N,N-Dimethyl-2-(perfluorophenoxy)ethanamine - ≥98% , CAS No.2044704-44-9

CAS: 2044704-44-9 Cat. No.: N993864 Formula: C₁₀H₁₀F₅NO Peso molecolare: 255.18 PubChem CID: 122198509

QUALITÀ & PUREZZA ≥98%

Storage

Room temperature

Specifiche

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

Sorrisi canonici

CN(C)CCOC1=C(C(=C(C(=C1F)F)F)F)F

IUPAC Name

N,N-dimethyl-2-(2,3,4,5,6-pentafluorophenoxy)ethanamine

InChIKey

ZBONATRDQBOWML-UHFFFAOYSA-N

INCHI

1S/C10H10F5NO/c1-16(2)3-4-17-10-8(14)6(12)5(11)7(13)9(10)15/h3-4H2,1-2H3

PubChem CID

122198509

Peso molecolare

255.18

Proprietà chimiche e fisiche

• Peso molecolare: 255.180 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 255.068 Da
• Monoisotopic Mass: 255.068 Da
• Topological Polar Surface Area: 12.500 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 227.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No item-specific, validated application protocols are provided for this product. As a general synthetic building block:

• For quaternization screens: dissolve 0.5–1.0 mmol of the amine in 2–3 mL MeCN, add 1.1–1.5 equiv of alkyl halide, stir at 40 °C, monitor by LCMS. Upon completion, concentrate and triturate with MTBE/Et2O to induce precipitation of the ammonium salt.
• For salt formation (HCl): dissolve the amine in anhydrous EtOAc (0.1–0.2 M), cool to 0–5 °C, add 2 M HCl in dioxane dropwise until pH paper indicates acidity and precipitation forms. Filter, wash with cold EtOAc, dry under vacuum.
• For analytical confirmation: acquire 1H NMR (expect NMe2 singlet ~2.2–2.4 ppm, ethylene multiplets ~2.6–3.9 ppm), 19F NMR for the C6F5 pattern (characteristic multiplets), and HRMS for [M+H]+.

These are general starting points and should be adjusted based on scale, equipment, and safety assessments. Always consult the SDS and perform appropriate risk assessments before commencing work.

Biological Roles

This product is intended for research use only. No biological or clinical claims are made for this substance.

General, non-clinical context (literature-based):

• Small tertiary amines can interact with biological membranes when protonated, increasing aqueous solubility and potentially acting as cationic surfactant precursors after quaternization. However, this compound is not characterized here for any biological activity.
• The perfluorinated aryl ether imparts hydrophobic/fluorophilic character, sometimes leveraged in materials interfacing with biomolecules (e.g., surface coatings). Such uses depend on formulation and are outside the scope of this product listing.
• No metabolic or enzymatic roles are known or implied; this is a synthetic building block. If exposure studies are planned, conduct independent toxicological assessments and follow institutional safety protocols.

If a biologically compatible salt form is required (e.g., HCl, mesylate) for specific in vitro workflows, it should be generated and qualified by the user. Always consult your institution’s EHS office and the SDS prior to any work involving cells or biological matrices.

Buffer Applications

This compound is not a buffering reagent and is not typically used to prepare defined pH buffer systems.

• Relevance note: As a tertiary amine, it can be protonated and thus exerts basicity, but its buffering range, solubility, and ionic strength characteristics have not been established for biochemical buffer use. Dedicated buffers (e.g., Tris, HEPES, MOPS) are preferred for precise pH control.
• Practical pointer: If present as an impurity or additive in aqueous systems, anticipate pH shifts upon protonation; evaluate compatibility with buffer components and consider using its protonated salt for aqueous manipulations to improve handling.

