Acetamide

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Acetamide
Names
IUPAC names
Acetamide
Ethanamide
Other names
acetic acid amide
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.430 Edit this at Wikidata
EC Number
  • 200-473-5
KEGG
RTECS number
  • AB4025000
UNII
  • InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) checkY
    Key: DLFVBJFMPXGRIB-UHFFFAOYSA-N checkY
  • InChI=1/C2H5NH2/c1-2(3)4/h1H3,(H2,3,4)
    Key: DLFVBJFMPXGRIB-UHFFFAOYAC
  • O=C(N)C
Properties
C2H5NO
Molar mass 59.068 g·mol−1
Appearance colorless, hygroscopic
Odor odorless
mouse-like with impurities
Density 1.159 g/cm3
Melting point 79 to 81 °C (174 to 178 °F; 352 to 354 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
trigonal
Hazards
GHS labelling:
GHS08: Health hazard
Warning
H351
P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3
1
1
Flash point 126 °C (259 °F; 399 K)
Lethal dose or concentration (LD, LC):
7000 mg/kg (rat, oral)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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.

On 30 July 2015, scientists reported that upon the first touchdown of the Philae lander on comet 67/P's surface, measurements by the COSAC and Ptolemy instruments revealed sixteen organic compounds, four of which were seen for the first time on a comet, including acetamide, acetone, methyl isocyanate and propionaldehyde.[6][7][8]

In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.[9][10]

Acetamide crystal structure

References

  1. ^ a b c d The Merck Index, 14th Edition, 36
  2. ^ a b "Acetic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_045.pub2. ISBN 978-3527306732.
  3. ^ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Organic Syntheses. 3: 3{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, 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. ^ Jordans, Frank (30 July 2015). "Philae probe finds evidence that comets can be cosmic labs". The Washington Post. Associated Press. Retrieved 30 July 2015.
  7. ^ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015.
  8. ^ Bibring, J.-P.; Taylor, M.G.G.T.; Alexander, C.; Auster, U.; Biele, J.; Finzi, A. Ercoli; Goesmann, F.; Klingehoefer, G.; Kofman, W.; Mottola, S.; Seidenstiker, K.J.; Spohn, T.; Wright, I. (31 July 2015). "Philae's First Days on the Comet - Introduction to Special Issue". Science. 349 (6247): 493. Bibcode:2015Sci...349..493B. doi:10.1126/science.aac5116. Retrieved 30 July 2015.
  9. ^ "Acetamide". Mindat.org.
  10. ^ "Acetamide" (pdf). Handbook of Mineralogy. RRUFF Project.

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Acetamide&oldid=721040587"