| Identification | More | [Name]
N-Methylhydroxylamine hydrochloride | [CAS]
4229-44-1 | [Synonyms]
HYDROXYLAMINOMETHANE HYDROCHLORIDE
N-METHYLHYDROXYLAMINE HCL
N-METHYLHYDROXYLAMINE HYDROCHLORIDE
N-METHYLHYDROXYLAMMONIUM CHLORIDE
Methanamine,N-hydroxy-,hydrochloride
n-hydroxy-methanaminhydrochloride
N-Methylhydroxyaminehydrochloride
N-Methylhydroxylaminehydrochloride,98%
N-METHYLHYDROXYAMINEHCL
Methyl hydroxylamine .HCL
Methylhydroxylammonium chloride
N-Hydroxymethanamine hydrochloride | [EINECS(EC#)]
224-181-2 | [Molecular Formula]
CH6ClNO | [MDL Number]
MFCD00012597 | [Molecular Weight]
83.52 | [MOL File]
4229-44-1.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
1759 | [WGK Germany ]
3
| [F ]
3-10 | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
III | [HS Code ]
29280090 |
| Hazard Information | Back Directory | [Chemical Properties]
The substance appears as white to almost white crystals or crystalline powder. It exhibits solubility in water. | [Uses]
N-Methylhydroxylamine is used as an inorganic catalyst used in the transamidation of primary amides with amines. | [Preparation]
N-methylhydroxylamine hydrochloride (N-MHA) was synthesized by a high pressure catalytic hydrogenation method using noble metal Pd/C and Pt-Rh/C as the catalyst. During the synthesis process, the catalyst was easily poisoned and the products would be deeply reduced to methylamine. Therefore, the purity of N-MHA is low and the cost is high. An industrial electrolytic cell was designed for the electrochemical synthesis of N-methylhydroxylamine hydrochloride (N-MHA). Copper was used as the cathode, graphite as the anode, and a cation membrane as the separator. The results show that N-MHA with a high purity of 99% can be electrosynthesized directly from nitromethane in HCl solution. | [Reactions]
N-methylhydroxylamine hydrochloride[4229-44-1] was widely used in the 1,3-dipolar cycloaddition and N-methylation reaction. For example, it has been considered an extremely important intermediate in the synthesis of biological active azetidinone and isoxazole compounds such as piperylone, isopyrine, and muscimole.
| [References]
A. Gibson and S. Mirzazadeh. N-methylhydroxylamine inhibits and M&B 22948 potentiates relaxations of the mouse anococcygeus to non-adrenergic, non-cholinergic field stimulation and to nitrovasodilator drugs.British Journal of Pharmacology.1989, 96 637-644. DOI:10.1111/j.1476-5381.1989.tb11863.x
J. R. Ochoa Gomez. Electrosynthesis of N-methylhydroxylamine.Journal of Applied Electrochemistry.1991, 21 331-334. DOI:10.1007/BF01020218
Reacts with aldehydes and ketones to give nitrones, which undergo 1,3-dipolar addition reactions with alkenes. Cycloaddition to trimethylvinylsilane has been used in a 2-carbon extension of aldehydes to ɑ?-unsaturated aldehydes: J. Org. Chem., 49, 3421 (1984). DOI:10.1021/jo00192a047
Intramolecular cycloaddition has been used as a route to bicyclic systems, e.g. from citronellal: Org. Synth. Coll., 6, 670 (1988).
Reviews: 1,3-Dipolar cycloadditions of nitrones: Synthesis, 205 (1975). The [3+2] nitrone-olefin cycloaddition reaction: Org. React., 36, 1 (1988). Synthetic applications of nitrones: Org. Prep. Proced. Int., 17, 25 (1985).
For conversion to, and reactions of, the N,O-bis(TMS) derivative, see: J. Chem. Soc., Perkin 1, 1823 (1989). |
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