2,2,2-Trifluoroethanol
[CAS# 75-89-8]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 2,2,2-Trifluoroethanol
• Synonyms: Trifluoroethanol; TFE
• Molecular Formula: C₂H₃F₃O
• Molecular Weight: 100.04
• CAS Registry Number: 75-89-8
• EC Number: 200-913-6
• SMILES: C(C(F)(F)F)O

Properties

• Density: 1.393 g/mL
• Melting point: -44 ºC
• Boiling point: 77-80 ºC
• Refractive index: 1.2907
• Flash point: 30 ºC

Safety Data

• Hazard Symbols: GHS02;GHS05;GHS06;GHS07;GHS08 Danger
• Hazard Statements: H226-H301+H331-H301-H312-H315-H318-H331-H332-H335-H360-H360F-H373
• Precautionary Statements: P203-P210-P233-P240-P241-P242-P243-P260-P261-P264-P264+P265-P270-P271-P280-P301+P316-P302+P352-P303+P361+P353-P304+P340-P305+P354+P338-P316-P317-P318-P319-P321-P330-P332+P317-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	3	H226
Serious eye damage	Eye Dam.	1	H318
Acute toxicity	Acute Tox.	3	H301
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Acute toxicity	Acute Tox.	4	H312
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H331
Acute toxicity	Acute Tox.	4	H332
Specific target organ toxicity - single exposure	STOT SE	3	H335
Reproductive toxicity	Repr.	1B	H360
Reproductive toxicity	Repr.	1B	H360F
Acute toxicity	Acute Tox.	4	H302
Reproductive toxicity	Repr.	2	H361
Acute toxicity	Acute Tox.	3	H311
Reproductive toxicity	Repr.	1A	H360
Eye irritation	Eye Irrit.	2	H319

• Transport Information: UN 1993;UN 1986

Discovory and Applicatios

2,2,2-Trifluoroethanol, with the chemical formula C₂HF₃OH, is a fluorinated alcohol that has been recognized for its unique chemical properties and diverse applications in both laboratory and industrial settings. This compound is characterized by the presence of three fluorine atoms attached to a central carbon atom, alongside a hydroxyl group. Its properties, which include a strong hydrogen bonding potential and high polarity, make it a valuable solvent and reagent in various chemical processes.

The discovery of 2,2,2-trifluoroethanol dates back to the mid-20th century when the exploration of fluorinated organic compounds became more widespread. Researchers were particularly interested in the chemical behavior of alcohols containing fluorine, as these compounds exhibited distinctive reactivity due to the electron-withdrawing effect of the fluorine atoms. The synthesis of 2,2,2-trifluoroethanol has been described in numerous studies, particularly highlighting its preparation through the reduction of 2,2,2-trifluoroacetaldehyde using reducing agents like sodium borohydride.

One of the primary applications of 2,2,2-trifluoroethanol is as a solvent in organic synthesis. Its strong hydrogen bonding ability, combined with its high polarity, makes it an excellent solvent for a variety of reactions, particularly those involving polar organic compounds. The solvent properties of 2,2,2-trifluoroethanol are often utilized in reactions where standard solvents would either not dissolve the reactants or would interfere with the reaction mechanism. Its use is most common in reactions involving nucleophilic substitution, esterification, and other processes requiring a highly polar medium.

Another important application of 2,2,2-trifluoroethanol is in the synthesis of organofluorine compounds. The compound's unique structure, with three fluorine atoms attached to a central carbon, imparts distinct chemical reactivity. As a result, 2,2,2-trifluoroethanol serves as an intermediate in the synthesis of various fluorinated organic compounds, which have a wide range of uses in pharmaceuticals, agrochemicals, and other specialty chemicals.

2,2,2-Trifluoroethanol is also used as a reagent in chemical reactions, especially in processes requiring the selective introduction of a trifluoromethyl group. For example, it can participate in reactions where the trifluoromethyl group from 2,2,2-trifluoroethanol is transferred to another organic molecule, modifying its properties or enhancing its stability. This application is especially important in the development of new fluorinated materials and molecules with specialized properties.

In addition to its synthetic uses, 2,2,2-trifluoroethanol plays a role in materials science, where it is employed in the development of new coatings, adhesives, and polymers. Its ability to form strong hydrogen bonds and its compatibility with fluorine-containing polymers make it useful in these applications, particularly when the need arises for materials with unique chemical or thermal properties. It has also been studied for its potential in the modification of existing polymeric materials to enhance their performance under various conditions.

Furthermore, 2,2,2-trifluoroethanol has been studied for its behavior as a stabilizing agent in certain chemical processes. Its ability to solvate both polar and nonpolar molecules allows it to stabilize reaction intermediates, thus improving the efficiency and selectivity of reactions. It has been reported to be effective in stabilizing highly reactive species, such as organometallic compounds, during chemical synthesis.

In conclusion, 2,2,2-trifluoroethanol is an important compound in both synthetic chemistry and industrial applications. Its ability to act as a solvent and reagent in a variety of reactions, its use in the synthesis of organofluorine compounds, and its role in materials science all contribute to its widespread use. The compound's unique chemical properties, particularly its strong hydrogen bonding and high polarity, make it an invaluable tool in modern chemical synthesis and material development.

References

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DOI: 10.1007/s00726-024-03428-z

1948. Trifluoroethanol. Journal of the American Chemical Society, 70(5).
DOI: 10.1021/ja01185a508