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{{chembox {{Chembox
| Watchedfields = changed
| verifiedrevid = 443363765
| verifiedrevid = 477238560
| ImageFileL1=Acetamide skeletal.svg
| ImageFileL1 = Acetamide skeletal.svg
| ImageSizeL1=100px
| ImageFileR1=Acetamide-3D-balls.png | ImageFileR1 = Acetamide-3D-balls.png
| 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>
| ImageSizeR1=120px
| IUPACName=Acetamide<br />Ethanamide | SystematicName = Ethanamide
| OtherNames = acetic acid amide | OtherNames = Acetic acid amide<br>Acetylamine
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| IUPHAR_ligand = 4661
| Abbreviations = | Abbreviations =
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
Line 18: Line 19:
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = DLFVBJFMPXGRIB-UHFFFAOYSA-N | StdInChIKey = DLFVBJFMPXGRIB-UHFFFAOYSA-N
| CASNo=60-35-5 | CASNo = 60-35-5
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| EINECS = | EINECS = 200-473-5
| PubChem = 178 | PubChem = 178
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
Line 28: Line 29:
| SMILES = O=C(N)C | SMILES = O=C(N)C
| InChI = 1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) | InChI = 1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
| RTECS = | RTECS = AB4025000
| MeSHName = | MeSHName =
| ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI_Ref = {{ebicite|correct|EBI}}
Line 34: Line 35:
| KEGG_Ref = {{keggcite|correct|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C06244 | KEGG = C06244
}}
| ATCCode = }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C=2|H=5|N=1|O=1 | C=2 | H=5 | N=1 | O=1
| Appearance = colorless, ] solid
| MolarMass=
| Odor = odorless <br> mouse-like with impurities
| Appearance =
| Density=1.16 g/cm³ | Density = 1.159&nbsp;g&nbsp;cm<sup>&minus;3</sup>
| MeltingPtCL=79 | MeltingPtC = 79 to 81
| BoilingPtC = 221.2
| MeltingPtCH=81
| BoilingPt_notes = (decomposes)
| BoilingPtC=222
| Solubility=2 g/mL<ref>'']'', 11th Edition, '''36'''</ref> | Solubility = 2000&nbsp;g&nbsp;L<sup>&minus;1</sup><ref name=Merck>'']'', 14th Edition, '''36'''</ref>
| SolubleOther = ] 500&nbsp;g&nbsp;L<sup>&minus;1</sup><ref name=Merck/><br> ] 166.67&nbsp;g&nbsp;L<sup>&minus;1</sup><ref name=Merck/><br> soluble in ], ], ]<ref name=Merck/>
| SolubleOther =
| Solvent = Water | 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 = ] | isbn = 9781498754293 | pages=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref>
| pKa =
| pKb =
| IsoelectricPt = | IsoelectricPt =
| SpecRotation = | SpecRotation =
| RefractIndex = | RefractIndex = 1.4274
| VaporPressure = 1.3&nbsp;Pa
| Viscosity =
| Viscosity = 2.052&nbsp;cP (91&nbsp;°C)
| Dipole = }}
| LogP = &minus;1.26
| Section3 = {{Chembox Structure
| MagSus = &minus;0.577&nbsp;×&nbsp;10<sup>−6</sup>&nbsp;cm<sup>3</sup>&nbsp;g<sup>&minus;1</sup>
| CrystalStruct =
}}
|Section3={{Chembox Structure
| CrystalStruct = trigonal
| Coordination = | Coordination =
| MolShape = | MolShape =
| Dipole = }} | Dipole =
}}
| Section4 = {{Chembox Thermochemistry | 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>
| DeltaHf =
| HeatCapacity = 91.3&nbsp;J·mol<sup>−1</sup>·K<sup>−1</sup>
| DeltaHc =
| Entropy = 115.0&nbsp;J·mol<sup>−1</sup>·K<sup>−1</sup>
| Entropy =
| DeltaHform = −317.0&nbsp;kJ·mol<sup>−1</sup>
| HeatCapacity = }}
| DeltaGfree =
| Section5 = {{Chembox Pharmacology
| DeltaHcombust =
| DeltaHfus =
| DeltaHvap =
| DeltaHsublim =
| HHV =
| LHV =
}}
|Section5={{Chembox Pharmacology
| Bioavail = | Bioavail =
| Metabolism = | Metabolism =
| HalfLife = | HalfLife =
| Excretion = | Excretion =
| Pregnancy_category =
| PregCat =
| AdminRoutes = }} | AdminRoutes =
}}
| Section6 = {{Chembox Explosive |Section6={{Chembox Explosive
| ShockSens = | ShockSens =
| FrictionSens = | FrictionSens =
| ExplosiveV = | DetonationV =
| REFactor = }} | REFactor =
}}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| GHSPictograms = {{GHS08}}
| ExternalMSDS =
| GHSSignalWord = Warning
| EUClass = Harmful ('''Xn''')<br />{{Carc3}}
| HPhrases = {{H-phrases|351}}
| EUIndex = 616-022-00-4
| PPhrases = {{P-phrases|201|202|281|308+313|405|501}}
| MainHazards = | MainHazards =
| NFPA-H = 3 | NFPA-H = 3
| NFPA-F = 1 | NFPA-F = 1
| NFPA-R = 1 | NFPA-R = 1
| NFPA-O = &nbsp; | NFPA-S = -
| RPhrases = {{R40}} | FlashPtC = 126
| AutoignitionPtC =
| SPhrases = {{S2}} {{S36/37}}
| RSPhrases =
| FlashPt =
| Autoignition =
| ExploLimits = | ExploLimits =
| PEL = | PEL =
| LD50 = 7000&nbsp;mg&nbsp;kg<sup>&minus;1</sup> (rat, oral)
| ExternalMSDS = }}
| ExternalSDS =
| Section8 = {{Chembox Related
}}
|Section8={{Chembox Related
| OtherAnions = | OtherAnions =
| OtherCations = | OtherCations =
| OtherFunctn = | OtherFunction =
| OtherFunction_label =
| Function =
| OtherCpds = }} | OtherCompounds =
}}
}} }}


