4-Br-1-Phenylethylammonium Bromide - ≥98%(4 Times Purification) , CAS No.B494336

CAS: B494336 Cat. No.: B494336 Formula: C₈H₁₁Br₂N Molecular Weight: 280.99

GRADE & PURITY ≥98%(4 Times Purification)

Synonyms

4-Br-α-Methylbenzylammonium Bromide；p-Br-MBABr

Storage

Protected from light,Room temperature,Argon charged

Shipped In

Normal

Specifications

Synonyms

4-Br-α-Methylbenzylammonium Bromide；p-Br-MBABr

Specifications & Purity

≥98%(4 Times Purification)

Storage

Protected from light,Room temperature,Argon charged

Shipped In

Normal

Purity

≥98%(4 Times Purification)

Names and Identifiers

Molecular Weight

280.99

Chemical and Physical Properties

• Solubility: Soluble in mostly organic solvent
• Sensitivity: Moisture sensitive；Air sensitive；Light sensitive

Application Protocols

No application protocols are specified for this item.

• General starting points (informational)
  • Perovskite thin films: Prepare filtered precursor inks in DMF:DMSO or greener alternatives; spin-coat with antisolvent drip; anneal 80–120 °C; characterize by XRD/PL/UV–Vis.
  • Salt-to-free amine: Basify in water, extract to organic, protect amine if needed, and proceed to cross-coupling.

Refer to primary literature and internal SOPs for procedure validation and optimization. For research use only.

Biological Roles

This compound is a synthetic arylalkylammonium bromide intended for materials and synthetic chemistry applications. It does not have a recognized physiological role.

• General notes
  • Primary ammonium salts can participate in ionic and hydrogen-bonding interactions with biomolecules, but this product is not designed or qualified for biological assays.
  • If used in exploratory bio-related research, confirm purity, counterion suitability, and endotoxin/bioburden requirements independently; none are specified for this item.

No medical, diagnostic, or therapeutic applications are claimed or supported. For research use only.

Buffer Applications

Not typically used as a buffering agent. Primary ammonium bromides do not provide defined conjugate acid/base pairs with suitable pKa spacing for classical buffer systems. If pH control is required in a workflow, select established buffers (e.g., phosphate, acetate, HEPES) appropriate to your system and solvent.

Green Alternatives

Greener choices relate mainly to solvent systems and processing, as the organic cation identity is tied to target material properties.

• Solvent strategy (general guidance)

  • Replace DMF with less hazardous options where feasible: DMSO/GBL blends, N-butylpyrrolidone (NBP), or alcohol-rich systems (e.g., IPA with salts pre-dissolved in minimal DMSO) can reduce worker exposure. Antisolvent crystallization using ethyl acetate or anisole instead of chlorinated solvents is an additional lever.
  • Use lower-toxicity antisolvents: Ethyl acetate, IPA, or anisole rather than toluene or chlorobenzene where device architecture allows.

• Processing improvements

  • Lower temperature drying/annealing and reduced solvent volumes via slot-die or blade coating improve EHS profiles at scale compared to repeated spin-coating.
  • Inline solvent recovery and closed coating systems reduce VOC emissions.

• Comparison (general) | Aspect | Conventional | Greener-leaning option | Trade-offs | |---|---|---|---| | Perovskite ink solvent | DMF or DMF:DMSO | GBL:DMSO, NBP, or alcohol-assisted DMSO | Viscosity/solubility changes; need re-optimization | | Antisolvent | Chlorobenzene, toluene | Ethyl acetate, IPA, anisole | Different crystallization kinetics, morphology tuning required | | Cleaning | Acetone, DMF | IPA, EtOAc, water (where compatible) | May need longer soak/time |

Note: Any substitution should be validated for film quality, device metrics, and long-term stability.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided for this product. It is offered for research use only.

• General considerations (informational)
  • Primary ammonium salts of benzylic amines are sometimes intermediates en route to APIs or functional materials, but this listing is not qualified for GMP use and has no stated compliance with pharmacopoeias.
  • If leveraging as a synthetic intermediate in a medicinal chemistry program, confirm residual solvent/counterion content and perform appropriate salt screening to identify pharmaceutically acceptable forms (e.g., HCl, sulfate) at a later stage.

