This compound belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
291.140 g/mol
XLogP3
3.500
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
4
Exact Mass
289.994 Da
Monoisotopic Mass
289.994 Da
Topological Polar Surface Area
26.300 Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
236.000
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
Lösungsrechner
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Application Protocols
Not applicable. No biological assay or immunoassay application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent.
Synthetic usage note (general)
For reaction setup, dry glassware and an inert atmosphere (N2/Ar) are recommended, particularly for moisture/air-sensitive transformations (e.g., phosphine-based Pd couplings, Wittig reactions).
Conduct small-scale pilots to refine solvent/base/catalyst combinations before scale-up.
Refer to the Reaction Conditions tab for literature starting points relevant to this compound class.
Biological Roles
This material is a synthetic organic intermediate and is not known to possess inherent biological roles or to be a metabolite.
General context (literature/general)
Aromatic aldehydes can form reversible adducts (Schiff bases) with primary amines in biomolecules under certain conditions, which is exploited in bioconjugation chemistry rather than representing a native biological role.
Aryl bromides are common handles in medicinal chemistry for diversification via cross-coupling; the bromide itself is not a biological functional group.
Research-use framing
The aldehyde functionality can be used to derivatize amine-bearing biomolecules (e.g., to generate oximes/hydrazones with hydroxylamine/hydrazide reagents) in chemical biology workflows; however, such applications require appropriate optimization and controls.
No medical, therapeutic, or physiological claims are made for this product. It is supplied strictly for research and laboratory use.
Buffer Applications
Not typically applicable. 4-[(3-Bromophenyl)methoxy]benzaldehyde is a hydrophobic organic building block rather than a buffering agent. It does not participate in defined acid–base equilibria suitable for pH control.
Practical guidance
For aqueous bioconjugation (e.g., oxime/hydrazone formation with the aldehyde), select appropriate buffers such as acetate (pH 4–5.5) or anilinium-catalyzed systems; maintain organic cosolvent (e.g., DMSO <10–20%) to aid solubility.
Avoid primary amine buffers (e.g., Tris) during aldehyde ligation steps, as they can compete with the intended nucleophile.
For standard buffering needs, use established systems (phosphate, HEPES, acetate) and refer to bioconjugation literature for specific protocols.
Green Alternatives
While this product is a solid/synthetic intermediate rather than a process solvent, greener choices can be made in its use and transformations.
Solvent selection (literature/general)
Prefer 2-MeTHF or cyclopentyl methyl ether (CPME) over THF/MTBE where compatible, offering better renewability and lower peroxide concerns (still monitor peroxides).
Ethyl acetate or toluene can substitute for dichloromethane in many carbonyl reactions; acetonitrile or propylene carbonate may replace DMF/DMAc for some couplings.
Catalysis and bases
Employ ligand-optimized Pd catalysts enabling lower catalyst loadings and aqueous or micellar media (e.g., surfactant-enabled Suzuki couplings) to reduce organic solvent use.
Use inorganic carbonate bases (K2CO3, Cs2CO3) or aqueous NaOH in biphasic systems to minimize amine base waste.
Protection strategies
Avoid unnecessary protection of the aldehyde when reaction conditions can be tuned (e.g., buffered imine formation in ethanol) to reduce steps and solvent consumption.
Energy and workup
Conduct couplings under flow or microwave conditions to shorten reaction times and energy input.
Replace silica-intensive purifications with crystallization or precipitation when feasible; consider reverse-phase scavenging for catalyst/ligand removal.
Comparison snapshot (general)
Traditional: DCM, DMF, THF; homogeneous Pd(0) with high loadings; multiple protection steps.
Greener alternative: EtOAc/2-MeTHF/aqueous micellar media; ppm-level Pd with modern ligands; minimized protection/deprotection and telescoped sequences.
All recommendations are general green-chemistry strategies; applicability depends on the specific transformation and should be validated at lab scale.
Pharmaceutical Uses
This product is not an excipient and has no pharmacopeial monograph indicated in the Product Data. It is supplied for research use only.
Research and process chemistry context (general)
Serves as a bifunctional intermediate in medicinal chemistry campaigns: the aryl bromide enables late-stage diversification via cross-coupling, while the aldehyde enables formation of imines/oximes or further elaboration to alcohols/acids.
Can be incorporated into structure–activity relationship (SAR) libraries by coupling on the brominated ring, followed by aldehyde transformations to modulate polarity and binding vectors.
