This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
External Descriptors
Not available
1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.
In situ free-base generation: Suspend the hydrobromide salt in MeCN, add 1.1–1.5 equiv triethylamine at 0–25 °C, stir 10–30 min, then add nucleophile/base for the intended transformation. Monitor for complete neutralization (disappearance of pyridinium N–H in 1H NMR if sampled).
SN2 example setup: Dissolve substrate and 1.5–3.0 equiv nucleophile (e.g., NaN3) in dry DMSO at 25–60 °C; include 0.5 equiv Et3N to scavenge HBr. Quench into water, extract, and purify by chromatography.
Elimination example setup: Dissolve in dry THF, cool to 0 °C, add t-BuOK (1.2–1.5 equiv) under N2, then warm to RT and stir 1–3 h. Quench with NH4Cl, extract, and distill/short-path the resulting 4-vinylpyridine or convert in situ.
These are illustrative, literature-style outlines and not item-specific validated procedures. Optimize conditions for your substrate/capabilities.
Biological Roles
This product is a synthetic heteroaromatic salt intended for laboratory research and synthesis. No endogenous biological role is associated with 4-(1-bromoethyl)pyridine or its hydrobromide.
Structural motif: The pyridine ring occurs widely in natural products and cofactors (e.g., the pyridinium core of NAD+/NADP+ in biochemistry), but the 4-(1-bromoethyl) substitution is not a known biological building block.
Reactivity considerations: As an electrophilic alkyl bromide, it may alkylate nucleophilic biomolecules in vitro; experiments involving biological matrices should be conducted with appropriate containment and controls.
Use domain: Suitable for chemical biology or probe synthesis where a pyridyl handle is desired, but the compound itself is not a buffer, ligand, or metabolite.
Research Use Note: For research use only. Not for drug, household, diagnostic, or other clinical uses.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biochemical buffers. The hydrobromide salt form is acidic, but it does not provide a defined conjugate acid/base pair suitable for buffer systems.
For buffer needs, select established systems (e.g., phosphate, HEPES, MOPS, Tris) matched to your target pH.
If employing this material in aqueous reaction media, adjust pH independently using appropriate buffers and monitor ionic strength to manage solubility and reaction rates.
Green Alternatives
Greener strategy focuses on solvent and base choice, as the intrinsic functionality (secondary alkyl bromide) is not readily “green-replaceable.” Options (literature/general):
Solvent optimization:
Replace polar aprotic reprotoxic solvents where possible:
DMF/NMP → alternatives: Cyrene, propylene carbonate, dimethyl carbonate, ethyl acetate, or MeCN depending on reaction class and nucleophile.
DMSO is acceptable in many green guides, albeit with odor; it remains a strong option for substitution chemistry.
Aqueous or water-lean micellar systems (e.g., TPGS-750-M) can enable SN1/SN2 with reduced organic solvent use; validate compatibility with pyridinium salts.
Base and acid scavenging:
Use carbonate or bicarbonate bases in biphasic water/organic systems to minimize strong base usage, capturing HBr benignly. Phase-transfer catalysts can accelerate reactions at milder pH.
Halide management:
Design workups to recover/recycle bromide where feasible (ion-exchange or crystallization), particularly at scale.
Energy and safety:
Favor room-temperature substitutions in high-permittivity solvents to reduce heating requirements.
Continuous flow for exothermic neutralizations or eliminations can improve heat/mass transfer and minimize solvent volumes.
Tradeoffs:
Greener solvents may reduce solubility of the salt; in situ free-base generation followed by extraction into greener media (EtOAc, MeCN) balances EHS with performance.
Strong non-nucleophilic bases (e.g., t-BuOK) are effective but less green; DBU or carbonate systems may suffice with longer times.
Pharmaceutical Uses
No pharmacopeial status or excipient role is specified for this item.
Formulation context (general): Hydrobromide salts are common for increasing solubility of amines; however, 4-(1-bromoethyl)pyridine hydrobromide is supplied for R&D use as a synthetic intermediate/alkylating building block rather than as a pharmaceutical ingredient.
