O-methylhydroxylamine hydrochloride

• ChemBase ID: 69545
• Molecular Formular: CH6ClNO
• Molecular Mass: 83.51744
• Monoisotopic Mass: 83.0137915
• SMILES: NOC.Cl
• Canonical SMILES: CON.Cl
• InChI: InChI=1S/CH5NO.ClH/c1-3-2;/h2H2,1H3;1H
• InChIKey: XNXVOSBNFZWHBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: O-methylhydroxylamine hydrochloride
• IUPAC Traditional name: O-methylhydroxylamine hydrochloride
• Synonyms: METHOXYAMINE HYDROCHLORIDE; Methoxyamine hydrochloride; Methoxylamine hydrochloride; O-Methylhydroxylamine hydrochloride; Methoxylamine hydrochloride; O-Methylhydroxylamine hydrochloride 98%; Methoxylammonium Chloride; O-METHYLHYDROXYLAMINE HYDROCHLORIDE; METHOXYAMINE; Methoxylamine hydrochloride solution; (Aminooxy)methane Hydrochloride; Hydroxylamine Methyl Ether Hydrochloride; Methoxyammonium Chloride; N-Methoxylamine Hydrochloride; O-Methoxyamine Hydrochloride; Methoxylamine Hydrochloride; O-甲胲 盐酸盐; 甲氧基胺 盐酸盐; 甲氧胺 盐酸盐; 甲氧胺盐酸盐; 甲氧基胺 盐酸盐 溶液

Database IDs

• CAS Number: 593-56-6
• EC Number: 209-798-7
• MDL Number: MFCD00012951
• Beilstein Number: 3589723
• Merck Index: 145989
• PubChem SID: 24853598; 162035271; 24885282; 24853502
• PubChem CID: 521874

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.39036477
• LogD (pH = 7.4): -0.36289734
• Log P: -0.36253566
• Molar Refractivity: 12.331 cm^3
• Polarizability: 4.8056803 Å^3
• Polar Surface Area: 35.25 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 145-151°C; 147-149°C; 151-154 °C; 151-154 °C(lit.); 151-155°C; ca 148°C dec.
• Density: 1.1 g/mL at 25 °C
• Refractive Index: n20/D 1.4021

Safety Information

• Storage Condition: Refrigerator; Room Temperature (15-30°C), Desiccate
• Storage Warning: Corrosive/Hygroscopic; Hygroscopic; IRRITANT
• RTECS: NC3980000
• European Hazard Symbols: Corrosive (C); Nature polluting (N); X
• UN Number: 1759; 3261; 3265; UN3261
• German water hazard class: 3
• Hazard Class: 8
• Packing Group: 2; II; III
• Australian Hazchem: 2X
• Risk Statements: 22-34-43-50; 34; 34-50; 35-37-50; R:34
• Safety Statements: 26-36/37/39-45; 26-36/37/39-45-61; S:26-27/28-36/37/39-46-64
• EU Classification: C10
• EU Hazard Identification Number: 8B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false; 是
• GHS Pictograms: GHS05; GHS06; GHS07; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H317-H314-H318-H400; H314-H335-H400; H314-H400
• GHS Precautionary statements: P260-P301+P310-P303+P361+P353-P305+P351+P338-P405-P501A; P261-P273-P280-P305 + P351 + P338-P310; P273-P280-P305 + P351 + P338-P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges; Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 3261 8/PG 2; UN 3265 8/PG 2

Product Information

• Purity: ≥98.0% (AT); 95+%; 98%; 98+%
• Concentration: 25-30 wt. % in H2O
• Grade: purum
• Salt Data: HCl
• Impurities: <5% NH4Cl <5%, CH3ONHCH3·HCl <3%
• Linear Formula: CH3ONH2 · HCl

DETAILS

MP Biomedicals - 02155405

Hydrochloride

MP Biomedicals - 05208450

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 225517

Packaging
25, 100 g in glass bottle

Sigma Aldrich - 226904

Application
Reagent for the preparation of O-methyl oximes.1,2 Used to make O-methyl oximes from aldehydes3 or ketones.4
Packaging
1, 5 g in glass bottle
25 g in poly bottle
100 g in glass bottle

Sigma Aldrich - 67546

Other Notes
Reagent for the protection of the keto group in 1,4-diene-3-one systems1; Reagent for the derivatization of keto-groups of steroids for the detection by GLC2; Reagent for the rapid determination of neutral sugars and amino sugars in glycoproteins by GC3; Reagent used in the stereoselective reduction of ketones4

Toronto Research Chemicals - M262720

Methoxylamine is a methoxime derivative used as internal standard for Prostaglandin assays by gas chromatography-mass spectrometry.

REFERENCES

• Herold, D.A. et al.: Prostaglandins, 33, 599 (1987)
• In the presence of KO-t-Bu and a copper catalyst in DMF, aminates nitroarenes at the ortho (predominantly) and para positions: J. Org. Chem., 61, 442 (1996).
• Reacts with aldehydes and ketones to give O-methyloximes: J. Org. Chem., 27, 914 (1962); 28, 1523 (1963); Anal. Biochem., 22, 284 (1968). Open-chain aldoses have been prepared by ozonolysis of the methoximes of fully-acylated sugars: J. Org. Chem., 54, 4957 (1989).
• As with oximes, the lithiation of methoximes results in abstraction of a proton syn to the oxygen function (coordination stabilization): J. Org. Chem., 41, 439 (1976). For a review of the alkylation of carbonyl compounds via their nitrogen-containing derivatives, see: Synthesis, 517 (1983).