≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Store at 2-8°C,Protected from light,Argon charged Ships Wet ice Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 36 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Descripción general
Application
Employed in palladium-catalyzed mono- and bis-arylation of 3,4-(ethylenedioxy)thiophenes. Also used in a cross-coupling study with potassium vinyltrifluoroborate.
This compound belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
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.
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Application Protocols
Not applicable. No antibody/assay protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For practical usage, consult the Reaction Conditions section for representative synthetic procedures (e.g., cross-couplings, olefinations, reductive aminations) and adjust stoichiometry, catalyst loading, and temperature based on your substrates and scale.
Biological Roles
This product is intended strictly for research and laboratory use. It does not have an established biological role. The following information is general context about aromatic aldehydes and is not a claim about this specific product in biological systems.
Reactivity with biomolecules (general)
Aldehydes can reversibly form Schiff bases with primary amines (e.g., lysine side chains), which underlies common bioconjugation strategies in vitro when anilines or aliphatic amines are present. Such reactions are typically stabilized by reduction (e.g., NaBH3CN) to secondary amines.
Metabolic considerations (general literature)
Simple benzaldehydes may be oxidized by aldehyde dehydrogenases to the corresponding benzoic acids in vivo; halogen substitution can modulate rates and distribution, but detailed metabolism is substrate-specific and beyond the scope of this listing.
Materials/bioconjugation interface
The para-bromide allows further derivatization (e.g., installation of linkers or reporter groups) before applying carbonyl chemistry for conjugation, supporting stepwise assembly of probes or polymer–small-molecule hybrids in research settings.
No biological, diagnostic, or therapeutic use is intended or implied. For any work involving biological matrices, ensure removal of residual catalysts/solvents and confirm biocompatibility separately.
Buffer Applications
Not typically applicable. p-Bromobenzaldehyde is a hydrophobic organic building block rather than a buffering agent. It does not serve as a pH buffer in aqueous systems. For practical use in aqueous-phase reactions (e.g., aqueous Suzuki couplings), select an appropriate buffer/base system (e.g., K2CO3, K3PO4) primarily for the reaction rather than buffering capacity, and refer instead to the Solvent Selection and Reaction Conditions sections for guidance.
Green Alternatives
As a substrate, p-bromobenzaldehyde is not readily replaced; greening efforts target solvent/catalyst choices and protection strategies.
Greener solvent choices (literature/general)
Replace DCM/CHCl3 with EtOAc or MTBE for workups; use toluene or 2-MeTHF in place of THF/diethyl ether where feasible.
For Suzuki couplings, ethanol/water or 2-propanol/water with a mild base (K2CO3, K3PO4) can replace high-boiling amide solvents (DMF, NMP).
For imine formation, solvent-free or azeotropic water removal in bio-derived solvents (2-MeTHF) can reduce waste.
Catalyst and process intensification
Employ ligand-efficient Pd systems (ppm-level loadings) or heterogeneous catalysts (Pd/C, Pd on reusable supports) to minimize metal waste.
Explore nickel-catalyzed couplings for reduced Pd usage, noting sensitivity to aldehydes (consider acetal protection).
Energy and protection strategy
Microwave or flow synthesis can reduce reaction time/energy.
Use temporary acetals that can be hydrolyzed under mild, aqueous acidic conditions to minimize harsh reagents.
Comparison (general guidance)
| Scenario | Conventional | Greener alternative | Trade-offs |
|---|---|---|---|
| Extraction | DCM | EtOAc or MTBE | Slightly slower phase separation; safer profile |
| Ether solvents | THF | 2-MeTHF/CPME | Peroxide risk persists; better renewability and separations |
| Coupling medium | DMF/dioxane | EtOH/H2O | Substrate/catalyst solubility limits; often mitigated by surfactants or phase-transfer |
Note: Validate catalyst/solvent compatibility with aldehydes to avoid side reactions.
Pharmaceutical Uses
This product is for research use only. It is not an excipient or drug substance as supplied. The following notes provide general formulation/manufacturing context for aromatic aldehyde building blocks; they are not specific to this SKU.
Role in process chemistry (general)
p-Bromobenzaldehyde can serve as a key intermediate for synthesizing biaryl, styrenyl, or alkynyl-aryl aldehydes that are elaborated into API candidates. The para-bromo handle enables cross-coupling to construct frameworks, while the aldehyde enables downstream reductive amination or oxidation to acids for amide couplings.
