Acetamide

Acetamide

Names
IUPAC names Acetamide Ethanamide
Other names acetic acid amide
Identifiers
CAS Registry Number	Y
ChEBI	Y
ChEMBL	Y
ChemSpider	Y
DrugBank	Y
EC number	200-473-5
InChI InChI=1S/C2H5NO/c1-2(3)4/h1H3,(H2,3,4) Y Key: DLFVBJFMPXGRIB-UHFFFAOYSA-N Y InChI=1/C2H5NH2/c1-2(3)4/h1H3,(H2,3,4) Key: DLFVBJFMPXGRIB-UHFFFAOYAC
IUPHAR/BPS
Jmol-3D images	Image
KEGG	Y
PubChem
RTECS number	AB4025000
SMILES O=C(N)C
UNII	Y
Properties
Chemical formula	C2H5NO
Molar mass	59.07 g·mol−1
Appearance	colorless, hygroscopic
Odor	odorless mouse-like with impurities
Density	1.159 g/cm3
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[1]
Solubility	ethanol 500 g L−1[1] pyridine 166.67 g L−1[1] soluble in chloroform, glycerol, benzene[1]
log P	-1.26
Vapor pressure	1.3 Pa
Acidity (pKa)	16.5
Refractive index (nD)	1.4274
Viscosity	2.052 cP (91 °C)
Structure
Crystal structure	trigonal
Hazards
Safety data sheet	External MSDS
EU classification (DSD)	Harmful (Xn) Carc. Cat. 3
R-phrases	R40
S-phrases	(S2) S36/37
NFPA 704	1 3 1
Flash point	126 °C (259 °F; 399 K)
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	700 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y  (: Y/N?)

Acetamide (amide derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent.^[2] The related compound N,N-dimethylacetamide (DMA) is more widely used, but it is not prepared from acetamide.

Production

Laboratory scale

Acetamide can be produced in the laboratory by dehydrating ammonium acetate:^[3]

CH₃COONH₄ → CH₃C(O)NH₂ + H₂O

Alternatively acetamide can be obtained in excellent yield via ammonolysis of acetylacetone under conditions commonly used in reductive amination.^[4]

Industrial scale

In a similar fashion to some laboratory methods, acetamide is produced dehydrating ammonium acetate or via the hydrolysis of acetonitrile, a byproduct of the production of acrylonitrile:^[2]

CH₃CN + H₂O → CH₃C(O)NH₂

Use

• A precursor to thioacetamide

Occurrence

Acetamide has been detected near the center of the Earth) can form in space.

On 30 July 2015, scientists reported that upon the first touchdown of the acetone, methyl isocyanate and propionaldehyde.^[6][7][8]

In addition, acetamide is found infrequently on burning coal dumps, as a mineral of the same name.^[9][10]

Acetamide crystal structure

References

1. ^ ^{a b c d} The Merck Index, 14th Edition, 36
2. ^ ^{a b} "Acetic Acid",  
3. ^ Coleman, G. H.; Alvarado, A. M. (1923). "Acetamide".  
4. ^ Schwoegler, Edward J.; Adkins, Homer (1939). "Preparation of Certain Amines". Journal of the American Chemical Society 61 (12): 3499–3502.  
5. ^ Hollis, J. M.; Lovas, F. J.; Remijan, A. J.; Jewell, P. R.; Ilyushin, V. V.; Kleiner, I. (2006). ): The Largest Interstellar Molecule with a Peptide Bond"₂CONH₃"Detection of Acetamide (CH (pdf). The Astrophysical Journal 643 (1): L25–L28.  
6. ^ Jordans, Frank (30 July 2015). "Philae probe finds evidence that comets can be cosmic labs". The Washington Post. Associated Press. Retrieved 30 July 2015. 
7. ^ "Science on the Surface of a Comet". European Space Agency. 30 July 2015. Retrieved 30 July 2015. 
8. ^ 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".  
9. ^ "Acetamide". Mindat.org. 
10. ^ "Acetamide" (pdf). Handbook of Mineralogy. RRUFF Project. 

External links

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

Molecules detected in outer space Molecules Diatomic Aluminium monochloride Aluminium monofluoride Aluminium monoxide Argon hydride Carbon monophosphide Carbon monosulfide Carbon monoxide Carborundum Cyanogen radical Diatomic carbon Fluoromethylidynium 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 Hydrogen isocyanide (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 Silicon naphthalocyanine 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 Cyanodiacetylene Ethylene oxide 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 Buckminsterfullerene (C60 fullerene) ("bucky-ball") 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 Extraterrestrial life Extraterrestrial liquid water Forbidden mechanism Helium hydride ion Homochirality Intergalactic dust Interplanetary medium Interstellar medium Iron–sulfur world theory Kerogen Life 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 Book:Chemistry Category:Astrochemistry Category:Molecules Portal:Astrobiology Portal:Chemistry

Categories

• Chemboxes which contain changes to watched fields
• Acetamides
• Hazardous air pollutants
• IARC Group 2B carcinogens
• Plasticizers