2,2-Difluoroethanol
[CAS# 359-13-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Fatty alcohol
• Name: 2,2-Difluoroethanol
• Molecular Formula: C₂H₄F₂O
• Molecular Weight: 82.05
• CAS Registry Number: 359-13-7
• EC Number: 670-547-3
• SMILES: C(C(F)F)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.296 g/mL (Expl.)
• Melting point: -28 ºC (Expl.)
• Index of Refraction: 1.3, Calc.^*, 1.338 (Expl.)
• Boiling Point: 95.5 ºC (760 mmHg), Calc.^*, 95-96 ºC (Expl.)
• Flash Point: 0.4±23.2 ºC, Calc.^*, 3 ºC (Expl.)

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

Safety Data

• Hazard Symbols: GHS02;GHS06;GHS07 Danger
• Hazard Statements: H225-H226-H300-H301-H302+H312+H332-H302-H311-H312-H315-H319-H330-H332-H335
• Precautionary Statements: P210-P233-P240-P241-P242-P243-P260-P261-P262-P264-P264+P265-P270-P271-P280-P284-P301+P316-P301+P317-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P316-P317-P319-P320-P321-P330-P332+P317-P337+P317-P361+P364-P362+P364-P370+P378-P403+P233-P403+P235-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Flammable liquids	Flam. Liq.	2	H225
Skin irritation	Skin Irrit.	2	H315
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H311
Eye irritation	Eye Irrit.	2	H319
Eye irritation	Eye Irrit.	2A	H319
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	2	H330
Acute toxicity	Acute Tox.	4	H312
Flammable liquids	Flam. Liq.	3	H226
Acute toxicity	Acute Tox.	4	H332

Discovory and Applicatios

2,2-Difluoroethanol (C₂H₃F₂OH) is a fluorinated alcohol, where two fluorine atoms are substituted at the second carbon of the ethyl alcohol molecule. This modification imparts unique physical and chemical properties to the compound, making it valuable in various industrial and chemical applications.

The compound was first synthesized and studied in the context of fluorinated alcohols, which are known for their stability and reactivity due to the strong electronegativity of fluorine. 2,2-Difluoroethanol was synthesized as part of efforts to explore the effects of fluorine substitution on the properties of alcohols, particularly their solvent characteristics, reactivity, and potential applications in chemical synthesis.

In terms of its applications, 2,2-difluoroethanol is primarily used as a solvent and intermediate in organic synthesis. Its ability to solvate a variety of organic compounds, especially those containing polar groups, makes it a useful solvent in synthetic chemistry, particularly in reactions that require a polar, yet non-protic, environment. It is employed in reactions such as nucleophilic substitution, where the fluorine atoms can influence the reactivity of the compound. Additionally, the alcohol group in 2,2-difluoroethanol allows it to participate in reactions such as esterifications and transesterifications, making it useful in the production of fluorinated esters.

Another key application of 2,2-difluoroethanol is its use as a fluorinating agent in the preparation of other fluorinated organic compounds. The presence of two fluorine atoms on the alcohol molecule allows it to act as a precursor to other fluorinated derivatives, which can be useful in the development of materials with unique properties, such as improved chemical stability, hydrophobicity, or resistance to heat and wear. In particular, it is used in the synthesis of fluorinated intermediates for pharmaceuticals and agrochemicals.

2,2-Difluoroethanol has also been explored for use in liquid-phase reactions in the synthesis of fluorinated compounds. The presence of fluorine atoms in organic molecules often imparts desirable properties such as enhanced chemical stability, and the reactivity of 2,2-difluoroethanol makes it a versatile tool for designing molecules with specific performance characteristics.

The compound is also of interest in the development of new materials, particularly in the context of advanced polymers and coatings. Fluorinated alcohols like 2,2-difluoroethanol can be used as building blocks for the synthesis of polymers that exhibit superior resistance to solvents, oils, and high temperatures. As such, it has been studied in relation to the formulation of coatings for electronic components and other materials exposed to harsh environments.

From an environmental and safety perspective, 2,2-difluoroethanol is subject to regulatory scrutiny due to the presence of fluorine, which can have persistent environmental effects. Fluorinated compounds, in general, are resistant to degradation, which raises concerns regarding their potential impact on ecosystems if they are not properly disposed of. As a result, its use in industrial applications must comply with environmental regulations to mitigate any adverse effects.

In summary, 2,2-difluoroethanol is a valuable fluorinated alcohol with diverse applications in organic synthesis, chemical manufacturing, and material science. Its properties as a solvent, reagent, and precursor to other fluorinated compounds make it an important intermediate in the production of specialty chemicals and advanced materials. However, its environmental and safety considerations necessitate careful management during its use and disposal to minimize potential ecological impacts.

References

2011. Intermolecular interactions, disorder and twinning in ciprofloxacin-2,2-difluoroethanol (2/3) and ciprofloxacin-water (3/14.5). Acta crystallographica. Section C, Crystal structure communications, 67(Pt 3).
DOI: 10.1107/s0108270111005488

2009. Conformational stability, r 0 structural parameters, barriers to internal rotation, ab initio calculations, and vibrational assignment for 2,2-difluoroethanol. Structural Chemistry, 20(3).
DOI: 10.1007/s11224-009-9446-8

1995. Thermodynamic properties of liquid 2,2-difluoroethanol. International Journal of Thermophysics, 16(4).
DOI: 10.1007/bf02093472