Protecting-group considerations
Temporary acetal protection may be used during basic or nucleophilic steps; deprotection under mild aqueous acid conditions simplifies workup and reduces harsh reagents.
Impurity control (general)
Oxidation to 4-bromobenzoic acid and reduction to 4-bromobenzyl alcohol are typical degradants; process controls and storage under inert atmosphere/light protection mitigate formation.
Regulatory note
No pharmacopeial monograph is implied. For any GMP application, source lot-specific CoA, impurity profile, and residual solvent/metal data, and qualify analytical methods per ICH Q2.
Physical Properties
Item-specific physical specifications are not provided for this SKU. The following are typical literature values for 4-bromobenzaldehyde and are supplied for reference only; they are not guaranteed specifications for this item.
Phase/appearance (literature): typically a white to off-white crystalline solid
Melting point (literature): ~57–60 °C
Boiling point (literature): ~240–250 °C at 1 atm (compound is often handled below mp; distillation typically under reduced pressure)
Density (literature): ~1.6–1.7 g/cm³ (solid; temperature-dependent)
Solubility (literature/general):
Water: low solubility (aromatic aldehyde with halogen, hydrophobic character)
Organic solvents: soluble in ethanol, methanol, acetone, ethyl acetate, dichloromethane, THF; very soluble in chlorinated and aromatic solvents (e.g., toluene)
LogP (literature): estimated ~2.5–3, consistent with para-bromoaryl aldehydes
pKa (literature): not applicable (no ionizable protic functionality under neutral conditions); aldehyde hydrate equilibrium possible in water
UV–Vis (literature): weak π→π* absorption in near-UV due to benzaldehyde chromophore; typically used as a reactant rather than as a chromophore standard
Refractive index: Not applicable to solid; not commonly reported
Item-specific values (purity grade UV cutoff, water/peroxide ppm, metals): Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
If designated as “Reagent/AR grade,” typical expectation is suitability for most synthetic applications with tight limits on common impurities (e.g., halides, residual solvents, water). If “HPLC grade,” solvents are optimized for low UV absorbance—less relevant for solids like this aldehyde, where “assay” and impurity profile matter more than UV cutoff.
For cross-coupling and organometallic transformations, low levels of halide scrambling, protodehalogenation products, residual metals, and oxidized byproducts (4-bromobenzoic acid or benzyl alcohol) are desirable. If you require metal-sensitive performance (e.g., Pd-catalyzed steps at low loading), request a CoA with detailed trace metal and residual solvent data.
Light and oxygen sensitivity: The product is supplied argon charged and specified to be protected from light, which helps preserve aldehyde integrity (minimizing oxidation to 4-bromobenzoic acid and polymeric byproducts). Upon opening, minimize headspace oxygen, promptly recap, and consider inert-atmosphere storage for long-term use.
For analytical verification, common QC methods include: 1H/13C NMR for aldehyde formyl signal (~9.8–10.2 ppm, literature), GC/GC–MS or HPLC for assay, and IR for carbonyl stretch (~1690–1710 cm⁻¹, literature).
Reaction and Applications
This substrate is a versatile bifunctional building block in organic synthesis and materials workflows, valued in the materials science domain for installing functional aromatic motifs and conjugated linkers.
Sonogashira couples terminal alkynes to build ethynyl-aryl aldehydes for conjugated scaffolds.
Orthogonality and protecting-group strategy
The aldehyde can be transiently protected as an acetal (e.g., ethylene acetal) to enhance compatibility with basic or nucleophilic couplings.
Sequential logic: (1) protect aldehyde, (2) cross-couple at Ar–Br, (3) deprotect to restore –CHO for final elaboration.
Representative downstream utilities
Synthesis of dyes, ligands, MOF linkers (via oxidation to acids then coupling), and advanced intermediates for small-molecule libraries.
Tips: Maintain inert atmosphere and exclude moisture/strong base when aldehyde integrity is critical; consider light protection during prolonged reactions to limit oxidation.
Reaction Conditions
The following conditions are representative literature guidance for 4-bromobenzaldehyde and should be optimized per substrate and scale. They are not product specifications.
