Product Introduction: N,N-Dimethylacetoacetamide (CAS 2044-64-6)

N,N-Dimethylacetoacetamide is a chemical compound belonging to the class of amides. It is widely recognized and utilized as a versatile organic intermediate or building block in various chemical syntheses, particularly for the preparation of sulfur-containing compounds like thioamides

Basic Information

• Chemical Name: N,N-Dimethylacetoacetamide
• CAS Registry Number: 2044-64-61
• EINECS Number: 218-059-81
• Molecular Weight: 129.16 g/mol1

Physical and Chemical Properties

Here is a summary of the key physical properties:

Applications

The primary application of N,N-Dimethylacetoacetamide is as a chemical reagent and organic synthetic intermediate

• Thioamide Synthesis: It is notably used for the preparation of thioamide derivatives. Thioamides are important sulfur-based compounds with broad applications in:
  • Pharmaceuticals: Used as intermediates in drug synthesis.
  • Agrochemicals: Used in the production of pesticides.
  • Industrial Chemistry: Employed as stabilizers, inhibitors, catalysts, vulcanizing agents, and flotation collectors
• Example Synthesis: The search results provide an example where it is reacted with phenyl isothiocyanat and potassium carbonate in ethanol to yield 3-Anilino-N,N-dimethyl-3-oxothiopropionamide with a reported yield of 88.6%

Basic Information

• Product Name: N,N-Dimethylacetoacetamide
• Alias: DMAA; Acetoacetic acid dimethylamide; 2,4-Dioxo-N,N-dimethylbutanamide
• Chemical Formula: C6H11NO2
• Molar Mass: 129.16 g/mol
• CAS Number: 2044-64-6

Physical Properties

• Appearance: Colorless to pale yellow transparent liquid or crystalline solid (at lower temperatures), with no strong pungent odor.
• Melting Point: 21-23°C (store as a liquid to avoid crystallization).
• Boiling Point: 214-216°C (decomposes upon heating under atmospheric pressure).
• Density: 1.04 g/cm³ (25°C).
• Solubility: Highly soluble in water, ethanol, acetone, chloroform, and other polar solvents; miscible with most organic solvents.
• Refractive Index: n20D 1.452

Applications

• Pharmaceutical Intermediates:
  • Synthesis of anti-inflammatory drugs (e.g., pyrazolone derivatives like metamizole);
  • Preparation of antibiotics (e.g., cephalosporin side chains);
  • Key intermediate for antimalarial agents (e.g., chloroquine analogs).
• Agrochemicals:
  • Used in synthesizing herbicides, fungicides, and insecticides (e.g., pyrazole-based pesticides).
• Polymer Chemistry:
  • As a crosslinking agent or modifier for polymers (e.g., polyurethanes, polyesters);
  • Precursor for functional polymers with β-dicarbonyl groups.
• Organic Synthesis:
  • Building block for heterocycles (e.g., pyridines, pyrimidines) via cyclization reactions;
  • Used in the synthesis of dyes, pigments, and photographic chemicals.

Safety and Storage
Hazards

• Health Risks:
  • Skin/Eye Contact: May cause irritation, redness, and pain; prolonged exposure may lead to burns.
  • Inhalation/Ingestion: Harmful if inhaled or swallowed; may cause respiratory irritation, nausea, or vomiting.
  • Toxicity: LD50 (rat, oral) ≈ 1500 mg/kg (moderate toxicity).
• Environmental Risks:
  • Persistent in water; may be toxic to aquatic organisms.
  • Avoid release into soil or water systems.
• Fire and Explosion:
  • Combustible liquid; flash point ≈ 96°C.
  • Keep away from open flames and heat sources.

Safety Measures

• Protection:
  • Wear chemical-resistant gloves, safety goggles, and protective clothing.
  • Use in a well-ventilated area or fume hood to prevent vapor inhalation.
• Storage:
  • Store in a tightly sealed container in a cool, dry place.
  • Keep away from strong acids, bases, and oxidizing agents.
• Emergency Handling:
  • For spills, absorb with inert material (e.g., sand) and dispose of properly.
  • In case of fire, use dry chemical, CO2, or foam extinguishers.

Derivatives and Analogues

• Common Derivatives:
  • N,N-Dimethyl-3-oxobutanethioamide: Sulfur analog for preparing thiazole derivatives.
  • N,N-Dimethyl-3-oxopentanamide: Homologue with an additional methyl group (C7H13NO2).
• Comparison with Related Compounds:

Packaging can be customized according to customer requirements.