hydroxy(methyl)azanium chloride

• ChemBase ID: 301903
• Molecular Formular: CH5ClNO
• Molecular Mass: 82.5095
• Monoisotopic Mass: 82.00596647
• SMILES: C[NH+]O.[Cl-]
• Canonical SMILES: C[NH+]O.[Cl-]
• InChI: InChI=1S/CH5NO.ClH/c1-2-3;/h2-3H,1H3;1H
• InChIKey: RGZRSLKIOCHTSI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: hydroxy(methyl)azanium chloride
• IUPAC Traditional name: hydroxy(methyl)azanium chloride
• Synonyms: N-Methylhydroxylamine hydrochloride; N-甲基羟基胺盐酸盐

Database IDs

• CAS Number: 4229-44-1
• EC Number: 224-181-2
• MDL Number: MFCD00012597
• Beilstein Number: 3541409

CALCULATED PROPERTIES

• Acid pKa: 16.820272
• H Acceptors: 1
• H Donor: 2
• LogD (pH = 5.5): -0.61248004
• LogD (pH = 7.4): -0.51816565
• Log P: -0.5168203
• Molar Refractivity: 22.9762 cm^3
• Polarizability: 4.6925015 Å^3
• Polar Surface Area: 36.84 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 80-86°C

Safety Information

• Storage Warning: Hygroscopic
• European Hazard Symbols: Irritant (Xi)
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A

Product Information

• Purity: 98%

REFERENCES

• 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):
  
• 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).