Formulation relevance
None; not intended as an API or excipient. Any handling in pharmaceutical R&D would be at the discovery/synthesis stage only.
No clinical or therapeutic claims are made. For GMP or regulatory applications, source appropriate qualified materials and documentation.
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values (non-spec item data)
Empirical formula (computed from structure): C14H11BrO2
Formula weight (computed): ~291.14 g/mol
Physical state/volatility (literature expectation): Aromatic aldehyde/aryl bromide of this size typically presents as a low-melting solid or viscous oil with low volatility.
Solubility profile (literature/general):
Practically insoluble in water; soluble in common organic solvents (e.g., dichloromethane, chloroform, THF, acetonitrile, ethyl acetate, toluene, DMF, DMSO).
Ether linkage and two aryl rings confer hydrophobicity; aldehyde adds modest polarity enabling good solubility in polar aprotic media.
Partitioning (qualitative): Expected lipophilic character (aryl/aryl ether/aryl bromide), consistent with strong retention on nonpolar stationary phases and high logP relative to simple benzaldehydes (no numeric value asserted).
UV-Vis (qualitative): Conjugated aromatic aldehyde chromophore absorbs in near-UV; suitable for TLC visualization under 254 nm.
Acidity/basicity: Non-basic; aldehyde can hydrate weakly in water; no titratable groups in neutral range.
Practical handling properties (general)
Crystallization often feasible from hexanes/ethyl acetate or toluene/EtOAc mixtures.
Thin-layer chromatography: typically Rf mid-to-high in hexanes/EtOAc (3:1 to 9:1), depending on matrix; visualizable with UV and 2,4-DNPH spray for aldehydes.
No item-specific values (mp/bp/density/RI) are provided; consult the CoA/Spec Sheet for definitive specifications.
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.
Interpreting typical grades (general guidance)
Research-grade aromatic building blocks are commonly offered at ≥95–98% purity by HPLC/GC/NMR for reliable performance in synthesis.
Higher grades (e.g., 99%+) reduce side-product formation in sensitive transformations (e.g., cross-couplings, enantioselective reactions) and can lower background in analytical development.
Impurity considerations for this class (general)
Potential impurities: residual starting materials (4-hydroxybenzaldehyde derivatives, 3-bromobenzyl species), isomeric ethers, oxidation products (acids from aldehyde), and hydrodebrominated analogs.
Aldehyde stability: Gradual oxidation to the corresponding benzoic acid can occur on air exposure; trace acid or base can induce self-condensation. Fresh bottles and inert-atmosphere storage help maintain assay.
Analytical verification (general practices)
Identity/purity: 1H/13C NMR (diagnostic aldehyde proton ~9.7–10.1 ppm), IR (C=O ~1680–1720 cm−1), LC/GC purity, HRMS for exact mass confirmation.
Residual solvents and moisture: Karl Fischer for moisture; GC-HS for solvents when required for sensitive steps.
For purchasing lots, consult the Aladdin CoA/Spec Sheet for exact purity, test methods, and acceptance criteria applicable to SKU B1071764.
Reaction and Applications
As a dual-functional building block, 4-[(3-bromophenyl)methoxy]benzaldehyde integrates an aryl bromide (for cross-coupling) and an aromatic aldehyde (for carbonyl chemistry), connected by a benzylic ether.
Transformations leveraging the aldehyde (literature)
Wittig/Horner–Wadsworth–Emmons olefinations to install vinyl linkers or styrenes; typically retain the aryl bromide intact under mild Pd-free conditions.
Imine/oxime/hydrazone formation (Schiff bases) with amines, hydroxylamine, hydrazines; platforms for reductive amination or traceless ligations.
Aldol/Knoevenagel condensations with active methylenes (e.g., malononitrile, Meldrum’s acid) to generate push–pull chromophores or conjugated linkers.
Acetal protection (e.g., ethylene glycol, TsOH) for orthogonal manipulations followed by deprotection.
Transformations at the aryl bromide (literature)
Suzuki–Miyaura coupling with boronic acids/esters to elaborate the distal ring while conserving the aldehyde.
Buchwald–Hartwig C–N coupling to introduce anilines/carbazoles; aldehyde can be masked as acetal if sensitive.
Sonogashira coupling to install alkynes; proceed under base/amine conditions with aldehyde protection as needed.
Lithium–halogen exchange is generally discouraged without protecting the aldehyde; can cause side reactions.
