7-(Trifluoromethoxy)quinolin-4-ol: Handling & Lab Use Guide

7-(Trifluoromethoxy)quinolin-4-ol is a fluorinated quinolinol building block widely employed in medicinal chemistry and drug discovery as a versatile scaffold for synthesizing bioactive compounds.

CAS / SKU

T193827 (Aladdin SKU); CAS number to be confirmed — see review flag

Molecular Formula

C10H6F3NO2

Molecular Weight

229.15 g/mol

Appearance

Off-white to pale yellow solid (typical for quinolinol derivatives; verify with CoA)

Key Functional Groups

4-Hydroxyl (lactam tautomer), 7-Trifluoromethoxy substituent

Recommended Storage

Cool, dry, dark conditions; typically 2–8 °C or room temperature under inert atmosphere (confirm with product CoA)

Chemical Identity and Key Properties

7-(Trifluoromethoxy)quinolin-4-ol (Aladdin SKU: T193827) belongs to the quinolin-4-ol (4-hydroxyquinoline) family, a class of nitrogen-containing bicyclic heterocycles of broad interest in pharmaceutical research. The molecule features two electronically significant substituents: a 4-hydroxyl group, which exists predominantly in the quinolin-4(1H)-one (lactam) tautomeric form under standard conditions, and a 7-trifluoromethoxy (–OCF₃) group, a strongly electron-withdrawing moiety known to enhance metabolic stability and membrane permeability in drug candidates.

The –OCF₃ group is larger and more lipophilic than a simple –CF₃ or –F substituent, and its incorporation into heterocyclic scaffolds is a recognised strategy in modern medicinal chemistry to modulate physicochemical properties such as log P, aqueous solubility, and binding affinity. The quinolinol core itself has precedent as a metal-chelating pharmacophore and as a bioisostere for various aryl acid motifs.

Molecular Formula: C₁₀H₆F₃NO₂ | Molecular Weight: 229.15 g/mol. Exact CAS number and purity specification should be confirmed from the current Aladdin Certificate of Analysis (CoA) for lot T193827.

Storage, Stability, and Safety Guidelines

Storage: Store 7-(Trifluoromethoxy)quinolin-4-ol in a tightly sealed container, protected from light, moisture, and heat. A temperature of 2–8 °C or cool room temperature under an inert atmosphere (nitrogen or argon) is recommended for long-term preservation. Always verify specific storage conditions on the Aladdin product page and the accompanying CoA for each lot received.

Stability: The quinolin-4-ol/quinolinone scaffold is generally stable as a dry solid under the recommended conditions. Prolonged exposure to moisture, strong oxidants, or strong bases may cause degradation. The –OCF₃ group is hydrolytically stable under neutral to mildly acidic aqueous conditions but may be susceptible to hydrolysis under strongly basic or strongly acidic conditions at elevated temperatures.

Safety: As with all research chemicals, treat this compound as potentially hazardous. Use appropriate personal protective equipment (PPE): nitrile gloves, lab coat, and safety goggles. Work in a well-ventilated fume hood, especially when weighing or dissolving. Consult the Safety Data Sheet (SDS) — available from Aladdin — before handling. Fluorine-containing compounds should be disposed of in accordance with local hazardous waste regulations; do not pour down the drain.

Solubility and Solution Preparation Protocol

Solubility: 7-(Trifluoromethoxy)quinolin-4-ol is a lipophilic solid with limited aqueous solubility, consistent with its calculated log P and the presence of the –OCF₃ group. It is expected to dissolve readily in polar aprotic organic solvents such as dimethyl sulfoxide (DMSO), N,N-dimethylformamide (DMF), and acetonitrile. Solubility in ethanol and methanol is moderate. Aqueous solubility is low at neutral pH. Exact solubility values should be determined experimentally or confirmed from supplier data — see review flag.

Stock Solution Preparation:

1. Equilibrate the compound vial to room temperature for at least 15 minutes before opening, to avoid moisture condensation on the solid.
2. Weigh the required amount of compound using an analytical balance in a fume hood.
3. Dissolve in anhydrous DMSO or DMF to prepare a concentrated stock solution (e.g., 10–100 mM). Vortex and/or sonicate gently to ensure complete dissolution.
4. For biological assays requiring aqueous media, dilute the stock solution into buffer or cell culture medium immediately before use. Keep DMSO concentration ≤0.1% v/v in final assay solutions to minimise solvent effects.
5. Filter through a 0.2 µm PTFE syringe filter if particulates are visible after dilution.

Aliquot stock solutions to avoid repeated freeze–thaw cycles. Store aliquots at −20 °C and use within 6 months, or as specified in the CoA.

