{{Chembox | Watchedfields = changed | verifiedrevid = 477238560 | ImageFileL1 = Acetamide skeletal.svg | ImageClassL1 = skin-invert-image | ImageFileR1 = Acetamide-3D-balls.png | ImageClassR1 = bg-transparent | PIN = Acetamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 841 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> | SystematicName = Ethanamide | OtherNames = Acetic acid amide<br>Acetylamine |Section1={{Chembox Identifiers | IUPHAR_ligand = 4661 | Abbreviations = | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 8XOE1JSO29 | InChIKey = DLFVBJFMPXGRIB-UHFFFAOYAC | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 16081 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = DLFVBJFMPXGRIB-UHFFFAOYSA-N | CASNo = 60-35-5 | CASNo_Ref = {{cascite|correct|CAS}} | EINECS = 200-473-5 | PubChem = 178 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 173 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB02736 | SMILES = O=C(N)C | InChI = 1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) | RTECS = AB4025000 | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 27856 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C06244 }} |Section2={{Chembox Properties | C=2 | H=5 | N=1 | O=1 | Appearance = colorless, hygroscopic solid | Odor = odorless <br> mouse-like with impurities | Density = 1.159 g cm<sup>−3</sup> | MeltingPtC = 79 to 81 | BoilingPtC = 221.2 | BoilingPt_notes = (decomposes) | Solubility = 2000 g L<sup>−1</sup><ref name=Merck>''The Merck Index'', 14th Edition, '''36'''</ref> | SolubleOther = ethanol 500 g L<sup>−1</sup><ref name=Merck/><br> pyridine 166.67 g L<sup>−1</sup><ref name=Merck/><br> soluble in chloroform, glycerol, benzene<ref name=Merck/> | Solvent = | pKa = 15.1 (25 °C, H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = CRC Press | isbn = 9781498754293 | pages=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref> | IsoelectricPt = | SpecRotation = | RefractIndex = 1.4274 | VaporPressure = 1.3 Pa | Viscosity = 2.052 cP (91 °C) | LogP = −1.26 | MagSus = −0.577 × 10<sup>−6</sup> cm<sup>3</sup> g<sup>−1</sup> }} |Section3={{Chembox Structure | CrystalStruct = trigonal | Coordination = | MolShape = | Dipole = }} | Section4 = {{Chembox Thermochemistry | Thermochemistry_ref = <ref name="crc">{{cite book |author1=John Rumble |title=CRC Handbook of Chemistry and Physics |date=June 18, 2018 |publisher=CRC Press |isbn=978-1138561632 |pages=5–3|edition=99th |language=English}}</ref> | HeatCapacity = 91.3 J·mol<sup>−1</sup>·K<sup>−1</sup> | Entropy = 115.0 J·mol<sup>−1</sup>·K<sup>−1</sup> | DeltaHform = −317.0 kJ·mol<sup>−1</sup> | DeltaGfree = | DeltaHcombust = | DeltaHfus = | DeltaHvap = | DeltaHsublim = | HHV = | LHV = }} |Section5={{Chembox Pharmacology | Bioavail = | Metabolism = | HalfLife = | Excretion = | Pregnancy_category = | AdminRoutes = }} |Section6={{Chembox Explosive | ShockSens = | FrictionSens = | DetonationV = | REFactor = }} |Section7={{Chembox Hazards | GHSPictograms = {{GHS08}} | GHSSignalWord = Warning | HPhrases = {{H-phrases|351}} | PPhrases = {{P-phrases|201|202|281|308+313|405|501}} | MainHazards = | NFPA-H = 3 | NFPA-F = 1 | NFPA-R = 1 | NFPA-S = - | FlashPtC = 126 | AutoignitionPtC = | ExploLimits = | PEL = | LD50 = 7000 mg kg<sup>−1</sup> (rat, oral) | ExternalSDS = [http://www.sigmaaldrich.com/MSDS/MSDS/DisplayMSDSPage.do?country=US&language=en&productNumber=A0500&brand=SIAL&PageToGoToURL=http%3A//www.sigmaaldrich.com/catalog/search%3Finterface%3DAll%26term%3Dacetamide%26lang%3Den%26region%3DUS%26focus%3Dproduct%26N%3D0%2B220003048%2B219853269%2B219853286%26mode%3Dmatch%2520partialmax External MSDS] }} |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = }} }}
