| Revision as of 16:01, 6 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').← Previous edit |
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{{chembox |
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{{Chembox |
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| verifiedrevid = 408940143 |
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| verifiedrevid = 477238560 |
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| ImageFileL1=Acetamide skeletal.svg |
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| ImageFileL1 = Acetamide skeletal.svg |
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| ImageFileR1 = Acetamide-3D-balls.png |
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| ImageSizeL1=100px |
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| PIN = Acetamide<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 841 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter }}</ref> |
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| ImageFileR1=Acetamide-3D-balls.png |
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| SystematicName = Ethanamide |
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| ImageSizeR1=120px |
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| OtherNames = Acetic acid amide<br>Acetylamine |
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| IUPACName=Acetamide<br />Ethanamide |
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|Section1={{Chembox Identifiers |
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| OtherNames = acetic acid amide |
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| IUPHAR_ligand = 4661 |
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| Section1 = {{Chembox Identifiers |
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| Abbreviations = |
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| Abbreviations = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DLFVBJFMPXGRIB-UHFFFAOYSA-N |
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| StdInChIKey = DLFVBJFMPXGRIB-UHFFFAOYSA-N |
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| CASNo=60-35-5 |
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| CASNo = 60-35-5 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| EINECS = |
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| EINECS = 200-473-5 |
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| PubChem = 178 |
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| PubChem = 178 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 173 |
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| ChemSpiderID = 173 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB02736 |
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| DrugBank = DB02736 |
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| SMILES = O=C(N)C |
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| SMILES = O=C(N)C |
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| InChI = 1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) |
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| InChI = 1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) |
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| RTECS = |
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| RTECS = AB4025000 |
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| MeSHName = |
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| MeSHName = |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27856 |
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| ChEBI = 27856 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = C06244 |
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| KEGG = C06244 |
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}} |
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| ATCCode = }} |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=2|H=5|N=1|O=1 |
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| C=2 | H=5 | N=1 | O=1 |
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| Appearance = colorless, ] solid |
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| MolarMass= |
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| Odor = odorless <br> mouse-like with impurities |
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| Appearance = |
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| Density=1.16 g/cm³ |
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| Density = 1.159 g cm<sup>−3</sup> |
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| MeltingPtCL=79 |
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| MeltingPtC = 79 to 81 |
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| BoilingPtC = 221.2 |
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| MeltingPtCH=81 |
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| BoilingPt_notes = (decomposes) |
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| BoilingPtC=222 |
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| Solubility=2 g/mL<ref>'']'', 11th Edition, '''36'''</ref> |
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| Solubility = 2000 g L<sup>−1</sup><ref name=Merck>'']'', 14th Edition, '''36'''</ref> |
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| SolubleOther = ] 500 g L<sup>−1</sup><ref name=Merck/><br> ] 166.67 g L<sup>−1</sup><ref name=Merck/><br> soluble in ], ], ]<ref name=Merck/> |
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| SolubleOther = |
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| Solvent = Water |
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| Solvent = |
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| 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 = ] | isbn = 9781498754293 | pages=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref> |
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| pKa = |
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| pKb = |
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| IsoelectricPt = |
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| IsoelectricPt = |
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| SpecRotation = |
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| SpecRotation = |
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| RefractIndex = |
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| RefractIndex = 1.4274 |
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| VaporPressure = 1.3 Pa |
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| Viscosity = |
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| Viscosity = 2.052 cP (91 °C) |
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| Dipole = }} |
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| LogP = −1.26 |
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| Section3 = {{Chembox Structure |
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| MagSus = −0.577 × 10<sup>−6</sup> cm<sup>3</sup> g<sup>−1</sup> |
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}} |
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|Section3={{Chembox Structure |
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| CrystalStruct = trigonal |
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| Coordination = |
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}} |
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| Section4 = {{Chembox Thermochemistry |
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| Section4 = {{Chembox Thermochemistry |
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| 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> |
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| DeltaHf = |
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| HeatCapacity = 91.3 J·mol<sup>−1</sup>·K<sup>−1</sup> |
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| DeltaHc = |
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| Entropy = 115.0 J·mol<sup>−1</sup>·K<sup>−1</sup> |
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| Entropy = |
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| DeltaHform = −317.0 kJ·mol<sup>−1</sup> |
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| HeatCapacity = }} |
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| Section5 = {{Chembox Pharmacology |
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|Section5={{Chembox Pharmacology |
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| Section6 = {{Chembox Explosive |
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| Section7 = {{Chembox Hazards |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS08}} |
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| GHSSignalWord = Warning |
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| EUClass = Harmful ('''Xn''')<br />{{Carc3}} |