Green Alternatives

Because this molecule contains a perfluorinated aromatic ring, its environmental profile warrants consideration. While highly useful in synthesis and materials, perfluorinated motifs are generally persistent. Options to reduce environmental impact (general guidance):

• Substrate design alternatives:

  • Replace perfluorophenyl (C6F5) with non-fluorinated phenyl or partially fluorinated rings when the application tolerates reduced fluorophilicity/lipophilicity.
  • Consider bio-based aryl ethers or alkyl ethers that achieve similar polarity without extensive fluorination.

• Process solvent choices (if using this reagent):

  • Prefer greener solvents (MeCN, 2-MeTHF, CPME, EtOAc, propylene carbonate) over chlorinated solvents where feasible.

• Lifecycle and workup:

  • Capture and recycle mother liquors containing fluorinated organics; use adsorbents (activated carbon) where appropriate; segregate fluorinated waste streams for specialized disposal.

• Comparison snapshot (general, literature-based):

  • Perfluorophenyl tertiary amine vs. phenyl analogue:
    • Persistence: higher for perfluorinated variant; lower for phenyl.
    • Lipophilicity: higher for perfluorinated; moderate for phenyl.
    • Performance in fluorous media: favorable for perfluorinated; limited for phenyl.

Trade-offs: Reducing fluorination may alter solubility, phase behavior, and thermal/oxidative stability. If the perfluoroaryl is essential to performance (e.g., in fluorous separations or surface energy tuning), mitigate impact by minimizing scale, optimizing yields, and maximizing recovery/reuse.

Pharmaceutical Uses

No pharmacopeial status, excipient role, or GMP grade is provided for this item. It is supplied for research use only.

General, non-therapeutic context:

• Tertiary amines and their quaternary ammonium salts can serve as processing aids, antistatic agents, or phase-transfer catalysts in manufacturing contexts. Whether this specific perfluorophenoxy-substituted amine is appropriate depends on impurity profile, grade, and regulatory requirements.
• If formulation studies are contemplated (e.g., as a counterion donor or catalyst in a non-drug process), generate a full impurity and residual solvent profile and assess extractables/leachables relevant to the intended equipment and packaging.

Important: Do not use this material as an API, excipient, or in clinical applications without appropriate qualification and regulatory review. For any pharmaceutical-adjacent work, request extended QC data and regulatory documentation.

Physical Properties

Item-specific specifications are not provided in the Product Data. The values below are literature/computed guidance derived from the named structure and should not be treated as product specifications.

• Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula (computed from name): C10H10F5NO
• Molecular weight (computed): ~255.19 g/mol
• Boiling point (literature expectation for analogous tertiary aminoaryl ethers): often in the 200–260 °C range at 1 atm; actual BP depends on purity and may require reduced pressure due to thermal sensitivity of perfluoroaryl ethers. Use distillation under vacuum if purification is needed.
• Melting point: Not available in literature; likely liquid or low-melting solid near ambient based on structure; verify experimentally.
• Density: Not specified for this item; refer to CoA/Spec Sheet. Tertiary amine ethers with perfluoroaryl substituents typically show densities around 1.2–1.4 g/mL (literature trend), but confirm by measurement.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• pKaH of the conjugate acid (tertiary amine basicity, literature expectation): tertiary aliphatic amines pKaH ≈ 9–11; the electron-withdrawing perfluorophenoxy group (through-space/inductive, remote) may modestly reduce basicity, giving an estimated pKaH in the 8–10 range. Determine experimentally for exact value.
• LogP/logD (qualitative): Expected moderately lipophilic due to C6F5 ring; protonation will shift to hydrophilic logD at low pH.
• Solubility (qualitative, literature): typically soluble in common organic solvents (DCM, THF, MeCN, toluene, EtOAc). Free base shows low water solubility; protonated salts are water-soluble.

For any critical design or regulatory use, consult the product CoA/SDS for measured properties.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting grades (general guidance):

  • Research-grade or catalog-grade tertiary amine building blocks are typically suitable for synthesis, screening, and method development. When LC/GC/ICP trace limits, UV cutoffs, or water/peroxide specifications matter, request an up-to-date CoA.
  • If an assay/purity (e.g., ≥98%) is provided on the CoA, it usually reflects area% by HPLC/GC with volatile content (water, residual solvents) excluded unless otherwise noted.

