DIMETHYLACETOACETAMIDE

Dimethylacetoacetamide is a clear, colorless to yellow liquid used as a general purpose, low color generating co-promoter for many unsaturated polyester (FRP) resin formulations. 
Dimethylacetoacetamide is also used in the production of low VOC unsaturated polyester (FRP) systems for coatings and as an intermediate for the production of insecticides.
Dimethylacetoacetamide is an organic β-keto amide derived from acetoacetic acid.

CAS Number: 2044-64-6
Molecular Formula: C6H11NO2
Molecular Weight: 129.16
EINECS Number: 218-059-8

Synonyms: N,N-Dimethylacetoacetamide, N,N-Dimethyl-3-oxobutanamide, 2044-64-6, Butanamide N,N-dimethyl-3-oxo-, Dimethylacetoacetamide, Acetoacetamide N,N-dimethyl-, 7E2L0OAA4K, DTXSID8027454, NSC-524755, DMAAm cpd, RefChem:161274, 218-059-8, N,N-Dimethyl-3-oxobutyramide, MFCD00038243, Acetylacetamide N,N-dimethyl-, N-Acetoacetyldimethylamine, CAS-2044-64-6, Dimethyl acetoacetamide, EINECS 218-059-8, UNII-7E2L0OAA4K, Dimethylamid kyseliny acetoctove, N,N-dimethyl-3-oxo-butanamide, EC 218-059-8, SCHEMBL56374, Acetoacetic acid dimethylamide, 4-04-00-00260, Butanamide N-dimethyl-3-oxo-, CHEMBL3185062, SCHEMBL11685089, N,N-Dimethyl-3-oxobutanamide, Tox21_201898, Tox21_303265, SBB007704, STL183263, N,N-Dimethyl-2-acetoacetamide, AKOS000120991, NCGC00249133-01, NCGC00257209-01, NCGC00259447-01, SY008180, DB-080755, CS-0155066, D0642, NS00009956, EN300-17523, E75883, F324094, Q27268134, Z56948269, F0001-0723, Acetoacetamide, N,N-dimethyl-;Acetylacetamide, N,N-dimethyl-;Butanamide, N,N-dimethyl-3-oxo-;Butanamide,N,N-dimethyl-3-oxo-;Dimethylamid kyseliny acetoctove;dimethylamidkyselinyacetoctove;Acetoacetdimethylamide;N,N-Dimethylacetoacetamide (approx. 80% in water)

Dimethylacetoacetamide contains both a keto group (C=O) and a tertiary amide functional group, which gives it useful reactivity in organic synthesis.
It is typically a clear to pale liquid used as a chemical intermediate in pharmaceuticals, polymer chemistry, and specialty coatings.
Dimethylacetoacetamide is liquid containing 20% water, miscible in water and organic compounds. 

Dimethylacetoacetamide is used as a general-purpose low color-generating copromotor for many unsaturated polyester resin formulations.
Dimethylacetoacetamide is the organic compound with the formula CH3C(O)N(CH3)2. 
This colorless, water-miscible, high-boiling liquid is commonly used as a polar solvent in organic synthesis. 

Dimethylacetoacetamide is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.
Dimethylacetoacetamide is prepared commercially by the reaction of dimethylamine with acetic anhydride or acetic acid. 
Dehydration of the salt of Dimethylacetoacetamide and acetic acid also furnishes this compound: CH3CO2H·HN(CH3)2 → H2O + CH3CON(CH3)2

Dimethylacetoacetamide can also be produced by the reaction of dimethylamine with methyl acetate.
The separation and purification of the product is carried out by multistage distillation in rectification columns. 
Dimethylacetoacetamide is obtained with essentially quantitive (99%) yield referred to methyl acetate.[6]

Dimethylacetoacetamide is a β-keto tertiary amide belonging to the broader family of acetoacetamide derivatives, which are widely used as reactive intermediates in organic synthesis.
Its structure contains two key functional moieties: a tertiary amide group [–CON(CH₃)₂] that provides stability and basicity, and a keto carbonyl group at the β-position that imparts significant nucleophilicity and enol/enolate-forming ability.
Because of this dual-carbonyl system, the molecule participates efficiently in condensation, alkylation, and acylation reactions, making it valuable in the synthesis of fine chemicals, pharmaceuticals, and advanced polymeric materials.

Chemically, Dimethylacetoacetamide acts as an acetoacetylating agent, enabling the controlled introduction of acetoacetyl groups into polymer chains, dyes, and biologically active molecules.
It is typically encountered as a clear to slightly yellow, low-viscosity liquid with moderate volatility and a characteristic light amine-like odor.
Dimethylacetoacetamide dissolves readily in most polar and moderately non-polar organic solvents and shows partial solubility in water due to the polar amide functionality.

