methoxy(methyl)amine hydrochloride

• ChemBase ID: 69396
• Molecular Formular: C2H8ClNO
• Molecular Mass: 97.54402
• Monoisotopic Mass: 97.02944156
• SMILES: N(OC)C.Cl
• Canonical SMILES: CONC.Cl
• InChI: InChI=1S/C2H7NO.ClH/c1-3-4-2;/h3H,1-2H3;1H
• InChIKey: USZLCYNVCCDPLQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methoxy(methyl)amine hydrochloride
• IUPAC Traditional name: N,O-dimethylhydroxylamine hydrochloride
• Synonyms: N,O-Dimethylhydroxylamine hydrochloride; O,N-DIMETHYLHYDROXYLAMINE HYDROCHLORIDE; N,O-Dimethylhydroxylamine hydrochloride; N-Methoxymethylamine hydrochloride; O,N-DIMETHYLHYDROXYLAMINE; N,O-二甲基羟胺盐酸盐; N,O-二甲基羟胺 盐酸盐

Database IDs

• CAS Number: 6638-79-5
• EC Number: 229-642-1
• MDL Number: MFCD00012485
• Beilstein Number: 3650353
• PubChem SID: 162035122; 24865421; 24893502
• PubChem CID: 81138

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.33209413
• LogD (pH = 7.4): -0.14191397
• Log P: -0.13885958
• Molar Refractivity: 26.6585 cm^3
• Polarizability: 6.637073 Å^3
• Polar Surface Area: 21.26 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 111-115 °C; 112-115 °C; 112-115°C; 112-116°C

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant/Hygroscopic/Store under Argon; Hygroscopic; IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; 36/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥98.0% (AT); 95+%; 97%; 98%
• Grade: purum
• Linear Formula: CH3ONHCH3 · HCl

DETAILS

MP Biomedicals - 02157824

Hydrochloride
Crystalline

MP Biomedicals - 05212867

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D163708

Application
Reagent for the preparation of Weinreb amides recently used in the synthesis of 2-acyloxazoles from 2-oxazolemagnesium chloride.1
Packaging
1 kg in poly bottle
5 g in glass bottle
25, 100 g in poly bottle
5, 20 kg in fiber drum

Sigma Aldrich - 40706

Other Notes
Amides of this hydroxylamine can be selectively converted to ketones by addition of nucleophiles and to aldehydes by reduction1,2

REFERENCES

• The N-methoxy-N-methylamides (Weinreb amides) of carboxylic acids, N-protected amino acids and peptides are readily prepared from the acid chloride or mixed anhydride, or from the acid in the presence of 2-Chloro-1-methylpyridinium iodide, A12820: Synth. Commun., 25, 1277 (1995); or BOP Reagent (1H-Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, A16140): J. Org. Chem., 61, 4999 (1996). The products undergo a number of useful transformations, e.g.:
• Reaction with Grignard or organolithium reagents gives ketones: Tetrahedron Lett., 22, 3815 (1981). Reduction with Lithium aluminum hydride, A18116, gives the aldehyde: Synthesis, 676 (1983). For subsequent conversion of Boc-amino acid derived aldehydes and ketones to pyrrole derivatives, see: J. Org. Chem., 61, 4999 (1996). Coupling with alkyl acetoacetates gives ? δ -diketo esters: Tetrahedron Lett., 29, 6467 (1988). For conversion to ɑ -diketones or ɑ -keto esters, see: J. Org. Chem., 54, 3913 (1989).