ANQ-11125 TFA , CAS No.A1432265

CAS: A1432265 Cat. No.: A1432265 Formula: C₈₆H₁₂₅N₁₉O₂₁.xC₂HF₃O₂ Peso molecolare: 1761.03 (free acid)

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

ANQ-11125 TFA is a potent and selective antagonist of motilin , with the pK d of 8.24. ANQ-11125 TFA blocks motilide-induced contractions in vitro in the rabbit.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

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Tipo di azione

ANTAGONIST

Nomi e identificatori

Peso molecolare

1761.03 (free acid)

Application Protocols

Item-specific tested applications, assay types, or recommended dilutions: Not specified for this item.

General usage guidance in discovery settings (non-clinical)

• Stock preparation: Prepare a concentrated DMSO stock (e.g., 10–50 mM) based on free-base equivalents if known. Filter through a 0.22 μm PTFE filter if particulate is present.
• Plate-based assays: Dispense using calibrated liquid handlers; target final DMSO ≤0.1–0.5% v/v. Include vehicle controls and, if relevant, counterion-matched controls to assess TFA effects.
• Solubility check: Visual inspection after dilution; if precipitation occurs, reduce concentration, add solubilizing co-solvent (≤0.5% DMSO), or pre-exchange counterion.
• Data reporting: Document batch/lot, salt form, nominal purity, and concentration calculations (free-base vs. salt) for reproducibility.
• Stability: Minimize room-temperature exposure; return stocks to −20°C promptly and avoid repeated freeze–thaw cycles by aliquoting.

Biological Roles

Item-specific biological roles or targets: Not specified for this item; no target annotation is provided.

General considerations for small-molecule library members (non-clinical)

• Role in research: Such compounds are typically used as chemical probes or screening hits/leads in biochemical or cell-based assays to interrogate pathways, enzymes, receptors, or phenotypes.
• Counterion impact: The TFA counterion generally does not confer specific biological activity but can influence apparent potency in vitro by affecting pH, ionic strength, and solubility. For sensitive assays, consider desalting or counterion exchange and report concentrations as free-base equivalents.
• Adsorption and carryover: Cationic salts may adsorb to plastics or membranes; using low-bind labware and adding inert carrier protein (e.g., BSA) at low levels can mitigate losses in some assay formats (general practice).
• Off-target considerations: Without a defined structure, off-target profiles cannot be anticipated; comprehensive profiling requires empirical screening and orthogonal confirmation.
• Documentation: Maintain detailed records of batch, salt form, and exact mass used to ensure reproducibility across assays and between laboratories.

Buffer Applications

Not typically applicable.

• ANQ-11125 TFA is supplied as a small-molecule TFA salt for research screening and synthesis, not as a buffering reagent. The TFA counterion is a strong acid and is generally avoided as a buffer component due to poor buffering capacity near physiological pH.
• Practical note: If using in aqueous assays, adjust the final medium with appropriate buffers (e.g., phosphate, HEPES, MOPS; selection depends on target pH) and keep the contribution of TFA to ionic strength minimal by limiting the stock solution volume or by prior counterion exchange.

Green Alternatives

This section discusses greener choices around solvents and counterion management for TFA salts in research workflows (general guidance).

• Counterion considerations

  • TFA is a perfluorinated anion; while effective for salt formation, it can complicate waste streams. Alternatives include hydrochloride, sulfate, citrate, tartrate, mesylate, or acetate salts, chosen to balance solubility, crystallinity, and environmental profile.
  • Tradeoffs: HCl salts are widely accepted and MS-friendly but may be more hygroscopic; organic carboxylates (acetate, citrate) are less persistent environmentally but may afford oils rather than crystalline solids.

• Solvent choices for dissolution and processing

  • Prefer water, ethanol, isopropanol, and ethyl acetate where feasible over chlorinated solvents (e.g., DCM) and high-toxicity solvents (e.g., DMF, NMP). DMSO remains common for stocks; minimize final assay DMSO content.
  • Mobile phases: For LC, replace TFA with formic acid (0.1%) or volatile ammonium salts (e.g., ammonium formate/acetate) to improve MS compatibility and reduce persistent fluorinated waste.

• Workup and purification

  • Employ aqueous bicarbonate/carbonate to exchange out TFA, then recover the free base and re-salt with a greener acid if needed.
  • Crystallization in greener solvent systems (EtOAc/IPA/heptane) can reduce solvent footprint vs. DCM/MeOH.

• Comparative snapshot (general)

  • TFA salt: strong acidity, robust crystallization, but fluorinated waste.
  • HCl salt: strong acidity, common, MS-compatible; corrosive but non-fluorinated.
  • Acetate/citrate: milder, biodegradable conjugate base; may impact stability/solubility profiles.