Ether linker reactivity (literature)
Benzylic ether can be cleaved by hydrogenolysis (H2, Pd/C) to regenerate the phenol on ring A and release 3-bromotoluene derivatives; ensure bromide stability under chosen conditions.
Application examples (conceptual)
Convergent synthesis of biaryl aldehydes, donor–acceptor systems, fluorescent scaffolds, or linkers for conjugation chemistry where the aldehyde enables further bioconjugation.
Practical tip: Sequence planning often protects the aldehyde as an acetal prior to Pd-catalyzed couplings to avoid base- or amine-induced side reactions and to simplify purification.
Reaction Conditions
General literature guidance for typical transformations of this scaffold (optimize for your substrate and scale):
Suzuki–Miyaura coupling (on aryl Br)
Catalyst/base/solvent: Pd(PPh3)4 (1–2 mol%) or Pd2(dba)3/XPhos (0.5–1 mol% Pd); K2CO3 or K3PO4 (2–3 equiv); dioxane/H2O (4:1) or toluene/H2O; 70–100 °C; 4–16 h.
Notes: Aldehyde often tolerated; protect as acetal if basic or amine conditions cause side reactions.
Buchwald–Hartwig amination
Pd2(dba)3 (1 mol% Pd), BrettPhos or RuPhos (2–3 mol%), NaOtBu or Cs2CO3, toluene or dioxane, 80–100 °C, 6–18 h.
Notes: Monitor for imine formation with amine nucleophiles; aldehyde protection may improve yields/purity.
Sonogashira coupling
Pd(PPh3)2Cl2 (1–2 mol%), CuI (2–5 mol%), Et3N or i-Pr2NH, THF or DMF, 25–60 °C; 2–12 h.
Notes: Copper-free variants reduce side reactions; avoid Glaser coupling by oxygen exclusion.
Wittig/HWE olefination (aldehyde)
Ylide or phosphonate (1.2–1.5 equiv), THF or DCM, 0–25 °C; 1–6 h.
Notes: E/Z selectivity controlled by reagent choice; aryl bromide unaffected.
Reductive amination
Amine (1.1–2.0 equiv), NaBH3CN or picoline borane, MeOH/AcOH buffer, 0–25 °C; 2–16 h.
Notes: Control pH ~5–6; avoid strong bases that can affect coupling handles.
Deprotection: aqueous acid (e.g., 1 M HCl/THF), rt–reflux; monitor to avoid ether cleavage.
All parameters are literature-style starting points; adjust catalyst loading, base, solvent, and temperature to your specific substrates and desired chemoselectivity.
Safety and Handling
Item-specific hazard data (from Product Data)
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General hazards for aromatic aldehydes and aryl bromides (literature/general)
May cause skin and eye irritation; aldehydes can be sensitizers and respiratory irritants upon vapor/aerosol exposure.
Harmful if swallowed or inhaled; handle powders to avoid dust generation.
Wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to minimize inhalation exposure.
Incompatibilities and reactivity (general)
Strong oxidizing agents (risk of exothermic reactions/oxidation).
Strong bases and nucleophiles may promote aldol-like condensations or addition to the aldehyde.
Reducing conditions (e.g., catalytic hydrogenation) can reduce aldehyde to alcohol and may also debrominate the aryl bromide under forcing conditions.
First-aid overview (general)
Skin/eye contact: Rinse thoroughly with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire-fighting measures (general)
Use dry chemical, CO2, or foam; combustion may produce CO/CO2 and HBr-containing fumes.
Always consult the product-specific SDS for authoritative safety, toxicological, and regulatory information.
Solvent Selection
This compound is a moderately lipophilic aromatic aldehyde/aryl bromide. Solvent choice should balance solubility, reaction compatibility (for the aldehyde and aryl bromide), and workup ease.
Polarity/miscibility (general characteristics)
Poorly soluble in water; readily soluble in common organic solvents (DCM, CHCl3, THF, EtOAc, toluene, MeCN, DMF, DMSO).
Polar aprotic media (THF, MeCN, DMF, DMSO) provide excellent solubility for coupling and carbonyl transformations.
Typical use scenarios
Cross-coupling on the aryl bromide: DMF, DMAc, dioxane, THF, or toluene with aqueous base (for Suzuki) or alkoxide/amine base (for Buchwald–Hartwig). Mixtures of dioxane/H2O or toluene/EtOH/H2O are common (literature).
Carbonyl chemistry (Wittig, HWE, reductive amination, oxime formation): THF, DCM, or MeOH/EtOH (for imine/oxime formation) depending on catalyst and water management.
