593-77-1

Basic information

• Product Name: N-Methylhydroxylamine
• Synonyms: METHYLHYDROXYLAMINE;NCI C-60066;NCI-C-60066;N-MethylhydroxyaMine;Methanamine, N-hydroxy-
• CAS NO: 593-77-1
• Molecular Formula: CH₅NO
• Molecular Weight: 47.07
• Mol File: 593-77-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 87.5°C
• Boiling Point: 55.67°C (rough estimate)
• Appearance: /
• Density: 1.0003
• Refractive Index: 1.4164 (estimate)
• PKA: 14.00±0.30(Predicted)
• CAS DataBase Reference: N-Methylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Methylhydroxylamine(593-77-1)
• EPA Substance Registry System: N-Methylhydroxylamine(593-77-1)

Safety Data

• Hazardous Substances Data: 593-77-1(Hazardous Substances Data)

Usage

General Description

N-Methylhydroxylamine is a chemical compound with the formula CH3NHOH. It is a colorless, hygroscopic liquid that is soluble in water and polar organic solvents. N-Methylhydroxylamine is commonly used as a reagent in organic synthesis, particularly in the production of pharmaceuticals and agrochemicals. It is also employed in the manufacture of rubber and plastics. N-Methylhydroxylamine is a highly reactive compound and must be handled with caution due to its potential as an explosive, oxidizing, and flammable substance. It is important to follow strict safety protocols when working with this chemical.

InChI:InChI=1S/CH5NO/c1-2-3/h2-3H,1H3

Upstream product

• 81206-51-1 acetaldehyde-(N-methyl oxime ) 
• 76-06-2 chloropicrin 
• 109-02-4 4-methyl-morpholine 
• 5756-69-4 3-hydroxy-3-methyl-1-phenyl-1-triazene 
• 7647-01-0 hydrogenchloride 
• 75-52-5 nitromethane 
• 7664-93-9 sulfuric acid 
• 26817-00-5 1-hydroxy-1-methyl-3-phenyl-urea 
• 42449-48-9 4-methyl-benzophenone-(N-methyl oxime ) 
• 16089-77-3 methyl-(3-nitro-benzylidene-(seqcis))-amine oxide 
• 74-88-4 methyl iodide 
• 71-43-2 benzene 
• 861565-98-2 N-methyl-N-trityl-hydroxylamine 
• 108-24-7 acetic anhydride 

Downstream Products

• 145616-48-4 (1Z,2E)-N-methyl-3-phenylprop-2-en-1-imine oxide 
• 3016-84-0 ethyl hydroxyl(methyl)carbamate 
• 4950-03-2 N,O-Bis-aethoxycarbonyl-N-methyl-hydroxylamin 
• 861565-98-2 N-methyl-N-trityl-hydroxylamine 
• 98496-72-1 3-hydroxy-3-methyl-1-p-nitrophenyl-1-triazene 
• 52266-34-9 3-(hydroxy-methyl-amino)-1-phenyl-propan-1-one 
• 28809-12-3 1-methyl-3c-phenyl-(3ar,9bc)-1,3a,4,9b-tetrahydro-3H-chromeno[4,3-c]isoxazole 
• 64797-05-3 C₁₄H₂₁ClN₂O₂ 
• 145616-48-4 C-styryl-N-methyl nitrone 
• 137661-29-1 N-methyl-N-(3,5-diphenyl-4-isoxazolylmethyl)hydroxylamine 
• 91153-79-6 α-(o-crotyloxy)phenyl-N-methylnitrone 
• 105249-66-9 2-Biphenyl-4-yl-N-hydroxy-N-methyl-acetamide 
• 88793-55-9 (3-Hydroxy-1-methyl-6-oxo-1,6-dihydro-pyridazin-4-yl)-acetic acid 
• 88793-56-0 (6-Hydroxy-2-methyl-3-oxo-2,3-dihydro-pyridazin-4-yl)-acetic acid 

Relevant articles and documents

Electrochemical Reductive N-Methylation with CO2Enabled by a Molecular Catalyst

The development of benign methylation reactions utilizing CO2 as a one-carbon building block would enable a more sustainable chemical industry. Electrochemical CO2 reduction has been extensively studied, but its application for reductive methylation reactions remains out of the scope of current electrocatalysis. Here, we report the first electrochemical reductive N-methylation reaction with CO2 and demonstrate its compatibility with amines, hydroxylamines, and hydrazine. Catalyzed by cobalt phthalocyanine molecules supported on carbon nanotubes, the N-methylation reaction proceeds in aqueous media via the chemical condensation of an electrophilic carbon intermediate, proposed to be adsorbed or near-electrode formaldehyde formed from the four-electron reduction of CO2, with nucleophilic nitrogenous reactants and subsequent reduction. By comparing various amines, we discover that the nucleophilicity of the amine reactant is a descriptor for the C-N coupling efficacy. We extend the scope of the reaction to be compatible with cheap and abundant nitro-compounds by developing a cascade reduction process in which CO2 and nitro-compounds are reduced concurrently to yield N-methylamines with high monomethylation selectivity via the overall transfer of 12 electrons and 12 protons.

ELECTROREDUCTION OF NITROMETHANE ON HYDROPHOBIZED COPPER ELECTRODES IN A HYDROCHLORIC ACID ELECTROLYTE

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Mesylhydroxylamines, V. Polysubstituted N-Mesylhydroxylamines

The preparation and characterization of the following N-mesylhydroxylamines are reported: (CH3SO2)2NOSO2CH3 (1), (CH3SO2)2NOCH3 (2), CH3SO2N(CH3)OSO2CH3 (3), CH3SO2N(H)OCH3 (4), Na(1+)*CH3SO2NOCH3(1-)*1/2H2O (5), CH3SO2N(CH3)OCH3 (6). - Keywords: Methane Sulfonic Acid Derivatives, Hydroxylamines