Pharmaceutical Uses

Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet. This product is for research use only and is not for human or veterinary use.

General formulation/manufacturing context (non-clinical)

• Salt selection: Converting free-base amines to salts enhances crystallinity, stability, and manufacturability. While TFA salts are common in discovery and purification, pharmaceutically developed forms more often employ non-fluorinated counterions (e.g., HCl, sulfate, fumarate, maleate) due to regulatory and environmental considerations.
• Process utility: TFA salts can aid in isolation after preparative chromatography (elution with TFA-containing mobile phases) and can be convenient intermediates before final salt exchange.
• Analytical considerations: Report dose levels as free-base equivalents to allow cross-comparison between salt forms; perform salt screening to identify optimal polymorphs and hydrate/solvate states for advanced development.
• Residuals and extractables: For any material intended for translational studies, control residual solvents, inorganic counterions, and verify TFA content by validated methods; however, this product is not supplied for such applications.

Physical Properties

Item-specific properties (from Product Data)

• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, logP/logD, pKa, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance for organic TFA salts

• Physical state: Many amine·TFA salts are crystalline or amorphous solids that can be hygroscopic, though behavior varies with the cation.
• Solubility (typical): Enhanced solubility in polar protic solvents (water, MeOH, EtOH) and highly polar aprotics (DMSO, DMF). Solubility in less polar solvents (EtOAc, MTBE, hydrocarbons) is often reduced relative to the free base.
• pKa considerations: TFA is a strong organic acid (pKa ~0.3 in water, literature), so amine·TFA salts typically exist predominantly as the protonated cation in aqueous media below neutral pH; conversion to free base occurs upon basification (literature guidance).
• Thermal behavior: TFA salts can decompose or lose TFA upon strong heating or under high vacuum with base present; always confirm stability by TGA/DSC for process work (general practice).
• Spectroscopy cues: 19F NMR often shows a singlet for CF3 near −75 ppm; IR shows strong C=O stretch of carboxylate ~1670–1600 cm−1 and C–F stretches ~1200 cm−1 (literature ranges). These are general indicators and not specifications for this item.

Quality and Grades

Item-specific quality information

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

How to interpret grade in the context of small-molecule TFA salts (general guidance)

• Research grade: Appropriate for discovery chemistry, screening, and non-GLP studies. Purity typically reported by HPLC/UPLC area % and/or NMR qNMR; salt stoichiometry (e.g., 1.0 eq TFA) may be listed separately.
• Chromatography data: For LC-based purity, ensure the method and detection wavelength are provided on the CoA; TFA-containing analytes can show stronger UV at low wavelengths (e.g., 210–220 nm).
• Residual solvents: Libraries often specify compliance with general residual solvent limits (e.g., ICH Q3C classes); check CoA.
• Counterion content: For TFA salts, percent TFA or equivalents per mole of base is commonly reported (e.g., via ion chromatography or 19F NMR). Verify mono- vs. di-protonation if multiple basic sites exist in the cation.
• Water content: If Karl Fischer is provided, confirm hydration state; hygroscopic salts can vary in apparent assay by weight.
• Implications for use: For bioassay screening, consistency of salt form and concentration matters; normalize dosing to free-base equivalents if comparing across counterions.
• Documentation: For regulated or scale-up work, request full specification sheet, batch-specific CoA, and, when necessary, impurity profiles.

Reaction and Applications

Item-specific application claims (from Product Data)

• Manufacturer Applications: Not specified.

General applications relevant to TFA salts of small molecules

• Discovery screening: TFA salts provide stable, weighable forms for library members; convenient for high-throughput screening, hit validation, and SAR comparisons when normalized to free-base equivalents.
• Handling and formulation: Salts reduce volatility and may improve bench stability of amines and N-heterocycles, facilitating storage and dosing accuracy.
• Synthetic manipulations:
  • Free-base generation: Neutralize with a non-nucleophilic base (e.g., Na2CO3, K2CO3, or aqueous NH3) and extract to obtain the free base for coupling or metalation steps.
  • Salt metathesis: Exchange TFA for other counterions (HCl, fumarate, tartrate, mesylate) to optimize crystallinity or solubility; commonly achieved by dissolution in minimal solvent followed by treatment with the desired acid and recrystallization.
  • Protection/deprotection logic: While TFA is not a protecting group here, the salt form can temporarily modulate basicity/nucleophilicity during workups and purifications.
• Analytical workflows: Expect strong 19F NMR signal from TFA; confirm salt stoichiometry by 19F qNMR or ion chromatography. For LC/MS, TFA can suppress ionization; consider formic acid or ammonium acetate eluents when monitoring the cation.
• Practical tips
  • If performing base-sensitive transformations, liberate and isolate the free base to avoid acid-promoted side reactions.
  • For scale-up, map a reproducible salt formation protocol (acid equivalents, solvent, temperature) to ensure consistent polymorph/solvate, if any.