Process chemistry: The salt form can simplify handling during route scouting for pyridine-containing APIs or intermediates, enabling substitution or elimination to access 4-vinylpyridine or benzylic derivatives.
Compliance note: Research use only. Not intended for human or veterinary use, diagnostic procedures, or as a drug substance/excipient.
Physical Properties
Item-specific numerical specifications are not provided in the Product Data. Where applicable below, values are qualitative or literature-type guidance for this class of compound; do not treat them as specifications.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Pyridinium hydrobromide salts are typically crystalline solids with relatively high MPs; literature trend.)
Boiling point: Not applicable for salts (they decompose before boiling; literature trend).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable (solid); Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature/general):
Expected to be readily soluble in water and polar protic solvents (MeOH, EtOH) due to pyridinium hydrobromide salt form.
Typically soluble in highly polar aprotic media (DMSO, DMF). Solubility in less polar organic solvents (EtOAc, toluene) is limited in salt form; conversion to the free base increases organic solubility.
pKa (context, literature): Protonated pyridinium conjugate acids commonly have pKa (for deprotonation to free base) in the 5–6 range; exact value for this specific salt is not specified.
LogP: Not specified for this item; refer to CoA/Spec Sheet. (Salt form reduces apparent partitioning into nonpolar phases.)
Always confirm item-specific physical constants on the CoA/Spec Sheet before process design or scale-up.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
When grade/purity is unspecified, Aladdin supplies research-grade material intended for laboratory R&D use only (see Research Use Note). For sensitive applications (e.g., mechanistic studies, asymmetric catalysis, or formulation), request the current CoA to verify assay, residual solvents, water content, halide content, and trace-metal profile if critical to your process.
Hydrobromide salt form: The presence of a counterion (Br−) is intrinsic to the product identity; it is not a “stabilizer.” If your route requires the free base 4-(1-bromoethyl)pyridine, plan an in situ neutralization immediately prior to use to avoid side reactions or decomposition.
Typical analytical controls to expect on CoA (examples; not item-specific specs):
Identification by 1H NMR/13C NMR (pyridinium shifts), IR (pyridinium bands), and MS of the free base or salt adduct.
Assay by qNMR or HPLC.
Water (Karl Fischer) and residual inorganic bromide (as total halide) may be reported for salts; request if relevant to downstream catalysis.
Contact Technical Support for batch-specific CoAs and additional documentation (e.g., stability or impurity profiles) if needed.
Reaction and Applications
This reagent is a versatile benzylic secondary bromide embedded in a 4-substituted pyridine and supplied as its hydrobromide salt. Key application families (literature/general):
Nucleophilic substitution (SN1/SN2):
Alcohols (ROH) → 4-(1-alkoxyethyl)pyridine derivatives under solvolytic or base-assisted conditions.
Azide, cyanide, thiolates, and carboxylates can displace bromide to access 4-(1-substituted-ethyl)pyridine scaffolds. Choice of solvent (DMSO/DMF) and nucleophile hardness guides SN2 vs SN1 pathways.
Practical tip: Neutralize the pyridinium salt to the free base before reactions sensitive to acid; triethylamine or DIPEA often suffice in situ. Control temperature to balance substitution vs elimination.
Elimination to 4-vinylpyridine (E2):
Strong, non-nucleophilic bases (e.g., t-BuOK, DBU) can effect dehydrohalogenation to give para-vinylpyridine, a valuable monomer/coupling partner. Conduct under anhydrous conditions; monitor for polymerization of vinylpyridine.
Radical pathways: Under photoredox or initiator conditions, bromide abstraction can generate benzylic radicals for Giese-type additions or Minisci-adjacent methodologies (literature trend).
Polymer/ligand precursor:
The 4-vinylpyridine derived from elimination is a handle for radical polymerization or post-polymer modification, furnishing pyridyl-functional materials and ligands for metal coordination.
Notes:
The salt form provides handling convenience but may necessitate pre-basification for water- or base-sensitive downstream chemistry.
Monitor for HBr evolution; include suitable acid scavengers when needed.
Reaction Conditions
General, literature-style guidance for transformations of benzylic secondary bromides bearing a pyridyl ring; verify and optimize for your system. No item-specific specs are implied.
