Methoxyamine

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Methoxyamine
Methoxyamine.svg
Methoxyamine-3D.jpg
Names
Preferred IUPAC name
O-Methylhydroxylamine [1]
Other names
Methoxylamine; (Aminooxy)methane
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.600 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-660-1
PubChem CID
UNII
  • InChI=1S/CH5NO/c1-3-2/h2H2,1H3
    Key: GMPKIPWJBDOURN-UHFFFAOYSA-N
  • CON
Properties
CH5NO
Molar mass 47.057 g·mol−1
AppearanceColorless 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]
GHS-pictogram-acid.svg GHS-pictogram-exclam.svg
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)
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).

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]

Contents

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−

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] Methoxyamine

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

Related Research Articles

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References

  1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 994. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. 1 2 3 Kokko, Bruce J.; Edmondson, Scott D. (14 March 2008). "O -Methylhydroxylamine". Encyclopedia of Reagents for Organic Synthesis: rm192m.pub2. doi:10.1002/047084289X.rm192m.pub2. ISBN   978-0471936237.
  3. ↑ "O-Methylhydroxylamine". pubchem.ncbi.nlm.nih.gov.
  4. ↑ Review: Houben-Weyl, Methoden der organische Chemie, vol 10.1, p 1186. Patent: Klein, Ulrich; Buschmann, Ernst; Keil, Michael; Goetz, Norbert; Hartmann, Horst "Process for preparing O-substituted hydroxylammonium salts." Ger. Offen. to BASF, (1994), DE 4233333 A1 19940407.
  5. ↑ Kokko, Bruce J.; Edmondson, Scott D. (2008). "O-Methylhydroxylamine". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rm192m.pub2. ISBN   978-0471936237.
  6. ↑ NCI
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