Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent.[5] The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between acetone, which has two methyl (CH3) groups either side of the carbonyl (CO), and urea which has two amide (NH2) groups in those locations. Acetamide is also a naturally occurring mineral[6] with the IMA symbol: Ace.[7]
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| Names | |||
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| Preferred IUPAC name
Acetamide[1] | |||
| Systematic IUPAC name
Ethanamide | |||
| Other names
Acetic acid amide | |||
| Identifiers | |||
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3D model (JSmol) |
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| ChEMBL | |||
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| DrugBank |
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| ECHA InfoCard | 100.000.430 
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| EC Number |
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| KEGG |
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PubChem CID |
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| RTECS number |
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| UNII | |||
CompTox Dashboard (EPA) |
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| Properties | |||
| C2H5NO | |||
| Molar mass | 59.068 g·mol−1 | ||
| Appearance | colorless, hygroscopic solid | ||
| Odor | odorless mouse-like with impurities | ||
| Density | 1.159 g cm−3 | ||
| 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[2] | |||
| Solubility | ethanol 500 g L−1[2] pyridine 166.67 g L−1[2] soluble in chloroform, glycerol, benzene[2] | ||
| log P | −1.26 | ||
| Vapor pressure | 1.3 Pa | ||
| Acidity (pKa) | 15.1 (25 °C, H2O)[3] | ||
| −0.577 × 10−6 cm3 g−1 | |||
Refractive index (nD) |
1.4274 | ||
| Viscosity | 2.052 cP (91 °C) | ||
| Structure | |||
| trigonal | |||
| Thermochemistry[4] | |||
Heat capacity (C) |
91.3 J·mol−1·K−1 | ||
Std molar |
115.0 J·mol−1·K−1 | ||
Std enthalpy of |
−317.0 kJ·mol−1 | ||
| Hazards | |||
| GHS labelling: | |||
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| Warning | |||
| H351 | |||
| P201, P202, P281, P308+P313, P405, P501 | |||
| NFPA 704 (fire diamond) | |||
| Flash point | 126 °C (259 °F; 399 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose) |
7000 mg kg−1 (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). | |||
Acetamide can be produced in the laboratory from ammonium acetatebydehydration:[9]
Alternatively acetamide can be obtained in excellent yield via ammonolysisofacetylacetone under conditions commonly used in reductive amination.[10]
It can also be made from anhydrous acetic acid, acetonitrile and very well dried hydrogen chloride gas, using an ice bath, alongside more valuable reagent acetyl chloride. Yield is typically low (up to 35%), and the acetamide made this way is generated as a salt with HCl.
In a similar fashion to some laboratory methods, acetamide is produced by dehydrating ammonium acetate or via the hydrationofacetonitrile, a byproduct of the production of acrylonitrile:[5]
Acetamide is used as a plasticizer and an industrial solvent.[5] Molten acetamide is good solvent with a broad range of applicability. Notably, its dielectric constant is higher than most organic solvents, allowing it to dissolve inorganic compounds with solubilities closely analogous to that of water.[11] Acetamide has uses in electrochemistry and the organic synthesis of pharmaceuticals, pesticides, and antioxidants for plastics.[12] It is a precursor to thioacetamide.[13]
Acetamide has been detected near the center of the Milky Way galaxy.[14] 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 – acetamide, acetone, methyl isocyanate, and propionaldehyde[15][16][17] – were seen for the first time on a comet.
In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.[18][19]
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