N,N-dimethylacetamide

• ChemBase ID: 103204
• Molecular Formular: C4H9NO
• Molecular Mass: 87.12036
• Monoisotopic Mass: 87.06841391
• SMILES: CN(C)C(=O)C
• Canonical SMILES: CC(=O)N(C)C
• InChI: InChI=1S/C4H9NO/c1-4(6)5(2)3/h1-3H3
• InChIKey: FXHOOIRPVKKKFG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N,N-dimethylacetamide
• IUPAC Traditional name: dimethylacetamide
• Synonyms: Dimethylacetamide; DMA; N,N-Dimethylacetamide, HPLC Grade; N,N-DIMETHYLACETAMIDE; N,N-DIMETHYLACETAMIDE, HPLC/SPECTRO GRADE; N,N-DIMETHYLACETAMIDE, ANHYDROSOLV GRADE; N,N-DIMETHYLACETAMIDE, CERTIFIED GRADE; N,N-Dimethylacetamide; N,N-Dimethylacetamide-d9; N,N-二甲基乙酰胺, HPLC级; N,N-二甲基乙酰胺; N,N-二甲基乙酰胺-d9

Database IDs

• CAS Number: 116057-81-9; 127-19-5
• EC Number: 204-826-4
• MDL Number: MFCD00008686
• Beilstein Number: 1737614
• Merck Index: 143227
• PubChem SID: 24856380; 24864224; 24864225; 24850431; 24886390; 24856426; 162090444; 24849477; 24874272; 24893416
• PubChem CID: 31374
• CHEMBL: 11873
• Chemspider ID: 29107
• MeSH Name: dimethylacetamide
• Unique Ingredient Identifier: JCV5VDB3HY
• Wikipedia Title: Dimethylacetamide

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): -0.5829362
• LogD (pH = 7.4): -0.58293617
• Log P: -0.58293617
• Molar Refractivity: 24.2593 cm^3
• Polarizability: 9.313932 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Miscible in water
• Apperance: Colorless liquid; Liquid
• Melting Point: -20 °C; -20 °C(lit.); -20°C; -20°C
• Boiling Point: 164.5-166 °C(lit.); 164-166 °C(lit.); 165 °C at 1013 hPa; 165.05°C (438.2K); 165-166°C
• Flash Point: 158 °F; 63 °C (closed cup); 63 °C; 70 °C; 70°C(158°F)
• Auto Ignition Point: 400 °C (DIN 51794); 490 °C; 914 °F
• Density: .94 g/cm^3 at 20 °C; 0.937 g/mL at 25 °C(lit.); 0.940; 1.033 g/mL at 25 °C; 937 mg mL^-1
• Refractive Index: 1.4375; 1.4385; n20/D 1.437; n20/D 1.437(lit.); n20/D 1.438; n20/D 1.438(lit.)
• Vapor Pressure: 1.76 hPa at 20 °C; 2 mmHg ( 25 °C); 300 Pa; 4 mmHg ( 38 °C)
• Vapor Density: 3 (vs air); 3.01 (air = 1)
• Partition Coefficient: -0.253
• Absorption Wavelength: 270 nm; λ: 270 nm Amax: 1.0; λ: 270 nm Amax: 1.00; λ: 280 nm Amax: 0.3; λ: 280 nm Amax: 0.30; λ: 290 nm Amax: 0.15; λ: 300 nm Amax: 0.1; λ: 310 nm Amax: 0.05; λ: 320 nm Amax: 0.03; λ: 360 nm Amax: 0.005; λ: 360 nm Amax: 0.01; λ: 360-400 nm Amax: 0.01
• Viscosity: 1.956 mPa s
• Odor: Ammoniacal
• Heat Capacity: 178.2 J K^-1 mol^-1
• Std enthalpy of combustion: -2.5835–-2.5805 MJ mol^-1
• Std enthalpy of formation: -300.1 kJ mol^-1
• Absorbance: 1.00

Safety Information

• Storage Condition: Room Temperature (15-30°C), Desiccate
• RTECS: AB7700000
• European Hazard Symbols: Toxic (T); Harmful (Xn)
• German water hazard class: 1; 3
• Risk Statements: 20/21-36/37/38-62; 61-20/21; 61-20/21-36; R:20/21-61; r61, r20/21
• Safety Statements: 23-26-36; 53-45; S:45-53; s45
• TSCA Listed: 是
• EU Index: 616-011-00-4
• GHS Pictograms: GHS exclamation mark; GHS health hazard; GHS07; GHS08
• GHS Signal Word: DANGER; Danger; Warning
• NFPA704:
  