No clinical or therapeutic claims are made.

Physical Properties

Item-specific physicochemical specifications are not provided in the product data.

• Item-specific specs

  • Melting point, density, solubility, refractive index, logP, pKa, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature expectations for benzylic primary ammonium bromide salts (informational)

  • Physical state: Typically crystalline solids; often hygroscopic due to the –NH3+ functionality and halide counterion.
  • Solubility: Generally highly soluble in polar protic solvents (water, methanol, ethanol) and polar aprotics (DMSO, DMF); limited solubility in nonpolar hydrocarbons. Actual solubility depends on substitution and salt lattice; verify experimentally.
  • Thermal behavior: Ammonium halide salts may show decomposition or loss of HBr at elevated temperatures prior to clear boiling; drying and gentle heating under vacuum are preferred when needed.
  • Acid/base: Exists as the protonated ammonium; basification with aqueous alkali liberates the corresponding free amine (which is typically more volatile and less water-soluble).

Note: Use the CoA/Spec Sheet for lot-specific measured properties when available.

Quality & Grades

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

• Practical implications

  • In materials science workflows (e.g., solution-processed thin films), purity of organic ammonium salts can strongly influence film morphology, defect density, and optoelectronic properties. Metal and halide impurity levels, water content, and residual inorganic salts are particularly relevant.
  • When grade is unspecified, we recommend validating suitability by small-scale trials and including purification/drying steps as needed (e.g., recrystallization from alcohols/ethers, vacuum drying at mild temperature) while monitoring via NMR and halide titration/ion chromatography.

• Typical grades (general guidance)

  • Research grade: Adequate for most exploratory syntheses and materials screening; verify by NMR/HRMS.
  • Electronic/materials grade: Emphasizes low ionic/metal contaminants and controlled residual water; preferred for perovskite device fabrication.

• Stabilizers and additives

  • No stabilizer information is provided. If stabilizers are present in certain lots, their identity and level should appear on the CoA/Spec Sheet. Stabilizers can influence crystallization and film growth; account for them in processing.

• Documentation

  • For compliance and reproducibility, retain batch CoA/Spec Sheet and SDS and record storage atmosphere and opening dates (due to potential hygroscopic mass gain).

Reaction & Applications

• Materials science (general; category-relevant)

  • Layered (2D) and quasi-2D metal halide perovskites: Arylalkylammonium bromides serve as bulky spacer cations that template Ruddlesden–Popper phases (e.g., (R–NH3)2A(n−1)BnX(3n+1)). Para-bromo substitution can modulate intermolecular interactions, crystallization kinetics, and film optical properties. When combined with PbBr2 or mixed PbX2, this salt can help form bromide-rich perovskite layers for LEDs and photodetectors. Literature reports use related phenethyl/benzyl ammonium salts to control n-value distributions and suppress ion migration.
  • Crystal growth/additives: As a structure-directing cation, it can influence grain orientation and passivate surface/edge defects via ammonium hydrogen bonding/ionic interactions.

• Synthetic chemistry (general)

  • Precursor to the free amine (4-bromo-1-phenylethylamine) upon basification; the free amine is a useful chiral/benzylic amine (racemic unless resolved) for further derivatization.
  • The aryl bromide enables cross-coupling after deprotection: Suzuki–Miyaura, Buchwald–Hartwig (via amide/urea masks), Heck, and Sonogashira on the aromatic ring, expanding the library of aryl-substituted benzylic amines.
  • Salt metathesis: Exchange of Br– for other anions (e.g., PF6–, BF4–, OTf–) to tune solubility, crystallinity, or to generate ion-pairing catalysts or electrolyte candidates.

• Practical tips

  • Dry the salt before precision solution prep (vacuum, mild heat, inert gas) to minimize water carryover.
  • For perovskite inks, filter final solutions (0.2 μm PTFE/NYLON depending on solvent) before coating to remove particulates and dust.

Reaction Conditions

The following are general, literature-style conditions relevant to the two principal uses: (a) conversion to the free amine for cross-coupling chemistry and (b) formation of layered bromide perovskite films. These are example conditions only and must be optimized per system.

