This compound belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
279.910 g/mol
XLogP3
3.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
279.856 Da
Monoisotopic Mass
277.858 Da
Topological Polar Surface Area
37.300 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
151.000
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
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Recensioni
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Application Protocols
No item-specific, application-validated protocols are provided in the Product Data.
General handling protocols (literature-oriented; not product specifications):
Stock solution preparation for screening chemistry: Dissolve in anhydrous DMSO or DMF to 10–50 mM under inert atmosphere if prolonged storage is intended; filter (0.2 µm PTFE) if particulate is present.
Imine formation (small-scale): Mix aldehyde (1.0 eq) with amine (1.1 eq) in EtOH with 3Å molecular sieves; stir at RT–50 °C for 2–6 h; monitor by TLC/HPLC; concentrate and triturate/crystallize.
Suzuki coupling (microscale): Combine aryl bromide (1.0 eq), boronic acid (1.2 eq), Pd catalyst (1–2 mol%), K3PO4 (2.5 eq) in 1,4-dioxane/H2O (4:1); heat to 90 °C for 6–12 h; quench, extract, and purify.
For any regulated or scale-up use, develop and validate process-specific SOPs. Always consult the SDS before designing experimental protocols.
Biological Roles
This product is a small-molecule synthetic building block and is not intended for biological use in living systems.
General/literature context (not product claims):
Salicylaldehyde derivatives are widely used as ligands (via Schiff-base formation) for metal complexes that can serve as model systems in bioinorganic chemistry. These complexes can mimic coordination environments relevant to metalloenzymes but are used in vitro.
Phenolic aldehydes can engage in hydrogen bonding and π–π interactions, features often exploited in supramolecular assemblies and sensors (e.g., colorimetric/fluorimetric probes upon imine formation). Incorporation of bromines enhances heavy-atom effects, sometimes used in crystallography (anomalous scattering) or to promote intersystem crossing in photophysical studies.
Metabolism/biotransformation considerations are not typically applicable because this material is for research and synthetic use only and not for in vivo administration.
Research Use Only: As noted by the manufacturer, this product is for research use only and not for diagnostic, therapeutic, or other clinical applications.
Buffer Applications
Not typically applicable. 4,5-Dibromo-2-hydroxybenzaldehyde is a hydrophobic organic building block rather than a buffering reagent. It lacks acid/base pairs with suitable pKa spacing and aqueous solubility for preparing laboratory buffers. For experimental use involving this compound, dissolve in an appropriate organic solvent (e.g., DMSO, DMF, MeCN, EtOH) and, if needed, introduce into aqueous systems via co-solvent strategies or surfactants.
Green Alternatives
While 4,5-dibromo-2-hydroxybenzaldehyde itself is a halogenated aromatic building block (and thus not “green” by inherent composition), process greening can be achieved via solvent and reagent choices.
Greener process choices (literature guidance):
Solvents for condensations/imine formation: Ethanol or isopropanol (renewable, low toxicity) in place of DMF/DMSO when solubility allows; employ azeotropic water removal or molecular sieves.
Cross-coupling media: 2-MeTHF or CPME can replace THF/toluene in some Pd-catalyzed couplings; aqueous micellar catalysis (TPGS-750-M, Savie) in water/ppm Pd has growing precedent for aryl bromides.
Bases: K3PO4 or K2CO3 over strong inorganic hydroxides to reduce hazards; organic superbases avoided unless necessary.
Catalysis: Modern ligand systems (e.g., XPhos, SPhos) permit low-Pd loadings (≤0.5 mol%) at moderate temperatures, cutting metal footprint.
Workup/waste minimization: Telescoping imine formation and coupling sequences; crystallization-induced purification rather than chromatographic silica waste.
Greener: EtOH/2-MeTHF/water, micellar media; ≤0.5 mol% Pd or Ni; carbonate/phosphate bases. Pros: lower E-factor, safer. Cons: may need re-optimization for solubility/reactivity.
Note: Selection must balance EHS gains against solubility challenges of this dibromo substrate.
Pharmaceutical Uses
Not an excipient or pharmacopeial buffer. As a halogenated aromatic building block, 4,5-dibromo-2-hydroxybenzaldehyde may be used in medicinal chemistry research workflows strictly as a synthetic intermediate.