• Stabilizers and additives:

  • No stabilizer information is provided for this product. For tertiary amines, stabilizers are uncommon; however, salts (e.g., HCl) may be offered to improve handling where volatility/odor is a concern. Verify the exact form on the label/CoA.

• Typical analytical controls (general):

  • Identity by 1H/13C/19F NMR and HRMS; purity by HPLC/GC; water by KF if hygroscopicity is a concern; residual solvents by GC; and confirmation that the free base vs. salt form matches the label.

• Implications for synthetic use:

  • Trace acids or peroxides can quench nucleophiles; ensure materials are neutral and inhibitor-free for base-sensitive steps. For catalysis or salt formation, knowledge of amine content (titration) is useful.

For definitive, lot-specific details, rely on the CoA/Spec Sheet supplied with the product.

Reaction and Applications

N,N-Dimethyl-2-(perfluorophenoxy)ethanamine functions primarily as a fluorinated tertiary amine building block. Key application spaces (literature/general) include:

• Quaternization to ammonium salts:

  • Alkylation with alkyl halides, sulfates, or triflates generates quaternary ammonium salts. The perfluoroaryl ether can modulate lipophilicity and thermal stability of the resulting onium species (potential phase-transfer agents, surfactants, or ionic liquid precursors). Typical conditions: MeCN or acetone, 20–60 °C.

• Salt formation and counterion screening:

  • Rapid, reversible protonation with mineral or organic acids affords crystalline salts (HCl, HBr, p-toluenesulfonate) useful for handling, purification, and property tuning (solubility, melting point).

• Oxidation to amine oxides:

  • H2O2 or m-CPBA can afford the corresponding amine oxide, useful as a ligand variant or surfactant-like additive. Control temperature to avoid over-oxidation and preserve the aryl ether.

• Nucleophilic catalysis/base:

  • As a tertiary amine, it can serve as a base or nucleophilic catalyst in acylation (e.g., Steglich-type contexts) or Michael additions, recognizing that basicity may be slightly attenuated by the electron-poor aryl ether remote group.

• Fluorophilicity and materials interfaces:

  • The C6F5 ring increases affinity for fluorinated environments, which can be leveraged in separations (fluorous biphasic systems) or surface modification work where partial fluorous character is beneficial.

Practical tips:

• Drying: Use molecular sieves or distill over CaH2 for water-sensitive applications.
• Avoid strong nucleophiles that could, under forcing conditions, engage in SNAr on the perfluoroaryl ring; while the ether is robust, highly basic conditions at elevated temperatures can induce ring transformations.
• Verify free base vs. salt form before stoichiometric use.

Reaction Conditions

General, literature-style conditions for common transformations of tertiary amines like N,N-dimethyl-2-(perfluorophenoxy)ethanamine. These are not product specifications and should be optimized per substrate.

• Quaternization (onium salt formation):

  • Reagents: alkyl halides (MeI, BnBr), dialkyl sulfates (Me2SO4), or triflates.
  • Solvents: MeCN, acetone, or neat; optional catalytic KI.
  • Conditions: 20–60 °C, 2–24 h. Isolate salts by filtration or solvent switch. Typical yields often >80% for unhindered electrophiles (literature).

• Amine oxide formation:

  • Reagents: 30% H2O2 (aqueous) or m-CPBA (DCM/CH2Cl2) at 0–25 °C.
  • Control exotherm; quench excess oxidant with Na2SO3. Purify by crystallization or chromatography.

• Salt formation/crystallization:

  • Bubble dry HCl gas into anhydrous ether/EtOAc solution at 0–5 °C or add 2–4 M HCl in dioxane to anhydrous solution. Precipitated ammonium salts are filtered and dried under vacuum.