'''Acetamide''' (systematic name: '''ethanamide''') is an organic compound with the formula CH<sub>3</sub>CONH<sub>2</sub>. It is an amide derived from ammonia and acetic acid. It finds some use as a plasticizer and as an industrial solvent.<ref name = ullmann/> 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 (CH<sub>3</sub>) groups either side of the carbonyl (CO), and urea which has two amide (NH<sub>2</sub>) groups in those locations. Acetamide is also a naturally occurring mineral<ref>[https://www.mindat.org/min-13.html Mindat: Naturally occurring acetamide]</ref> with the IMA symbol: Ace.<ref>{{Cite journal|last=Warr|first=L.N.|date=2021|title=IMA-CNMNC approved mineral symbols|journal=Mineralogical Magazine|volume=85|issue=3|pages=291–320|doi=10.1180/mgm.2021.43|bibcode=2021MinM...85..291W|s2cid=235729616|doi-access=free}}</ref>
==Production== [[File:CSD CIF ACEMID06.jpg|thumb|288 px|left|Structure of acetamide hydrogen-bonded dimer from X-ray crystallography. Selected distances: C-O: 1.243, C-N, 1.325, N---O, 2.925 Å. Color code: red = O, blue = N, gray = C, white = H.<ref>{{cite journal |doi=10.1107/S1600536803019494 |title=A new refinement of the orthorhombic polymorph of acetamide |date=2003 |last1=Bats |first1=Jan W. |last2=Haberecht |first2=Monika C. |last3=Wagner |first3=Matthias |journal=Acta Crystallographica Section E |volume=59 |issue=10 |pages=o1483–o1485 }}</ref>]]
===Laboratory scale=== Acetamide can be produced in the laboratory from ammonium acetate by dehydration:<ref>{{OrgSynth | author1 = Coleman, G. H. | author2 = Alvarado, A. M. | title = Acetamide | volume = 3 | pages = 3 | collvol = 1 | collvolpages = 3 | year = 1923 | prep = cv1p0003 | doi = 10.15227/orgsyn.003.0003}}</ref> : [NH<sub>4</sub>][CH<sub>3</sub>CO<sub>2</sub>] → CH<sub>3</sub>C(O)NH<sub>2</sub> + H<sub>2</sub>O
Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination.<ref>{{cite journal|last1=Schwoegler|first1=Edward J.|last2=Adkins|first2=Homer|author-link2=Homer Burton Adkins|title=Preparation of Certain Amines|journal=J. Am. Chem. Soc.|year=1939|volume=61|issue=12|pages=3499–3502|doi=10.1021/ja01267a081}}</ref>
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:<ref name = ullmann>{{ Ullmann | last1= Cheung |first1=H. |last2=Tanke |first2=R. S. |last3=Torrence |first3=G. P. | title = Acetic Acid | doi = 10.1002/14356007.a01_045.pub2}}</ref> : CH<sub>3</sub>CN + H<sub>2</sub>O → CH<sub>3</sub>C(O)NH<sub>2</sub>