General/literature context (no medical claims):
Role in discovery: The aldehyde enables rapid generation of imine/oxime libraries; the dibromo motif supports parallel Suzuki/Sonogashira diversification for SAR exploration.
Formulation relevance: When used in screening libraries, compounds derived from this scaffold are commonly handled as DMSO stock solutions (e.g., 10–50 mM) for high-throughput assays; however, this product itself is not formulated for administration.
Regulatory status: No pharmacopeial monograph known for this specific compound. Any GMP or clinical manufacturing use would require dedicated quality development and controls beyond standard research grade.
For any application intersecting regulated environments, request detailed quality documentation (full CoA, residual solvents, elemental impurities profile) and perform appropriate qualification.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (typical for this compound; not product specifications):
Molecular formula: C7H4Br2O2 (computed from structure)
Molecular weight: ~279.91 g/mol (computed)
Physical state: Typically a crystalline solid (literature)
Color: Often off-white to light yellow solid (literature)
Melting point: Reports in the ~150–170 °C range depending on polymorph and purity (literature; values vary by source)
Boiling point: Decomposes before boiling at ambient pressure (literature expectation for polyhalogenated aromatics)
Density: Not broadly reported for the solid; typically >1 g/cm³ due to dibromo substitution (qualitative, literature)
Solubility: Sparingly soluble in water; soluble in common organic solvents such as ethanol, methanol, acetonitrile, acetone, ethyl acetate, DCM, THF; highly soluble in polar aprotic media (DMF, DMSO) (literature)
LogP: Expected moderate-to-high due to dibromination; reported cLogP often ~2–3 (literature/estimates)
pKa (phenolic OH): Generally ~9–10 for salicylaldehydes; dibromination may modestly acidify (literature trend)
UV-Vis: Aromatic band ~200–300 nm; intramolecular H-bonded salicylaldehyde chromophore shows characteristic n→π* near ~320–360 nm (solvent-dependent; literature)
Refractive index, water content, metals, or UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
Research grade: Suitable for most synthetic and analytical R&D. If UV transparency or LC/MS background is critical, request HPLC or LC/MS grade specifications.
Purity reporting: For building blocks such as halogenated salicylaldehydes, purity is often reported by HPLC/GC and corroborated by NMR. Residual solvents, inorganic halides, and positional isomers are typical impurity classes.
Stabilizers: None are typically added to this class; if any stabilizer or inhibitor is used, it will be listed on the CoA/SDS. Absence of an inhibitor means the aldehyde functionality may slowly oxidize—store properly.
Trace metals / halides: If the material is intended for cross-coupling, low residual metal and halide salts can matter for catalysis and analytical endpoints. For catalytic applications or high-sensitivity assays, request a metal-screened lot.
Documentation: For specific acceptance criteria (assay %, NMR identity, water content, residual solvent limits), consult the lot-specific CoA/Spec Sheet. Do not substitute literature values for product specifications.
Reaction and Applications
This dihalogenated salicylaldehyde serves as a versatile bifunctional building block, combining an electrophilic aldehyde with two aryl bromides and a directing/chelating phenolic OH.
Representative application families (literature):
Imination/Schiff bases: Condensation with primary amines to give salicylidene imines (often form stable, H-bonded ligands). Water removal (Dean–Stark in toluene) or molecular sieves enhances conversion.
Knoevenagel/aldol-type condensations: Reaction with activated methylenes (e.g., malononitrile, cyanoacetates) under basic catalysis (piperidine, ammonium acetate) affords electron-poor styryl derivatives.
O-acylation/O-alkylation: Phenolic OH enables formation of esters/ethers for protecting-group strategy or property tuning; typical bases: K2CO3, Cs2CO3, NaH.
Cross-coupling at C–Br: Suzuki–Miyaura (boronic acids/esters), Sonogashira (terminal alkynes), Buchwald–Hartwig (amines) allow diversification at the 4- and 5-positions. Orthogonal use with aldehyde-protecting groups can enable sequential functionalization.
