N-O DIMETHYLHYDROXYLAMINE HCL IS FREQUENTLY USED AS A PROTECTING AGENT FOR ALDEHYDES.

N-O Dimethylhydroxylamine HCl is frequently used as a protecting agent for aldehydes.

N-O Dimethylhydroxylamine HCl is frequently used as a protecting agent for aldehydes.

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N-O Dimethylhydroxylamine Hydrochloride (N-O Dimethylhydroxylamine HCl)

N,O-Dimethylhydroxylamine HCL

1. Chemical Identity and Nomenclature

  • Chemical Name: N-O Dimethylhydroxylamine Hydrochloride

    • Other Names: N,N-Dimethylhydroxylamine hydrochloride, DMHA·HCl

    •  Molecular Formula: C2H7ClN

  • Molecular Weight: 97.54 g/mol

  • CAS Number: 3283-24-3 (commonly referenced)

2. Molecular Structure

  • The compound consists of a hydroxylamine (–NHOH) moiety where the nitrogen atom is substituted with two methyl groups (–CH3).

  • The hydrochloride salt is formed by protonation of the nitrogen atom and association with chloride ion (Cl⁻).

  • Structural formula:

    (CH3)2N–OH · HCl

  • This gives the compound both nucleophilic and slightly basic characteristics.

3. Physical Properties

Property Description
Appearance White to off-white crystalline solid
Melting Point Typically around 120–130 °C (decomposes)
Solubility Highly soluble in water and alcohols
Stability Stable under normal conditions but sensitive to strong acids and oxidizers

4. Synthesis

  • Preparation Methods:

    • Usually synthesized via methylation of hydroxylamine or hydroxylamine hydrochloride with methylating agents such as dimethyl sulfate, methyl iodide, or via reductive methylation methods.

    • Reaction must be carefully controlled to avoid over-methylation or side reactions.

    • Purification involves crystallization or solvent extraction techniques.

5. Chemical Behavior and Reactivity

  • The molecule exhibits nucleophilicity primarily at the nitrogen and oxygen atoms due to lone pairs, allowing it to react with electrophiles.

  • The N–O bond is a distinctive feature that can participate in redox and condensation reactions.

  • The hydrochloride salt form enhances stability and solubility, facilitating its use in aqueous or polar media.

6. Applications

  • Organic Synthesis Intermediate:
    Used extensively as a reagent or intermediate for introducing the N–O functional group in various synthetic pathways.

  • Oximation Reactions:
    Useful in preparing oximes by reaction with aldehydes or ketones, which are important in pharmaceuticals and agrochemical synthesis.

  • Pharmaceutical Industry:
    Employed in the manufacture of drugs where N-O functionalities are required.

  • Agrochemicals and Fine Chemicals:
    Used as a building block or modifying reagent.

7. Handling and Safety

  • Hazards:
    Can cause irritation to skin, eyes, and respiratory tract.
    May be harmful if swallowed or inhaled.

  • Precautions:
    Handle in a well-ventilated environment or fume hood.
    Use personal protective equipment such as gloves and safety goggles.

  • Storage:
    Store in a cool, dry place, tightly sealed to avoid moisture uptake and decomposition.
    Keep away from strong oxidizing agents and acids.

8. Summary

N-O Dimethylhydroxylamine Hydrochloride is a valuable intermediate in organic chemistry due to its nucleophilic and functional versatility. Its stable hydrochloride salt form makes it easier to handle and incorporate into various chemical synthesis processes, especially those involving N–O bond formation, oximes, and nitrogen-containing compounds.

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