==Uses== Acetamide is used as a plasticizer and an industrial solvent.<ref name="ullmann" /> 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.<ref>{{Cite journal|last=Stafford|first=O. F.|date=1933|title=Acetamide as a Solvent|journal=J. Am. Chem. Soc.|volume=55|issue=10|pages=3987–3988|doi=10.1021/ja01337a011}}</ref> Acetamide has uses in electrochemistry and the organic synthesis of pharmaceuticals, pesticides, and antioxidants for plastics.<ref>{{Cite book|last=Wagner|first=Frank S.|title=Kirk-Othmer Encyclopedia of Chemical Technology|publisher=John Wiley & Sons|year=2002|isbn=9780471238966|doi=10.1002/0471238961.0103052023010714.a02.pub2}}</ref> It is a precursor to thioacetamide.<ref>{{OrgSynth|author=Schwarz, G.|title=2,4-Dimethylthiazole|volume=25|pages=35|collvol=3|collvolpages=332|year=1945|prep=cv3p0332}}</ref>
==Occurrence== Acetamide has been detected near the center of the Milky Way galaxy.<ref>{{ cite journal |author1=Hollis, J. M. |author2=Lovas, F. J. |author3=Remijan, A. J. |author4=Jewell, P. R. |author5=Ilyushin, V. V. |author6=Kleiner, I. | title = Detection of Acetamide (CH<sub>3</sub>CONH<sub>2</sub>): The Largest Interstellar Molecule with a Peptide Bond | journal = Astrophys. J. | year = 2006 | volume = 643 | issue = 1 | pages = L25–L28 | doi = 10.1086/505110 | bibcode = 2006ApJ...643L..25H | doi-access = free }}</ref> 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<ref name="wapo20150730">{{cite news |url=https://www.washingtonpost.com/world/philae-probe-finds-evidence-that-comets-can-be-cosmic-labs/2015/07/30/63a2fc0e-36e5-11e5-ab7b-6416d97c73c2_story.html |archive-url=https://web.archive.org/web/20181223235109/https://www.washingtonpost.com/world/philae-probe-finds-evidence-that-comets-can-be-cosmic-labs/2015/07/30/63a2fc0e-36e5-11e5-ab7b-6416d97c73c2_story.html |url-status=dead |archive-date=23 December 2018 |title=Philae probe finds evidence that comets can be cosmic labs |newspaper=The Washington Post |agency=Associated Press |first=Frank |last=Jordans |date=30 July 2015 |access-date=30 July 2015}}</ref><ref name="esa20150730">{{cite web |url=http://www.esa.int/Our_Activities/Space_Science/Rosetta/Science_on_the_surface_of_a_comet |title=Science on the Surface of a Comet |publisher=European Space Agency |date=30 July 2015 |access-date=30 July 2015}}</ref><ref name="SCI-20150731">{{cite journal |last1=Bibring |first1=J.-P. |last2=Taylor |first2=M.G.G.T. |last3=Alexander |first3=C. |last4=Auster |first4=U. |last5=Biele |first5=J. |last6=Finzi |first6=A. Ercoli |last7=Goesmann |first7=F. |last8=Klingehoefer |first8=G. |last9=Kofman |first9=W. |last10=Mottola |first10=S. |last11=Seidenstiker |first11=K.J. |last12=Spohn |first12=T. |last13=Wright |first13=I. |title=Philae's First Days on the Comet - Introduction to Special Issue |date=31 July 2015 |journal=Science |volume=349 |number=6247 |page=493 |doi=10.1126/science.aac5116 |bibcode=2015Sci...349..493B |pmid=26228139|doi-access=free }}</ref> – 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.<ref>{{ cite web | url = http://www.mindat.org/min-13.html | title = Acetamide | publisher = Mindat.org }}</ref><ref>{{ cite web | url = http://rruff.geo.arizona.edu/doclib/hom/acetamide.pdf | title = Acetamide | work = Handbook of Mineralogy | publisher = RRUFF Project }}</ref>
==References== {{reflist}}
==External links== {{Wiktionary}} * {{ICSC|0233|02}} * {{cite web|url=http://www.webmineral.com/data/Acetamide.shtml#.YbXGi73MLIW|title=Acetamide|publisher=Webmineral.org}} {{Molecules detected in outer space}} {{Authority control}}
Category:Acetamides Category:IARC Group 2B carcinogens Category:Plasticizers Category:Organic minerals