3-Methoxyphenylethylammonium Bromide - ≥99%(4 Times Purification) , CAS No.60189-29-9

CAS: 60189-29-9 Cat. No.: M494132 Summenformel: C₉H₁₄BrNO Molekulargewicht: 232.12

Synonyms

3-MeOPEABr

Storage

Protected from light,Room temperature,Argon charged

Shipped In

Normal

Specifications

Synonyme

3-MeOPEABr

Spezifikationen & Reinheit

≥99%(4 Times Purification)

Storage

Protected from light,Room temperature,Argon charged

Verschickt in

Normal

Namen und Kennungen

• Molekulargewicht: 232.12
• Reaxy-Rn: 22887988
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=22887988&ln=

Chemische und physikalische Eigenschaften

• Löslichkeit: Soluble in mostly organic solvent
• Empfindlichkeit: Moisture sensitive;air sensitive;light sensitive

Application Protocols

No vendor‑validated bioassay protocols are provided for this product. For materials applications (e.g., perovskite surface passivation), users typically develop process‑specific protocols involving solution preparation in alcohols, substrate cleaning, deposition (spin/dip/coat), and post‑treatments. Refer to the literature for starting points and adjust to your device architecture and environmental controls.

Biological Roles

This product is intended for materials and synthetic chemistry applications. It is not supplied for biological or clinical use.

General chemistry context (not item specifications):

• The cation derives from 3‑methoxyphenethylamine, a simple aromatic ethanolamine analogue; such small organic ammonium ions do not possess defined physiological roles as supplied and are not endogenous metabolites.
• In biochemical settings, primary ammonium salts may interact nonspecifically with biomacromolecules via electrostatics and hydrophobic/aromatic interactions, but this material is not characterized for biological assays.

Research Use Note: For research use only. No medical, diagnostic, or therapeutic use is intended or implied.

Buffer Applications

Not typically used as a buffering agent. Primary ammonium bromide salts lack well‑defined, practical buffering ranges in aqueous systems compared to dedicated buffers (e.g., phosphate, Tris, HEPES). If pH control is required in processes involving this compound, select an appropriate buffer system separately and verify compatibility with ammonium salts and any device substrates.

Green Alternatives

Greener practice with this ammonium bromide focuses on solvent and process choices rather than replacing the active cation.

• Prefer bio‑derived alcohols (ethanol, isopropanol) or water/alcohol blends for solution processing where feasible, instead of high‑hazard solvents (DMF, NMP). Dry, low‑residue grades minimize film defects.
• Use antisolvent‑free or low‑waste deposition strategies (e.g., blade/slot‑die coating with controlled humidity), minimizing solvent volumes.
• Implement closed‑loop solvent recovery for alcohols and acetonitrile.
• Consider halide alignment with device needs: bromide has a more moderate environmental profile than iodide in some contexts, but all lead‑halide systems require rigorous EHS controls for Pb exposure and end‑of‑life handling (if used with lead salts).

Concise comparison (literature/general):

• Traditional approach: DMF/DMSO inks; high boiling, worker exposure concerns; excellent solvation and film uniformity.
• Greener approach: EtOH/IPA or ACN systems; lower toxicity and easier recovery; may need process tuning (additives, humidity control) to match film morphology.

Trade‑offs:

• Faster‑evaporating green solvents can challenge film formation window; optimize concentration, temperature, and substrate motion.
• Water incorporation can alter perovskite phase; use anhydrous alcohols for moisture‑sensitive stacks.

Pharmaceutical Uses

No pharmacopeial or excipient status is specified for this item; refer to CoA/Spec Sheet if GMP or compendial compliance is required.

Context (general, non‑clinical):

• Organic ammonium bromide salts like this compound are occasionally used in process research as isolable amine forms to facilitate handling, purification, or salt‑screening studies. However, this specific material is supplied for research use only and is not intended for human or veterinary applications.
• If employing in formulation science experiments (e.g., model ion‑pairing studies), thoroughly assess solubility, hygroscopicity, and compatibility with excipients; no claims of safety, efficacy, or regulatory acceptance are made.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point, boiling point, density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations (for context only; not item specifications):

• Physical state: Organic ammonium bromide salts are typically crystalline solids with relatively high melting points compared to their free‑base amines.
• Solubility: Such salts are generally highly soluble in polar protic solvents (water, methanol, ethanol, isopropanol) and moderately soluble in polar aprotic media (DMF, DMSO, acetonitrile), with limited solubility in nonpolar solvents. Actual solubility for this item must be verified experimentally.
• Acid–base: Represents the conjugate acid (ammonium) of 3‑methoxyphenethylamine (free‑base pKaH+ often near 9–10 for phenethylamines; literature), implying the salt dissociates in water to give the ammonium and bromide ions.

Notes for practitioners:

• Hygroscopic uptake can affect measured mass fraction if handling is prolonged in ambient humidity; minimize open‑air exposure.
• If precise physical constants are required for process design or QC, consult the lot‑specific CoA and conduct in‑house verification.

