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

1. Chemical Identity

• Chemical Name: N-O Dimethylhydroxylamine Hydrochloride

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

• Molecular Formula: C₂H₇ClNO

• Molecular Weight: 97.54 g/mol

• CAS Number: 3283-24-3

2. Molecular Structure

The compound consists of a hydroxylamine (–NHOH) group where the nitrogen atom is substituted with two methyl groups (-CH₃). The compound exists as a hydrochloride salt formed by protonation of the nitrogen and association with a chloride ion.

• Structural formula:

  H | CH3–N–O·HCl | CH3

• Description:
  The nitrogen atom carries two methyl groups and is bonded to an oxygen atom (N–O bond). The protonated nitrogen forms the hydrochloride salt with Cl⁻.

3. Physical and Chemical Properties

4. Synthesis

N-O Dimethylhydroxylamine hydrochloride is generally prepared by:

• Methylation of hydroxylamine hydrochloride using methylating agents like dimethyl sulfate or methyl iodide under controlled conditions to selectively attach methyl groups to the nitrogen atom.

• Careful control of reaction conditions is necessary to prevent over-methylation or decomposition.

5. Applications

• Widely used as a key intermediate in organic synthesis, especially in the preparation of compounds containing N–O functional groups.

• Utilized for the synthesis of oximes, which are important intermediates in pharmaceuticals and agrochemicals.

• Used in the manufacture of various fine chemicals where introducing a dimethylhydroxylamine moiety is required.

6. Chemical Reactivity

• Exhibits nucleophilic properties at the nitrogen and oxygen atoms, allowing it to react with electrophiles.

• The N–O bond can undergo transformations useful in synthetic pathways, including condensation and oxidation-reduction reactions.

7. Safety and Handling

• Should be handled with care as it can be an irritant to the skin, eyes, and respiratory system.

• Use personal protective equipment such as gloves, goggles, and work in a well-ventilated area or fume hood.

• Store in a cool, dry place, away from strong oxidizers and acids.

8. Summary

N-O Dimethylhydroxylamine Hydrochloride is a stable, water-soluble crystalline compound widely used in organic synthesis to introduce N–O functionality. Its hydrochloride salt form improves stability and ease of handling, making it a valuable reagent and intermediate in pharmaceuticals, agrochemicals, and fine chemical industries.