Reaction Conditions

Item-specific reaction conditions: Not specified for this item; refer to CoA/Spec Sheet for any batch notes.

General literature/practice for manipulating TFA salts of amines/heterocycles

• Free-base liberation
  • Conditions: Dissolve salt in water or MeOH/H2O; add Na2CO3 or K2CO3 to pH 9–11; extract with EtOAc or MTBE. Dry and concentrate to obtain the free base. Typical quantitative conversion within minutes to 1 h, depending on phase transfer.
  • Alternative: Use Amberlite IRA-400 (OH− form) or similar basic resin for gentle, solvent-compatible deprotonation.
• Salt metathesis
  • Conditions: Dissolve in minimal solvent (EtOH, IPA, MeOH) and treat with equimolar target acid (e.g., HCl in IPA/ether, fumaric/maleic acid in alcohol). Induce crystallization by antisolvent addition (MTBE/heptane) and cooling. Characterize stoichiometry by titration or 19F NMR (loss of TFA signal).
• Workup and drying
  • Keep temperatures modest (≤40°C) to avoid decomposition; co-evaporate with toluene or acetonitrile to strip residual TFA after basification.
• Analytical monitoring
  • TLC/UPLC under non-TFA acidic modifiers (formic acid) improves MS detection of the cation. 19F NMR serves as a rapid check for remaining TFA.
• Yields
  • Neutralization and salt exchange steps are typically high-yielding (literature: often >80–95%), governed mainly by solubility and crystallization efficiency rather than intrinsic reactivity.

Safety and Handling

Item-specific safety data

• GHS classification, signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.

General safety considerations for organic TFA salts

• Hazards: Depending on the cation, salts may cause irritation to skin, eyes, and respiratory tract. Trifluoroacetate counterions are acidic; dusts/solutions can be irritating.
• PPE: Use lab coat, safety glasses or goggles, and appropriate chemically resistant gloves (e.g., nitrile). Employ weighing in a fume hood to minimize inhalation of dust/aerosol.
• Handling: Avoid moisture ingress if the salt is hygroscopic. Keep containers tightly closed. Use clean, dry tools to prevent adventitious base contamination that may liberate free base and TFA.
• Incompatibilities: Strong bases (can liberate free base and trifluoroacetate), strong oxidizers (general caution), and reactive acylating agents (may alter the cation). Avoid heating to decomposition.
• First aid (overview; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice if irritation continues.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Spill/accidental release: Avoid dust generation, collect mechanically or with damp disposable towels/HEPA vacuum, and dispose of in accordance with institutional and local regulations.
• Waste: Collect as organic laboratory waste; salts containing fluorinated anions should not be discharged to drain. Follow institutional EHS guidance.
• Always consult the SDS for authoritative, product-specific safety information.

Solvent Selection

Item-specific solubility/miscibility: Not specified for this item; refer to CoA/Spec Sheet.

General solvent guidance for organic TFA salts

• Polarity class: Typically polar ionic solids; most TFA salts of amines show improved solubility in polar protic and highly polar aprotic media versus the corresponding free bases.
• Common solvents for stock solutions:
  • Aqueous: Water, buffer (acidic to neutral pH) often improves dissolution; avoid strong base if you need to maintain the salt form.
  • Organic: DMSO (most universal for screening stocks), methanol, ethanol; DMF for particularly challenging cases.
• Practical tips
  • Start with DMSO to prepare concentrated cryostocks (e.g., 10–50 mM), then dilute into assay buffer or media to limit DMSO to ≤0.1–0.5% v/v.
  • If dissolution is slow, gentle warming (≤40°C) and sonication can help. Avoid prolonged heating that may promote counterion exchange or degradation.
  • For LC/MS or preparative work, be aware that residual TFA can suppress electrospray ionization and affect peak shape; consider exchanging the counterion (e.g., to HCl or acetate) when MS sensitivity is critical.
• Choosing vs. alternatives
  • If low aqueous solubility persists, convert to the free base (carefully basify, extract into an organic phase) or to a different salt (HCl, mesylate, citrate) to tune solubility/pH behavior.
  • For biological assays sensitive to TFA, perform desalting or counterion exchange prior to dosing.