'''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. '''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>


==Production and use== ==Production==
]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>]]
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>
: CH<sub>3</sub>COONH<sub>4</sub> → CH<sub>3</sub>C(O)NH<sub>2</sub> + H<sub>2</sub>O


===Laboratory scale===
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>
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>
: → CH<sub>3</sub>C(O)NH<sub>2</sub> + H<sub>2</sub>O

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>

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.

===Industrial scale===
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>
: CH<sub>3</sub>CN + H<sub>2</sub>O → CH<sub>3</sub>C(O)NH<sub>2</sub> : 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 ] 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>


==Occurrence== ==Occurrence==
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.
Acetamide has been detected near the center of the ] galaxy.<ref>{{cite journal
| author=J. M. Hollis, F. J. Lovas, Anthony J. Remijan, P. R. Jewell, V. V. Ilyushin, and I. Kleiner
| title=Detection of Acetamide (CH3CONH2): The Largest Interstellar Molecule with a Peptide Bond
| journal=The Astrophysical Journal
| year=2006
| volume=643
| issue=2
| pages=L25–L28
| doi=10.1086/505110
| 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.


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 &ndash; 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> &ndash; 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>, Mindat.org</ref><ref></ref>


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>
==Safety==
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>


==References== ==References==
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==External links== ==External links==
{{Wiktionary}}
* {{ICSC|0233|02}} * {{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}}


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Latest revision as of 18:53, 20 October 2024

Acetamide
Names
Preferred IUPAC name Acetamide
Systematic IUPAC name Ethanamide
Other names Acetic acid amide
Acetylamine
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.430 Edit this at Wikidata
EC Number
  • 200-473-5
IUPHAR/BPS
KEGG
PubChem CID
RTECS number
  • AB4025000
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)Key: DLFVBJFMPXGRIB-UHFFFAOYSA-N
  • 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
Appearance colorless, hygroscopic solid
Odor odorless
mouse-like with impurities
Density 1.159 g cm
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
Solubility ethanol 500 g L
pyridine 166.67 g L
soluble in chloroform, glycerol, benzene
log P −1.26
Vapor pressure 1.3 Pa
Acidity (pKa) 15.1 (25 °C, H2O)
Magnetic susceptibility (χ) −0.577 × 10 cm g
Refractive index (nD) 1.4274
Viscosity 2.052 cP (91 °C)
Structure
Crystal structure trigonal
Thermochemistry
Heat capacity (C) 91.3 J·mol·K
Std molar
entropy
(S298)
115.0 J·mol·K
Std enthalpy of
formation
fH298)
−317.0 kJ·mol
Hazards
GHS labelling:
Pictograms GHS08: Health hazard
Signal word Warning
Hazard statements H351
Precautionary statements P201, P202, P281, P308+P313, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
3 1 1
Flash point 126 °C (259 °F; 399 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose) 7000 mg kg (rat, oral)
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkverify (what is  ?) 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. 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 with the IMA symbol: Ace.

Production

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.

Laboratory scale

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

→ CH3C(O)NH2 + H2O

Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination.

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:

CH3CN + H2O → CH3C(O)NH2

Uses

Acetamide is used as a plasticizer and an industrial solvent. 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. Acetamide has uses in electrochemistry and the organic synthesis of pharmaceuticals, pesticides, and antioxidants for plastics. It is a precursor to thioacetamide.

Occurrence

Acetamide has been detected near the center of the Milky Way galaxy. 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 – 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.

References

  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. ^ 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. ^ 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.
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  18. "Acetamide". Mindat.org.
  19. "Acetamide" (PDF). Handbook of Mineralogy. RRUFF Project.

External links

Molecules detected in outer space
Molecules
Diatomic







Triatomic
Four
atoms
Five
atoms
Six
atoms
Seven
atoms
Eight
atoms
Nine
atoms
Ten
atoms
or more
Deuterated
molecules
Unconfirmed
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