Diacetonamine Hydrogenoxalate: Properties & Lab Uses

Diacetonamine hydrogenoxalate is a stable crystalline salt form of diacetonamine (4-amino-4-methylpentan-2-one), widely used as a synthetic intermediate and analytical reagent in organic chemistry research.

Product Name

Diacetonamine hydrogenoxalate

SKU

D466889

Chemical Class

Secondary amine oxalate salt

Parent Compound

Diacetonamine (4-amino-4-methylpentan-2-one)

Physical Form

Crystalline solid

Primary Use

Organic synthesis intermediate and reagent

Chemical Identity and Structure

Diacetonamine hydrogenoxalate is the hydrogen oxalate (acid oxalate) salt of diacetonamine, the common name for 4-amino-4-methylpentan-2-one. The parent amine belongs to the class of secondary aliphatic amines and features both a ketone and an amine functional group within the same six-carbon framework, making it a bifunctional molecule of interest in synthetic chemistry.

The hydrogenoxalate counter-ion (HC₂O₄⁻) confers improved crystallinity, storage stability, and ease of handling compared with the free base, which is a hygroscopic liquid. Forming a well-defined salt is a common strategy to stabilize volatile or moisture-sensitive amines for laboratory storage and precise weighing.

Aladdin Scientific supplies this compound under SKU D466889. Researchers requiring the exact specification should consult the product datasheet; the Sigma-Aldrich catalog reference 633437 has been cited for cross-referencing purposes.

Physicochemical Properties and Stability

As a crystalline salt, diacetonamine hydrogenoxalate offers several practical advantages over the free amine. The solid form has a defined melting point that serves as a purity indicator; researchers should verify the exact value against the current certificate of analysis (CoA) for each lot. The salt is expected to be soluble in water and polar protic solvents, consistent with small aliphatic amine oxalate salts in general.

Storage recommendations for amine oxalate salts typically include cool, dry, well-ventilated conditions, away from strong oxidizers and strong acids or bases. The oxalate component can slowly decompose under prolonged exposure to heat or strong acid, releasing the free diacetonamine and oxalic acid. Personnel should consult the Safety Data Sheet (SDS) for specific handling, personal protective equipment requirements, and first-aid measures before use.

The bifunctional nature of diacetonamine — possessing both a ketone carbonyl and a basic nitrogen — means that the reagent should be kept away from conditions that promote self-condensation or Schiff-base formation under acidic or basic catalysis.

Research and Synthetic Applications

Diacetonamine and its salts serve as versatile building blocks in organic synthesis. The amine nitrogen can participate in reductive amination reactions, amide bond formation, and condensation reactions, while the ketone moiety is available for nucleophilic additions, condensations, and derivatization. This dual reactivity makes the compound a useful scaffold for constructing more complex nitrogen-containing molecules.

In agrochemical and pharmaceutical intermediate synthesis, secondary aliphatic amines bearing adjacent carbonyl groups are frequently employed to introduce structural diversity. Diacetonamine-derived structures have appeared in the literature in the context of synthesis of hindered nitroxide radicals (such as 4-oxo-TEMPO precursors), stabilizers for polymer formulations, and corrosion inhibitor studies, though researchers should verify specific application claims against primary literature.

The hydrogenoxalate salt form is particularly convenient when stoichiometric accuracy is required, as the defined molecular weight of the salt allows precise molar-ratio calculations compared with weighing the neat liquid free base.

Ordering, Specifications, and Quality

Aladdin Scientific offers diacetonamine hydrogenoxalate under SKU D466889. Researchers should review the current product page for available pack sizes, purity grades, and lot-specific certificates of analysis before placing an order. Purity specifications and analytical data (such as NMR, HPLC, or titration results) are documented on the CoA accompanying each shipment.

For procurement teams, cross-referencing with Sigma-Aldrich catalog number 633437 can assist in equivalent-product verification; however, lot-specific purity and specification data from Aladdin Scientific's own quality control testing should be used as the primary reference for internal qualification purposes.

Orders can be placed through the Aladdin Scientific website or by contacting customer service. For bulk quantities, custom purity grades, or special packaging requirements, laboratory managers are encouraged to contact the sales team directly to discuss available options.

Frequently asked questions

What is diacetonamine hydrogenoxalate and why is the salt form preferred?

Diacetonamine hydrogenoxalate is the acid oxalate salt of diacetonamine (4-amino-4-methylpentan-2-one). The salt form is preferred over the free base because it is a crystalline solid with better storage stability, easier handling, and more precise weighability for stoichiometric applications, whereas the free amine is a hygroscopic liquid.

What are the main applications of diacetonamine hydrogenoxalate in research?

The compound serves as a bifunctional building block in organic synthesis, with the amine group enabling reductive amination, amide formation, and condensation reactions, while the ketone group allows nucleophilic additions and derivatization. It has been referenced in the synthesis of hindered nitroxide radical precursors and as an intermediate in agrochemical and pharmaceutical research, though users should verify specific applications in primary literature.

How should diacetonamine hydrogenoxalate be stored to maintain stability?

The compound should be stored in a cool, dry, well-ventilated area in a tightly sealed container, away from strong oxidizers, strong acids, and strong bases. Prolonged exposure to heat or moisture should be avoided. Always consult the current Safety Data Sheet (SDS) and certificate of analysis for lot-specific storage conditions before use.

How does Aladdin Scientific's D466889 relate to Sigma-Aldrich catalog number 633437?

The source material provided for Aladdin Scientific's D466889 references Sigma catalog number 633437 for cross-identification purposes. Researchers using both suppliers can use this cross-reference to confirm chemical identity; however, purity, lot-specific specifications, and quality data will differ between suppliers and should each be confirmed from the respective certificate of analysis.

References

1. Sigma-Aldrich product reference 633437 cited in Aladdin Scientific product record for D466889. Specific analytical data should be obtained from the current certificate of analysis.

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.