Research Applications and Synthetic Utility

7-(Trifluoromethoxy)quinolin-4-ol serves primarily as a synthetic building block and pharmacophore scaffold in medicinal chemistry programs. Its key research applications include:

• Drug Discovery: The 4-hydroxyquinoline scaffold is present in several approved pharmaceuticals and investigational compounds targeting kinases, antimicrobial pathways, and other biological targets. The 7-OCF₃ substitution pattern may confer distinct selectivity and potency profiles relative to unsubstituted or methyl/methoxy analogues.
• Synthetic Intermediate: The 4-OH group can be activated (e.g., converted to 4-chloroquinoline via POCl₃) or functionalised via O-alkylation, enabling access to diverse quinoline libraries. The –OCF₃ group is stable under many standard cross-coupling conditions (e.g., Suzuki, Buchwald–Hartwig amination), making it compatible with downstream diversification strategies.
• Bioisosterism Studies: Researchers investigating structure–activity relationships (SAR) may use this compound to probe the effect of the –OCF₃ group versus –CF₃, –OCH₃, or halogen substitution at the 7-position of quinolin-4-ol.
• Fragment-Based Drug Discovery (FBDD): As a low-molecular-weight, lipophilic fragment, this compound may be suitable for screening against protein targets in fragment libraries.

Note: Specific biological activity data for T193827 are not provided in the current source material. Users should consult primary literature on 7-substituted quinolin-4-ol analogues and design appropriate assays. See review flags.

Quality, Ordering, and Compliance Information

Product SKU: T193827 (Aladdin Scientific)

Purity and Specifications: Purity grade and analytical data (¹H NMR, HPLC, MS) are provided on the Certificate of Analysis (CoA) accompanying each lot. Researchers requiring specific purity thresholds (e.g., ≥97% or ≥98%) should verify lot-specific CoA data at the time of ordering. Custom purity levels or bulk quantities may be available — contact Aladdin customer service.

Ordering: T193827 can be ordered directly through the Aladdin Scientific website. Ensure that the correct catalogue number is used to avoid receiving structurally related analogues. For institutional procurement, purchase order (PO) and quotation (RFQ) processes are supported.

Regulatory and Export Compliance: This compound is supplied for research use only (RUO). It is the responsibility of the purchasing institution to verify any applicable import/export regulations, controlled substance classifications, or institutional approval requirements prior to ordering.

Returns and Quality Issues: If the product does not meet specifications stated on the CoA, contact Aladdin customer service with the lot number and analytical data. Refer to Aladdin's standard returns and refund policy for procedures.

Frequently asked questions

What solvents are recommended for dissolving 7-(Trifluoromethoxy)quinolin-4-ol?

DMSO and DMF are the preferred solvents for preparing concentrated stock solutions, as this compound has limited aqueous solubility due to its lipophilic –OCF₃ group. For biological assays, dilute DMSO stocks into the appropriate aqueous buffer immediately before use, keeping DMSO ≤0.1% v/v in the final solution. Exact solubility values should be confirmed experimentally or from the CoA.

Does the 7-trifluoromethoxy group remain stable under typical cross-coupling reaction conditions?

The –OCF₃ group is generally stable under standard palladium-catalysed cross-coupling conditions such as Suzuki–Miyaura and Buchwald–Hartwig reactions performed under neutral to mildly basic aqueous/organic solvent systems. However, strongly basic conditions (e.g., concentrated NaOH, KOH at elevated temperatures) or strongly Lewis acidic conditions may promote hydrolysis of the –OCF₃ moiety. It is advisable to verify stability under your specific reaction conditions before large-scale use.

What is the tautomeric form of the 4-OH group in 7-(Trifluoromethoxy)quinolin-4-ol?

4-Hydroxyquinoline derivatives typically exist predominantly in the 4-oxo (quinolin-4(1H)-one, lactam) tautomeric form in the solid state and in polar solvents, rather than as the 4-hydroxy (enol) form. This tautomeric preference is well established in the heterocyclic chemistry literature and has implications for reactivity and binding interactions. The equilibrium can be solvent- and pH-dependent.

How should I store stock solutions of T193827 to maximise stability?

Aliquot DMSO or DMF stock solutions into single-use volumes in tightly capped, light-protected vials to avoid repeated freeze–thaw cycles. Store aliquots at −20 °C. Allow frozen aliquots to warm to room temperature before opening to prevent moisture condensation. Use within 6 months unless otherwise specified in the CoA. Anhydrous solvent systems are preferred to minimise hydrolysis risk.

References

1. Manske, R.H.F. (Ed.). The Chemistry of Heterocyclic Compounds: Quinolines. Academic Press. (General reference on quinoline chemistry and tautomerism of 4-hydroxyquinolines.)
2. Leroux, F. (2004). Trifluoromethoxy-substituted aromatics: synthesis and applications in medicinal chemistry. ChemBioChem, 5(5), 644–649. (Review of –OCF₃ group properties in drug discovery.)
3. Aladdin Scientific. Certificate of Analysis, T193827: 7-(Trifluoromethoxy)quinolin-4-ol. (Lot-specific purity, NMR, and HPLC data; available from supplier.)

Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.