SN2 substitutions:
Solvents: DMSO, DMF, or MeCN (dry). Temperature: 0–60 °C depending on nucleophile strength. Typical bases: none or mild tertiary amine to scavenge HBr. Reaction time: 1–24 h. Notes: Use excess nucleophile; minimize water to avoid hydrolysis.
Solvolysis/SN1:
Solvents: Alcohols (MeOH, EtOH) or mixed HFIP/MeCN to stabilize cations. Temperature: ambient to reflux of solvent. Acidic medium may accelerate but risks side reactions; the hydrobromide salt provides inherent acidity.
Elimination (E2 to 4-vinylpyridine):
Bases: t-BuOK (THF/t-BuOH), DBU (MeCN, toluene), or potassium carbonate with phase-transfer in polar aprotic solvent. Temperature: 20–80 °C. Reaction time: 1–6 h. Notes: Anhydrous conditions; trap or vent HBr; inhibit polymerization of vinylpyridine (add radical inhibitor, low temp, rapid workup).
Hydrolysis to benzylic alcohol:
Aqueous acetone/MeCN with carbonate base, 20–50 °C, 2–12 h. Followed by oxidation (e.g., MnO2, TEMPO/NaOCl) to 4-acetylpyridine (general sequence).
Workup considerations:
For salt-to-free-base toggling: Basify with NaHCO3/Na2CO3 and extract into EtOAc/MTBE. Remove residual bromide by water washes or brief passage through an anion-exchange resin if required for catalysis.
Always run small-scale trials and monitor by TLC/LC–MS or NMR; control acid/base balance to steer substitution vs elimination.
Safety and Handling
Safety data specific to this catalog item is not provided in the Product Data; consult the product SDS for authoritative information.
GHS classification, signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
General hazard considerations for structure/class (literature/general):
Alkyl halide functionality: The 1-bromoethyl group can act as an electrophile/alkylating agent; such compounds may be harmful if inhaled, ingested, or in contact with skin and can cause irritation to eyes/skin/respiratory tract.
Acidic salt: As a hydrobromide, material may be acidic and corrosive to metals in moist environments; can release HBr on strong heating or with bases.
Wear appropriate PPE: lab coat, safety glasses or face shield, and chemical-resistant gloves (e.g., nitrile). Use within a fume hood to avoid inhalation of vapors/aerosols or HBr fumes during neutralization.
Avoid contact with strong bases or nucleophiles unless intended; exotherm and HBr evolution possible.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention.
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention immediately.
Waste: Collect halogenated organic/acidic waste per institutional and regulatory guidance.
Solvent Selection
Use-case-driven solvent choice depends on whether you employ the salt directly or first generate the free base.
Polarity class (general): As a pyridinium hydrobromide, the material is highly polar and typically dissolves in water, alcohols, DMSO, and DMF. Solubility in less polar media (MeCN, acetone) can vary; verify experimentally.
Working with the salt (hydrobromide):
Aqueous or mixed aqueous–organic systems enable phase-controlled reactions (e.g., substitution with water-soluble nucleophiles). Alcoholic solvents (MeOH/EtOH) promote solvolysis to the corresponding 1-alkoxyethyl derivative.
DMSO/DMF are suitable for SN1/SN2 transformations with ionic nucleophiles; include a base scavenger if HBr formation is problematic.
Generating the free base in situ:
Neutralization with a non-nucleophilic base (e.g., triethylamine, DIPEA, or bicarbonate in biphasic media) followed by extraction into a polar aprotic solvent (MeCN, THF, or DCM) can increase compatibility with organometallic or anhydrous conditions.
Comparison (general guidance):
DMSO vs DMF: DMSO often affords higher rates for substitution with hard nucleophiles; DMF offers easier removal and lower odor but may require stringent drying.
MeCN: Useful compromise for SN1-type solvolysis or for reactions with moderately lipophilic nucleophiles; lower donor number than DMSO/DMF may reduce competing elimination.
Drying/conditioning:
For base- or moisture-sensitive transformations, rigorously dry solvents (3Å molecular sieves) and pre-dry glassware; residual water exacerbates HBr formation and competing hydrolysis.
