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

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

Uses

Used in Organic Synthesis:
N-Methylhydroxylamine is used as a reagent in organic synthesis for the production of pharmaceuticals and agrochemicals. Its reactivity allows it to participate in various chemical reactions, making it a valuable component in the synthesis of a wide range of compounds.
Used in Rubber and Plastics Manufacturing:
N-Methylhydroxylamine is also employed in the manufacture of rubber and plastics, where it serves as a crucial ingredient in the production process. Its presence can influence the properties and performance of the final products.
Safety Precautions:
Due to the potential hazards associated with N-Methylhydroxylamine, it is essential to follow strict safety protocols when working with this chemical. This includes handling it with care to prevent accidental reactions and ensuring proper storage conditions to minimize the risk of explosions or fires.

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

Upstream product

• 81206-51-1 acetaldehyde-(N-methyl oxime ) 
• 60-29-7 diethyl ether 
• 2421-26-3 2-chloro-2-nitrosopropane 
• 544-97-8 dimethyl zinc(II) 
• 75-52-5 nitromethane 
• 76-06-2 chloropicrin 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 10557-03-6 (Z)-N-(1-phenylethylidene)methanamine N-oxide 
• 203731-09-3 4-methoxybenzylidenemethylamine N-oxide 
• 74-88-4 methyl iodide 
• 79566-22-6 N-(3-Benzyl-2-methyl-4-phenyl-isoxazolidin-5-yl)-N-methyl-hydroxylamine 
• 80653-57-2 N,O-Dimesyl-N-methylhydroxylamin 
• 109-02-4 4-methyl-morpholine 
• 91328-48-2 (Z)-N-(n-heptylidene)methylamine N-oxide 

Downstream Products

• 145616-48-4 (1Z,2E)-N-methyl-3-phenylprop-2-en-1-imine oxide 
• 98496-72-1 3-hydroxy-3-methyl-1-p-nitrophenyl-1-triazene 
• 5756-69-4 3-hydroxy-3-methyl-1-phenyl-1-triazene 
• 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 
• 3376-23-6 N-methyl-α-phenylnitrone 
• 203731-09-3 4-methoxybenzylidenemethylamine N-oxide 
• 16817-96-2 N-methyl-O-benzoylbenzohydroxamic acid 
• 2446-50-6 N-hydroxy-N-methylbenzamide 
• 26817-00-5 1-hydroxy-1-methyl-3-phenyl-urea 
• 2614-48-4 N-methyl-N-(4-methoxybenzoyl)hydroxylamine 
• 191991-32-9 N-(4-dimethylamino-benzyl)-N-methyl-hydroxylamine 
• 15058-52-3 benzyl hydroxy(methyl)carbamate 

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.

Spontaneous dehydration mechanism of aromatic aldehyde reactions with hydroxyl and non-hydroxyl amines

The plot of rate constants vs. pH for the dehydration step of the reaction between furfural and 5-nitrofurfural with hydroxylamine, N-methylhydroxylamine, and O-methylhydroxylamine, shows two regions corresponding to the oxonium ion-catalyzed and spontaneous dehydration. The oxonium ion-catalyzed dehydration region of the reaction of furfural with the above mentioned hydroxylamines exhibits general acid catalysis with excellent Bronsted correlation (Bronsted coefficients: 0.76 (r = 0.986), 0.68 (r = 0.987), and 0.67 (r = 0.993) respectively). However, the rate constants of the spontaneous dehydration of these hydroxylamines, where water is considered the general acid catalyst, exhibit a large positive deviation from the Bronsted line. This fact was not observed in the reaction of non-hydroxyl amines with different aromatic aldehydes by other authors, thus supporting that the spontaneous dehydration steps for these reactions proceed by intramolecular catalysis. The mechanism of intramolecular catalysis might be stepwise. First, a zwitterionic intermediate is formed. It can then evolve in the second step by loss of water, or follow a concerted pathway, with the transference of a proton through a five-membered ring (general intramolecular acid catalysis). In the case of non-hydroxyl amines, data suggested the possibility of a mechanism of intramolecular proton transfer through one or two water molecules, from the nitrogen of the amine to the leaving hydroxide ion.

Hydrolysis of Di- and Trimesylhydroxylamines and their Methylated Derivatives

The mesylhydroxylamines (CH3SO2)2NOH, (CH3SO2)2NOCH3, CH3SO2N(H)OSO2CH3, CH3SO2N(CH3)OSO2CH3 (1-4) and (CH3SO2)2NOSO2CH3 (5) were treated with basic, neutral, and acidic aqueous solutions.The reaction products were identified.Possible decomposition mechanisms were discussed.

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

Kinetics and Mechanism of the Oxidation of N-Methylmorpholine by Alkaline Hexacyanoferrate(III) Ion

The kinetics of hexacyanoferrate(III) ion oxidation of N-methylmorpholine in aqueous alkaline medium at constant ionic strength has been studied at four temperatures.The data show that the reaction follows first order kinetics with respect to each of the hexacyanoferrate(III) ion, N-methylmorpholine and hydroxide ion.The energy of activation and entropy of activation have been calculated to be 13.84 Kcal/mole and -23.81 e.u. respectively.The net rate of oxidation of N-methylmorpholine as measured by the consumption of hexacyanoferrate(III) ion, is given by -d3->/dt = k1k2/k-1**->*3->