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| HPhrases = {{H-phrases|351}} |
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| EUIndex = 616-022-00-4 |
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| PPhrases = {{P-phrases|201|202|281|308+313|405|501}} |
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| MainHazards = |
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| NFPA-H = 3 |
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| NFPA-H = 3 |
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| NFPA-F = 1 |
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| NFPA-F = 1 |
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| NFPA-R = 1 |
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| NFPA-R = 1 |
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| NFPA-O = |
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| NFPA-S = - |
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| RPhrases = {{R40}} |
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| FlashPtC = 126 |
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| SPhrases = {{S2}} {{S36/37}} |
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| LD50 = 7000 mg kg<sup>−1</sup> (rat, oral) |
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| Section8 = {{Chembox Related |
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'''Acetamide''' (]: '''ethanamide''') is an ] with the formula CH<sub>3</sub>CONH<sub>2</sub>. It is the simplest ] derived from ]. It finds some use as a ] and as an industrial solvent. The related compound ] (DMA) is more widely used, but it is not prepared from acetamide. |
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'''Acetamide''' (systematic name: '''ethanamide''') is an ] with the formula CH<sub>3</sub>CONH<sub>2</sub>. It is an ] derived from ] and ]. It finds some use as a ] and as an industrial solvent.<ref name = ullmann/> The related compound ] (DMA) is more widely used, but it is not prepared from acetamide. Acetamide can be considered an intermediate between ], which has two methyl (CH<sub>3</sub>) groups either side of the carbonyl (CO), and ] which has two amide (NH<sub>2</sub>) groups in those locations. Acetamide is also a naturally occurring mineral<ref></ref> with the ] ]: 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> |
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==Production and use== |
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==Production== |
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]ed dimer from ]. 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>]] |
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Acetamide can be produced in the laboratory by ] ]:<ref>{{OrgSynth | collvol = 1 | collvolpages = 3 | year = 1941 | prep = cv1p003 | author = G. H. Coleman and A. M. Alvarado | title = Acetamide}}</ref> |
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: CH<sub>3</sub>COONH<sub>4</sub> → CH<sub>3</sub>C(O)NH<sub>2</sub> + H<sub>2</sub>O |
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===Laboratory scale=== |
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In industry, it is typically obtained by ] of ], a byproduct of the production of ]:<ref>Hosea Cheung, Robin S. Tanke, G. Paul Torrence “Acetic Acid” in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. {{DOI|10.1002/14356007.a01_045}}</ref> |
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Acetamide can be produced in the laboratory from ] by ]:<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> |
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: → CH<sub>3</sub>C(O)NH<sub>2</sub> + H<sub>2</sub>O |
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Alternatively acetamide can be obtained in excellent yield via ] of ] under conditions commonly used in ].<ref>{{cite journal|last1=Schwoegler|first1=Edward J.|last2=Adkins|first2=Homer|author-link2=Homer Burton Adkins|title=Preparation of Certain Amines|journal=]|year=1939|volume=61|issue=12|pages=3499–3502|doi=10.1021/ja01267a081}}</ref> |
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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 ]. Yield is typically low (up to 35%), and the acetamide made this way is generated as a salt with HCl. |
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===Industrial scale=== |
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In a similar fashion to some laboratory methods, acetamide is produced by ] ammonium acetate or via the ] of ], a byproduct of the production of ]:<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> |
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: CH<sub>3</sub>CN + H<sub>2</sub>O → CH<sub>3</sub>C(O)NH<sub>2</sub> |
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: CH<sub>3</sub>CN + H<sub>2</sub>O → CH<sub>3</sub>C(O)NH<sub>2</sub> |
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==Uses== |
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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 ] is higher than most organic solvents, allowing it to dissolve ]s with solubilities closely analogous to that of water.<ref>{{Cite journal|last=Stafford|first=O. F.|date=1933|title=Acetamide as a Solvent|journal=]|volume=55|issue=10|pages=3987–3988|doi=10.1021/ja01337a011}}</ref> Acetamide has uses in electrochemistry and the ] 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 ].<ref>{{OrgSynth|author=Schwarz, G.|title=2,4-Dimethylthiazole|volume=25|pages=35|collvol=3|collvolpages=332|year=1945|prep=cv3p0332}}</ref> |
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==Occurrence== |
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==Occurrence== |
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Acetamide has been detected near the center of the ] 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 = ] | 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 ]) can form in space. |
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Acetamide has been detected near the center of the ] galaxy.<ref>{{cite journal |
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| author=J. M. Hollis, F. J. Lovas, Anthony J. Remijan, P. R. Jewell, V. V. Ilyushin, and I. Kleiner |
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| title=Detection of Acetamide (CH3CONH2): The Largest Interstellar Molecule with a Peptide Bond |
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| journal=The Astrophysical Journal |
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| year=2006 |
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| volume=643 |
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| issue=2 |
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| pages=L25–L28 |
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| doi=10.1086/505110 |
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| bibcode=2006ApJ...643L..25H}}</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 ]) can form in space. |
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On 30 July 2015, scientists reported that upon the first touchdown of the '']'' lander on ] ]{{'s}} surface, measurements by the COSAC and Ptolemy instruments revealed sixteen ]s, four of which – acetamide, ], ], and ]<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=] |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. |
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In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.<ref>, Mindat.org</ref><ref></ref> |
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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> |
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==Safety== |
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In the U.S., the ] added acetamide to the list of compounds known to cause cancer or reproductive toxicity, for the purposes of ].<ref>, ]</ref> |
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==References== |
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==References== |
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==External links== |
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==External links== |
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{{Wiktionary}} |
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* {{ICSC|0233|02}} |
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* {{ICSC|0233|02}} |
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* {{cite web|url=http://www.webmineral.com/data/Acetamide.shtml#.YbXGi73MLIW|title=Acetamide|publisher=Webmineral.org}} |
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{{Molecules detected in outer space}} |
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{{Authority control}} |
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