Shipping: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for pyridinium hydrobromide salts (literature/common practice):
Keep tightly closed in the original container with a desiccant if available; salts of this type can be hygroscopic and may cake upon moisture uptake.
Protect from prolonged exposure to air and strong light to minimize discoloration or decomposition. Store away from bases and oxidizers.
If long-term storage is anticipated, consider secondary containment and inert headspace where possible.
Reconstitution/Preparation:
For aqueous work: Dissolve directly in deionized water or alcohol/water mixtures; adjust pH separately as required for your process.
For anhydrous organic reactions: Generate the free base in situ with a non-nucleophilic tertiary amine (e.g., Et3N, DIPEA) in dry solvent (MeCN, THF, DCM). Filter or phase-separate salts prior to use if needed.
Solution stability: Prepare solutions fresh for moisture/base-sensitive transformations. If a stock solution is required, store at 2–8 °C under inert atmosphere and use within a few days (general recommendation; verify experimentally).
Always refer to the current CoA/SDS for definitive storage and handling instructions.
Structure and Identity
Brief description: 4-(1-Bromoethyl)pyridine hydrobromide is a para-substituted pyridine bearing a secondary bromoethyl group; the material is isolated as the hydrobromide salt (protonated pyridinium with Br− counterion).
Product name (catalog): 4-(1-Bromoethyl)pyridine hydrobromide (SKU: B953737)
CAS: 89694-53-1
PubChem CID: 45792237 (literature identifier)
InChIKey (provided): 450937 (note: appears truncated/atypical; verify against CoA/SDS)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general, literature-based):
Core ring: pyridine (C5H4N) with the substituent at the 4-position (para to the ring nitrogen).
Side chain: 1-bromoethyl (–CH(Br)–CH3) attached to the aromatic ring; the benzylic carbon is secondary and chiral. Commercial material is typically racemic unless otherwise stated.
Salt form: hydrobromide (protonated pyridinium N; Br− as counterion). This increases polarity and aqueous solubility versus the free base.
2D description: a six-membered aromatic ring containing one nitrogen (position 1). At position 4 is a –CH(Br)–CH3 group. The ring nitrogen is protonated in the hydrobromide, balancing with an external bromide anion.
Identity notes:
Verify exact stereochemical composition and any additional identifiers on the item’s CoA.
Being a salt, analytical methods (NMR, HRMS) should account for protonation state and counterion.
Synthetic Utility
Key functional elements and their reactivity (literature/general):
Benzylic secondary bromide:
Undergoes SN2 with hard nucleophiles in polar aprotic media; neighboring aryl stabilization permits SN1 pathways with solvolysis or soft nucleophiles.
E2 elimination provides 4-vinylpyridine, a versatile handle for polymerization and further functionalization (e.g., hydroboration/oxidation, epoxidation, cross-metathesis).
Pyridine ring (para-substitution):
Directs electronics; the ring nitrogen can be coordinated or protected/deprotected via protonation states, impacting reactivity and selectivity.
After substitution at the benzylic center, the pyridyl moiety serves as a ligand or directing group in C–H activation chemistry (via subsequent transformations).
Retrosynthetic value:
Access to 4-acylpyridines: Benzylic alcohol formation followed by oxidation yields 4-acetylpyridine, a common intermediate.
Access to 4-alkenyl/alkyl pyridines: Elimination or substitution with organometallic nucleophiles (e.g., organocuprates with careful conditions) enables C(sp3)–C bond construction.
Practical notes:
Neutralize the hydrobromide to the free base prior to strong-base or organometallic chemistry to avoid acid quench of reagents and competitive elimination/hydrolysis.
Control stereochemistry if relevant: reactions at the secondary center may proceed with inversion (SN2) or racemization (SN1); plan chiral outcomes accordingly.
Residual inorganic bromide may influence catalytic systems; include aqueous washes or ion-exchange cleanup when necessary.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological macromolecule, antibody, or affinity reagent. No target binding specificity, clone, isotype, or species reactivity is associated with this catalog item.
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