N-methylhydroxylamine hydrochloride

• ChemBase ID: 76242
• Molecular Formular: CH6ClNO
• Molecular Mass: 83.51744
• Monoisotopic Mass: 83.0137915
• SMILES: N(C)O.Cl
• Canonical SMILES: CNO.Cl
• InChI: InChI=1S/CH5NO.ClH/c1-2-3;/h2-3H,1H3;1H
• InChIKey: RGZRSLKIOCHTSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-methylhydroxylamine hydrochloride
• IUPAC Traditional name: N-methylhydroxylamine hydrochloride
• Synonyms: N-Methylhydroxylamine hydrochloride; N-Methylhydroxylamine hydrochloride; N-METHYLHYDROXYLAMINE HCl; N-METHYLHYDROXYLAMINE; Methylhydroxylamine Hydrochloride; Methylhydroxylammonium Chloride; N-Hydroxy-N-methanamine Hydrochloride; N-Hydroxy-N-methylammonium Chloride; N-Hydroxymethanamine Hydrochloride; N-Methylhydroxylamine Hydrochloride; N-Methylhydroxylammonium Chloride; N-甲基羟胺 盐酸盐

Database IDs

• CAS Number: 4229-44-1
• EC Number: 224-181-2
• MDL Number: MFCD00012597
• Beilstein Number: 3541409
• PubChem SID: 24896973; 162041149; 24885281
• PubChem CID: 77906

CALCULATED PROPERTIES

• Acid pKa: 16.820272
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.61248004
• LogD (pH = 7.4): -0.51816565
• Log P: -0.5168203
• Molar Refractivity: 22.1762 cm^3
• Polarizability: 4.7371387 Å^3
• Polar Surface Area: 32.26 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, very faintly yellow
• Melting Point: 82-84 °C; 83-84°C; 86 - 88°C; 86-88 °C(lit.)
• Hydrophobicity(logP): -1.104

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• Storage Warning: Irritant/Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (AT); 95%; 98%
• Grade: purum
• Linear Formula: CH3NHOH · HCl

DETAILS

MP Biomedicals - 05216923

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02155575

Hydrochloride Crystalline

Sigma Aldrich - M50400

Packaging
5, 10 g in glass bottle
Application
Used to construct hydroxamates, important functional groups for the complexation of iron.1

Sigma Aldrich - 67545

Other Notes
Formation of a nitrone with formaldehyde and [2+3]-cycloaddition with olefins1

Toronto Research Chemicals - M312780

N-Methylhydroxylamine is used as an inorganic catalyst used in the transamidation of primary amides with amines.

REFERENCES

• Allen, C.L. et al.: Ange. Chem. Int. Ed., 51, 1383 (2012)