• Ether stability window:

  • Avoid strong bases/nucleophiles at high temperature (e.g., molten alkoxides, NaNH2 in liquid ammonia) that could promote SNAr on the C6F5 ring. Typical neutral-to-mildly basic conditions (pH ≤ 11) are generally well tolerated.

• Purification tips:

  • Free base: may tail on silica; add 0.1–1% Et3N to eluents or use basic alumina.
  • Salts: often crystalline; wash with non-solvents (MTBE, hexanes) to remove organic impurities.

Always run small-scale trials and monitor by 1H/13C/19F NMR, LCMS, and TLC to confirm reaction progress and stability.

Safety and Handling

• GHS/CLP information (item-specific):

  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements (H-codes): Not specified for this item; refer to SDS.
  • GHS classification/pictograms: Not specified for this item; refer to SDS.

• General hazards for tertiary amines and perfluoroaryl ethers (literature, not product-specific):

  • Tertiary amines are typically skin/eye irritants and may cause respiratory irritation; amines can have strong odors.
  • Forms salts with acids; heat generation upon neutralization. Avoid contact with strong oxidizers. Amines may attack certain plastics and soft metals (e.g., copper alloys) and can absorb CO2 from air to form ammonium carbamates.
  • Perfluoroaryl ethers are generally thermally stable but may release toxic fumes (HF, COx, NOx) under fire/thermal decomposition.

• PPE and handling:

  • Wear safety glasses or goggles, lab coat, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to control vapors/odors.
  • Avoid inhalation and direct contact. Keep away from acids and oxidizing agents. Ground/bond equipment if handling bulk liquids.

• First aid (general guidance; defer to SDS):

  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

• Fire fighting (general): Use dry chemical, CO2, or foam. Combustion may produce hydrogen fluoride from fluorinated aryl moieties—firefighters should wear self-contained breathing apparatus.

Always consult the product SDS for authoritative safety information.

Solvent Selection

This compound is a moderately lipophilic tertiary amine bearing a perfluorinated aryl ether. Solvent selection hinges on its acid–base state and the operation (reaction vs. workup vs. purification).

• Polarity/miscibility (literature expectations):

  • Free base: readily soluble in dichloromethane, chloroform, THF, ethyl acetate, acetone/MeCN, and aromatic solvents (toluene). Limited solubility in water at neutral/basic pH.
  • Protonated salts (e.g., HCl): significantly more water-soluble; also dissolve in alcohols and polar aprotics.

• Choosing solvents by task:

  • Nucleophilic substitutions, quaternization: acetonitrile, acetone, or DMF/DMSO support SN2 reactions with alkyl halides; MeCN often preferred for ease of workup and lower boiling point.
  • Salt formation and extractions: use biphasic systems (water/EtOAc or water/MTBE). Protonate in aqueous acid to drive partitioning to the aqueous phase; basify to recover free base.
  • Chromatography: normal-phase silica may tail with basic amines; add 0.1–1% Et3N to eluents or use basic alumina/reverse-phase methods.

• Comparative notes (general):

  • Versus non-fluorinated analogs, fluorinated aryl ethers exhibit higher affinity for halogenated and aromatic solvents and can show reduced volatility; plan evaporation conditions accordingly.
  • If odor control and worker comfort are priorities, select higher-boiling, low-odor solvents (e.g., MeCN, EtOAc) over chlorinateds when compatible.

These are general solvent guidelines based on structure; confirm solubility experimentally for your specific conditions.

Storage and Reconstitution

• Storage (item-specific from Product Data): Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General handling and storage guidance:

• Keep container tightly closed in a dry, well-ventilated place. Minimize headspace to reduce odor and CO2 uptake. Store away from strong acids, oxidizers, and reactive halogenating agents.
• If long-term storage is planned, consider using amber glass and inert gas blanket for sensitive applications. Secondary containment is recommended for liquid forms.
• If supplied as the free base and a crystalline salt is preferred for handling, prepare an acid addition salt (e.g., HCl) immediately prior to use; document conversion on labels.