Industrial usage is often based on its ability to form enamines and stable intermediates that enable heterocyclic ring construction, particularly in pharmaceutical precursor manufacturing.
It also serves as a modifier in coatings and adhesives, where the acetoacetyl group enhances crosslinking capacity, UV-resistance, and adhesion strength.
In short, dimethylacetoacetamide is a versatile molecular building block that bridges practical industrial chemistry and advanced synthetic transformations due to its reactive β-keto amide framework.

Melting point: −55 °C
Boiling point: 105 °C (lit.)
Density: 1.067 g/mL (25 °C)
Vapor pressure: 19.84 hPa (25 °C)
Refractive index: n20/D 1.447
Flash point: 252 °F
Storage temperature: Inert atmosphere, room temperature
Solubility: H₂O: soluble
Form: Clear liquid
pKa: 12.82 ± 0.46 (predicted)
Color: APHA ≤ 350
Water solubility: Hydrolyzes slowly
BRN: 1755038
LogP: 0.91 (25 °C)

Dimethylacetoacetamide is an organic β-keto tertiary amide derived from acetoacetic acid, where the amide nitrogen is substituted with two methyl groups.
This structure places it in the acetoacetamide family, well-known for their reactive β-dicarbonyl systems that can form enol and enolate intermediates.
This dual-carbonyl arrangement — a keto group and a amide carbonyl separated by one carbon — gives the molecule a high degree of chemical versatility.

In solution, Dimethylacetoacetamide tends to exist in a keto–enol equilibrium, enabling it to act both as a nucleophile (via enolate formation) and as an electrophile (via the carbonyls).
This amphoteric nature allows the compound to undergo condensation, Michael addition, acylation, and alkylation reactions, making it a highly useful synthetic building block.
Its tertiary amide functionality increases hydrolytic stability compared to primary or secondary amides, while still enabling coordination with catalysts — this makes it valuable in transition-metal-catalyzed reactions.

The electron-withdrawing effect of the carbonyl group next to the amide enhances reactivity at the α- and β-positions, enabling controlled C–C and C–N bond formation, especially during heterocycle synthesis for pharmaceutical intermediates.
Industrially, Dimethylacetoacetamide plays a major role as an acetoacetylating reagent used to incorporate acetoacetyl groups into polymers such as waterborne acrylic latex resins, improving crosslinking density, weatherability, and UV-stability in coatings.
Its reactivity also facilitates production of functional dyes, pigments, agrochemical actives, and photopolymer additives.

In physical form, it typically appears as a clear-to-light yellow, moderately viscous liquid with a faint amide odor.
It is miscible with common organic solvents, such as alcohols, ketones, and esters, and exhibits moderate volatility that requires storage away from strong oxidizers or reactive bases.
The compound is generally stable but may slowly decompose under strong acidic or alkaline conditions, where hydrolysis can form dimethylamine and acetoacetic derivatives.

Dimethylacetoacetamide is regarded as a chemically robust yet highly functionalized intermediate, bridging polymer chemistry and advanced organic synthesis, and continues to be a key reagent in materials development driven by the β-keto amide’s unique electronic and structural profile.
The chemical reactions of Dimethylacetoacetamide are typical of N,N-disubstituted amides. Hydrolysis of the acyl-N bond occurs in the presence of acids: CH3CON(CH3)2 + H2O + HCl → CH3COOH + (CH3)2NH2+Cl−

However, it is resistant to bases. 
For this reason Dimethylacetoacetamide is a useful solvent for reactions involving strong bases such as sodium hydroxide.
Dimethylacetoacetamide is commonly used as a solvent for fibers (e.g., polyacrylonitrile, spandex) or in the adhesive industry.

Dimethylacetoacetamide is also employed in the production of pharmaceuticals and plasticizers as a reaction medium.
A solution of lithium chloride in DMAc (LiCl/DMAc) can dissolve cellulose. Unlike many other cellulose solvents, LiCl/DMAc gives a molecular dispersion, i.e. a "true solution". 

For this reason, it is used in gel permeation chromatography to determine the molar mass distribution of cellulose samples.
Dimethylacetoacetamide is also used as an excipient in drugs, e.g. in Vumon (teniposide), Busulfex (busulfan) or Amsidine (amsacrine).

Uses Of Dimethylacetoacetamide:
Dimethylacetoacetamide is used as intermediate for the production of insecticides, e.g. dicrotophos and as a promoter in unsaturated polyester resins.
Dimethylacetoacetamide is an organic intermediate that can be used to prepare thioamide compounds. 
As an important thiocarboxylic acid derivative, thioamide compounds have received extensive attention in pharmaceutical synthesis, chemical engineering and related fields. 

Dimethylacetoacetamide and its derivatives have a wide range of applications in analysis, materials, and electrochemistry. 
They are not only used in the production of polymerization inhibitors, catalysts, stabilizers, pesticides, etc., but also in the production of pharmaceutical raw materials, vulcanizing agents, and chemicals.
Dimethylacetoacetamide is used as a reactant in the asymmetric hydrogenation of functionalized ketones in presence of chiral bis(diphenylphosphino)binaphthyl ruthenium complex.

