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Acetamide - Wikipedia

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Acetamide

Names

Preferred IUPAC name

Acetamide^[1]

Systematic IUPAC name

Ethanamide

Other names

Acetic acid amide
Acetylamine

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

RTECS number

AB4025000

UNII

8XOE1JSO29^Y

CompTox Dashboard (EPA)

DTXSID7020005

InChI

InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)^Y
Key: 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 (pK_a)

15.1 (25 °C, H₂O)^[3]

Magnetic susceptibility (χ)

−0.577 × 10⁻⁶ cm³ g⁻¹

Refractive index (n_D)

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 molar
entropy (S^⦵₂₉₈)

115.0 J·mol⁻¹·K⁻¹

Std enthalpy of
formation (Δ_fH^⦵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)

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).

verify (what is ^YN ?)

Infobox references

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

Laboratory scale

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

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

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

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

^ "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.
^ ^a ^b ^c ^d The Merck Index, 14th Edition, 36
^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 9781498754293.
^ John Rumble (June 18, 2018). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
^ ^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.
^ Mindat: Naturally occurring acetamide
^ 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.
^ 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.
^ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Organic Syntheses. 3: 3. doi:10.15227/orgsyn.003.0003; Collected Volumes, vol. 1, p. 3.
^ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". J. Am. Chem. Soc. 61 (12): 3499–3502. doi:10.1021/ja01267a081.
^ Stafford, O. F. (1933). "Acetamide as a Solvent". J. Am. Chem. Soc. 55 (10): 3987–3988. doi:10.1021/ja01337a011.
^ Wagner, Frank S. (2002). Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons. doi:10.1002/0471238961.0103052023010714.a02.pub2. ISBN 9780471238966.
^ Schwarz, G. (1945). "2,4-Dimethylthiazole". Organic Syntheses. 25: 35; Collected Volumes, vol. 3, p. 332.
^ 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.
^ 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.
^ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015.
^ 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.
^ "Acetamide". Mindat.org.
^ "Acetamide" (PDF). Handbook of Mineralogy. RRUFF Project.

External links

Look up acetamide in Wiktionary, the free dictionary.

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

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
Four atoms	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
Five atoms	Ammonium ion Butadiynyl Carbodiimide Cyanamide Cyanoacetylene Cyanoformaldehyde Cyanomethyl Cyclopropenylidene Formic acid Isocyanoacetylene Ketene Methane Methoxy radical Methylenimine Propadienylidene Protonated formaldehyde Silane Silicon-carbide cluster
Six atoms	Acetonitrile Cyanobutadiynyl radical E-Cyanomethanimine Cyclopropenone Diacetylene Ethylene Formamide HC₄N Ketenimine Methanethiol Methanol Methyl isocyanide Pentynylidyne Propynal Protonated cyanoacetylene
Seven atoms	Acetaldehyde Acrylonitrile Vinyl cyanide Cyanodiacetylene Ethylene oxide Glycolonitrile Hexatriynyl radical Propyne Methylamine Methyl isocyanate Vinyl alcohol
Eight atoms	Acetic acid Aminoacetonitrile Cyanoallene Ethanimine Glycolaldehyde Hexapentaenylidene Methylcyanoacetylene Methyl formate Acrolein
Nine atoms	Acetamide Cyanohexatriyne Dimethyl ether Ethanol Methyldiacetylene Octatetraynyl radical Propene Ethanethiol Propionitrile N-Methylformamide
Ten atoms or 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

Deuterated
molecules

Unconfirmed

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