Butyramide

Butyramide is the amide of butyric acid. It has the molecular formula C3H7CONH2. It is a white solid that is freely soluble in water and ethanol, but slightly soluble in diethyl ether. At room temperature, butyramide is a crystalline solid and in contrast to butyric acid, it is devoid of an unpleasant, rancid smell.

Butyramide[1]
Names
Preferred IUPAC name
Butanamide
Other names
Butyramide
n-Butylamide
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
DrugBank
ECHA InfoCard 100.007.980
PubChem CID
UNII
InChI
  • InChI=1S/C4H9NO/c1-2-3-4(5)6/h2-3H2,1H3,(H2,5,6) Y
    Key: DNSISZSEWVHGLH-UHFFFAOYSA-N Y
  • InChI=1/C4H9NO/c1-2-3-4(5)6/h2-3H2,1H3,(H2,5,6)
    Key: DNSISZSEWVHGLH-UHFFFAOYAW
SMILES
  • CCCC(N)=O
  • O=C(N)CCC
Properties
Chemical formula
 C4H9NO
Molar mass 87.122 g·mol−1
Density 1.03 g/cm3
Melting point 115 to 116 °C (239 to 241 °F; 388 to 389 K)
Boiling point 216 °C (421 °F; 489 K)
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

Synthesis

Butyramide can be synthesized by:

  • catalytic hydration of butyronitrile;
  • reaction of butyryl chloride with ammonium salts;
  • reduction of butyraldoxime.

Derivatives

Some of its derivatives have shown preliminary strong anticonvulsive activity and inhibitory action on histone deacetylases, which are crucial enzymes controlling the proliferative or differentiation status of most cells.

See also
  • Isobutyramide

References
  1. Merck Index, 11th Edition, 1592
  • Jiang J et al. PLos One 2012; 7(3): e34283
  • Liu WH et al. Yao Xue Xue Bao 2012 Feb; 47(2): 194-99.
  • Vitorivic-Todorovic MD et al. Bioorg Med Chem 2010 Feb; 18(3): 1181-93.
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