Quality and Grades

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

Interpretation and guidance:

• In the absence of a declared grade (e.g., AR, HPLC, electronic/OPV), rely on the CoA for assay, residual solvents, halide content, and impurity profile. For optoelectronic use, vendors often monitor halide stoichiometry and trace metal content; confirm these if critical to device performance.
• Materials science use: For perovskite and thin‑film research, low levels of colored or UV‑active impurities can influence film absorption and photoluminescence. If your application is photophysical, request low‑UV background and trace metal data when available.
• Stabilizers/additives: None are specified for this listing. If stabilizers were present, they could influence film morphology or interfacial chemistry; verify “additive‑free” status on the CoA if needed.
• Batch consistency: For device fabrication, small variations (moisture content, particle size, residual free base) may affect solubility and film formation. Implement incoming QC (Karl Fischer, PXRD, NMR) per your lab’s SOPs.

Reaction and Applications

Materials science (literature/context):

• Perovskite optoelectronics: Aryl‑ethylammonium halides are widely used as bulky spacer cations to form 2D Ruddlesden–Popper phases (e.g., A2PbBr4‑type), surface passivators for 3D perovskites, and defect suppressors in LEDs and photovoltaics. The 3‑methoxy substituent can influence intermolecular interactions and film energetics versus unsubstituted phenethylammonium.
• Surface passivation: Post‑treatments from alcoholic solutions can reduce nonradiative recombination at grain boundaries by quenching halide vacancies and coordinating under‑coordinated lead. Typical practice uses dilute solutions in IPA/EtOH followed by brief spin or dip exposure (literature).
• Halide management: As a bromide salt, this reagent supports fabrication of Br‑rich perovskites (green/blue‑emissive). Mixed‑halide systems may undergo halide migration; careful process control is advised.

Synthetic/chemical (general):

• Precursor to the free base: Basification liberates 3‑methoxyphenethylamine for further transformations (amide formation with coupling reagents, urea/thiourea synthesis, reductive amination partners). Using the bromide salt simplifies weighing and handling versus volatile free bases.
• Ion‑pairing and crystallization: The ammonium–bromide pairing can aid in crystallization or temporary protection of the amine functionality during multistep sequences.

Practical tips:

• Employ dry, oxygen‑ and moisture‑controlled environments for sensitive optoelectronic work.
• Filter solutions (0.2 μm) before film deposition to remove particulates.
• Validate halide stoichiometry (e.g., by ion chromatography or XPS) when device performance is sensitive to Br− content.

Reaction Conditions

Guidance below is general/literature-based for typical uses; these are not item specifications.

• Liberation of free base: Dissolve the salt in water or MeOH/EtOH and add a mild base (e.g., NaHCO3/Na2CO3) to pH >10; extract the free amine into an organic phase (DCM/EtOAc). In anhydrous systems, use iPr2NEt or Et3N in MeCN/THF/DMF to generate the free base in situ.
• Amide couplings (from liberated amine): Common conditions: HATU or EDC·HCl with DIPEA in DMF/MeCN/DCM, 0–25 °C, 1–12 h (literature); monitor by LC/MS. Carbodiimide couplings benefit from HOAt/HOBt or Oxyma.
• Urea formation: CDI (1.1–2.0 equiv) with the free amine in THF/DMF, 0–50 °C; add second amine after intermediate formation.
• Reductive amination: Condense free amine with aldehyde/ketone (3 Å MS, MeOH/EtOH or toluene/MeCN), then reduce with NaBH3CN (pH ~6–7 aqueous/MeOH) or BH3·THF at 0–25 °C.
• Perovskite passivation/2D phase formation: Prepare 1–20 mg/mL solutions in IPA/EtOH (literature ranges); apply by spin/dip/brush coating onto pre‑formed lead‑halide perovskite films; brief exposures (seconds to minutes) followed by drying/annealing (60–120 °C, few minutes) are typical optimization variables.

Always optimize stoichiometry, temperature, and time for your substrate; confirm outcomes by NMR, IR, PXRD, UV–Vis/PL, or device metrics as appropriate.

Safety and Handling

• GHS Classification: Not specified for this item; refer to SDS.
• Signal word / H‑statements / Pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance (not a substitute for the SDS):

• Hazard profile (general): Organic ammonium bromide salts are typically nonflammable solids and may cause irritation to eyes, skin, and respiratory tract upon contact with dust or solutions.
• PPE: Wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust/aerosols.
• Handling: Avoid creating dust. Prevent contact with oxidizers and strong bases/acids that can alter the salt form or release the free amine. For perovskite applications, avoid contamination with halide‑exchangeable species if halide stoichiometry is critical.
• First aid (overview): • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation persists.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Stability: Bromide salts are generally stable; protect from moisture and light to preserve quality and prevent discoloration or degradation of trace impurities.
• Always consult the product’s SDS for authoritative hazard, toxicological, and disposal information.

