Hexanoyl chloride

Hexanoyl chloride
Names
	Preferred IUPAC name Hexanoyl chloride
	Other names Caproyl chloride
Identifiers
CAS Number	142-61-0;
3D model (JSmol)	Interactive image;
ChemSpider	60671;
ECHA InfoCard	100.005.045
EC Number	205-549-1;
PubChem CID	67340;
UNII	I7GE8HG3B2;
CompTox Dashboard (EPA)	DTXSID8059718 ;
	InChI InChI=1S/C6H11ClO/c1-2-3-4-5-6(7)8/h2-5H2,1H3 Key: YWGHUJQYGPDNKT-UHFFFAOYSA-N;
	SMILES CCCCCC(=O)Cl;
Properties
Chemical formula	C6H11ClO
Molar mass	134.60 g·mol−1
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Maybe toxic and corrosive
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H226, H302, H314, H335
Precautionary statements	P210, P233, P240, P241, P242, P243, P260, P264, P270, P271, P280, P301+P312, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P330, P363, P370+P378, P403+P233, P403+P235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Hexanoyl chloride is a six-carbon acyl chloride with a straight-chain structure that is used as a reagent in organic synthesis.^[1]^[2]^[3]^[4]

Structure and properties

Hexanoyl chloride consists of a six-carbon aliphatic chain attached to an acyl chloride functional group (–COCl). Like other acyl chlorides, it is highly electrophilic and readily undergoes nucleophilic acyl substitution reactions.

The compound is typically a colorless to pale yellow liquid with a pungent odor. It is moisture-sensitive and hydrolyzes rapidly in the presence of water to produce hexanoic acid and hydrogen chloride:

CH3(CH2)4COCl + H2O → CH3(CH2)4COOH + HCl

Preparation

Hexanoyl chloride is commonly prepared by the reaction of hexanoic acid with chlorinating agents such as:

A typical synthesis using thionyl chloride is:

CH3(CH2)4COOH + SOCl2 → CH3(CH2)4COCl + SO2 + HCl

Reactions

Hexanoyl chloride participates in many reactions characteristic of acyl chlorides:

Ester formation

Reaction with alcohols yields hexanoate esters:

R-OH + CH3(CH2)4COCl → CH3(CH2)4COOR + HCl

Amide formation

Reaction with ammonia or amines produces amides:

RNH2 + CH3(CH2)4COCl → CH3(CH2)4CONHR + HCl

Friedel–Crafts acylation

In the presence of a Lewis acid catalyst such as aluminium chloride, hexanoyl chloride can acylate aromatic compounds to form ketones.

Uses

Hexanoyl chloride is used in:

Organic synthesis laboratories as an acylating reagent.
Manufacture of pharmaceuticals and agrochemicals.
Production of specialty esters and amides.
Preparation of surfactants, fragrances, and fine chemicals.

Safety

Hexanoyl chloride is corrosive and reacts vigorously with water, releasing hydrogen chloride gas. Contact with skin, eyes, or mucous membranes may cause severe irritation or burns. Appropriate protective equipment should be used when handling the substance.

References

↑ "Hexanoyl chloride". Sigma-Aldrich. Retrieved 1 July 2017.
↑ Jeremy P. E. Spencer; Alan Crozier (24 April 2012). Flavonoids and Related Compounds: Bioavailability and Function. CRC Press. pp. 263–4. ISBN 978-1-4398-4827-2.
↑ Vijay Kumar Thakur; Amar Singh Singha (27 April 2015). Surface Modification of Biopolymers. John Wiley & Sons. p. 265. ISBN 978-1-118-66955-6.
↑ Robert Martin; Jean-Pierre Buisson (24 February 2015). Aromatic Hydroxyketones: Preparation & Physical Properties: Aromatic Hydroxyketones from Butanone (C4) to Dotriacontanone (C32). Springer. pp. 661 etc. ISBN 978-3-319-14185-5.

[Sigma-Aldrich-1] "Hexanoyl chloride". Sigma-Aldrich. Retrieved 1 July 2017.

[SpencerCrozier2012-2] Jeremy P. E. Spencer; Alan Crozier (24 April 2012). Flavonoids and Related Compounds: Bioavailability and Function. CRC Press. pp. 263–4. ISBN 978-1-4398-4827-2.

[ThakurSingha2015-3] Vijay Kumar Thakur; Amar Singh Singha (27 April 2015). Surface Modification of Biopolymers. John Wiley & Sons. p. 265. ISBN 978-1-118-66955-6.

[MartinBuisson2015-4] Robert Martin; Jean-Pierre Buisson (24 February 2015). Aromatic Hydroxyketones: Preparation & Physical Properties: Aromatic Hydroxyketones from Butanone (C4) to Dotriacontanone (C32). Springer. pp. 661 etc. ISBN 978-3-319-14185-5.

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