  2

  2

  0
• LD50: 2.24 g kg^-1 (dermal, rabbit); 4.3 g kg^-1 (oral, rat)
• Explode Limits: 1.8 %, 100 °F; 1.8–11.5%; 11.5 %, 160 °F
• GHS Hazard statements: 312, 332, 360; H312 + H332-H319-H360D; H312-H315-H319-H332-H335-H361; H312-H332-H360D; H360-H312-H332-H227
• GHS Precautionary statements: 280, 308+313; P201-P280-P305 + P351 + P338-P308 + P313; P201-P280-P308 + P313; P210-P261-P280-P302+P352-P405-P501A; P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Purity: ≥99%; ≥98.0% (GC); ≥99%; ≥99% (GC); ≥99.0%; ≥99.5% (GC); ≥99.8% (GC); ≥99.9%; ≥99.9% (GC); 99%; 99.5+%; 99.8%
• Grade: absolute; analytical standard; anhydrous; B&J Brand (product of Burdick & Jackson); CHROMASOLV® Plus; for HPLC; for peptide synthesis; for UV-spectroscopy; HPLC; puriss. p.a.; purum; ReagentPlus®; SAJ first grade; SAJ special grade; spectrophotometric grade
• Isotopic Purity: 99 atom % D
• Suitability: GC-Headspace tested; in accordance for amine test
• Evaporation Residue: <0.001%; ≤0.001%; ≤0.002%; ≤0.005%
• Impurities: <0.005% water; <0.030% water; <0.050% water; ≤0.005% water; ≤0.02% water; ≤0.03% water; ≤0.1% water
• Cation Traces: Al: ≤0.5 mg/kg; Ba: ≤0.1 mg/kg; Bi: ≤0.1 mg/kg; Ca: ≤0.5 mg/kg; Cd: ≤0.05 mg/kg; Co: ≤0.02 mg/kg; Cr: ≤0.02 mg/kg; Cu: ≤0.02 mg/kg; Fe: ≤0.1 mg/kg; K: ≤0.5 mg/kg; Li: ≤0.1 mg/kg; Mg: ≤0.1 mg/kg; Mn: ≤0.02 mg/kg; Mo: ≤0.1 mg/kg; Na: ≤0.5 mg/kg; Ni: ≤0.02 mg/kg; Pb: ≤0.1 mg/kg; Sr: ≤0.1 mg/kg; Zn: ≤0.1 mg/kg
• Shelf Life: (limited shelf life, expiry date on the label)
• Quality: over molecular sieve (H2O ≤0.01%)
• Mol. Weight: mol wt 96.20
• λ: 1 cm path, H2O reference; H2O reference
• Linear Formula: CD3CON(CD3)2; CH3CON(CH3)2

DETAILS

MP Biomedicals - 05202370

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150928

Purity: 99+%
1 ml = approx. 0.94 g
Cryoprotective properties

Sigma Aldrich - 17308

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REFERENCES

• Morris, J., et al., Biotechniques, 35: 956-968.
• Useful solvent in halex fluorinations of chloroarenes; compare Sulfolane, A13466.
• See also Sodium hydride, 13431, for warning.
• Dipolar aprotic solvent, cf N,N-Dimethylformamide, A13547, Dimethyl sulfoxide, A13280, 1-Methyl-2-pyrrolidinone, A12260.
• Undergoes Vilsmeier-type reactions (compare DMF), with reactive substrates, introducing an acetyl group: Chem. Ber., 97, 616 (1964).
• Reacts with alkyl and aryl Grignard reagents to give methyl ketones in good yields: Synthesis, 228 (1984).
• In the presence of triflic anhydride and 2,4,6-collidine, forms a highly-reactive keteniminium triflate, which undergoes a [2+2] cycloaddition reaction with terminal alkenes to give, after hydrolysis a 3-alkylcyclobutanone: J. Am. Chem. Soc., 107, 2192 (1985); Org. Synth. Coll., 8, 306 (1993):