2-Ethylhexyl chloroformate
[CAS# 24468-13-1]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester
• Name: 2-Ethylhexyl chloroformate
• Synonyms: 2-etylhexyl-chlorformiat
• Molecular Formula: C₉H₁₇ClO₂
• Molecular Weight: 192.68
• CAS Registry Number: 24468-13-1
• EC Number: 246-278-9
• SMILES: CCCCC(CC)COC(=O)Cl

Properties

• Density: 0.981
• Boiling point: 106-107 °C
• Refractive index: 1.431
• Flash point: 179 °F

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H290-H315-H317-H330-H332
• Safety Statements: P234-P260-P261-P264-P271-P272-P280-P284-P302+P352-P304+P340-P316-P317-P320-P321-P332+P317-P333+P317-P362+P364-P390-P403+P233-P405-P406-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	1	H330
Skin irritation	Skin Irrit.	2	H315
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Skin sensitization	Skin Sens.	1	H317
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Eye irritation	Eye Irrit.	2B	H319
Acute toxicity	Acute Tox.	2	H330
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	2	H310

• Transport Information: UN 2748

Discovery and Applications

2-Ethylhexyl chloroformate is an organic chemical compound with the molecular formula C9H17ClO2. It belongs to the class of chloroformates, which are widely used as intermediates in organic synthesis. This compound is typically a colorless liquid and is known for its reactivity, particularly in esterification and urethane formation reactions. The presence of both the chloroformate functional group and the 2-ethylhexyl chain provides versatility in various industrial and laboratory applications.

The discovery and synthesis of chloroformates, including 2-ethylhexyl chloroformate, originated from the need to develop reagents that could effectively introduce protective groups or modify chemical structures in a controlled manner. Chloroformates are useful due to their ability to react with alcohols and amines, forming esters and carbamates, respectively. 2-Ethylhexyl chloroformate, in particular, benefits from its branched alkyl chain, which influences its solubility and reactivity.

One of the primary applications of 2-ethylhexyl chloroformate is in the production of plasticizers and additives for polymers. Plasticizers improve the flexibility and durability of plastics, and 2-ethylhexyl chloroformate plays a key role in synthesizing compounds that are incorporated into these materials. Its ability to form stable urethanes and esters makes it a valuable intermediate in the chemical processes used to enhance the performance of polymeric products.

In addition to its role in polymer chemistry, 2-ethylhexyl chloroformate is used in the pharmaceutical and agrochemical industries. It is often employed in the synthesis of active pharmaceutical ingredients (APIs) and various agricultural chemicals. The reactivity of the chloroformate group allows for the creation of complex molecules with specific biological activities, making it a versatile reagent for drug development and crop protection.

2-Ethylhexyl chloroformate is also used in the preparation of surfactants and coatings. Surfactants are essential in detergents, emulsifiers, and dispersing agents, while coatings derived from 2-ethylhexyl chloroformate provide protective layers for various materials. These applications benefit from the compound’s ability to form stable bonds and impart desirable physical properties to the final product.

References

2018. Preparation, Crystal Structures and Hirshfeld Surface Analyses of Two Impurities of Azilsartan. *Journal of Chemical Crystallography*, 48(12).
DOI: 10.1007/s10870-018-0754-y

2007. Decarboxylation of Chloroformates. *Science of Synthesis*.
URL: https://science-of-synthesis.thieme.com/app/text/?id=SD-035-00056

1982. Determination of the components of waste water from bis(2-ethylhexyl)peroxydicarbonate production by gas-solid chromatography. *Fresenius' Zeitschrift für Analytische Chemie*, 311(1).
DOI: 10.1007/bf00483717