Pentanoyl chloride

Pentanoyl chloride
Names
	Preferred IUPAC name Pentanoyl chloride
	Other names Valeroyl chloride; n-Pentanoyl chloride
Identifiers
CAS Number	638-29-9 ;
3D model (JSmol)	Interactive image;
ECHA InfoCard	100.010.301
PubChem CID	61186;
UNII	KJ3B4CY5GG ;
CompTox Dashboard (EPA)	DTXSID2034091 ;
	SMILES CCCCC(=O)Cl;
Properties
Chemical formula	C5H9ClO
Molar mass	120.58 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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, valeryl 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

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

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

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