N-Methylacetamide

N-Methylacetamide
Names
Preferred IUPAC name
N-Methylacetamide
Other names
  • Methyl acetamide
  • Monomethylacetamide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.075
EC Number
  • 201-182-6
UNII
UN number 85335
  • InChI=1S/C3H7NO/c1-3(5)4-2/h1-2H3,(H,4,5)
    Key: OHLUUHNLEMFGTQ-UHFFFAOYSA-N
  • CC(=O)NC
Properties
C3H7NO
Molar mass 73.095 g·mol−1
Appearance Colourless solid with faint odour[1]
Density 0.94 g·cm−3[1]
Melting point 27–30.6 °C (80.6–87.1 °F; 300.1–303.8 K)[1][4]
Boiling point 206–208 °C (403–406 °F; 479–481 K)[1]
Solubility
Vapor pressure 1.1 hPa (50 °C)[1]
1.433 (20 °C)[3]
Hazards
GHS labelling:[1]
GHS08: Health hazard
Danger
H360D
P201, P202, P280, P308+P313, P405, P501[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

N-Methylacetamide is a chemical compound from the amides group. The compound is listed as very high concern by the European Chemicals Agency (ECHA).

Generation

N-methylacetamide can be obtained by reacting hot acetic acid or acetic anhydride with methylamine.[5][6] It can also be prepared by reacting N,N′-dimethylurea with acetic acid[6] or by reacting acetone oxime with sulfuric acid.[7]

Characteristics

N-Methylacetamide is a flammable, difficult to ignite, hygroscopic, crystalline, colourless solid with a faint odor that is soluble in water.[1] Several isomeric forms are known.[8][9] In solution, it is 97–100% present as the Z isomer with a polymeric structure.[10][4] The compound has a high dielectric constant of 191.3 at 32 °C.[11]

Use

N-Methylacetamide is used as an intermediate in the production of agrochemicals and as a solvent in electrochemistry.[2][5]

See also

References

  1. ^ a b c d e f g h i Record of N-Methylacetamid in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 2022-01-20.
  2. ^ a b N-Methylacetamide, 99% at AlfaAesar, accessed on {{{Datum}}} (PDF) (JavaScript required).
  3. ^ Sigma-Aldrich Co., product no. {{{id}}}.
  4. ^ a b J. F. Coetzee (2013). Recommended Methods for Purification of Solvents and Tests for Impurities International Union of Pure and Applied Chemistry. Elsevier. p. 50. ISBN 978-1-4831-3845-9.
  5. ^ a b NLM Hazardous Substances Data Bank entry for [ ]
  6. ^ a b D.R. Buhler, D.J. Reed (2013). Nitrogen and Phosphorus Solvents. Elsevier. p. 166. ISBN 978-1-4832-9020-1.
  7. ^ Joachim Buddrus, Bernd Schmidt (2015). Grundlagen der Organischen Chemie. Walter de Gruyter GmbH & Co KG. p. 581. ISBN 978-3-11-033105-9.
  8. ^ Noemi G. Mirkin, Samuel Krimm (1991). "Conformers of cis-N-methylacetamide". Journal of Molecular Structure: THEOCHEM. 236 (1–2): 97–111. doi:10.1016/0166-1280(91)87010-J. hdl:2027.42/29043.
  9. ^ Mirkin, Noemi G.; Krimm, Samuel (1991-12-01). "Ab initio vibrational analysis of hydrogen-bonded trans- and cis-N-methylacetamide". Journal of the American Chemical Society. 113 (26): 9742–9747. Bibcode:1991JAChS.113.9742M. doi:10.1021/ja00026a005.
  10. ^ K.-H. Hellwich (2013). Stereochemie Grundbegriffe. Springer-Verlag. p. 43. ISBN 978-3-662-10051-6.
  11. ^ A. Covington (2012). Physical Chemistry of Organic Solvent Systems. Springer Science & Business Media. p. 247. ISBN 978-1-4684-1959-7.
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