2-Ethylhexanoyl chloride
[CAS# 760-67-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Acid halide
• Name: 2-Ethylhexanoyl chloride
• Molecular Formula: C₈H₁₅ClO
• Molecular Weight: 162.66
• CAS Registry Number: 760-67-8
• EC Number: 212-081-1
• SMILES: CCCCC(CC)C(=O)Cl

Properties

• Density: 0.939
• Boiling point: 67-68 °C (11 mmHg)
• Refractive index: 1.4315-1.4335
• Flash point: 69 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H290-H302-H314-H317-H318-H330
• Safety Statements: P234-P260-P261-P264-P264+P265-P270-P271-P272-P280-P284-P301+P317-P301+P330+P331-P302+P352-P302+P361+P354-P304+P340-P305+P354+P338-P316-P317-P320-P321-P330-P333+P317-P362+P364-P363-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	1	H330
Skin sensitization	Skin Sens.	1	H317
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	4	H332
Skin corrosion	Skin Corr.	1C	H314
Skin corrosion	Skin Corr.	1A	H314

• Transport Information: UN 3265

Discovery and Applications

2-Ethylhexanoyl chloride, with the chemical formula C8H15ClO, is a versatile organic compound widely used in the chemical industry for its reactivity and utility in various synthetic applications. It is an acyl chloride derivative of 2-ethylhexanoic acid, characterized by its functional group, which consists of a chlorine atom bonded to an acyl group. This compound is recognized for its role in the synthesis of esters, polymers, and other organic chemicals.

The discovery of 2-ethylhexanoyl chloride is rooted in the study of acyl chlorides, which are important intermediates in organic synthesis. The synthesis of 2-ethylhexanoyl chloride typically involves the reaction of 2-ethylhexanoic acid with thionyl chloride or oxalyl chloride, resulting in the formation of the corresponding acyl chloride. This process allows for the introduction of the acyl chloride group, which is highly reactive and can participate in a range of chemical reactions.

One of the primary applications of 2-ethylhexanoyl chloride is in the production of esters. By reacting with alcohols, it forms 2-ethylhexyl esters, which are valuable in the manufacture of plasticizers, solvents, and other industrial chemicals. These esters are used to enhance the flexibility and durability of plastics and are integral to various applications in the plastics industry.

In addition to its role in ester synthesis, 2-ethylhexanoyl chloride is used in the synthesis of pharmaceuticals and agrochemicals. Its reactivity allows it to participate in the formation of various compounds that are important in drug development and agricultural chemistry. The ability to introduce the 2-ethylhexanoyl group into different molecules makes it a useful building block for creating compounds with specific properties and activities.

Furthermore, 2-ethylhexanoyl chloride is employed in the production of polymers and resins. Its acyl chloride group can react with other monomers to form copolymers and specialized resins used in coatings, adhesives, and other materials. These polymers benefit from the unique properties imparted by the 2-ethylhexanoyl group, including enhanced stability and performance in various applications.

In summary, 2-ethylhexanoyl chloride is a significant compound in organic synthesis due to its reactivity and versatility. Its applications span the production of esters, pharmaceuticals, agrochemicals, and polymers, highlighting its importance in both industrial and chemical research.

References

2003. Synthesis and chemical hydrolysis of surface-active esters. Journal of Surfactants and Detergents, 6(4).
DOI: 10.1007/s11743-003-0275-0

2020. Recent Advances in the Synthesis of Acyl Fluorides. Synthesis, 52(20).
DOI: 10.1055/s-0040-1705951

1988. Wetting properties of nonionics from branched fatty diamides. Journal of the American Oil Chemists' Society, 65(5).
DOI: 10.1007/bf02542540