Octanoyl chloride
[CAS# 111-64-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: Octanoyl chloride
• Synonyms: Capryloyl chloride
• Molecular Formula: C₈H₁₅ClO
• Molecular Weight: 162.66
• CAS Registry Number: 111-64-8
• EC Number: 203-891-6
• SMILES: CCCCCCCC(=O)Cl

Properties

• Density: 0.953
• Melting point: -63 °C
• Boiling point: 195 °C
• Refractive index: 1.434-1.436
• Flash point: 75 °C
• Water solubility: REACTS

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H290-H315-H317-H318-H330
• Safety Statements: P234-P260-P261-P264-P264+P265-P271-P272-P280-P284-P302+P352-P304+P340-P305+P354+P338-P316-P317-P320-P321-P332+P317-P333+P317-P362+P364-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	2	H330
Skin irritation	Skin Irrit.	2	H315
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	1	H330
Acute toxicity	Acute Tox.	4	H302
Skin corrosion	Skin Corr.	1C	H314

• Transport Information: UN 3265

Discovery and Applications

Octanoyl chloride, also known as capryloyl chloride, is an organic compound with the chemical formula C8H15ClO. It is a colorless liquid with a pungent odor and is classified as an acyl chloride. Octanoyl chloride is primarily used as a reagent in organic synthesis, particularly for introducing the octanoyl group into other chemical compounds. The reactive nature of the acyl chloride group makes it valuable in the formation of esters and amides, which are key components in a variety of chemical products.

The discovery of octanoyl chloride and related acyl chlorides came as organic chemists sought efficient methods to introduce acyl groups into molecules. Acyl chlorides, including octanoyl chloride, are highly reactive with nucleophiles such as alcohols and amines, facilitating the formation of esters and amides. This reactivity has been harnessed in a wide range of chemical reactions, particularly in the fields of pharmaceuticals, agrochemicals, and polymer chemistry.

One of the main applications of octanoyl chloride is in the synthesis of esters and amides, which are important in creating surfactants, emulsifiers, and active pharmaceutical ingredients. Octanoyl chloride is often used to modify molecules by introducing hydrophobic octanoyl groups, which can alter the solubility, stability, or biological activity of the target compound. In pharmaceutical chemistry, octanoyl chloride is employed in the synthesis of intermediates for drug molecules, where the octanoyl group contributes to the desired pharmacokinetic properties.

In addition to its use in pharmaceuticals, octanoyl chloride is applied in the production of specialty chemicals, such as lubricants and surfactants. The ability of octanoyl chloride to form stable esters makes it useful in creating compounds with specific performance characteristics, such as improved lubrication properties or enhanced emulsification. This has led to its use in the formulation of industrial products, including cosmetics and personal care items.

Octanoyl chloride is also used in polymer chemistry, where it is employed as a reagent to modify polymers or introduce functional groups that enhance the material's properties. Its role in modifying surfaces and adding hydrophobicity has made it valuable in materials science research and development.

Overall, octanoyl chloride plays a significant role in organic synthesis, particularly in the formation of esters and amides. Its reactivity and ability to introduce the octanoyl group make it a versatile reagent in both industrial and research applications.

References

2019. Esterification of starch in search of a biodegradable thermoplastic material. Journal of Polymer Research.
DOI: 10.1007/s10965-019-1983-2

2018. Development of Novel Octanoyl Chitosan Nanoparticles for Improved Rifampicin Pulmonary Delivery: Optimization by Factorial Design. AAPS PharmSciTech.
DOI: 10.1208/s12249-018-0972-9

1968. Reactions of fatty acid chlorides: II. Synthesis of monohydrazides or dihydrazides by acylation of hydrazine hydrate with saturated fatty acid chlorides. Journal of the American Oil Chemists’ Society.
DOI: 10.1007/bf02667173