This compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
231.040 g/mol
XLogP3
2.200
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
2
Exact Mass
229.958 Da
Monoisotopic Mass
229.958 Da
Topological Polar Surface Area
46.500 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
162.000
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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Application Protocols
Not applicable for bioassay protocols. This listing is a synthetic reagent, not supplied with validated protocols for WB, IHC, IF, FC, etc.
For chemical synthesis, see the “Reaction Conditions” and “Synthetic Utility” sections for general literature guidance and adapt to your substrates and scale.
Biological Roles
This product is a small organic synthetic intermediate without an inherent biological role.
General context (literature/general): Phenolic anisaldehydes can serve as precursors to ligands, fluorescent fragments, or pharmacophore-bearing scaffolds after further derivatization (e.g., cross-coupling at C2, condensation at –CHO).
Enzyme/biomolecule interactions: No specific physiological role is established for this compound; the phenol and aldehyde motifs may engage in noncovalent interactions or reversible imine formation with amines in biochemical assay development, but such use requires separate validation.
Research-only disclaimer:
Per Product Data, this material is for research use only and is not intended for use in humans or animals.
Buffer Applications
Not typically applicable. This is a neutral organic building block rather than a buffering agent.
If dissolution in aqueous systems is required for screening or assays, prepare stock solutions in DMSO or MeCN, then dilute into buffered media while monitoring for precipitation. Adjust pH only if phenolate formation (basic pH) is intended for specific reactivity studies.
Green Alternatives
As a solid building block, the molecule itself is fixed; greener choices focus on solvents, bases, and catalysts.
Greener solvent swaps (literature/general):
Replace DMF/1,4-dioxane with 2-MeTHF or CPME for couplings and olefinations; consider Me-THF/H2O biphasic systems for Suzuki reactions.
Favor ethyl acetate or MeCN over CH2Cl2/CHCl3 when feasible; use toluene only with efficient recovery/reuse.
Base and aqueous media:
K2CO3/K3PO4 in water-containing systems can reduce solvent load; phase-transfer catalysis may enable milder conditions.
Catalysis:
Use precatalysts with bulky biaryl phosphines (e.g., XPhos, SPhos) for lower Pd loadings; explore Ni-catalyzed couplings for reduced precious-metal use when compatible with the substrate’s aldehyde and phenol.
Comparison (general considerations):
2-MeTHF vs THF: similar performance; 2-MeTHF is bio-based, higher boiling, more hydrophobic (easier workup), but peroxides can form—monitor accordingly.
CPME vs DCM: CPME is non-halogenated, broader liquid range, water tolerant; slightly less polar than DCM—may require temperature or catalyst adjustments.
Waste minimization:
Protect the aldehyde only when necessary; orthogonal reactivity often allows protection-free sequences, reducing steps and solvents.
Pharmaceutical Uses
No pharmacopeial excipient status is indicated for this item.
Formulation role: Not used directly as an excipient; instead, it can serve as a synthetic intermediate in medicinal chemistry programs where the aryl bromide enables diversification and the aldehyde allows rapid SAR via condensations.
CMC considerations (general): If intermediates are to be advanced, ensure control of aldehyde oxidation byproducts, residual palladium/nickel from couplings, and residual solvents per ICH Q3C/Q3D when relevant to later-stage development. These considerations do not apply to this catalog item as a research chemical unless your internal QA requires them.
Physical Properties
Item-specific property values are not provided in the Product Data. Where useful, general/literature expectations for closely related structures are noted for planning purposes only.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Melting point / Boiling point (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Density/Refractive index (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Solubility (literature/general):
Expected to be sparingly soluble in water due to aryl bromide and anisole motifs; phenolic OH may aid only slightly.
Typically soluble in common organic solvents such as DCM, chloroform, ethyl acetate, acetone, THF, acetonitrile; highly soluble in polar aprotic media (DMF, DMSO).
Acidity/basicity (literature/general): Phenolic OH pKa typically ~9–10 for substituted phenols; electron-withdrawing CHO/Br may slightly lower pKa relative to phenol.
Partitioning (literature/general): Substituted anisaldehydes/aryl bromides often show moderate hydrophobicity (logP in the 1.5–3 range), but exact value for this molecule is not specified here.
Always confirm critical parameters experimentally or via the item’s CoA/SDS for your lot.
Quality and Grades
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Context for professional use:
For synthetic applications (e.g., Pd-catalyzed couplings, carbonyl condensations), typical research grades are sufficient, but trace halide integrity, carbonyl purity (absence of acid/oxime), and water content can materially impact outcomes.
If applying in trace-catalyst cross-coupling, consider lots with documented low metal contaminants and verified halogen content by elemental analysis or HRMS.
If using in photochemical or oxidative contexts, verify absence of auto-oxidation products (e.g., corresponding benzoic acid) by HPLC/GC.
What to look for on the CoA/Spec Sheet:
Identity confirmation (1H/13C NMR, HRMS, or GC–MS), chromatographic purity, and any residual solvent profile.
