogenchloride; Equilibrium constant; effect of pH on nitrosation;

DOI:10.1248/cpb.30.3399

Reference yield:

ethyl N-nitrosocarbamate tetrabutylammonium salt + methyl iodide (74-88-4) → methoxy-diazenecarboxylic acid ethyl ester + ethyl N-methyl-N-nitrosocarbamate (615-53-2) + C4H8N2O3

Guidance literature:

In dichloromethane-d2; at 0 ℃; Further Variations:; Solvents; Reaction partners; Product distribution;

DOI:10.1021/ja0209058

Reference yield:

chloroformic acid ethyl ester (541-41-3) + (Z)-potassium methanediazotate (3058-37-5) → ethyl N-methyl-N-nitrosocarbamate (615-53-2)

Guidance literature:

In diethyl ether;

upstream raw materials:

Ethyl N-methylcarbamate

chloroformic acid ethyl ester

(Z)-potassium methanediazotate

methyl iodide

Downstream raw materials:

thiepan-4-one

1-oxa-6-thiaspiro<2.5>octane

ethyl N,N-dimethylcarbamate

ethyl phenylhydrazocarboxylate

Refernces

• 1、 Benin, Vladimir,Kaszynski, Piotr,Radziszewski, J. George. "Ambident ethyl N-nitrosocarbamate anion: Experimental and computational studies of alkylation and thermal stability". . p. 14115 - 14126. Retrieved 2007/10/03.
• 2、 Takeda,Kanaya. "A screening procedure for the formation of nitroso derivatives and mutagens by drug-nitrite interaction". . p. 3399 - 3404. Retrieved 2007/10/02.