Directed ortho-metalation (DoM)/halogen–lithium exchange: The o-hydroxy and aldehyde direct metallation; Br–Li exchange (t-BuLi, n-BuLi) at low temperature followed by electrophile trapping gives access to otherwise difficult substitution patterns.
Heterocycle formation: Condensation with 1,2-diamines yields salicylidene diimines; with hydrazines yields hydrazones; aldehyde participates in multicomponent reactions (e.g., Biginelli variants) when compatibility permits.
Practical tips:
Protect –CHO (as acetal) or –OH (as benzyl/THP ether) to avoid side reactions during strong-base or Pd-catalyzed steps.
For couplings, use bases that do not deprotonate the phenol excessively unless desired; include ligand choices that tolerate phenolic substrates.
Intramolecular H-bonding can slow imine hydrolysis, aiding isolation of Schiff bases.
Reaction Conditions
Typical conditions (literature; general guidance only):
Schiff base formation:
Reagents: Primary amine (1.0–1.2 eq), catalytic acid (AcOH) or base (piperidine); 3Å MS or Dean–Stark to remove water.
Solvent: EtOH, toluene, or MeCN.
Temperature/time: RT–80 °C, 1–16 h.
Notes: Intramolecular H-bonding stabilizes the imine; monitor by IR (C=O loss/C=N gain) or NMR.
Reagents: Phosphonium ylide or phosphonate (1.2–1.5 eq), base (NaH, KOtBu).
Solvent: THF, DMF, or toluene.
Temperature/time: 0–25 °C to reflux, 1–6 h.
Yields are substrate- and condition-dependent; consult primary literature for optimization on this dibrominated substrate.
Safety and Handling
Item-specific hazard details:
Signal Word: Not specified for this item; refer to SDS.
H-Statements / GHS Classification / Pictograms: Not specified for this item; refer to SDS.
General safety guidance (for halogenated aromatic aldehydes; literature best practices):
Likely hazards: Irritation to skin, eyes, and respiratory tract; harmful if swallowed. Aldehydes can be sensitizers/irritants; phenolic OH can enhance dermal absorption. Handle as a harmful organic solid.
PPE: Lab coat, nitrile gloves, splash goggles. Consider double-gloving for extended handling. Use in a chemical fume hood to avoid inhalation of dust or solvent vapors.
Engineering controls: Local exhaust ventilation; avoid aerosolization when weighing.
Incompatibilities: Strong bases (can promote aldol/condensation or phenolate formation), strong oxidizers (may over-oxidize or brominate), strong reducing agents (may reduce –CHO); avoid prolonged contact with reactive metals.
Stability considerations: Aromatic aldehydes can slowly oxidize to acids; minimize air/moisture exposure for long-term quality. Dibromo aromatics are generally stable thermally, but avoid high heat that may produce HBr-containing fumes.
First aid (overview; consult SDS): Eye/skin contact—rinse with water for ≥15 min; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical attention. Provide SDS to responders.
Waste: Collect halogenated organic waste separately per institutional and regulatory protocols.
Always defer to the product SDS and institutional EHS guidelines for authoritative safety information.
Solvent Selection
Applicability: This compound is a moderately polar, halogenated aromatic aldehyde with a phenolic OH. It is a solid reagent/building block rather than a bulk solvent; this section focuses on dissolution and reaction media.
General/literature guidance:
Polarity and hydrogen bonding: The o-hydroxyaldehyde can form intramolecular H-bonds; dissolution improves in polar aprotic solvents (DMF, DMSO, NMP, MeCN) and moderately polar protic solvents (MeOH, EtOH).
Common dissolution media (stock solutions): DMSO or DMF at 10–100 mM for screening; EtOH/MeCN for synthetic operations.
Water miscibility: Poor. Use co-solvents or phase-transfer strategies if aqueous conditions are required (e.g., micellar catalysis).
Solvent choices by use case:
Schiff base/Knoevenagel condensations: EtOH, i-PrOH, toluene, or acetonitrile depending on base and water-removal strategy.
Cross-couplings on the aryl bromides: Dioxane, toluene, THF, or MeCN with water/EtOH as co-solvent for base solubility.
Metalation/electrophile quench: Anhydrous THF or Et2O at low temperature.
Brief comparison (literature):
DMF/DMSO: Highest solubility; challenging workup and sustainability.
