acetamide

Acetamide
IUPAC name	Acetamide Ethanamide
Identifiers
CAS number	60-35-5 Y
PubChem	178
SMILES	O=C(N)C
InChI	1/C2H5NO/c1-2(3)4/h1H3,(H2,3,4)
InChI key	DLFVBJFMPXGRIB-UHFFFAOYAC
ChemSpider ID	173
Properties
Molecular formula	C2H5NO
Molar mass	59.07 g mol−1
Density	1.16 g/cm³
Melting point	79-81°C
Boiling point	222 °C
Solubility in water	2g/1ml
Hazards
MSDS	External MSDS
EU Index	616-022-00-4
EU classification	Harmful (Xn) Carc. Cat. 3
R-phrases	R40
S-phrases	(S2), S36/37
NFPA 704	1 3 1
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Acetamide (or acetic acid amide or ethanamide), CH₃CONH₂, the amide of acetic acid, is a white crystalline solid in pure form. It is produced by dehydrating ammonium acetate:^[1]

CH₃COONH₄ → CH₃CONH₂ + H₂O

It is used as a plasticizer and in the synthesis of many other organic compounds.

Acetamide is not extremely combustible, but releases irritating fumes when ignited. It is toxic by inhalation (of dust), ingestion, skin and eye contact. Skin or eye contact may cause redness and pain.

The derivative N,N-dimethylacetamide (DMA), which has two methyl groups replacing the amine protons, is used as a solvent. N-methylacetamide is often used as the simplest model in studies of the peptide bond.

Recent work on the Robert C. Byrd Green Bank Telescope has resulted in the discovery of several organic (carbon-based) compounds near the center of the Milky Way galaxy. Acetamide has been detected. This is particularly important as acetamide has an amide bond, similar to the essential bond between amino acids in proteins. This supports the theory that organic molecules that can lead to life (as we know it on Earth) can form in space.

In addition, acetamide is rarely found on burning coal dumps, as a mineral of the same name.^[2][3]

Cancer link

Acetamide has been found to cause cancer in laboratory animals. It is classified in Group 2B "possible human carcinogen" by the IARC.

References

1. ^ G. H. Coleman and A. M. Alvarado (1941), "Acetamide", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv1p003 ; Coll. Vol. 1: 3 
2. ^ http://www.mindat.org/min-13.html Mindat.org
3. ^ http://rruff.geo.arizona.edu/doclib/hom/acetamide.pdf Handbook of Mineralogy

• J. M. Hollis, F. J. Lovas, Anthony J. Remijan, P. R. Jewell, V. V. Ilyushin, and I. Kleiner (2006). "Detection of Acetamide (CH3CONH2): The Largest Interstellar Molecule with a Peptide Bond". The Astrophysical Journal 643 (2): L25–L28. doi:10.1086/505110. 

External links

• International Chemical Safety Card 0233
• Webmineral.org