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N.N-DIMETHYLACETAMIDE

N.N-Dimethylacetamide is a highly effective polar aprotic solvent widely used in industrial chemical and polymer processing.
N.N-Dimethylacetamide efficiently dissolves a wide range of substances, including high-molecular-weight polymers, enhancing production performance.
N.N-Dimethylacetamide requires careful handling due to its potential health risks despite its valuable industrial applications.

CAS Number: 127-19-5
EC Number: 204-826-4
Chemical Formula: C4H9NO
Molar Mass: 87.122 g/mol

Synonyms: 127-19-5, 204-826-4, Acetamide, N,N-dimethyl-, Acetic Acid Dimethylamide, Acetic acid N,N-dimethylamide, Degassed and low oxygen N.N-Dimethylacetamide, Dimethylacetamide, Dimethylamid kyseliny octove, DMA, DMAc, Ethanoic acid N,N-dimethylamide, N,N-Dimethyl acetamide, N,N-Dimethylacetamid, N.N-Dimethylacetamide, N,N-Diméthylacétamide, N.N-Dimethylacetamide ZerO2(R), N.N-Dimethylacetamide, 13462-90-3, 16727-10-9, 20255-66-7, 31591-08-9, 5Y9, 99%, 99.5%, acetamide, dimethyl-, Acetamide, N,N-dimethyl-, labeled with deuterium (9CI), Acetamide-2,2,2-d3, N,N-di(methyl-d3)-, Acetdimethylamide, Acetic acid dimethylamide, Acetyldimethylamine, DMA, Acetic acid, dimethylamide, Acetic acid-dimethylamide, Acetyl dimethylamine, Acetyl-trimethyl-azanium, Acetyldimethylamine, Dimethylacetone amide, Dimethylamide acetate, Dma (van), DMA, DMA, DMA204-826-4MFCD00008686, N.N-Dimethylacetamide, N.N-Dimethylacetamide, EP, N,N-dimethyl acetoamide, N,N-Dimethyl-acetamide, N,N-Dimethyl-d6-acetamide, N.N-Dimethylacetamide (BP, Ph. Eur.), N.N-Dimethylacetamide, 99.5%, Extra Dry, N.N-Dimethylacetamide, reagent, N.N-Dimethylacetamide, super dehydrated, N.N-Dimethylacetamide-1,2-13C2, N.N-Dimethylacetamide-2,2,2-d3, N.N-Dimethylacetamide-D9, N,N-Dimethylethanamide, N,N′-Dimethylacetamide, n-n-dimethylacetamide, n-n-dimethylacetamide (dmac), n，n-二甲基乙酰胺, ~{n},~{n}-Dimethylethanamide, 二甲基乙酰胺

N.N-Dimethylacetamide is a polar aprotic organic solvent widely used in chemical synthesis, polymer processing, and industrial formulations.
N.N-Dimethylacetamide appears as a clear, colorless liquid with a faint amine-like odor and is known for its excellent solvency power for a wide range of organic and inorganic substances.

N.N-Dimethylacetamide 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.

N.N-Dimethylacetamide is miscible with most other solvents, although it is poorly soluble in aliphatic hydrocarbons.
N.N-Dimethylacetamide is an organic solvent with blood-brain transmissibility and an FDA-approved drug excipient.

N.N-Dimethylacetamide exerts anti-inflammatory activity by inhibiting the NF-κB signaling pathway.
N.N-Dimethylacetamide can be used in studies of weight gain caused by a high-fat diet and neuroinflammation in Alzheimer's disease.

N.N-Dimethylacetamide is used as a polar solvent in organic synthesis as well as in reactions involving strong bases such as sodium hydroxide.
N.N-Dimethylacetamide is also used as a solvent for fibers like polyacrylonitrile, spandex, as an excipient in drugs viz. vumon, busulfex and in the adhesive industry.

N.N-Dimethylacetamide finds application as a reaction medium in the production of pharmaceuticals, agrochemicals, dyes and plasticizers.
N.N-Dimethylacetamide is widely used in polymer industry due to its high solving power for high molecular-weight polymers and synthetic resins.

N.N-Dimethylacetamide plays an important role as a catalyst in various reactions viz. cyclization, halogenation, cynidation, alkylation and dehydrogenation and increases the yield of main products.
N.N-Dimethylacetamide is also used as an extracting agent for oil and gases, in paint removers, in the production of photo-resist stripping compounds and as booster solvent in coatings.

N,N−Dimethylacetamide is a dipolar, aprotic, high-boiling, oily solvent and reagent.
N.N-Dimethylacetamide is miscible with water and most oxygen- and nitrogen-containing organic solvents.
N.N-Dimethylacetamide has a faint ammonia odor.