Hydrogenolysis of the benzylic ether (if desired): EtOH, MeOH, or EtOAc under H2 with Pd/C; avoid solvents that poison catalyst.
Comparison notes
DCM/CHCl3: fast dissolution, easy evaporation; environmental concerns require proper handling.
THF/2-MeTHF: good balance of solubility and reactivity; 2-MeTHF offers greener profile and better water immiscibility for extractions.
Toluene: high-boiling, nonpolar; useful for high-temperature couplings; lower polarity can limit rate in polar reactions.
For chromatography, start with hexanes/EtOAc (9:1 to 3:1) and adjust based on Rf; aldehyde functionality enables UV and DNPH visualization.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (per Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General best practices for aromatic aldehydes
Store tightly capped under inert gas (N2/Ar) if possible to minimize slow oxidation of the aldehyde to the corresponding acid.
Keep in a desiccator or with desiccant; protect from prolonged light and heat.
If extended storage is expected, consider refrigeration (2–8 °C) as a precaution; allow to warm to room temperature in a sealed container before opening to avoid moisture condensation.
Reconstitution/handling
No reconstitution required. Dissolves readily in common organic solvents (e.g., DCM, THF, MeCN, EtOAc, toluene, DMF, DMSO). Prepare stock solutions freshly, or store aliquots at low temperature and protect from air/moisture.
For weighed solids: minimize exposure to ambient humidity; promptly recap and purge headspace with inert gas after use.
Stability notes (general)
Avoid prolonged exposure to strong bases/acids which can induce degradation (aldolization, acetalization/cleavage).
Under Pd-catalyzed hydrogenation, aldehyde reduction and possible debromination may occur; adjust conditions to maintain integrity when not intended.
Always consult the product CoA/Spec Sheet and SDS for lot-specific guidance.
Structure and Identity
A bifunctional aromatic building block featuring an aldehyde on one ring and an aryl bromide on the second ring linked through a benzylic ether.
Substitution pattern: para-formyl relative to the ether on ring A; meta-bromine on ring B relative to the benzylic CH2
2D description
Ring A (benzaldehyde): para positions occupied by –CHO and –O–CH2–aryl; other ring positions hydrogenated
Ring B (3-bromophenyl): bears Br at the meta position; bonded to the benzylic –CH2– of the ether; remaining positions hydrogenated
Note: Numeric identity fields not listed under Product Data are provided as literature/computed references only and are not item specifications.
Synthetic Utility
Key value arises from orthogonal reactivity of its handles and the stability of the aryl–O–CH2–aryl ether under many conditions.
Functional handle 1: Aromatic aldehyde
Enables formation of C=C (Wittig/HWE), C–N (imines → reductive amination), C–O/N (oximes/hydrazones), and C–C (Knoevenagel/aldol) bonds.
Can be selectively reduced to the benzyl alcohol (NaBH4, DIBAL) or oxidized to the benzoic acid (e.g., Pinnick oxidation) without affecting aryl bromide under mild conditions.
Functional handle 2: Aryl bromide (meta to benzylic attachment on the distal ring)
Readily participates in Pd-catalyzed couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Stille). The aldehyde is often compatible or can be protected as an acetal.
Allows installation of heteroaryl, alkenyl, alkynyl, or amine substituents to generate diverse analogs.
Linker: Benzylic ether
Chemoselective cleavage by hydrogenolysis to access the corresponding 4-hydroxybenzaldehyde derivatives when needed; also stable to many basic coupling conditions.
Retrosynthetic perspective
Disconnection strategies separate the target into (a) electrophilic aldehyde platform and (b) cross-coupling diversification point, simplifying library synthesis.
Purification/analytics tips (general)
Aldehyde proton (~9.7–10.1 ppm) and benzylic –CH2– (~5.0–5.3 ppm) are diagnostic in 1H NMR. IR C=O stretch ~1700 cm−1 confirms aldehyde integrity post-reaction.
Overall, the molecule is a versatile node for rapid diversification with good compatibility across carbonyl and cross-coupling manifolds.
Target Specificity
Not applicable. This product is a small-molecule organic building block and is not an antibody, protein, or biological targeting reagent. No target, epitope, clone, isotype, or species reactivity information applies.
Häufig gestellte Fragen
What is the purity of this product?
This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 588676-02-2, the molecular formula is C14H11O2Br, and the molecular weight is 291.13 g/mol. InChIKey RNVLQBDBEJCTRG-UHFFFAOYSA-N.
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.
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