16339-12-1

Basic information

• Product Name: N-NITROSO-N-METHYL-O-METHYL-HYDROXYLAMINE
• Synonyms: N-NITROSO-N-METHYL-O-METHYL-HYDROXYLAMINE;Methylmethoxynitrosamine;N-Methoxy-N-nitrosomethylamine
• CAS NO: 16339-12-1
• Molecular Formula: C₂H₆N₂O₂
• Molecular Weight: 90.10
• Mol File: 16339-12-1.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 167.26°C (rough estimate)
• Flash Point: °C
• Appearance: /
• Density: 1.3348 (rough estimate)
• Vapor Pressure: 342mmHg at 25°C
• Refractive Index: 1.4462 (estimate)
• PKA: -8.61±0.70(Predicted)
• CAS DataBase Reference: N-NITROSO-N-METHYL-O-METHYL-HYDROXYLAMINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-NITROSO-N-METHYL-O-METHYL-HYDROXYLAMINE(16339-12-1)
• EPA Substance Registry System: N-NITROSO-N-METHYL-O-METHYL-HYDROXYLAMINE(16339-12-1)

Safety Data

• Hazardous Substances Data: 16339-12-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C2H6N2O2/c1-4(3-5)6-2/h1-2H3

Upstream product

• 1117-97-1 N,0-dimethylhydroxylamine 
• 7732-18-5 water 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 

Downstream Products

• 67-56-1 methanol 
• 115-10-6 Dimethyl ether 
• 631-61-8 ammonium acetate 
• 6998-30-7 methylamine acetate 
• 50-00-0 formaldehyd 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 25843-45-2 (Z)-1-n-butyl-2-methyldiazene-1-oxide 

Relevant articles and documents

Synthesis of 14C-labelled compounds. III. Synthesis of N-nitroso-O,N-14C-dimethyl-hydroxylamine

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N-nitroso-N,O-dialkylhydroxylamines: Preparation, structure, and mechanism of the hydronium ion catalysed solvolytic nitrous oxide extrusion reaction

Eleven N-nitroso-N,O-dialkylhydroxylamines, RN(NO)OR′, have been prepared and the mechanisms of their hydronium ion catalysed solvolyses in aqueous solution which liberate nitrous oxide have been investigated. All reactions are first-order in substrate and first-order in hydronium ion, and the second-order rate constants at 25°C vary over a range of less than 140 in spite of considerable variation in substrate structure (R ranges from methyl to 4-methoxybenzyl to 2-adamantyl, for example) and changes in solvent composition (water with up to 50% methanol or 66% acetonitrile). Enthalpies and entropies of activation are qualitatively similar throughout the range (ΔH?= 72-93 kJ mol-1 and ΔS? = -19 to -57 J K-1 mol-1) which, with the product analyses, are accommodated by a mechanism involving pre-equilibrium protonation of the substrates followed by rate-limiting dissociation to give RN2O+ and HOR′. The oxodiazonium ion intermediate, RN2O+, then dissociates further to give the carbenium ion intermediate, R+, or suffers direct nucleophilic displacement of N2O by solvent (the external nucleophile) or by R′OH (the internal nucleophile liberated in the initial fragmentation). The carbenium ion, R+ (if formed), suffers nucleophilic capture either by solvent or by R′OH. When acetonitrile is the co-solvent (rather than methanol) for the N-(2-adamantyl) substrate 3g, the product of the Ritter reaction, 2-acetamidoadamantane, is detected. These nitrous oxide liberating reactions are compared with the nitric oxide liberating reactions of related N-nitrosohydroxylamines, and the origin of the difference between them is identified. The N(1)-nitroso group in the N,O-dibenzyl compound 3c is shown by X-ray crystallography to be essentially coplanar with the C and O atoms also bonded to N(1).

THE FORMATION OF AZOXYALKANES IN REACTIONS OF SOME ORGANOMETALLIC REAGENTS WITH N-nitroso-O,N-DIALKYLHYDROXYLAMINES: THE NONPHOTOCHEMICAL SYNTHESIS OF AN ACYCLIC (E)-AZOXYALKANE

Azoxyalkanes were found to be regiospecifically formed in the reactions of some alkyllithium and Grignard reagents with N-nitroso-O,N-dialkylhydroxylamines.Remarkably, although (Z)-stereomers were usually produced, in one case the (E)-isomer was predominant.