Acetamide

Acetamide  |  |

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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

EC Number |

* 200-473-5

IUPHAR/BPS

* 4661

KEGG |

* C06244 Y

PubChem CID

* 178

RTECS number |

* AB4025000

UNII |

* 8XOE1JSO29 Y

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

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[3]

Heat capacity (C)

| 91.3 J·mol−1·K−1

Std molar
entropy (S ~~o~~ 298)

| 115.0 J·mol−1·K−1

Std enthalpy of
formation (ΔfH⦵298)

| −317.0 kJ·mol−1
Hazards
Safety data sheet | External MSDS
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H351

GHS precautionary statements

| P201, P202, P281, P308+313, 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)

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

Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent.[4] 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[5] with the IMA symbol: Ace.[6]

## Contents

* 1 Production
* 1.1 Laboratory scale
* 1.2 Industrial scale
* 2 Uses
* 3 Occurrence
* 4 References
* 5 External links

## 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.[7]

### Laboratory scale

Acetamide can be produced in the laboratory from ammonium acetate by dehydration:[8]

[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.[9]

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:[4]

CH3CN + H2O → CH3C(O)NH2

## Uses

Acetamide is used as a plasticizer and an industrial solvent.[4] 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.[10] Acetamide has uses in electrochemistry and the organic synthesis of pharmaceuticals, pesticides, and antioxidants for plastics.[11] It is a precursor to thioacetamide.[12]

## Occurrence

Acetamide has been detected near the center of the Milky Way galaxy.[13] 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[14][15][16] - 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.[17][18]

## 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. ↑ 2.0 2.1 2.2 2.3 The Merck Index, 14th Edition, 36
3. ↑ John Rumble (June 18, 2018) (in English). CRC Handbook of Chemistry and Physics (99th ed.). CRC Press. pp. 5–3. ISBN 978-1138561632.
4. ↑ 4.0 4.1 4.2 "Ullmann's Encyclopedia of Industrial Chemistry". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a01_045.pub2.
5. ↑ Mindat: Naturally occurring acetamide
6. ↑ Warr, L.N. (2021). "IMA-CNMNC approved mineral symbols". Mineralogical Magazine 85 (3): 291–320. doi:10.1180/mgm.2021.43. Bibcode: 2021MinM...85..291W.
7. ↑ 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.
8. ↑ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide". Organic Syntheses 3: 3. doi:10.15227/orgsyn.003.0003. http://www.orgsyn.org/demo.aspx?prep=cv1p0003. ;  Collective Volume, 1, pp. 3
9. ↑ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". J. Am. Chem. Soc. 61 (12): 3499–3502. doi:10.1021/ja01267a081.
10. ↑ Stafford, O. F. (1933). "Acetamide as a Solvent". J. Am. Chem. Soc. 55 (10): 3987–3988. doi:10.1021/ja01337a011.
11. ↑ Wagner, Frank S. (2002). Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons. doi:10.1002/0471238961.0103052023010714.a02.pub2. ISBN 9780471238966.
12. ↑ Schwarz, G. (1945). "2,4-Dimethylthiazole". Organic Syntheses 25: 35. http://www.orgsyn.org/demo.aspx?prep=cv3p0332. ;  Collective Volume, 3, pp. 332
13. ↑ 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. doi:10.1086/505110. Bibcode: 2006ApJ...643L..25H.
14. ↑ Jordans, Frank (30 July 2015). "Philae probe finds evidence that comets can be cosmic labs". The Washington Post. Associated Press. 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.
15. ↑ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. http://www.esa.int/Our_Activities/Space_Science/Rosetta/Science_on_the_surface_of_a_comet.
16. ↑ Bibring, J.-P.; Taylor, M.G.G.T.; Alexander, C.; Auster, U.; Biele, J.; Finzi, A. Ercoli; Goesmann, F.; Klingehoefer, G. et al. (31 July 2015). "Philae's First Days on the Comet - Introduction to Special Issue". Science 349 (6247): 493. doi:10.1126/science.aac5116. PMID 26228139. Bibcode: 2015Sci...349..493B.
17. ↑ "Acetamide". Mindat.org. http://www.mindat.org/min-13.html.
18. ↑ "Acetamide". Handbook of Mineralogy. RRUFF Project. http://rruff.geo.arizona.edu/doclib/hom/acetamide.pdf.

## External links

* International Chemical Safety Card 0233
* "Acetamide". Webmineral.org. http://www.webmineral.com/data/Acetamide.shtml#.YbXGi73MLIW.

