Ethyl chlorodifluoroacetate
[CAS# 383-62-0]

Identification

• Classification: Chemical reagent >> Organic reagent >> Ester >> Ethyl ester compound
• Name: Ethyl chlorodifluoroacetate
• Synonyms: Chlorodifluoroacetic acid ethyl ester
• Molecular Formula: C₄H₅ClF₂O₂
• Molecular Weight: 158.53
• CAS Registry Number: 383-62-0
• EC Number: 206-850-0
• SMILES: CCOC(=O)C(F)(F)Cl

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*, 1.252 g/mL (Expl.)
• Index of Refraction: 1.374, Calc.^*, 1.358 (Expl.)
• Boiling Point: 93.8±35.0 °C (760 mmHg), Calc.^*, 96-97.5 °C (Expl.)
• Flash Point: 28.9±15.1 °C, Calc.^*, 18 °C (Expl.)

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

Safety Data

• Hazard Symbols: GHS02;GHS06 Danger
• Risk Statements: H225-H314-H318
• Safety Statements: P210-P233-P240-P241-P242-P243-P260-P264-P264+P265-P280-P301+P330+P331-P302+P361+P354-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P321-P363-P370+P378-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Skin corrosion	Skin Corr.	1B	H314
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

• Transport Information: UN 2924

Discovery and Applications

Ethyl chlorodifluoroacetate (C₄HF₂O₂) is a fluorinated organic compound that features both a chlorodifluoroacetate group and an ethyl ester group. The compound has garnered attention for its utility in organic synthesis, particularly in the preparation of various fluorinated derivatives. The presence of the trifluoromethyl group and the ester functionality allows for a range of reactivity that makes this compound useful in various chemical applications.

The synthesis of ethyl chlorodifluoroacetate involves reactions between difluoroacetic acid derivatives and ethylating reagents, with subsequent chlorination. As part of the broader category of organofluorine compounds, ethyl chlorodifluoroacetate is primarily synthesized and used in specialized synthetic organic chemistry, where it serves as a precursor to more complex fluorinated chemicals.

One of the main applications of ethyl chlorodifluoroacetate lies in its use as a reagent in the preparation of fluorinated intermediates and compounds. Fluorine substitution is often employed in drug development to improve the bioactivity, metabolic stability, and lipophilicity of certain compounds. The chlorodifluoroacetate group in ethyl chlorodifluoroacetate is an important functional group in the synthesis of fluorinated organic molecules, especially those intended for use in the pharmaceutical, agrochemical, and polymer industries.

In pharmaceutical synthesis, ethyl chlorodifluoroacetate serves as an intermediate in the preparation of fluorinated compounds, which are known for their enhanced biological activity. The introduction of fluorine atoms into organic molecules can increase the metabolic stability and bioavailability of drugs. This makes fluorinated compounds useful in the design of therapeutics, particularly for diseases such as cancer and cardiovascular disorders. Fluorinated organic molecules are also employed in the synthesis of antibiotics and antiviral agents, where the improved stability and resistance to enzymatic degradation enhance the efficacy of the drug.

In the agrochemical industry, ethyl chlorodifluoroacetate can be used to synthesize fluorinated agrochemicals, such as herbicides, fungicides, and insecticides. Fluorinated agrochemicals are known for their enhanced chemical stability, which allows them to be effective for longer periods, thereby improving their performance in protecting crops against pests and diseases. The incorporation of fluorine atoms also improves the environmental persistence and reduces the rate of degradation, making these chemicals more effective in agricultural applications.

Ethyl chlorodifluoroacetate is also of interest in the development of specialty polymers and materials. Fluorinated polymers, in particular, are known for their resistance to solvents, high thermal stability, and mechanical properties. The presence of the chlorodifluoroacetate group in ethyl chlorodifluoroacetate allows for the creation of polymers with enhanced chemical resistance, making them suitable for use in demanding applications, including coatings, adhesives, and sealants. These polymers are especially useful in industries where materials must withstand aggressive chemicals and extreme conditions.

Moreover, the ability to incorporate the chlorodifluoroacetate group into other molecular structures has led to its application in the design of functional materials for use in electronics and optoelectronics. Fluorinated materials, including those derived from ethyl chlorodifluoroacetate, can exhibit improved stability under harsh conditions, making them suitable for applications in organic electronics, sensors, and other high-tech devices.

As with many fluorinated chemicals, the use of ethyl chlorodifluoroacetate must be carefully managed due to the environmental persistence of fluorinated compounds. The chlorodifluoroacetate group, while providing stability and reactivity, can also contribute to the environmental burden if not properly controlled. Efforts to minimize the environmental impact of such chemicals involve the development of safer disposal methods and more sustainable synthetic routes for the production of fluorinated compounds.

In conclusion, ethyl chlorodifluoroacetate is a versatile and valuable compound in organic synthesis. It is primarily used as a precursor in the preparation of fluorinated compounds with applications in pharmaceuticals, agrochemicals, and polymer industries. Its role as a reagent in the synthesis of fluorinated intermediates enables the development of compounds with enhanced stability, biological activity, and chemical resistance. While its use offers several benefits, careful consideration must be given to its environmental impact due to the persistence of fluorinated chemicals in the environment.

References

2016. Deployment of Small-Ring Azaheterocycles as Building Blocks for the Synthesis of Organofluorine Compounds. Synlett, 27(10).
DOI: 10.1055/s-0035-1561379

2013. A theoretical investigation on the kinetics and reactivity of the gas-phase reactions of ethyl chlorodifluoroacetate with OH radical and Cl atom at 298 K. Structural Chemistry, 24(6).
DOI: 10.1007/s11224-013-0312-3

2011. Synthesis of new fluorine-containing pyrazolo[3,4-b]pyridinones as promising drug precursors. Russian Chemical Bulletin, 60(4).
DOI: 10.1007/s11172-011-0114-y