Introduction
N,N-Diethylacetoacetamide (DEAA, CAS 2235-46-3), also written N,N-diethyl-3-oxobutanamide, is a yellow liquid beta-ketoamide. It combines a reactive methylene and a ketone with a tertiary amide, which makes it a versatile building block for dyes, pigments, and pharmaceutical and agrochemical synthesis. Unlike acetoacetanilide, the amide nitrogen carries two ethyl groups, so the molecule is non-aromatic, liquid, and readily soluble in many organic solvents.
Chemical and Physical Properties
N,N-Diethylacetoacetamide is the diethylamide of acetoacetic acid. It behaves as a beta-dicarbonyl compound: the methylene between the ketone and the amide is acidic and forms an enolate with base, and the 1,3-dicarbonyl pattern allows it to form heterocycles and metal chelates.
| Property | Value |
|---|---|
| CAS number | 2235-46-3 |
| Molecular formula | C8H15NO2 |
| Molecular weight | 157.21 g/mol |
| Appearance | Yellow liquid |
| SMILES | CCN(CC)C(=O)CC(C)=O |
Production
N,N-Diethylacetoacetamide is produced by reacting diethylamine with a beta-keto acylating agent. The most direct industrial route uses diketene, which adds across the N-H bond of diethylamine in a single exothermic step. Alternatively, diethylamine can be reacted with ethyl or methyl acetoacetate in a transamidation, where the alcohol is removed to drive the reaction to completion. In both routes the crude product is purified so that the color value, moisture, and iron content meet the specification.
Applications
Dyes and Pigments
DEAA is used as an intermediate for azo dyes and organic pigments. Its beta-ketoamide group can be coupled or condensed to build the chromophores used in disperse and solvent dyes, and its liquid, non-aromatic nature gives formulators flexibility in solvent-based processes.
Pharmaceutical and Agrochemical Synthesis
The beta-ketoamide pattern is a useful handle in medicinal and agrochemical chemistry, where the reactive methylene and the ketone provide sites for alkylation, condensation, and ring formation. DEAA is used to introduce an acetoacetyl group or to build intermediates that carry the 1,3-dicarbonyl functionality.
Heterocycle and Chelate Building Block
Condensation with hydrazines gives pyrazolones and related heterocycles, and the 1,3-dicarbonyl arrangement lets DEAA act as a ligand for metal ions. These properties make it useful where a soluble beta-diketone equivalent is needed.
Quality and Specifications
Typical commercial specifications for N,N-diethylacetoacetamide are shown below. Assay, moisture, pH, color value, and iron content are the parameters most commonly specified.
| Parameter | Specification |
|---|---|
| Appearance | Yellow liquid |
| Assay | 98% min |
| Moisture | 0.3% max |
| pH | 5 – 7 |
| Color value | 7.0 max |
| Iron | 3 ppm max |
Low moisture and low iron are important because both can affect the color and the performance of the downstream dye or pigment, while pH indicates the amount of residual acid or amine in the product.
Handling and Storage
Store N,N-diethylacetoacetamide in a cool, dry, well-ventilated place with the container tightly closed, away from heat, moisture, and strong oxidants. Use appropriate personal protective equipment and follow the safety data sheet when handling the material.
Frequently Asked Questions about N,N-Diethylacetoacetamide
What is N,N-diethylacetoacetamide used for?
It is used mainly as an intermediate for azo dyes and organic pigments, and as a building block in pharmaceutical and agrochemical synthesis.
How is N,N-diethylacetoacetamide produced?
Industrially it is made by reacting diethylamine with diketene, or by transamidation of ethyl or methyl acetoacetate with diethylamine, followed by purification.
What is the difference between N,N-diethylacetoacetamide and acetoacetanilide?
Both are acetoacetamides, but DEAA carries two ethyl groups on the amide nitrogen and is a liquid, while acetoacetanilide carries an aromatic ring and is a solid used widely as a pigment intermediate.
How should N,N-diethylacetoacetamide be stored?
Keep it cool, dry, and tightly sealed, away from heat, moisture, and strong oxidants.
Where can I buy N,N-diethylacetoacetamide?
PolyBlueChem supplies N,N-diethylacetoacetamide (CAS 2235-46-3) with COA and MSDS. Contact our team for specifications, packaging, and a quotation.
References
- PubChem Compound Summary for N,N-diethylacetoacetamide (CAS 2235-46-3).
- Technical literature on beta-ketoamides and acetoacetamide intermediates.
- Supplier specifications for industrial-grade N,N-diethylacetoacetamide.
Disclaimer: This article is provided for general informational purposes only and does not constitute technical, regulatory, or safety advice. Always refer to the current safety data sheet and applicable regulations before handling this material.
PolyBlueChem, as the chemical supplier of all categories, is the supplier of N,N-diethylacetoacetamide (CAS 2235-46-3) as well. Contact our team for specifications, packaging and a quotation.