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Not to be confused with N-Methylhydroxylamine.
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).

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, an alkoxyamine. 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.

Synthesis

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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

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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

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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

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  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. ^ a b c Kokko, Bruce J.; Edmondson, Scott D. (14 March 2008). "O -Methylhydroxylamine". Encyclopedia of Reagents for Organic Synthesis. pp. 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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📚 Artikel Terkait di Wikipedia

N-Methylhydroxylamine

replacing one of the hydrogens of the amino group. It is an isomer of methoxyamine and aminomethanol. It decomposes in an exothermic reaction (-63 kJ/mol)

N,O-Dimethylhydroxylamine

is then liberated by acid hydrolysis followed by neutralization. Methoxyamine N-methylhydroxylamine N,O-Dimethylhydroxylamine hydrochloride at Sigma-Aldrich

Alkoxyamines

R2 are an organyl or hydrogen. They are O-substituted hydroxylamines. Methoxyamine Ethoxyamine O-Octadecylhydroxylamine IUPAC, Compendium of Chemical Terminology

Relugolix

reacted with CDI, and the resulting imidazolide was further treated with methoxyamine [67-62-9] to give the urea [737789-92-3] (8). A cyclization reaction

Arecoline

Although the first step is not very high yielding, if one substitutes methoxyamine for hydroxylamine procedure could be used for a one-pot synthesis of

CH5NO

(molar mass: 47.057 g/mol) may refer to: Aminomethanol, or methanolamine Methoxyamine, or O-methylhydroxylamine N-Methylhydroxylamine, or methylhydroxylamine

Pydiflumetofen

reduction reaction converts it to a ketone which forms an ketoxime with methoxyamine. This, in turn, is reduced with sodium cyanoborohydride to give the amine

Anthony Cashmore

Brown at Cambridge University, Cashmore demonstrated that the reagent methoxyamine reacted with a limited number of cytosine residues in tRNA. Later, Cashmore