MeCN/EtOH: Good balance of solubility and ease of removal; greener than DMF/DMSO.
Toluene/dioxane: Favor cross-coupling; remove easily; lower polarity may limit solubility—use heat or co-solvent.
Storage and Reconstitution
Item-specific storage/shipping:
Storage Conditions: Room temperature (as provided).
Shipped In: Normal (ambient) conditions.
General handling and stability (literature guidance; not product specifications):
Container: Store in a tightly sealed, light-resistant container to minimize oxidation of the aldehyde and any photodegradation.
Atmosphere: For long-term storage, consider a dry inert atmosphere (argon/nitrogen) and include a desiccant to limit moisture uptake and imine-forming side reactions with adventitious amines.
Shelf life: Aromatic aldehydes are generally stable for months at RT when protected from moisture/air; periodic QC (e.g., NMR for hydrate/acid formation) is advisable for critical applications.
Reconstitution/dissolution:
Solubility: Readily dissolved in DMSO, DMF, MeCN, EtOH; poorly soluble in water (literature).
Preparing stock solutions: For discovery workflows, 10–100 mM stocks in anhydrous DMSO/DMF are typical; filter-sterilize through PTFE if required. Label with solvent, concentration, and date.
Freeze–thaw: If solutions are frozen, avoid repeated freeze–thaw cycles; aliquot into single-use vials.
Always refer to the lot-specific CoA/Spec Sheet and SDS for definitive storage and handling instructions.
Research Use Note: For research use only.
Structure and Identity
Overview: 4,5-Dibromo-2-hydroxybenzaldehyde is a dihalogenated salicylaldehyde scaffold featuring an ortho-phenolic OH and an aldehyde on a brominated benzene ring.
Product Data (item-specific)
SKU: D1349863
Product Name: 4,5-Dibromo-2-hydroxybenzaldehyde
CAS: 156089-67-7
InChIKey: 417722 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Category: 化学和生化试剂 (research chemicals)
Storage Conditions: Room temperature
Shipped In: Normal
Structure description (general/literature)
Core: Benzene ring bearing three adjacent substituents in a 1,2,3-pattern.
Functional groups: Phenolic hydroxyl (–OH) at the ortho position relative to the aldehyde (–CHO); two bromine atoms at the 4- and 5-positions of the ring (para and para+1 relative to –CHO), giving a deactivated but cross-coupling-ready aryl bromide motif.
Notes: The ortho –OH and –CHO enable intramolecular H-bonding, often influencing spectral features (e.g., downfield OH in NMR) and reactivity (Schiff-base formation).
Synthetic Utility
Functional handles and their uses (literature):
Aldehyde (–CHO):
Condensation to imines, hydrazones, oximes; reductive amination to benzylamines.
Wittig/Horner–Wadsworth–Emmons to install alkenes; selectivity modulated by base/solvent.
Acetalization to protect during metal-catalyzed or strong-base steps.
Phenolic OH (ortho to –CHO):
Protect as benzyl/methyl/THP ether or as esters; enables chelation control in metalations and cyclizations.
Acts as directing site for DoM; forms salicylidene ligands.
Two aryl bromides (4- and 5-positions):
Platform for sequential/orthogonal cross-couplings (Suzuki, Sonogashira, Buchwald–Hartwig). Electronic/steric differences sometimes allow site-selective activation.
Halogen–lithium exchange followed by electrophile quench; access to CF3, formyl, nitrile, or borylated derivatives.
Retrosynthetic value:
Serves as a convergent node: derive diverse di-substituted salicylaldehydes by coupling two fragments while retaining the aldehyde for late-stage diversification.
Enables bifunctional ligands and macrocyclizations via di-coupling then imine/oxime formation.
Practical notes:
Protect –CHO before strong base or prolonged Pd/Ni catalysis; deprotection under mild acid afterward.
Use mild bases (K2CO3, Cs2CO3) for O-alkylations to preserve C–Br bonds.
For selectivity in di-couplings, adjust ligand/temperature and consider temporary masking of one C–Br via borylation–protodeborylation strategies.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent (e.g., antibody, enzyme inhibitor with defined biological target), and no target specificity data are provided in the Product Data.
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