3,3,3-Trifluoro-1-Propanol

• CAS: 65545-80-4
• Catalog Number: ACM65545804-1
• Category: Main Products
• Molecular Weight: 114.07
• Molecular Formula: C3H5F3O
• Synonyms: 3,3,3-trifluoropropanol
• Appearance: Yellow liquid

Case Study

Enhancing Hydrophobicity and Durability of Polyurethane Clearcoats Using 3,3,3-Trifluoro-1-Propanol as a Modifier

Zuo, Zongzheng, et al. Polymer 313 (2024): 127735.

This study examined the application of 3,3,3-trifluoro-1-propanol (TEOH1) as a fluorinated modifier in the synthesis of hydrophobic two-component polyurethane (2K PU) clearcoats. TEOH1 was used to functionalize a polyisocyanate hardener, imparting enhanced surface properties and environmental resistance to the coating system. TEOH1, along with longer-chain analogues (TEOH4 and TEOH6), was also evaluated for its ability to enhance coating performance under extended outdoor exposure.
Key Findings
· The hydrophobic 2K PU clearcoats exhibit the highest water contact angles (WCAs) of 91.9°, 101.6°, and 106° when perfluoro alcohol is applied at dosages of 10%, 20%, and 20% for TEOH1, TEOH4, and TEOH6, respectively, all without haze and with a non-sticky surface.
· To assess the durability of hydrophobicity in these perfluoro alcohol-modified coatings, accelerated weathering and outdoor exposure tests were conducted, alongside monitoring dirt pick-up resistance (DPUR) in outdoor conditions. Although the WCAs of all coatings decreased during weathering tests, those with at least 20% TEOH4 and 5% TEOH6 retained their hydrophobicity after 228 days of outdoor exposure.
· The incorporation of perfluoro alcohol significantly improved the DPUR of the 2K PU clearcoat, particularly for formulations with TEOH4 and TEOH6 at appropriate dosages. Overall, longer fluoroalkyl chains enhance hydrophobicity, hydrophobic durability, and outdoor dirt resistance.

3,3,3-Trifluoro-1-Propanol as a Fluorinated Building Block for an Amino-Activatable 19F-MRI Nanoprobe

Huang, Pingsheng, et al. ACS applied materials & interfaces 10.22 (2018): 18532-18542.

19F-MRI agents require dense fluorine content and sufficient molecular mobility to produce detectable signals in biological environments. The reported nanoprobe architecture places trifluoromethyl-containing segments inside a hydrophobic core so that 19F signals are initially quenched. This work described the use of 3,3,3-trifluoro-1-propanol (TFP) as the fluorinated alcohol reagent in the synthesis of an AMA-DNBS-F monomer that provided compactly packed trifluoromethyl motifs for a reducing-microenvironment-activated 19F-MRI nanoprobe.
Integration of the TFP-derived motif into a stimuli-responsive nanoprobe architecture permitted switching of 19F MRI signal upon biologically relevant triggering (biothiol cleavage), demonstrating a viable route to water-soluble, high-sensitivity 19F imaging agents.
Synthetic Workflow of AMA-DNBS-F Monomer
· 2-((2,4-dinitrophenyl)sulfonamido)ethyl methacrylate (AMA-DNBS) was prepared from 2-aminoethyl methacrylate and 2,4-dinitrobenzenesulfonyl chloride (60% yield), then subjected to Mitsunobu coupling with TFP, triphenylphosphine, and DEAD in THF to give 2-((2,4-dinitro-N-(3,3,3-trifluoropropyl)phenyl)sulfonamido)-ethyl methacrylate (AMA-DNBS-F) monomer after cold precipitation and silica purification (70% yield).
· TFP served as the fluorinated alcohol in a Mitsunobu coupling to introduce the 3,3,3-trifluoropropyl group into the AMA-DNBS scaffold, providing the trifluoromethyl-dense segment necessary for strong 19F content while remaining NMR-silent until probe activation.

Custom Q&A

What is the molecular formula of 3,3,3-Trifluoro-1-Propanol?

The molecular formula is C3H5F3O.

What are the synonyms for 3,3,3-Trifluoro-1-Propanol?

The synonyms are 3,3,3-Trifluoropropan-1-ol and 3,3,3-trifluoropropanol.

What is the molecular weight of 3,3,3-Trifluoro-1-Propanol?

The molecular weight is 114.07 g/mol.

When was the compound created and modified?

The compound was created on March 27, 2005, and last modified on October 21, 2023.

What is the IUPAC name of 3,3,3-Trifluoro-1-Propanol?

The IUPAC name is 3,3,3-trifluoropropan-1-ol.

What is the InChI key for 3,3,3-Trifluoro-1-Propanol?

The InChI key is HDBGBTNNPRCVND-UHFFFAOYSA-N.

What is the Canonical SMILES notation for 3,3,3-Trifluoro-1-Propanol?

The Canonical SMILES notation is C(CO)C(F)(F)F.

What are the CAS numbers associated with 3,3,3-Trifluoro-1-Propanol?

The CAS numbers are 2240-88-2 and 65530-60-1.

What is the XLogP3 value of 3,3,3-Trifluoro-1-Propanol?

The XLogP3 value is 0.4.

How many hydrogen bond acceptors and donors are there in 3,3,3-Trifluoro-1-Propanol?

There are 4 hydrogen bond acceptors and 1 hydrogen bond donor in 3,3,3-Trifluoro-1-Propanol.