N.N-Dimethylacetamide traces its roots at least as far back as 1914, when Marc Tiffeneau* and K. Fuhrer at Hôpital Boucicaut1 (Paris) identified it as a product of heating N,N-dimethylbenzylamine2 and acetic anhydride3 to 200 °C in a sealed tube.
Then, in 1931, in a treatise on the synthesis of aliphatic amides, James A. Mitchell and E. Emmet Reid at Johns Hopkins University (Baltimore) described preparing N.N-Dimethylacetamide in 84% yield by heating acetic acid and dimethylamine4 at 150 °C for 3 h.
This, along with using acetic anhydride or methyl acetate5 instead of the acid, is the process for manufacturing N.N-Dimethylacetamide today.

N.N-Dimethylacetamide is used as a solvent for producing fibers and for synthesizing organic compounds, notably pharmaceuticals.
N.N-Dimethylacetamide's broad range of miscibility makes it useful in mixed solvents.

N.N-Dimethylacetamide is also stable to strong bases; but it hydrolyzes in the presence of acids.
As the hazard information table shows, N.N-Dimethylacetamide must be handled with care.

Applications of N.N-Dimethylacetamide:
N.N-Dimethylacetamide is used in the production of synthetic fibers, films, and coatings, particularly in processes involving polyacrylonitrile, polyurethanes, and other polymers.
N.N-Dimethylacetamide is also applied as a reaction solvent in pharmaceuticals, agrochemicals, and specialty chemicals, and as a processing aid in adhesives and resins.

Reactions and Applications of N.N-Dimethylacetamide:
The chemical reactions of N.N-Dimethylacetamide 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, N.N-Dimethylacetamide is resistant to bases.
For this reason N.N-Dimethylacetamide is a useful solvent for reactions involving strong bases such as sodium hydroxide.

N.N-Dimethylacetamide is commonly used as a solvent for fibers (e.g., polyacrylonitrile, spandex) or in the adhesive industry.
N.N-Dimethylacetamide is also employed in the production of pharmaceuticals and plasticizers as a reaction medium.

A solution of lithium chloride in N.N-Dimethylacetamide (LiCl/DMAc) can dissolve cellulose.
Unlike many other cellulose solvents, LiCl/DMAc gives a molecular dispersion, i.e. a "true solution".
For this reason, N.N-Dimethylacetamide is used in gel permeation chromatography to determine the molar mass distribution of cellulose samples.

N.N-Dimethylacetamide is also used as an excipient in drugs, e.g. in Vumon (teniposide), Busulfex (busulfan) or Amsidine (amsacrine).

Synthesis and Production of N.N-Dimethylacetamide:
N.N-Dimethylacetamide is prepared commercially by the reaction of dimethylamine with acetic anhydride or acetic acid.

Dehydration of the salt of dimethylamine and acetic acid also furnishes this compound:
CH3CO2H·HN(CH3)2 → H2O + CH3CON(CH3)2

N.N-Dimethylacetamide 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.
N.N-Dimethylacetamide is obtained with essentially quantitive (99%) yield referred to methyl acetate.

Regulation of N.N-Dimethylacetamide:
In 2011, N.N-Dimethylacetamide was identified in the EU as a Substance of very high concern (SVHC) because of its reproductive toxicity.
In 2014, the European Commission has started an investigation to restrict the use of N.N-Dimethylacetamide in the EU according to REACH.

Handling and Storage of N.N-Dimethylacetamide:

Handling:
Avoid inhalation of vapors.
And contact with skin and eyes.

Storage:
Store in a tightly closed container.
In a cool, dry, well-ventilated area.

Protection:
Keep away from heat.
Sparks.
And open flames.

Stability and Reactivity of N.N-Dimethylacetamide:

Chemical stability:
Stable under recommended storage conditions.

Reactivity:
May react with strong oxidizing agents.

Conditions to avoid:
Excessive heat.
And moisture.

Incompatible materials:
Strong acids.
Bases.
And oxidizers.

Hazardous decomposition products:
Nitrogen oxides.
And carbon oxides under fire conditions.

First Aid Measures of N.N-Dimethylacetamide:

Inhalation:
Move to fresh air.
And seek medical attention if symptoms occur.

Skin contact:
Wash thoroughly with soap and water.

Eye contact:
Rinse cautiously with water for several minutes.

Ingestion:
Seek immediate medical attention.

Firefighting Measures of N.N-Dimethylacetamide:

Extinguishing media:
Foam.
Dry chemical.
Carbon dioxide.

Hazards:
Produces toxic fumes when burned.

Protective equipment:
Use full protective gear.
And self-contained breathing apparatus.

Accidental Release Measures of N.N-Dimethylacetamide:

Personal precautions:
Use protective equipment.
And avoid exposure.

Spill response:
Absorb with inert material.
And collect in a suitable container.

Environmental precautions:
Prevent entry into drains.
And waterways.

Exposure Controls/Personal Protection of N.N-Dimethylacetamide:

Respiratory protection:
Use appropriate respirator if needed.

Eye protection:
Safety goggles recommended.

Hand protection:
Chemical-resistant gloves.

Hygiene measures:
Avoid prolonged exposure.
And wash after handling.