Storage and Reconstitution

Item-specific storage and shipping

• Storage conditions: Store at −20°C (per Product Data). Keep container tightly closed, dry, and protected from light where practical.
• Shipped in: Ice chest + ice pads (per Product Data) to maintain cold chain.

General guidance for this product class

• Stability: Many small-molecule TFA salts are stable at −20°C for extended periods when protected from moisture. Hygroscopicity varies; opening in a low-humidity environment is recommended.
• Aliquoting: Upon first receipt, if solid, divide into single-use portions under dry conditions to minimize cumulative moisture uptake.
• Reconstitution
  • Solvent choice: Start with anhydrous DMSO for concentrated stocks; water, methanol, or ethanol may also be suitable depending on the cation (solubility for this specific item is not specified; consult CoA/Spec Sheet).
  • Concentration: Calculate on a free-base equivalent basis if molecular weight and salt stoichiometry are known. If unknown, determine by 19F NMR or acid-base titration prior to critical dosing.
  • Filtration: If needed, sterile-filter through 0.22 μm PTFE/nylon for cell-based assays; avoid cellulose esters with strong organic solvents.
• Freeze–thaw management: Store reconstituted stocks in small aliquots at −20°C or −80°C to avoid repeated freeze–thaw cycles; record preparation date and solvent.
• Light/air sensitivity: If the cation is air/light sensitive (unknown here), use amber vials and inert atmosphere. Confirm stability experimentally for long-term studies.

Structure and Identity

Item-specific facts (from Product Data)

• SKU: A1432265
• Product name: ANQ-11125 TFA
• Category: Small molecules and compound libraries (小分子和化合物库)
• Storage: Store at −20°C (as supplied)
• Shipping: Ice chest + ice pads
• Research use: For research use only
• Chemical identifiers (CAS, CID, InChIKey, SMILES, molecular formula, molecular weight): Not specified for this item; refer to CoA/Spec Sheet.

General/literature notes about “TFA” salt form

• The “TFA” suffix typically denotes a trifluoroacetate salt, most commonly formed with basic amines or heteroaromatics. In such salts, the organic cation is paired with the trifluoroacetate anion (CF3COO−).
• Structural features often implied: a protonatable functionality (e.g., primary/secondary/tertiary amine, amidine, imidazole-like N) that forms the salt; however, the exact scaffold for ANQ-11125 is not provided.

How to describe likely 2D features (general guidance)

• Cationic center at a protonated nitrogen (if present) paired with the TFA counterion.
• Trifluoroacetate comprises a carbonyl (C=O) adjacent to a CF3 group; the anion is resonance-stabilized between two oxygen atoms.

Traceability and identity confirmation (procedural guidance)

• For definitive identity, consult the item’s CoA/SDS for batch-specific: molecular formula, exact mass, salt stoichiometry (mono-/di-TFA), and any stereochemical assignments.
• Recommended orthogonal ID methods (general): 1H/13C NMR (look for TFA anion signals ~−75 to −77 ppm in 19F NMR and ~116–120 ppm in 13C q, depending on reference), HRMS (m/z of free base vs. salt adduct), and LC/MS retention under acidic and neutral mobile phases.

Synthetic Utility

General synthetic value of a small-molecule TFA salt (structure not specified)

• Access to the free base: Neutralization releases the free amine/heterocycle, enabling nucleophilic substitutions, acylations (acid chlorides/anhydrides), sulfonylations, carbamoylations, urea/thiourea formations, and metal-catalyzed couplings where a neutral nitrogen is required.
• Purification handle: Formation of the TFA salt can simplify isolation from basic or neutral impurities (e.g., by selective precipitation or crystallization) and can improve chromatographic behavior.
• Counterion exchange: Strategic conversion from TFA to HCl/mesylate/benzenesulfonate can fine-tune crystallinity and downstream processing.
• Protection strategy adjunct: While not a protecting group per se, protonation modulates basicity/reactivity, which can suppress undesired coordination to catalysts or reduce volatility during distillation/evaporation.
• Analytical leverage: 19F NMR quantification of TFA provides a convenient assay for salt stoichiometry; this assists in calculating equivalents for subsequent reactions.
• Workflow tip: Prior to moisture- or base-sensitive steps (e.g., strong base metalations, organometallic additions), isolate the meticulously dried free base (azeotrope with toluene) to avoid acid-induced side reactions. Re-form the desired salt at the end of the sequence for storage stability.

Target Specificity

Item-specific target data (antigen/epitope/clone/isotype/species): Not applicable. This product is a small-molecule TFA salt with no antibody or biological macromolecule specifications provided.