CAS 6638-79-5|N,O-dimethylhydroxylamine hydrochloride|N,O-Dimethylhydroxylamine hydrochloride|methoxy(methyl)amine hydrochloride|O,N-DIMETHYLHYDROXYLAMINE HYDROCHLORIDE|N-Methoxymethylamine hydrochl...

General Information

Structure

Molecular Formula

C₂H₈ClNO

Molecular Mass

97.54402

Exact Mass

97.02944156

Charge

InChI

InChI=1S/C2H7NO.ClH/c1-3-4-2;/h3H,1-2H3;1H

InChIKey

USZLCYNVCCDPLQ-UHFFFAOYSA-N

Canonic Smiles

CONC.Cl

Isomeric Smiles

N(OC)C.Cl

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-0.33209413

LogD (pH = 7.4)

-0.14191397

Log P

-0.13885958

Molar Refractivity

26.6585

Polarizability

6.637073

Polar Surface Area

21.26

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

N,O-Dimethylhydroxylamine hydrochlorideO,N-DIMETHYLHYDROXYLAMINE HYDROCHLORIDEN-Methoxymethylamine hydrochlorideO,N-DIMETHYLHYDROXYLAMINEN,O-Dimethylhydroxylamine hydrochlorideN,O-二甲基羟胺盐酸盐N,O-二甲基羟胺盐酸盐

IUPAC name

methoxy(methyl)amine hydrochloride

IUPAC Traditional name

N,O-dimethylhydroxylamine hydrochloride

Names and Identifiers

Registration numbers

MDL Number

Beilstein Number

EC Number

CAS Number

PubChem SID

2486542116203512224893502

PubChem CID

81138

Registration numbers

Properties

Physical Property

112-116°C

112-115 °C

111-115 °C

112-115°C

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

MP Biomedicals

02157824

Hydrochloride
Crystalline

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

40706

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

Molecule Details

References

PubChem Literature

From Data Sources

• 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).

• 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.:

References

Bioactivity

PubChem BioAssay

Bioactivity