pentanoyl chloride
{{Chembox
| ImageFile = Pentanoyl chloride.svg
| ImageSize = 200px
| PIN = Pentanoyl chloride
| OtherNames = Valeroyl chloride; n-Pentanoyl chloride
| Section1 = {{Chembox Identifiers
| CASNo = 638-29-9
| CASNo_Ref = {{cascite|correct|CAS}}
| ChEMBL = 1607711
| ChemSpiderID = 55132
| EC_number = 211-330-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = KJ3B4CY5GG
| PubChem = 61186
| UNNumber = 2502
| StdInChI=1S/C5H9ClO/c1-2-3-4-5(6)7/h2-4H2,1H3
| StdInChIKey = XGISHOFUAFNYQF-UHFFFAOYSA-N
| SMILES = CCCCC(=O)Cl
}}
| Section2 = {{Chembox Properties
| C=5|H=9|Cl=1|O=1
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
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| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
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|Section8={{Chembox Related
| OtherCompounds = Butyryl chloride
Hexanoyl chloride
}}
}}
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.{{cite journal|title=n-Butyryl Chloride|first1=B. |last1=Helferich|first2=W.|last2=Schaefer|journal=Org. Synth. |year=1929|volume=9|page=32|doi=10.15227/orgsyn.009.0032}}
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