(Perfluoroheptyl)methanol
[CAS# 307-30-2]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyrimidine compound >> Alcohol
• Name: (Perfluoroheptyl)methanol
• Synonyms: 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctan-1-ol
• Molecular Formula: C₇F₁₅CH₂OH
• Molecular Weight: 400.08
• CAS Registry Number: 307-30-2
• EC Number: 206-197-1
• SMILES: C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)O

Properties

• Density: 1.7±0.1 g/cm³ Calc.^*
• Boiling point: 164.0 °C 760 mmHg (Calc.)^*
• Flash point: 49.2±27.3 °C (Calc.)^*
• Index of refraction: 1.285 (Calc.)^*

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

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
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Skin irritation	Skin Irrit.	2	H315

Discovery and Applications

(Perfluoroheptyl)methanol is an organofluorine compound featuring a perfluorinated seven-carbon alkyl chain (perfluoroheptyl group) attached to a hydroxymethyl functional group. Its molecular formula is generally represented as C₈F₁₅OH. The structure consists of a fully fluorinated linear alkyl chain with a terminal primary alcohol group, combining the unique properties of perfluoroalkyl chains with the reactivity of an alcohol functional group.

The synthesis of (perfluoroheptyl)methanol typically involves the reduction or hydrolysis of perfluoroalkyl halides or esters bearing the perfluoroheptyl moiety. One common approach is the reaction of perfluoroheptyl iodide or bromide with formaldehyde derivatives under basic conditions, followed by subsequent reduction steps to yield the primary alcohol. The perfluorination of the alkyl chain imparts considerable chemical and thermal stability to the molecule, as well as hydrophobicity and lipophobicity due to the strong carbon-fluorine bonds.

(Perfluoroheptyl)methanol finds its primary applications in specialty chemical synthesis, particularly as a building block for fluorinated surfactants, lubricants, and materials with low surface energy. The perfluoroalkyl chain provides exceptional resistance to heat, chemical attack, and oxidation, while the hydroxyl group allows for further functionalization and incorporation into polymers, coatings, and surface modifiers.

One important area of application is the development of fluorinated surfactants and emulsifiers. These compounds utilize (perfluoroheptyl)methanol as a precursor to generate amphiphilic molecules capable of lowering surface tension in challenging environments such as high-temperature or chemically aggressive media. The alcohol group is often converted into ether, ester, or urethane linkages, enabling incorporation into more complex molecules tailored for specific industrial applications.

In materials science, derivatives of (perfluoroheptyl)methanol are used to modify surfaces to achieve hydrophobic and oleophobic properties, improving stain resistance, chemical inertness, and durability. Such modifications are valuable in textiles, electronics, and coatings industries where resistance to water, oils, and solvents is required.

Moreover, (perfluoroheptyl)methanol serves as a precursor in the synthesis of fluoroalkylated polymers and copolymers, which exhibit enhanced thermal and chemical stability compared to their hydrocarbon counterparts. These polymers are used in applications ranging from membranes and seals to advanced composite materials.

Environmental considerations related to (perfluoroheptyl)methanol and related perfluoroalkyl substances have been subject to increasing regulatory scrutiny due to the persistence and bioaccumulative potential of perfluorinated compounds. Consequently, the use and disposal of (perfluoroheptyl)methanol require adherence to safety and environmental guidelines to minimize ecological impact.

In summary, (perfluoroheptyl)methanol is a chemically stable fluorinated primary alcohol valued for its role as a versatile intermediate in the synthesis of fluorinated surfactants, polymers, and surface modifiers. Its unique combination of fluorinated chain stability and reactive hydroxyl functionality underpins its utility in various advanced material and chemical applications.

References

1999. 4 Halogen Containing Organic Compounds, C7 to C10, Vapor Pressure and Antoine Constants for Hydrocarbons, and S, Se, Te, and Halogen Containing Organic Compounds (8)
DOI: 10.1007/10680373_16

2008. Intelligent polymeric surfaces through molecular self-assembly, Journal of Coatings Technology and Research (5)
DOI: 10.1007/s11998-008-9125-5