• Liberation of free amine (general)

  • Procedure: Dissolve the ammonium salt in water; add 1–2 equivalents of NaOH or saturated Na2CO3 at 0–25 °C; extract the liberated amine with MTBE or Et2O (3×); dry (Na2SO4), filter, and concentrate at ≤30 °C. Protect (Boc/Cbz) prior to Pd-catalyzed couplings.
  • Notes: Keep temperature low to minimize racemization at the benzylic center if chirality is a concern. Work under inert gas to limit oxidation.

• Representative cross-coupling (literature-style example)

  • Suzuki–Miyaura on the para-bromo arene (from the protected amine): Pd(PPh3)4 (1–3 mol%), K2CO3 or K3PO4 (2–3 equiv), dioxane/H2O (4:1), 80–100 °C, 4–16 h. Typical literature yields for analogous substrates: 70–90% after optimization.

• Perovskite film processing (general)

  • Ink: Dissolve organic ammonium bromide with PbBr2 and/or mixed PbX2 in DMF:DMSO (or GBL/NBP variants) to 0.5–1.2 M per total lead; filter 0.2 μm.
  • Coating: Spin 1000–4000 rpm, 30–60 s with antisolvent drip (e.g., EtOAc or IPA) near the end of the spin.
  • Anneal: 80–120 °C for 5–20 min depending on substrate tolerance.
  • Notes: Humidity (<30% RH) and substrate temperature strongly affect phase purity and n-value distribution in quasi-2D films.

Safety & Handling

• GHS and hazard statements

  • Signal word, H-statements, pictograms, classification: Not specified for this item; refer to the SDS for authoritative safety data.

• General safety considerations for arylalkylammonium halide salts (informational)

  • Hazards: May cause irritation to skin, eyes, and respiratory tract. Avoid inhalation of dust and contact with eyes/skin.
  • Special risks: Hygroscopicity and water uptake can alter mass and concentration in solution; handle quickly in ambient air or under dry inert gas as provided.
  • Incompatibilities: Strong bases (will deprotonate to free amine; may release amine vapors). Strong oxidizers. Silver salts and other soft-metal salts (precipitation of AgBr). Avoid mixing with nitrites in acidic media due to potential N-nitrosamine formation with free amine.

• PPE and handling

  • Wear lab coat, nitrile gloves, and splash goggles. Handle powders in a fume hood or ventilated enclosure to minimize dust exposure.
  • Use dedicated, dry tools. Keep containers tightly closed under inert gas as provided.

• First-aid overview (general)

  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product SDS for definitive hazard, exposure limits, and spill/firefighting guidance.

Solvent Selection

As an ionic organic ammonium bromide, this material is best handled and processed in polar solvents. Choice depends on target application (e.g., perovskite precursor solutions, salt metathesis, or conversion to the free amine).

• Polarity/miscibility (general)

  • High affinity for polar protic: water, methanol, ethanol, isopropanol (typical good solubility).
  • Polar aprotic: DMSO, DMF, NMP typically dissolve well and are widely used in thin-film processing; acetonitrile varies by salt lattice—test empirically.
  • Poor solubility expected in nonpolar solvents (hexanes, toluene) unless converted to the free base.

• Selection tips by task

  • Perovskite precursor inks: DMSO and DMF (or mixed DMF:DMSO) are common; green-leaning alternatives include GBL, IPA, MeOAc as antisolvent; consider binary solvent engineering to tune drying/coordination.
  • Salt metathesis/ion exchange: Water/alcohol media streamline phase separation and filtration of inorganic coproducts (e.g., AgBr precipitation if exchanging Br–).
  • Liberation to free amine: Perform basification in a biphasic system (aq. Na2CO3/NaOH with an organic extractor like Et2O or MTBE) to transfer the neutral amine into the organic phase.

• Small comparison (general) | Solvent | Pros | Cons | |---|---|---| | DMSO | High solubility; film coordination control | High boiling, difficult drying | | DMF | Good solubility; widely reported | Regulatory scrutiny; moisture sensitive | | IPA/EtOH | Safer handling; fast drying | Lower solubility vs DMSO/DMF | | Water | Green; easy cleanup | Sensitive substrates may hydrolyze; slower drying in films |

Storage & Reconstitution

• Storage conditions (item-specific)

  • Protected from light; room temperature; argon charged (as provided in Product Data). Store tightly closed under inert gas in a desiccator or dry cabinet to minimize moisture uptake.
  • Shipped at ambient temperature (normal shipping).

