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Names | |
---|---|
Preferred IUPAC name
O-Methylhydroxylamine
[1] | |
Other names
Methoxylamine; (Aminooxy)methane
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.000.600 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 |
Refractive index (nD)
|
1.4164 |
Hazards | |
GHS labelling: [3] | |
![]() ![]() | |
Danger | |
H302, H312, H314, H332 | |
P260, P261, 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) | |
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).
|
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. It decomposes in an exothermic reaction (-56 kJ/mol) to methane and azanone unless stored as a hydrochloride salt. [2]
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]
The other broad method involves methanolysis of hydroxylamine sulfonates:
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]
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.
![]() | |
![]() | |
Names | |
---|---|
Preferred IUPAC name
O-Methylhydroxylamine
[1] | |
Other names
Methoxylamine; (Aminooxy)methane
| |
Identifiers | |
3D model (
JSmol)
|
|
ChEMBL | |
ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.000.600 |
EC Number |
|
PubChem
CID
|
|
UNII | |
CompTox Dashboard (
EPA)
|
|
| |
| |
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 |
Refractive index (nD)
|
1.4164 |
Hazards | |
GHS labelling: [3] | |
![]() ![]() | |
Danger | |
H302, H312, H314, H332 | |
P260, P261, 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) | |
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).
|
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. It decomposes in an exothermic reaction (-56 kJ/mol) to methane and azanone unless stored as a hydrochloride salt. [2]
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]
The other broad method involves methanolysis of hydroxylamine sulfonates:
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]
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.