Suzuki–Miyaura coupling (Ar–Br)
Catalyst: Pd(PPh3)4 (1–2 mol%) or Pd-precatalyst with phosphine/biarylphosphine ligand
Base: K2CO3 or K3PO4 (2–3 equiv)
Solvent: EtOH/H2O (1:1) or dioxane/H2O; 60–90 °C under N2/Ar, 2–12 h
Note: Protect aldehyde as acetal if base-sensitive nucleophiles are present
Heck coupling
Catalyst: Pd(OAc)2 (1–2 mol%) with PPh3 (4–6 mol%)
Base: Et3N or DIPEA (2–3 equiv)
Solvent: DMF, NMP, or toluene; 90–130 °C, 4–16 h
Sonogashira coupling
Catalyst/co-catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (5–10 mol%)
Base: Et3N or i-Pr2NH
Solvent: THF, toluene, or EtOH; rt–60 °C, 2–10 h; protect aldehyde if needed
Wittig olefination
Reagents: Ph3P=CHR (generated from phosphonium ylide)
Solvent: THF or toluene; 0–25 °C to reflux; 2–8 h
Tip: Use stabilized ylides for E-selectivity; protect aldehyde in multi-step sequences
HWE olefination
Reagents: Phosphonate (1.2–1.5 equiv), base (NaH, DBU)
Solvent: THF/DMF; 0–25 °C, 2–6 h; often higher E-selectivity
Nucleophilic addition (Grignard)
Reagents: RMgX (1.2–1.5 equiv)
Solvent: THF or 2-MeTHF; −78 to 0 °C; quench with NH4Cl
Imine formation/reductive amination
Solvent: Toluene (Dean–Stark) or EtOH; acid catalyst (AcOH, p-TsOH); rt–reflux; then NaBH3CN/NaBH(OAc)3 for reduction
Typical isolated yields vary with coupling partners and conditions and often range from moderate to high in literature reports.
Safety and Handling
Safety data in this section are general for aryl aldehydes and brominated aromatics. Item-specific GHS and hazard statements are Not specified for this item; refer to the product SDS for authoritative information.
Product Data storage and transport
Store at 2–8 °C, protected from light, argon charged (provided)
Shipped on wet ice (provided)
Typical hazards (general literature guidance)
Irritant: Aldehydes can cause skin/eye irritation and respiratory irritation upon dust or vapor exposure.
Sensitization: Some aldehydes may cause skin sensitization; handle with care to avoid repeated contact.
Combustible organic solid; avoid ignition sources and dust formation.
Reactivity: Aldehydes can oxidize to corresponding acids on exposure to air/light; argon blanket and light protection help limit degradation.
Incompatibilities (general)
Strong oxidizers (risk of exothermic oxidation)
Strong bases and nucleophiles (can induce aldol-type side reactions, Cannizzaro with non-enolizable aldehydes, or imine formation with amines)
Reducing agents (unwanted reduction to alcohol)
PPE and engineering controls
Use in fume hood; wear lab coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Avoid inhalation of dust.
First-aid overview (general)
Skin/eye contact: Rinse with water for ≥15 min; remove contaminated clothing; seek medical attention as needed.
Inhalation: Move to fresh air; provide oxygen if needed; seek medical attention.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Always consult the SDS for this SKU for definitive GHS classification, pictograms, and first-aid measures.
Solvent Selection
p-Bromobenzaldehyde is moderately hydrophobic and readily soluble in common organic solvents. Solvent choice should reflect the reaction mode (carbonyl vs. aryl–Br handle) and green chemistry priorities.
Polarity/miscibility profile (literature/general)
Poor water solubility; favors aprotic organics: DCM, chloroform, THF, EtOAc, toluene, acetonitrile. Soluble in lower alcohols (MeOH, EtOH) but can participate in acetal formation under acidic conditions.
For nucleophilic additions (e.g., Grignard), ethers (Et2O, THF, 2-MeTHF) are typical.
For cross-couplings, polar aprotics (DMF, DMAc, NMP) or mixed aqueous alcohol systems (EtOH/H2O) with a base (K2CO3) are common.
Practical selection guidance
Carbonyl transformations (Wittig/HWE, imine formation): THF, toluene, or MeCN are robust; alcohols can be used with care to avoid acetalization.
Cross-coupling at aryl–Br: EtOH/H2O or toluene/EtOH with Pd catalysts for Suzuki–Miyaura; DMF or dioxane for more challenging couplings.
Workup/extraction: EtOAc or MTBE provide efficient partitioning from aqueous media; avoid prolonged basic aqueous exposure to limit Cannizzaro-type side reactions (though aromatic aldehydes are less prone).
