Sodium chlorodifluoroacetate
[CAS# 1895-39-2]

Identification

• Classification: Organic raw materials >> Organometallic salt
• Name: Sodium chlorodifluoroacetate
• Synonyms: Chlorodifluoroacetic acid sodium salt
• Molecular Formula: C₂ClF₂NaO₂
• Molecular Weight: 152.46
• CAS Registry Number: 1895-39-2
• EC Number: 217-586-0
• SMILES: C(=O)(C(F)(F)Cl)[O-].[Na+]

Properties

• Melting point: 196-198 °C (Expl.)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Sodium chlorodifluoroacetate (C₂ClF₂NaO₂) is an organofluorine compound that has been studied for its role as a synthetic intermediate in the production of fluorinated chemicals. It is the sodium salt of chlorodifluoroacetic acid and contains both halogen and carboxylate functional groups, which influence its chemical reactivity and stability. The presence of fluorine and chlorine in the molecular structure imparts unique physicochemical properties, making it useful in various industrial applications.

The synthesis of sodium chlorodifluoroacetate typically involves the reaction of chlorodifluoroacetic acid with sodium hydroxide or a similar base to yield the corresponding sodium salt. Alternatively, it can be prepared through fluorination reactions using chlorinated precursors and fluorinating agents. The stability of the compound under different conditions depends on factors such as pH, temperature, and the presence of moisture.

One of the primary applications of sodium chlorodifluoroacetate is in the synthesis of fluorinated organic molecules. It serves as a precursor for the production of various fluorinated intermediates used in pharmaceuticals, agrochemicals, and materials science. The presence of the chlorodifluoromethyl (-CClF₂) group allows for selective transformations in organic synthesis, including substitution and elimination reactions.

In pharmaceutical research, fluorinated compounds are often employed to enhance metabolic stability, bioavailability, and binding interactions with target biomolecules. While sodium chlorodifluoroacetate itself is not a drug, its derivatives have been explored in medicinal chemistry for their potential applications. Similarly, in the agrochemical industry, fluorinated intermediates derived from this compound are used in the synthesis of pesticides and herbicides, where fluorine can modulate biological activity and environmental persistence.

The use of sodium chlorodifluoroacetate in polymer chemistry has also been investigated. Fluorinated monomers derived from this compound contribute to the development of high-performance materials with desirable properties such as chemical resistance, low surface energy, and thermal stability. These materials are applied in coatings, electronics, and specialized industrial applications.

Handling and storage of sodium chlorodifluoroacetate require appropriate safety precautions due to its reactivity and potential decomposition under extreme conditions. It should be stored in sealed containers under controlled temperature and humidity to prevent hydrolysis or degradation. Standard laboratory safety protocols, including the use of gloves and protective eyewear, should be followed when working with the compound.

Sodium chlorodifluoroacetate remains an important intermediate in fluorine chemistry, supporting the synthesis of a variety of functionalized organic molecules. Its well-characterized reactivity and role in industrial and research applications contribute to its continued relevance in synthetic and applied chemistry.

References

2021. Multicomponent Reactions Based on In Situ Generated Isocyanides for the Construction of Heterocycles. Chemistry of Heterocyclic Compounds, 57(8).
DOI: 10.1007/s10593-021-02972-w

2019. N-Difluoromethylation of monosubstituted polydentate azoles. Chemistry of Heterocyclic Compounds, 55(4-5).
DOI: 10.1007/s10593-019-02465-x

2015. Difluoromethylation of 2-hydroxychalcones using sodium 2-chloro-2,2-difluoroacetate as difluoromethylating agent. Chemical Research in Chinese Universities, 31(3).
DOI: 10.1007/s40242-015-4456-0