Pentanoyl chloride

Last updated
Pentanoyl chloride
Pentanoyl chloride.svg
Names
Preferred IUPAC name
Pentanoyl chloride
Other names
Valeroyl chloride; n-Pentanoyl chloride
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.010.301 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-330-1
PubChem CID
UNII
UN number 2502
  • InChI=1S/C5H9ClO/c1-2-3-4-5(6)7/h2-4H2,1H3
    Key: XGISHOFUAFNYQF-UHFFFAOYSA-N
  • CCCCC(=O)Cl
Properties
C5H9ClO
Molar mass 120.58 g·mol−1
Related compounds
Related compounds
 Butyryl chloride
Hexanoyl chloride
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pentanoyl chloride is an acyl chloride derived from pentanoic acid. It is a colorless liquid that is used to attach the valeroyl group. It is usually produced by chlorination of valeric acid. [1]

Reactions

Like related acyl chlorides, valeroyl chloride hydrolyzes readily:

CH3(CH2)3C(O)Cl + H2O → CH3(CH2)3CO2H + HCl

Alcohols react to give esters:

CH3(CH2)3C(O)Cl + ROH → CH3(CH2)3CO2R + HCl

Amines react to give amides:

CH3(CH2)3C(O)Cl + R2NH → CH3(CH2)3C(O)NR2 + HCl

Benzene reacts under conditions of the Friedel-Crafts reaction to give valerophenone:

CH3(CH2)3C(O)Cl + C6H6 → CH3(CH2)3C(O)C6H5 + HCl

References

  1. ↑ Helferich, B.; Schaefer, W. (1929). "n-Butyryl Chloride". Org. Synth. 9: 32. doi:10.15227/orgsyn.009.0032.
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