Used in pharmaceutical synthesis to introduce β-keto groups into drug intermediates. 
This enables formation of valuable heterocyclic systems like pyridones and quinolinones. 
Dimethylacetoacetamide also supports enamine chemistry for controlled C–C and C–N bond formation.

Used in polymer chemistry and high-performance coatings as a reactive monomer or intermediate. 
The acetoacetyl groups enable strong crosslinking reactions with excellent curing behavior. 
This results in coatings with improved adhesion, flexibility, chemical resistance, and long-term UV stability.

Used in dye and pigment manufacturing to modify chromophores with acetoacetyl groups. 
These modifications enhance light fastness and color strength. 
They also improve dispersion stability in ink and textile formulations.

Used in agrochemical synthesis to produce active pesticide and herbicide components. 
Dimethylacetoacetamide enables stable β-dicarbonyl bonding, which supports biological activity. 
This allows fine-tuning of molecule performance in real agricultural conditions.

Used in specialty fine chemical production for fragrances, flavors, and advanced building blocks. 
Its dual-carbonyl system allows selective transformations and controlled reactivity. 
This makes it a versatile intermediate for high-value molecules.

Used in photopolymer and electronic materials to enhance crosslinking under UV curing. 
Dimethylacetoacetamide increases network density in optical resins and photoresists. 
This improves mechanical durability and performance in sensitive applications.

Dimethylacetoacetamide is used as a research reagent in β-keto amide chemistry and catalytic reaction development. 
It helps study enolate formation and nucleophilic additions. 
Researchers employ it to explore new synthetic pathways in academic and industrial labs.

Dimethylacetoacetamide is widely used in pharmaceutical synthesis for introducing β-keto functionalities into precursor molecules that later undergo cyclization. 
This supports the controlled formation of heterocycles with biological significance and improved stability profiles. 
Its enamine-forming ability enables further molecular expansion through catalytic coupling reactions.

Dimethylacetoacetamide is essential in polymer chemistry and functional coatings, where it serves as a reactive intermediate in acrylics, urethanes, and waterborne resins. 
Through acetoacetyl crosslinking, it delivers excellent curing speed and low-VOC performance. 
These improvements translate into coatings with superior mechanical resilience, weathering resistance, and long-term UV protection.

Dimethylacetoacetamide is applied in dye and pigment production, where acetoacetyl substitution enhances both molecular color strength and environmental durability. 
These structural modifications reinforce chromophore stability under light exposure. 
They also contribute to better pigment dispersion and consistency across printing and textile applications.

Dimethylacetoacetamide plays a crucial role in agrochemical development, where β-dicarbonyl groups support active herbicide and pesticide structures. 
The chemical stability it provides helps maintain the bioavailability and persistence of active compounds. 
This allows agrochemical formulations to perform reliably under diverse environmental conditions.

Dimethylacetoacetamide is important in specialty fine chemical manufacturing, particularly for constructing fragrances and advanced intermediates. 
The molecule’s dual-carbonyl system enables selective transformations without excessive by-product generation. 
This makes the compound highly efficient for building small yet sophisticated molecular frameworks.

Dimethylacetoacetamide is incorporated in photopolymer and electronic materials, where enhanced crosslinking is required for structural precision. 
Under UV or thermal curing, it generates tightly bonded polymer networks with minimal shrinkage. 
The resulting materials exhibit improved optical clarity, adhesion, and durability in electronic device components.

Dimethylacetoacetamide is utilized in synthetic and catalytic research, where its reactivity offers a controlled platform for studying β-keto amide behavior. 
Scientists examine its enolate-driven mechanisms to develop new reaction pathways. 
It consistently supports innovation in heterocycle formation, polymer modification, and transition-metal catalysis.

Safety Profile Of Dimethylacetoacetamide:
Dimethylacetoacetamide can cause skin irritation upon direct contact with the liquid. 
Prolonged exposure may lead to redness or mild chemical burns. 
Protective gloves and immediate washing are recommended during handling.

Vapors may produce eye irritation, especially in environments with poor ventilation. 
Splashes can lead to redness, tearing, or temporary discomfort. 
Eye protection must be worn to prevent accidental exposure.

Inhalation of high concentrations can irritate the respiratory tract. 
Dimethylacetoacetamide symptoms may include coughing, throat irritation, or a headache. 
Work in a fume hood or ensure sufficient airflow when using the substance.

Ingestion may be harmful and cause gastrointestinal discomfort or irritative symptoms. 
Accidental swallowing should be followed by medical attention. 
Eating, drinking, or smoking near the material must be avoided.

Dimethylacetoacetamide is a combustible liquid, capable of releasing flammable vapors at elevated temperatures. 
Ignition sources should be strictly controlled during storage and use. 
Store away from sparks, hot surfaces, and open flames.

Dimethylacetoacetamide may undergo decomposition under strong acidic or alkaline conditions, forming irritating or harmful byproducts. 
This breakdown can increase exposure risks if chemical stability is not maintained. 
Proper storage conditions are essential to minimize degradation.