N-Methylhydroxylamine

Base Information

• Chemical Name: N-Methylhydroxylamine
• CAS No.: 593-77-1
• Molecular Formula: CH5 N O
• Molecular Weight: 47.0568
• UNII: V8920J3L6R
• DSSTox Substance ID: DTXSID10208035
• Nikkaji Number: J2.699I
• Wikipedia: N-Methylhydroxylamine
• Wikidata: Q18378717
• ChEMBL ID: CHEMBL144761
• Mol file: 593-77-1.mol

Synonyms:N-methylhydroxylamine;N-methylhydroxylamine hydrochloride

Chemical Property of N-Methylhydroxylamine

Chemical Property:

• Melting Point: 87.5°C
• Refractive Index: 1.4164 (estimate)
• Boiling Point: 55.67°C (rough estimate)
• PKA: 14.00±0.30(Predicted)
• PSA: 32.26000
• Density: 1.0003
• LogP: -0.01410
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 47.037113783
• Heavy Atom Count: 3
• Complexity: 4.8

Purity/Quality:

98%Min ^*data from raw suppliers

N-METHYLHYDROXYLAMINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CNO
• General Description: N-Methylhydroxylamine is a key reagent in the synthesis of N-methyl-3-acylpyrroles, where it reacts with dimethylacetylene dicarboxylate (DMAD) to form an enamine intermediate, which subsequently reacts with acylchlorides to yield the target pyrrole derivatives. Its role in this multicomponent reaction highlights its utility as a versatile building block in organic synthesis, particularly for constructing heterocyclic compounds under mild conditions.

Technology Process of N-Methylhydroxylamine

There total 36 articles about N-Methylhydroxylamine 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:

chloropicrin (76-06-2) → dichloroformoxime (1794-86-1) + N-Methylhydroxylamine (593-77-1) + trichloronitrosomethane (3711-49-7) + methylamine (74-89-5)

Guidance literature:

Bei der elektrolytischen Reduktion entstehen je nach den Bedingungen wechselnde Menge;

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + N-methyl-α-phenylnitrone (3376-23-6) → N-Methylhydroxylamine (593-77-1) + benzaldehyde (100-52-7)

Guidance literature:

Reference yield:

N-methyl-α-phenylnitrone (3376-23-6) + furan-2,3,5(4H)-trione pyridine (1:1) → N-Methylhydroxylamine (593-77-1) + benzaldehyde (100-52-7)

Guidance literature:

upstream raw materials:

acetaldehyde-(N-methyl oxime )

diethyl ether

2-chloro-2-nitrosopropane

dimethyl zinc(II)

Downstream raw materials:

(1Z,2E)-N-methyl-3-phenylprop-2-en-1-imine oxide

3-hydroxy-3-methyl-1-p-nitrophenyl-1-triazene

3-hydroxy-3-methyl-1-phenyl-1-triazene

ethyl hydroxyl(methyl)carbamate

Refernces

A mild and facile one-pot synthesis of N-methyl-3-acyl- pyrroles

10.3390/molecules15052972

The research presents a mild and facile one-pot synthesis of N-Methyl-3-acylpyrroles through a multicomponent reaction involving dimethylacetylene dicarboxylate (DMAD), N-methylhydroxylamine, and various acylchlorides in the presence of KHCO3 as a catalyst. The study compares conventional and microwave protocols, finding that conventional heating at 40 oC in anhydrous dichloromethane yields good to excellent product yields. The reaction is clean and efficient, producing N-methyl-3-acylpyrroles with different substituents in good yields. The synthesized compounds were characterized using elemental analysis, IR, 1H-NMR, and 13C-NMR spectroscopy. The chemicals DMAD, N-methylhydroxylamine, acylchlorides, and KHCO3 played crucial roles in the synthesis, with DMAD and N-methylhydroxylamine forming an enamine intermediate that reacts with acylchlorides to produce the desired 3-acylpyrroles.