Identifiers of N.N-Dimethylacetamide:
CAS number: 127-19-5
EC index number: 616-011-00-4
EC number: 204-826-4
Hill Formula: C₄H₉NO
Chemical formula: CH₃CON(CH₃)₂
Molar Mass: 87.12 g/mol
HS Code: 2924 19 00

Product Number: D0641
Purity / Analysis Method : >99.0%(GC)
Molecular Formula / Molecular Weight: C4H9NO = 87.12
Physical State (20 deg.C): Liquid
Storage Temperature : Room Temperature (Recommended in a cool and dark place, <15°C)
CAS RN: 127-19-5
Reaxys Registry Number: 1737614
PubChem Substance ID: 87567287
SDBS (AIST Spectral DB): 448
Merck Index (14): 3227
MDL Number:
MFCD00008686

Linear Formula: CH3CON(CH3)2
CAS Number: 127-19-5
Molecular Weight: 87.12
NACRES: NA.21
PubChem Substance ID: 329751718
eCl@ss: 39031204
UNSPSC Code: 12352111
EC Number: 204-826-4
MDL number: MFCD00008686
Beilstein/REAXYS Number: 1737614
Assay: ≥99%
Form: liquid

CAS Number: 127-19-5
Abbreviations: DMA, DMAC, DMAc
Beilstein Reference: 1737614
ChEBI: CHEBI:84254
ChEMBL: ChEMBL11873
ChemSpider: 29107
ECHA InfoCard: 100.004.389
EC Number: 204-826-4
MeSH: dimethylacetamide
PubChem CID: 31374
RTECS number: AB7700000
UNII: JCV5VDB3HY
CompTox Dashboard (EPA): DTXSID5020499
InChI: InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3
Key: FXHOOIRPVKKKFG-UHFFFAOYSA-N
SMILES: CN(C)C(C)=O

Properties of N.N-Dimethylacetamide:
Chemical formula: C4H9NO
Molar mass: 87.122 g·mol−1
Appearance: Colorless liquid
Odor: Ammoniacal
Density: 0.937 g/mL
Melting point: −20 °C (−4 °F; 253 K)
Boiling point: 165.1 °C; 329.1 °F; 438.2 K
Solubility in waterÇ Miscible
log P: −0.253
Vapor pressure: 300 Pa
UV-vis (λmax): 270 nm
Refractive index (nD): 1.4375
Viscosity: 0.945 mPa·s

Boiling point: 165 - 166 °C (1013 hPa)
Density: 0.94 g/cm3 (20 °C)
Explosion limit: 1.7 - 11.5 %(V)
Flash point: 64 °C
Ignition temperature: 400 °C
Melting Point: -20 °C
pH value: 4 (200 g/l, H₂O, 20 °C)
Vapor pressure: 1.76 hPa (20 °C)
Solubility: >1000 g/l soluble

vapor density: 3 (vs air)
Quality Level: 100
vapor pressure: 2 mmHg ( 25 °C), 4 mmHg ( 38 °C)
product line: ReagentPlus®
assay: ≥99%
form: liquid
autoignition temp.: 914 °F
expl. lim.: 1.8 %, 100 °F, 11.5 %, 160 °F
refractive index: n20/D 1.437 (lit.)
pH: 4 (20 °C, 200 g/L)
bp: 164.5-166 °C (lit.)
mp: −20 °C (lit.)
density: 0.937 g/mL at 25 °C (lit.)
SMILES string: CN(C)C(C)=O
InChI: 1S/C4H9NO/c1-4(6)5(2)3/h1-3H3
InChI key: FXHOOIRPVKKKFG-UHFFFAOYSA-N

Molecular Weight: 348.48 g/mol
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 0
Exact Mass: 348.27365564 Da
Monoisotopic Mass: 348.27365564 Da
Topological Polar Surface Area: 81.2 Å²
Heavy Atom Count: 24
Complexity: 58.6
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 4
Compound Is Canonicalized: Yes

Melting Point: -20 °C
Boiling Point: 165 °C
Flash point: 63 °C
Specific Gravity (20/20): 0.94
Refractive Index: 1.44
Solubility in water: Completely miscible

Thermochemistry of N.N-Dimethylacetamide:
Heat capacity (C): 178.2 J/(K·mol)
Std enthalpy of formation (ΔfH⦵298): −300.1 kJ/mol
Std enthalpy of combustion (ΔcH⦵298): −2.5835–−2.5805 MJ/mol

Specifications of N.N-Dimethylacetamide:
Appearance: Colorless to Almost colorless clear liquid
Purity(GC): min. 99.0 %
NMR: confirm to structure

Assay (GC, area%): ≥ 99.0 % (a/a)
Density (d 20 °C/ 4 °C): 0.940 - 0.942
Water (K. F.): ≤ 0.30 %
Identity (IR): passes test

Related compounds of N.N-Dimethylacetamide:
dimethylformamide
acetamide
methylpyrrolidone

Names of N.N-Dimethylacetamide:

Preferred IUPAC name:
N.N-Dimethylacetamide