Acetamide

Acetamide
Names
IUPAC names
Acetamide
Ethanamide
Other names
acetic acid amide
Identifiers
60-35-5 Yes
ChEBI CHEBI:27856 Yes
ChEMBL ChEMBL16081 Yes
ChemSpider 173 Yes
DrugBank DB02736 Yes
EC number 200-473-5
Jmol-3D images Image
KEGG C06244 Yes
PubChem 178
RTECS number AB4025000
UNII 8XOE1JSO29 Yes
Properties
Molecular formula
 C2H5NO
Molar mass 59.07 g·mol−1
Appearance colorless, hygroscopic
Odor odorless
mouse-like with impurities
Density 1.159 g/cm3
Melting point 79 °C (174 °F; 352 K)
Boiling point 221.2 °C (430.2 °F; 494.3 K) (decomposes)
2000 g L−1[1]
Solubility ethanol 500 g L−1[1]
pyridine 166.67 g L−1[1]
soluble in chloroform, glycerol, benzene[1]
log P -1.26
Vapor pressure 1.3 Pa
Acidity (pKa) 16.5
1.4274
Viscosity 2.052 cP (91 °C)
Structure
Crystal structure trigonal
Hazards
MSDS External MSDS
EU Index 616-022-00-4
EU classification Harmful (Xn)
Carc. Cat. 3
R-phrases R40
S-phrases (S2) S36/37
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
1
3
1
Flash point 126 °C (259 °F; 399 K)
700 mg/kg (rat, oral)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Acetamide (IUPAC: ethanamide) is an organic compound with the formula CH3CONH2. It is the simplest amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent.[2] The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide.

Production

Laboratory scale

Acetamide can be produced in the laboratory by dehydrating ammonium acetate:[3]

CH3COONH4 → CH3C(O)NH2 + H2O

Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination.[4]

Industrial scale

In a similar fashion to some laboratory methods, acetamide is produced dehydrating ammonium acetate or via the hydrolysis of acetonitrile, a byproduct of the production of acrylonitrile:[2]

CH3CN + H2O → CH3C(O)NH2

Use

Occurrence

Acetamide has been detected near the center of the Milky Way galaxy.[5] This finding is potentially significant because acetamide has an amide bond, similar to the essential bond between amino acids in proteins. This finding lends support to the theory that organic molecules that can lead to life (as we know it on Earth) can form in space.

In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.[6][7]

Acetamide crystal structure

References

  1. ↑ 1.0 1.1 1.2 1.3 The Merck Index, 14th Edition, 36
  2. ↑ 2.0 2.1 "Acetic Acid", Ullmann's Encyclopedia of Industrial Chemistry, Weinheim: Wiley-VCH, 2005, doi:10.1002/14356007.a01_045.pub2
  3. ↑ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Org. Synth. 3: 3.; Coll. Vol. 1, p. 3
  4. ↑ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". Journal of the American Chemical Society 61 (12): 3499–3502. doi:10.1021/ja01267a081.
  5. ↑ Hollis, J. M.; Lovas, F. J.; Remijan, A. J.; Jewell, P. R.; Ilyushin, V. V.; Kleiner, I. (2006). "Detection of Acetamide (CH3CONH2): The Largest Interstellar Molecule with a Peptide Bond" (PDF). The Astrophysical Journal 643 (1): L25–L28. Bibcode:2006ApJ...643L..25H. doi:10.1086/505110.
  6. ↑ "Acetamide". Mindat.org.
  7. ↑ "Acetamide" (PDF). Handbook of Mineralogy. RRUFF Project.

External links