2,2,2-Trichloroethyl chloroformate
[CAS# 17341-93-4]

Identification

• Classification: Chemical reagent >> Organic reagent >> Halogenated aliphatic hydrocarbon
• Name: 2,2,2-Trichloroethyl chloroformate
• Molecular Formula: C₃H₂Cl₄O₂
• Molecular Weight: 211.86
• CAS Registry Number: 17341-93-4
• EC Number: 241-363-7
• SMILES: C(C(Cl)(Cl)Cl)OC(=O)Cl

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*, 1.539 g/mL (Expl.)
• Melting point: 0-2 °C °C (Expl.)
• Index of Refraction: 1.495, Calc.^*
• Boiling Point: 171.5 °C (760 mmHg), Calc.^*, 171-172 °C °C (Expl.)
• Flash Point: 82.1±24.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Risk Statements: H302-H314-H330-H3331
• Safety Statements: P260-P261-P264-P270-P271-P280-P284-P301+P317-P301+P330+P331-P302+P361+P354-P304+P340-P305+P354+P338-P316-P320-P321-P330-P363-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin corrosion	Skin Corr.	1B	H314
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Serious eye damage	Eye Dam.	1	H318
Substances or mixtures corrosive to metals	Met. Corr.	1	H290
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	2	H310
Specific target organ toxicity - single exposure	STOT SE	3	H335

• Transport Information: UN 3277

Discovery and Applications

2,2,2-Trichloroethyl chloroformate (C3H2Cl4O2) is a chemical compound that contains both a chloroformate group and a trichloroethyl group. This compound is widely used in organic synthesis due to its ability to introduce reactive functional groups into various molecules. The chloroformate group (-OC(O)Cl) in its structure makes it a useful reagent for the preparation of esters, carbonates, and carbamates.

2,2,2-Trichloroethyl chloroformate is typically synthesized by reacting trichloroethanol with phosgene, a key industrial chemical. In this reaction, the trichloroethanol undergoes a reaction with phosgene under mild conditions, resulting in the formation of 2,2,2-trichloroethyl chloroformate. The chloroformate group formed in this process is highly reactive, which makes it valuable for several chemical reactions.

One of the major applications of 2,2,2-trichloroethyl chloroformate is in the synthesis of esters and carbonates. The chloroformate group is highly reactive and can easily react with alcohols or phenols to form esters. This reaction is useful in the preparation of a wide range of compounds, including pharmaceuticals, agrochemicals, and fine chemicals. The ability to introduce a carbonate group into a molecule by reacting with alcohols also plays an important role in the synthesis of carbonates. These reactions are valuable in both industrial and laboratory settings.

Another significant application of 2,2,2-trichloroethyl chloroformate is in the preparation of carbamates. By reacting with amines, 2,2,2-trichloroethyl chloroformate can form carbamates. Carbamates are important intermediates in the synthesis of a variety of compounds, including insecticides, herbicides, and pharmaceuticals. The ability of 2,2,2-trichloroethyl chloroformate to introduce a carbamate group into a molecule is an essential process in the production of many chemicals used in agriculture and medicine.

2,2,2-Trichloroethyl chloroformate is also used as a protecting group in organic synthesis. The trichloroethyl group can serve as a protective group for certain functional groups, such as amines, during multi-step synthetic processes. By temporarily protecting these functional groups, the trichloroethyl group allows other reactions to occur without interfering with the protected functional group. Once the desired transformation is complete, the trichloroethyl group can be removed using hydrolysis or other methods.

In polymer chemistry, 2,2,2-trichloroethyl chloroformate has been used to modify polymers. The chloroformate group can react with polyols or other monomers to introduce the chloroformate functionality into polymer chains. This reaction is useful in the preparation of polycarbonates, which have applications in coatings, adhesives, and other materials. The ability to introduce chloroformate groups into polymer structures provides additional functionality to polymers, expanding their potential uses in various industries.

2,2,2-Trichloroethyl chloroformate is a versatile reagent in organic chemistry that plays a key role in the preparation of esters, carbonates, carbamates, and in polymer chemistry. Its reactivity and ability to introduce functional groups into molecules make it a valuable tool in both industrial and laboratory settings. The applications of this compound are well-established and widely utilized in the chemical industry for the synthesis of various chemicals and materials.

References

1976. Determination of pethidine in plasma by electron capture gas chromatography after reaction with trichloroethyl chloroformate. Journal of Chromatography A, 121(2).
DOI: 10.1016/s0021-9673(00)85019-0

2012. Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters. Russian Chemical Bulletin, 61(11).
DOI: 10.1007/s11172-012-0302-4

2015. Characterization of the designer drug bk‐2C‐B (2‐amino‐1‐(bromo‐dimethoxyphenyl)ethan‐1‐one) by gas chromatography/mass spectrometry without and with derivatization with 2,2,2‐trichloroethyl chloroformate, liquid chromatography/high‐resolution mass spectrometry, and nuclear magnetic resonance. Rapid Communications in Mass Spectrometry, 29(12).
DOI: 10.1002/rcm.7211