Acetamide - Wikipedia

Acetamide

Names
Preferred IUPAC name Acetamide[1]
Systematic IUPAC name Ethanamide
Other names Acetic acid amideAcetylamine
Identifiers
CAS Number	60-35-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:27856 Y
ChEMBL	ChEMBL16081 Y
ChemSpider	173 Y
DrugBank	DB02736 Y
ECHA InfoCard	100.000.430
EC Number	200-473-5
IUPHAR/BPS	4661
KEGG	C06244 Y
PubChem CID	178
RTECS number	AB4025000
UNII	8XOE1JSO29 Y
CompTox Dashboard (EPA)	DTXSID7020005
InChI InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) YKey: DLFVBJFMPXGRIB-UHFFFAOYSA-N Y InChI=1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)Key: DLFVBJFMPXGRIB-UHFFFAOYAC
SMILES O=C(N)C
Properties
Chemical formula	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)
Solubility in water	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]
Magnetic susceptibility (χ)	−0.577 × 10−6 cm3 g−1
Refractive index (nD)	1.4274
Viscosity	2.052 cP (91 °C)
Structure
Crystal structure	trigonal
Thermochemistry[4]
Heat capacity (C)	91.3 J·mol−1·K−1
Std molarentropy (S⦵298)	115.0 J·mol−1·K−1
Std enthalpy offormation (ΔfH⦵298)	−317.0 kJ·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H351
Precautionary statements	P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)	3 1 1
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). Y verify (what is YN ?) Infobox references

Chemical compound

Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is an amide derived from ammonia and 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]

Production

[edit]

Laboratory scale

[edit]

Acetamide can be produced in the laboratory from ammonium acetate by dehydration:[9]

[NH4][CH3CO2] → CH3C(O)NH2 + H2O

Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone 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.

Industrial scale

[edit]

In a similar fashion to some laboratory methods, acetamide is produced by dehydrating ammonium acetate or via the hydration of acetonitrile, a byproduct of the production of acrylonitrile:[5]

CH3CN + H2O → CH3C(O)NH2

Uses

[edit]

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]

Occurrence

[edit]

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]

References

[edit]

1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 841. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
2. ^ a b c d The Merck Index, 14th Edition, 36
3. ^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 9781498754293.
4. ^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
5. ^ a b c Cheung, H.; Tanke, R. S.; Torrence, G. P. "Acetic Acid". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_045.pub2. ISBN 978-3527306732.
6. ^ Mindat: Naturally occurring acetamide
7. ^ Warr, L.N. (2021). "IMA-CNMNC approved mineral symbols". Mineralogical Magazine. 85 (3): 291–320. Bibcode:2021MinM...85..291W. doi:10.1180/mgm.2021.43. S2CID 235729616.
8. ^ Bats, Jan W.; Haberecht, Monika C.; Wagner, Matthias (2003). "A new refinement of the orthorhombic polymorph of acetamide". Acta Crystallographica Section E. 59 (10): o1483–o1485. doi:10.1107/S1600536803019494.
9. ^ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Organic Syntheses. 3: 3. doi:10.15227/orgsyn.003.0003; Collected Volumes, vol. 1, p. 3.
10. ^ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". J. Am. Chem. Soc. 61 (12): 3499–3502. doi:10.1021/ja01267a081.
11. ^ Stafford, O. F. (1933). "Acetamide as a Solvent". J. Am. Chem. Soc. 55 (10): 3987–3988. doi:10.1021/ja01337a011.
12. ^ Wagner, Frank S. (2002). Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons. doi:10.1002/0471238961.0103052023010714.a02.pub2. ISBN 9780471238966.
13. ^ Schwarz, G. (1945). "2,4-Dimethylthiazole". Organic Syntheses. 25: 35; Collected Volumes, vol. 3, p. 332.
14. ^ 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". Astrophys. J. 643 (1): L25–L28. Bibcode:2006ApJ...643L..25H. doi:10.1086/505110.
15. ^ Jordans, Frank (30 July 2015). "Philae probe finds evidence that comets can be cosmic labs". The Washington Post. Associated Press. Archived from the original on 23 December 2018. Retrieved 30 July 2015.
16. ^ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015.
17. ^ 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. PMID 26228139.
18. ^ "Acetamide". Mindat.org.
19. ^ "Acetamide" (PDF). Handbook of Mineralogy. RRUFF Project.

External links

[edit] Look up acetamide in Wiktionary, the free dictionary.

• International Chemical Safety Card 0233
• "Acetamide". Webmineral.org.

v t e Molecules detected in outer space
Molecules	Diatomic Aluminium monochloride Aluminium monofluoride Aluminium(II) oxide Argonium Carbon cation Carbon monophosphide Carbon monosulfide Carbon monoxide Cyano radical Diatomic carbon Fluoromethylidynium Helium hydride ion Hydrogen chloride Hydrogen fluoride Hydrogen (molecular) Hydroxyl radical Iron(II) oxide Magnesium monohydride Methylidyne radical Nitric oxide Nitrogen (molecular) Imidogen Sulfur mononitride Oxygen (molecular) Phosphorus monoxide Phosphorus mononitride Potassium chloride Silicon carbide Silicon monoxide Silicon monosulfide Sodium chloride Sodium iodide Sulfanyl Sulfur monoxide Titanium(II) oxide Triatomic Aluminium(I) hydroxide Aluminium isocyanide Amino radical Carbon dioxide Carbonyl sulfide CCP radical Chloronium Diazenylium Dicarbon monoxide Disilicon carbide Ethynyl radical Formyl radical Hydrogen cyanide (HCN) Hydrogen isocyanide (HNC) Hydrogen sulfide Hydroperoxyl Iron cyanide Isoformyl Magnesium cyanide Magnesium isocyanide Methylene N2H+ Nitrous oxide Nitroxyl Ozone Methylidynephosphane Potassium cyanide Trihydrogen cation Sodium cyanide Sodium hydroxide Silicon carbonitride c-Silicon dicarbide SiNC Sulfur dioxide Thioformyl Thioxoethenylidene Titanium dioxide Tricarbon Water Fouratoms Acetylene Ammonia Isocyanic acid Cyanoethynyl Formaldehyde Fulminic acid HCCN Hydrogen peroxide Hydromagnesium isocyanide Isocyanic acid Isothiocyanic acid Ketenyl Methylene amidogen Methyl cation Methyl radical Propynylidyne Protonated carbon dioxide Protonated hydrogen cyanide Silicon tricarbide Thioformaldehyde Tricarbon monoxide Tricarbon monosulfide Thiocyanic acid Fiveatoms Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster Sixatoms Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC4N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene Sevenatoms Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol Eightatoms Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein Nineatoms Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide Tenatomsor more Acetone Benzene Benzonitrile Buckminsterfullerene (C60, C60+, fullerene, buckyball) C70 fullerene Cyanodecapentayne Ethylene glycol Ethyl formate Methyl acetate Methyl-cyano-diacetylene Methyltriacetylene Propionaldehyde Butyronitrile Pyrimidine Heptatrienyl radical
Deuteratedmolecules	Ammonia Ammonium ion Formaldehyde Formyl radical Heavy water Hydrogen cyanide Hydrogen deuteride Hydrogen isocyanide Propyne N2D+ Trihydrogen cation
Unconfirmed	Anthracene Dihydroxyacetone Methoxyethane Glycine Graphene Hemolithin H2NCO+ Linear C5 Naphthalene cation Phosphine Pyrene Silylidyne
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