Comparison snapshot (general)
DCM vs. EtOAc: DCM offers rapid dissolution and low bp; EtOAc is greener and often adequate for extractions and recrystallizations.
THF vs. 2-MeTHF: 2-MeTHF offers improved sustainability and water-immiscibility while supporting organometallic chemistry comparably to THF.
Storage and Reconstitution
Storage (from Product Data)
Store at 2–8 °C
Protect from light
Argon charged (maintain inert atmosphere to limit oxidation)
Shipped on wet ice
Handling and in-use guidance (general)
Minimize headspace oxygen and limit light exposure. After opening, promptly recap, optionally purge with argon or nitrogen, and return to cold storage.
Avoid prolonged exposure to strong bases or nucleophiles during storage; keep away from oxidizing agents.
Reconstitution/dissolution (general)
If supplied as a solid, dissolve the required amount in a dry, oxygen-free organic solvent compatible with your application (e.g., THF, toluene, DCM, EtOAc, MeCN, or alcohols). For air/moisture-sensitive work, perform transfers under inert atmosphere.
For solutions, prepare single-use aliquots to minimize repeated headspace exposure. Filter through a PTFE syringe filter (0.45 µm) if particulate is observed.
Stability notes (general)
Aldehydes may slowly oxidize to the corresponding acid; light and oxygen exclusion significantly improve shelf life. Consider periodic QC (e.g., 1H NMR, HPLC) for long-term stored material.
For item-specific shelf-life or solution stability claims, refer to the product CoA/Spec Sheet and SDS. Research use only.
Structure and Identity
p-Bromobenzaldehyde (4-bromobenzaldehyde) is a bifunctional aryl building block combining an electrophilic aldehyde with a para-positioned aryl bromide, enabling orthogonal reactivity in synthesis.
Item identifiers (from Product Data)
SKU: B419287
CAS: 1122-91-4
PubChem CID: 70741
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature identity data (for reference; not item-specific)
Example InChIKey (literature): commonly reported for 4-bromobenzaldehyde; consult primary databases for the exact key
Structural features (general description)
Aromatic ring: monosubstituted benzene core with para substitution pattern
Functional groups: one aryl bromide (C–Br) and one formyl group (–CHO) in the 1,4-relationship
Reactivity handles: aldehyde is strongly electrophilic at carbonyl carbon; aryl bromide undergoes Pd-catalyzed cross-couplings (Suzuki–Miyaura, Heck, Sonogashira)
2D structural description: A benzene ring bearing a bromine atom at the para position relative to an aldehyde group; the aldehyde carbonyl is conjugated with the ring, enhancing polarization and facilitating nucleophilic additions and olefination reactions.
Note: All structural identifiers that are not provided under Product Data are shown as literature reference values only and should be confirmed against the product CoA/Spec Sheet for lot-specific use.
Synthetic Utility
The dual functionality of p-bromobenzaldehyde provides orthogonal reaction manifolds that streamline route design.
Aldehyde handle (general/literature)
Electrophilic carbonyl undergoes: Wittig/HWE olefination (to styrenes), nucleophilic additions (RMgX/RLi → benzylic alcohols), reductive amination (amines → benzylamines), and condensation to oximes/hydrazones for further transformations (e.g., Beckmann-type chemistry after oxidation).
Oxidation to the carboxylic acid affords 4-bromobenzoic acid, enabling convergent amide/ester formation.
Aryl–Br handle (general/literature)
Suzuki–Miyaura: install aryl/heteroaryl groups to access biaryl aldehydes for ligand/dye/materials development.
Sonogashira: couple terminal alkynes to build ethynyl-aryl aldehydes; suitable for click-chemistry pipelines after alkyne functionalization.
Lithium–halogen exchange (at low temperature) enables formyl retention with careful quench; more commonly, protect aldehyde as acetal prior to organolithium steps.
Strategy
Protect–couple–deprotect sequences minimize side reactions of the aldehyde under basic/catalytic conditions, preserving chemoselectivity.
Divergent synthesis: From a single starting material, access acid, alcohol, imine, olefin, biaryl, and alkynyl derivatives, supporting library synthesis and materials diversification.
Target Specificity
Not applicable. This product is a small-molecule building block and does not possess biological target specificity parameters (e.g., antigen, epitope, isotype). Refer instead to the Reaction & Applications and Synthetic Utility sections for relevant use information.
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