Butyramide

Butyramide^[1]

Names
IUPAC name Butanamide
Other names Butyramide n-Butylamide
Identifiers
CAS Number	541-35-5
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:50724
ChemSpider	10464
DrugBank	DB02121
ECHA InfoCard	100.007.980
PubChem CID	10927
UNII	9J6OR937VR
CompTox Dashboard (EPA)	DTXSID8060248
InChI InChI=1S/C4H9NO/c1-2-3-4(5)6/h2-3H2,1H3,(H2,5,6) Key: DNSISZSEWVHGLH-UHFFFAOYSA-N 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).

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.

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

• 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.