* v
* t
* e

Molecules detected in outer space

Molecules|

| Diatomic|

* Aluminium monochloride
* Aluminium monofluoride
* Aluminium monoxide
* Argonium
* Carbon monophosphide
* Carbon monosulfide
* Carbon monoxide
* Carborundum
* Cyanogen radical
* Diatomic carbon
* Fluoromethylidynium
* Helium hydride ion
* Hydrogen chloride
* Hydrogen fluoride
* Hydrogen (molecular)
* Hydroxyl radical
* Iron(II) oxide
* Magnesium monohydride cation
* Methylidyne radical
* Nitric oxide
* Nitrogen (molecular)
* Nitrogen monohydride
* Nitrogen sulfide
* Oxygen (molecular)
* Phosphorus monoxide
* Phosphorus mononitride
* Potassium chloride
* Silicon carbide
* Silicon mononitride
* Silicon monoxide
* Silicon monosulfide
* Sodium chloride
* Sodium iodide
* Sulfur monohydride
* Sulfur monoxide
* Titanium oxide

|
|

Triatomic|

* Aluminium 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 radical
* N2H+
* Nitrous oxide
* Nitroxyl
* Ozone
* Phosphaethyne
* Potassium cyanide
* Protonated molecular hydrogen
* Sodium cyanide
* Sodium hydroxide
* Silicon carbonitride
* c-Silicon dicarbide
* SiNC
* Sulfur dioxide
* Thioformyl
* Thioxoethenylidene
* Titanium dioxide
* Tricarbon
* Water

Four
atoms|

* Acetylene
* Ammonia
* Cyanic acid
* Cyanoethynyl
* Cyclopropynylidyne
* Formaldehyde
* Fulminic acid
* HCCN
* Hydrogen peroxide
* Hydromagnesium isocyanide
* Isocyanic acid
* Isothiocyanic acid
* Ketenyl
* Methylene amidogen
* Methyl radical
* Propynylidyne
* Protonated carbon dioxide
* Protonated hydrogen cyanide
* Silicon tricarbide
* Thioformaldehyde
* Tricarbon monoxide
* Tricarbon sulfide
* Thiocyanic acid

Five
atoms|

* Ammonium ion
* Butadiynyl
* Carbodiimide
* Cyanamide
* Cyanoacetylene
* Cyanoformaldehyde
* Cyanomethyl
* Cyclopropenylidene
* Formic acid
* Isocyanoacetylene
* Ketene
* Methane
* Methoxy radical
* Methylenimine
* Propadienylidene
* Protonated formaldehyde
* 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
* Methylacetylene
* Methylamine
* Methyl isocyanate
* Vinyl alcohol

Eight
atoms|

* Acetic acid
* Aminoacetonitrile
* Cyanoallene
* Ethanimine
* Glycolaldehyde
* Heptatrienyl radical
* Hexapentaenylidene
* Methylcyanoacetylene
* Methyl formate
* Propenal

Nine
atoms|

* Acetamide
* Cyanohexatriyne
* Cyanotriacetylene
* Dimethyl ether
* Ethanol
* Methyldiacetylene
* Octatetraynyl radical
* Propene
* Propionitrile

Ten
atoms
or more|

* Acetone
* Benzene
* Benzonitrile
* Buckminsterfullerene (C60, C60+, fullerene, buckyball)
* C70 fullerene
* Cyanodecapentayne
* Cyanopentaacetylene
* Cyanotetra-acetylene
* Ethylene glycol
* Ethyl formate
* Methyl acetate
* Methyl-cyano-diacetylene
* Methyltriacetylene
* Propanal
* n-Propyl cyanide
* Pyrimidine

Deuterated
molecules|

* Ammonia
* Ammonium ion
* Formaldehyde
* Formyl radical
* Heavy water
* Hydrogen cyanide
* Hydrogen deuteride
* Hydrogen isocyanide
* Methylacetylene
* N2D+
* Trihydrogen cation

Unconfirmed|

* Anthracene
* Dihydroxyacetone
* Ethyl methyl ether
* Glycine
* Graphene
* H2NCO+
* Linear C5
* Naphthalene cation
* Phosphine
* Pyrene
* Silylidine

Related|

* Abiogenesis
* Astrobiology
* Astrochemistry
* Atomic and molecular astrophysics
* Chemical formula
* Circumstellar envelope
* Cosmic dust
* Cosmic ray
* Cosmochemistry
* Diffuse interstellar band
* Earliest known life forms
* Extraterrestrial life
* Extraterrestrial liquid water
* Forbidden mechanism
* Homochirality
* Intergalactic dust
* Interplanetary medium
* Interstellar medium
* Photodissociation region
* Iron–sulfur world theory
* Kerogen
* Molecules in stars
* Nexus for Exoplanet System Science
* Organic compound
* Outer space
* PAH world hypothesis
* Panspermia
* Polycyclic aromatic hydrocarbon (PAH)
* RNA world hypothesis
* Spectroscopy
* Tholin

* Category:Astrochemistry
*   *   *

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