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Acetamide

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Acetamide

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This page is a soft redirect. Names

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IUPAC names
Acetamide
Ethanamide
Other names
acetic acid amide
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This page is a soft redirect. Identifiers

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60-35-5 7pxY ChEBI CHEBI:27856 7pxY ChEMBL ChEMBL16081 7pxY ChemSpider 173 7pxY DrugBank DB02736 7pxY EC number 200-473-5 Jmol-3D images Image KEGG C06244 7pxY PubChem Template:Chembox PubChem/format RTECS number AB4025000 Template:Chembox UNII colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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This page is a soft redirect.- C2H5NO Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1 Appearance colorless, hygroscopic Odor odorless
mouse-like with impurities Density 1.159 g/cm3 Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". (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) colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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Crystal structure trigonal colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
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SDS 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

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Flash point Script error: No such module "convert". 700 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 14pxY verify (what is10pxY/10pxN?) 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]

File:Acetamide crystal structure.png
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, 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

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