Reconstitution:

• If received as a solid (e.g., salt form), dissolve in a compatible anhydrous solvent (MeCN, DCM, EtOAc, MeOH) to the desired concentration. For aqueous work, use the protonated salt to improve solubility.
• Warm gently to ambient and sonicate if needed. Filter through a PTFE or PES membrane (0.2–0.45 μm) to remove particulates before sensitive applications.

Note: For any unspecified storage constraints (light sensitivity, moisture sensitivity, inhibitor content), consult the lot-specific CoA/SDS. Product is for research use only.

Structure and Identity

N,N-Dimethyl-2-(perfluorophenoxy)ethanamine is a tertiary amine bearing a perfluorinated aryl ether. The molecule features a pentafluorophenyl ring (electron-poor) connected via an ether oxygen to a 2-dimethylaminoethyl chain.

• Item-specific identifiers from Product Data:
  • CAS: 2044704-44-9
  • CID: 122198509
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (catalog provided: "452605" appears incomplete)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed identity (for reference; verify against primary databases):
  • Proposed structure (from name): perfluorophenoxy–CH2–CH2–N(CH3)2
  • Typical/derived SMILES (literature-style, to be verified): CN(C)CCOc1c(F)c(F)c(F)c(F)c1F
  • Molecular formula (computed from name): C10H10F5NO
  • Molecular weight (computed): ~255.19 g/mol
• Key structural features (general description):
  • Aromatic ring: a pentafluorophenyl (C6F5–) ring, strongly electron-withdrawing, deactivating toward electrophilic substitution, but enabling SNAr chemistry at ring positions in other contexts.
  • Ether linkage: an aryl–O–alkyl ether connecting the ring to the ethylene spacer.
  • Tertiary amine: N,N-dimethylamino terminus (no N–H), readily quaternized; basicity tempered by the distant perfluoroaryl group.
  • 2D description: From left to right, a C6F5 ring bonded to an oxygen (para-oriented F pattern typical), followed by –CH2–CH2– tether ending at a dimethyl-substituted nitrogen.

Notes: All item-specific identity elements not explicitly listed in the Product Data should be confirmed on the CoA/Spec Sheet prior to regulatory or analytical use.

Synthetic Utility

Functional group set: tertiary aliphatic amine (N,N-dimethyl), aryl–O–alkyl ether, and a pentafluorophenyl ring.

• Basic/nucleophilic site (tertiary amine):

  • Readily forms quaternary ammonium salts with alkylating agents (useful for onium phase-transfer catalysis or ionic liquid exploration). Salt formation can also aid crystallinity and purification.
  • Acts as a non-nucleophilic to moderately nucleophilic base in acylation or conjugate addition catalysis; basicity is tunable via protonation.
  • Amenable to oxidation to the amine oxide, enabling different hydrogen-bonding and polarity profiles.

• Ether linkage and perfluoroaryl ring:

  • The C6F5 ring is strongly electron-withdrawing and deactivates typical electrophilic aromatic substitution; however, perfluoroaryl systems can undergo SNAr with strong nucleophiles under forcing conditions. While the aryl–O bond is generally robust, knowledge of potential vicarious substitution is useful when planning harsh reactions.
  • The perfluoroaryl increases lipophilicity and compatibility with halogenated/fluorous phases, which can be leveraged for partition-driven purifications or material assembly.

• Retrosynthetic considerations:

  • Disconnection at the ether: typically from pentafluorophenol and 2-dimethylaminoethyl halide/sulfonate via Williamson ether synthesis or Mitsunobu-type strategies.
  • Late-stage quaternization: maintain the free base through multistep sequences and install the desired counterion at the end to simplify workups.

Overall, this scaffold is a versatile handle for tuning polarity, phase behavior, and cationic character through simple, high-yielding transformations.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, isotype, or species reactivity information applies.