Solvent Selection

This compound is an organic ammonium bromide salt; solvent choice should reflect its ionic and polar character.

General solvent behavior (literature/general):

• High solubility (typical): Water, methanol, ethanol, isopropanol. These support rapid dissolution and solution processing for thin films and surface treatments.
• Moderate solubility (often): DMF, DMSO, acetonitrile. Common for perovskite precursor inks; co‑solvent systems with alcohols can improve wetting and film quality.
• Low solubility: Nonpolar solvents (toluene, hexane, chlorinated solvents) unless the ammonium is paired via ion pairing or used in mixed systems.

Selection tips:

• For spin‑coating/passivation on lead‑halide perovskites, isopropanol (IPA) and ethanol are frequently chosen to avoid dissolving underlying perovskite layers excessively, while still delivering the organic cation.
• For bulk salt processing or recrystallization, water/alcohol mixtures help control crystallization rate and particle size.
• If water sensitivity of your substrate is a concern, use dry alcohols or polar aprotics and maintain low moisture.

Quick comparison (general):

• IPA: good film wetting, moderate volatility, benign safety profile.
• Ethanol: faster drying, strong solvation, more hygroscopic.
• DMF/DMSO: strong solvation for multi‑component inks; slower drying; handle with care for toxicity.

Always verify actual solubility and compatibility experimentally under your conditions.

Storage and Reconstitution

• Storage conditions (from Product Data): Protected from light; Room temperature; Argon charged.
• Shipped: Normal (ambient) conditions.

Practical guidance:

• Keep container tightly sealed under inert gas to limit moisture and oxygen exposure; many organic ammonium salts are mildly hygroscopic. Reseal promptly after use. Store in a dry cabinet or desiccator when possible.
• Protect from light to preserve color and purity, especially for optoelectronic use where trace discoloration can matter.
• For solution preparation, use dry, oxygen‑free alcohols (IPA/EtOH) or polar aprotic solvents as needed. Filter solutions through 0.2 μm PTFE/NYLON filters before thin‑film processing.
• If preparing aqueous solutions, consider microbial controls for prolonged storage (sterile filtration); otherwise prepare fresh to minimize changes in pH or halide content via contamination.
• Avoid repeated freeze–thaw of solutions; store aliquots if necessary. Solid material is generally more stable than solution when kept dry and protected from light.

For any additional item‑specific instructions (e.g., exact shelf life, allowable humidity), consult the lot CoA/Spec Sheet and SDS.

Structure and Identity

A bromide salt of a protonated 3-methoxyphenethylamine, commonly used as an organic ammonium cation in materials science.

• Product name: 3-Methoxyphenylethylammonium Bromide (meta-anisyl‑ethylammonium bromide)
• CAS: 60189-29-9
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• CID: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Note (literature/inferred): The cation is the protonated form of 3‑methoxyphenethylamine; overall empirical formula for the salt is commonly written as C9H14NOBr (literature), subject to confirmation on the CoA.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Note (literature/inferred): ~232.12 g/mol for C9H14NOBr; verify on the CoA for this lot.

Structural features (general description):

• Functional groups: Anilide-type aryl ether (–OCH3) at the 3‑position of a phenyl ring; a two‑carbon ethylammonium chain (–CH2–CH2–NH3+); bromide counterion.
• 2D description: A benzene ring bearing a meta‑methoxy substituent and a –CH2–CH2–NH3+ substituent; the cation is primary ammonium; no stereocenters.
• Ionic character: Organic primary ammonium paired with Br−; typically crystalline and hygroscopic relative to the free base.

Synthetic Utility

Functional group and reactivity overview (general):

• Primary ammonium (as bromide salt): Easily converted to the free amine under basic conditions (e.g., Na2CO3, triethylamine) for subsequent coupling chemistry.
• Anisole (3‑methoxy) aryl ring: Electron‑donating substituent activates the ring toward electrophilic aromatic substitution at ortho/para relative to OMe (meta to the ethylamino chain), enabling further diversification if desired (literature context).
• Nucleophile precursor: The free amine participates in amide coupling (EDC/HATU/DIC), urea/thiourea formation (with phosgene equivalents or CDI), imine formation followed by reductive amination, and sulfonamide synthesis.

Use cases:

• Salt as a handling form: Enhanced stability and nonvolatility vs free base simplifies weighing and storage; dissolves well in polar solvents for homogeneous reactions after in situ neutralization.
• Temporary protection: As an ammonium salt, the amine nucleophilicity is suppressed, which can be advantageous in stepwise sequences where uncontrolled amine reactions are undesirable; deprotect by basification when needed.

Tips:

• Adjust base equivalents to fully liberate the free base in nonaqueous media (monitor by TLC/NMR).
• If residual bromide is problematic (e.g., for metal catalysis), consider aqueous workup or ion exchange before downstream steps.

Target Specificity

Not applicable. This product is a small‑molecule salt for materials/synthetic chemistry and does not have antigen/epitope/clone attributes. No species reactivity or isotype information applies.