Butyramide

Butyramide is the amide of butyric acid. It has the molecular formula C₃H₇CONH₂. It is a white solid that 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 unpleasant, rancid smell.

Butyramide[1]

Names
IUPAC name Butanamide
Other names Butyramide n-Butylamide
Identifiers
CAS Number	541-35-5^Y
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:50724^Y
ChemSpider	10464^Y
DrugBank	DB02121^Y
ECHA InfoCard	100.007.980
PubChem CID	10927
UNII	9J6OR937VR^Y
CompTox Dashboard (EPA)	DTXSID8060248
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/cm^3
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).
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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, 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.