• Stability considerations (general)

  • Ammonium bromide salts may be hygroscopic. Minimize headspace exposure, and record opening dates. If clumping or mass gain is observed, dry under vacuum at mild temperature (e.g., 25–40 °C) before preparing precise solutions.

• Reconstitution and solution preparation (general)

  • Solvents: Water, methanol, ethanol, isopropanol, DMSO, and DMF commonly dissolve arylalkylammonium bromides. Choose solvent based on downstream use (e.g., DMSO/DMF for perovskite inks; alcohols/water for salt metathesis).
  • Technique: Weigh rapidly, add solvent under inert atmosphere if possible, and mix until fully dissolved; filter through 0.2 μm for film applications.
  • Concentration: Prepare fresh solutions when possible; store working solutions in amber vials, under inert gas, protected from light.

• Shelf life

  • Not specified for this item; refer to CoA/Spec Sheet. Periodically confirm integrity by NMR or HPLC if long-term storage solutions are maintained.

For research use only.

Structure & Identity

A benzylic primary ammonium bromide salt featuring a para-brominated aryl ring and a chiral benzylic center. The cation is the protonated form of 4-bromo-1-phenylethylamine (p-bromo-α-methylbenzylamine), paired with bromide as counterion.

• Item-specific identifiers

  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • CAS: B494336 (catalog reference)
  • SKU: B494336

• Structural features (general description)

  • Aromatic ring bearing a para-bromo substituent (–Br) providing an aryl bromide handle for cross-coupling after deprotection to the free amine.
  • Benzylic stereocenter at the carbon bearing –CH3 and –NH3+ (racemic unless otherwise specified).
  • Primary ammonium (–NH3+) engages in strong hydrogen bonding and ion pairing with Br–; salt form enhances crystallinity and handling compared with the free base.
  • Counterion: bromide (Br–).

• 2D structure (verbal)

  • A para-bromobenzene ring attached at the benzylic carbon to a methyl group and a protonated amino group (–CH(CH3)–NH3+), balanced by an external bromide anion.

Synthetic Utility

This salt is a convenient, bench-stable form of a para-brominated benzylic amine precursor, enabling both ionic and covalent-chemistry pathways.

• Access to free base

  • Basification with Na2CO3/NaOH liberates 4-bromo-1-phenylethylamine, enabling downstream derivatizations (amide formation, reductive alkylation, carbamate protection, urea/thiourea synthesis). Enantiomeric enrichment can be pursued via resolution or asymmetric synthesis if chirality is critical.

• Aryl bromide reactivity (after deprotection as needed)

  • Suzuki–Miyaura cross-coupling to diversify aryl substituents (B(OH)2/boronate esters). Protect or transiently mask the benzylic amine (Boc, Cbz) to avoid catalyst poisoning.
  • Buchwald–Hartwig amination and Ullmann-type couplings for constructing diarylamines (again, usually from protected amine derivatives).
  • Heck/Sonogashira for vinyl/alkynyl installation on the para position, broadening electronic properties for materials targets.

• Ion exchange/salt engineering

  • Convert to PF6–, BF4–, OTf–, or organic sulfonates to tailor solubility, crystallinity, or to prepare ion-pair catalysts or electrolytes.

• Linking strategies

  • The benzylic amine allows attachment to surfaces/polymers via amide or imine linkages; the aryl bromide enables orthogonal diversification.

Practical note: Control moisture and residual acid/base during coupling work; amine/basic sites can coordinate to Pd/Cu catalysts—protection often improves yields and selectivity.

Target Specificity

Not applicable. This product is a small-molecule ammonium salt, not a biological targeting reagent or antibody. No antigen/epitope specificity, clone information, or species reactivity is associated with this item.

Frequently Asked Questions

How should this product be stored?

Store at room temperature, protected from light, under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is B494336, the molecular formula is C8H11Br2N, and the molecular weight is 280.99 g/mol.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.