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Acetamide

Acetamide
Acetamide skeletal.svg
Acetamide-3D-balls.png
Names
Preferred IUPAC name
Acetamide
Systematic IUPAC name
Ethanamide
Other names
Acetic acid amide
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.000.430
EC Number 200-473-5
KEGG
PubChem CID
RTECS number AB4025000
UNII
Properties
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)
2000 g L−1
Solubility ethanol 500 g L−1
pyridine 166.67 g L−1
soluble in chloroform, glycerol, benzene
log P -1.26
Vapor pressure 1.3 Pa
Acidity (pKa) 16.5
-.577−6 cm3/g
1.4274
Viscosity 2.052 cP (91 °C)
Structure
trigonal
Hazards
Safety data sheet External MSDS
GHS pictograms The health hazard pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word Warning
H351
P201, P202, P281, P308+313, P405, P501
Harmful (Xn)
Carc. Cat. 3
R-phrases R40
S-phrases (S2) S36/37
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 3: Short exposure could cause serious temporary or residual injury. E.g., chlorine gas Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 126 °C (259 °F; 399 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
7000 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Acetamide (systematic name: ethanamide) is an organic compound with the formula CH3CONH2. It is the simplest amide derived from 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 produced in the laboratory by dehydrating ammonium acetate:

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

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:

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.


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Wikipedia

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