Methoxyamine

Chemical compound From Wikipedia, the free encyclopedia

Methoxyamine is the organic compound with the formula CH3ONH2. Also called O-methylhydroxylamine, it is a colourless volatile liquid that is soluble in polar organic solvent and in water. It is a derivative of hydroxylamine with the hydroxyl hydrogen replaced by a methyl group. Alternatively, it can be viewed as a derivative of methanol with the hydroxyl hydrogen replaced by an amino group. It is an isomer of N-methylhydroxylamine and aminomethanol.

Quick facts Names, Identifiers ...
Methoxyamine
Methoxyamine
Methoxyamine
Methoxyamine
Methoxyamine
Names
Preferred IUPAC name
O-Methylhydroxylamine[1]
Other names
Methoxylamine; (Aminooxy)methane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.600 Edit this at Wikidata
EC Number
  • 200-660-1
UNII
  • InChI=1S/CH5NO/c1-3-2/h2H2,1H3
    Key: GMPKIPWJBDOURN-UHFFFAOYSA-N
  • CON
Properties
CH5NO
Molar mass 47.057 g·mol−1
Appearance Colorless liquid
Odor Ammoniacal
Melting point −86.4[2] °C (−123.5 °F; 186.8 K)
Boiling point 48.1[2] °C (118.6 °F; 321.2 K)
Miscible
Vapor pressure 297.5 mmHg at 25°C
1.4164
Hazards
GHS labelling:[3]
GHS05: CorrosiveGHS07: Exclamation mark
Danger
H302, H312, H314, H332
P260, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P362+P364, P363, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Safety data sheet (SDS) Santa Cruz (HCl)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

Methoxyamine is prepared via O-alkylation of hydroxylamine derivatives. For example, it is obtained by O-methylation of acetone oxime followed by hydrolysis of the O-methylated oxime:[4]

(CH3)2CNOCH3 + H2O → (CH3)2CO + H2NOCH3

The other broad method involves methanolysis of hydroxylamine sulfonates:

H2NOSO3− + CH3OH → H2NOCH3 + HSO4−

Commercial products are usually the hydrochloride salt.[2]

Reactions

Analogous to the behavior of hydroxylamine, methoxyamine condenses with ketones and aldehydes to give imines.

Methoxyamine is used as a synthon for NH2+. It undergoes deprotonation by methyl lithium to give CH3ONHLi. This N-lithio derivative is attacked by organolithium compounds to give, after hydrolysis, amines:[5]

H2NOCH3 + CH3Li → LiHNOCH3 + CH4
LiHNOCH3 + RLi → RNHLi + LiOCH3
RNHLi + H2O → RNH2 + LiOH

Uses

Methoxyamine has potential medicinal uses. It covalently binds to apurinic/apyrimidinic (AP) DNA damage sites and inhibits base excision repair (BER), which may result in an increase in DNA strand breaks and apoptosis.This agent may potentiate the anti-tumor activity of alkylating agents.[6]

Examples of drugs incorporating the methoxyamine unit are brasofensine and gemifloxacin.

References

External links

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