Stabilizer information (none listed for this item); if present in other lots, understand potential impacts on reactivity (e.g., phenol-blocking or aldehyde protection).
Reaction and Applications
Prized as a bifunctional building block that combines an aryl bromide (for cross-coupling) with a formyl handle (for C–C bond formation) and a phenolic OH (for further diversification).
Cross-coupling via Ar–Br (literature/general):
Suzuki–Miyaura: Couple with boronic acids/esters to access 2-substituted 6-hydroxy-4-methoxybenzaldehydes. Pd(PPh3)4, Pd2(dba)3/XPhos, or Pd-PEPPSI catalysts; bases K2CO3, K3PO4, Cs2CO3; solvents dioxane/H2O, toluene/H2O, 2-MeTHF. 50–100 °C.
Heck: Install alkenes at C2; ligands P(o-tol)3 or PPh3; bases Et3N or inorganic carbonates.
Buchwald–Hartwig: Though a phenol is present, C–N coupling at C2 requires amine nucleophiles and appropriate ligand (e.g., BrettPhos) if converting Ar–Br to anilines/amides.
Carbonyl transformations:
Wittig/Horner–Wadsworth–Emmons to form styrenes or acrylic derivatives on the anisole/phenol scaffold.
Knoevenagel with active methylene compounds (malononitrile, cyanoacetates) to generate electron-rich aryl alkenes.
Reductive manipulations: NaBH4 or catalytic hydrogenation reduce –CHO to benzyl alcohol; selective reductions can be tuned to avoid debromination.
Oxime/hydrazone formation for protecting/derivatizing the aldehyde.
Phenolic/O-chemistry:
O-alkylation/acylation for ether/ester libraries; careful base choice (K2CO3/Cs2CO3) to avoid aldehyde side reactions.
Demethylation (BBr3, AlCl3/thiols) can convert –OMe to a catechol analogue (with protection of the other OH as needed).
Applications (general): Useful in the synthesis of bioactive scaffolds, ligands, and functional materials where orthogonal handles enable stepwise diversification.
Reaction Conditions
General literature guidance for analogous substrates bearing Ar–Br, –CHO, and –OH:
Base: K2CO3 or K3PO4 (2–3 equiv) in dioxane/H2O (4:1) or 2-MeTHF/H2O.
Temp/Time: 60–90 °C, 2–12 h.
Notes: Free phenol can be tolerated; if problematic, protect as benzyl or silyl ether. Avoid strong bases that induce aldehyde side reactions; buffered aqueous systems often suffice.
Heck coupling:
Pd(OAc)2 (1–2 mol%) + P(o-tol)3 or PPh3; base Et3N or DIPEA; solvent DMF, MeCN, or toluene; 90–120 °C.
Wittig/HWE olefination of –CHO:
Wittig: Ph3P=CHR (1.2–1.5 equiv), solvent THF or toluene, 0–25 °C to rt, 2–6 h.
HWE: Diethyl phosphonate carbanion (NaH/KOtBu), solvent THF/DMF, 0–25 °C.
Notes: The phenol may need protection under strong base; milder Still–Gennari reagents can improve E-selectivity.
NaBH4 (1.2 equiv) in MeOH or EtOH at 0–25 °C yields benzyl alcohols rapidly; monitor to avoid over-reduction or debromination.
Yields vary with partners and conditions; consult the primary literature and perform small-scale optimization.
Safety and Handling
GHS/SDS status for this item: Not specified for this item; refer to the product SDS for definitive hazard classification, H-statements, and pictograms.
General hazard profile (literature/general for phenolic aldehydes and aryl bromides):
May cause skin/eye irritation; aldehydes can be respiratory/skin irritants and sensitizers in some cases.
Harmful if swallowed/inhaled; avoid dust or aerosols.
Phenolic OH imparts weak acidity; aryl bromides can be hazardous to aquatic life.
PPE: Lab coat, nitrile gloves, splash goggles; handle in a fume hood to avoid inhalation of vapors or particulates.
Handling advice:
Minimize exposure to air and light to limit aldehyde oxidation to the corresponding acid.
Avoid strong bases when unintended O-alkylation or Cannizzaro-type side reactions would be problematic (though aromatic aldehydes are generally resistant to Cannizzaro unless strongly activated and under concentrated base).
Keep containers tightly closed; purge headspace with inert gas if storing long-term.
Incompatibilities (general): Strong oxidizers (risk of over-oxidation), strong bases (phenolate formation), strong reducing agents (may reduce C=O or debrominate), and electrophiles that may react with the phenol.
First aid (overview; see SDS): Rinse eyes/skin with water for at least 15 minutes upon contact; move to fresh air if inhaled; seek medical attention if symptoms persist; do not induce vomiting after ingestion—consult medical professionals.
Always defer to the official SDS for authoritative safety information.
Solvent Selection
This compound is a moderately polar aromatic aldehyde with phenolic and methoxy substituents; it dissolves best in mid- to high-polarity organic solvents.
Limited in alcohols: Soluble in MeOH/EtOH; phenolic H can engage in H-bonding, aiding solubility.
Poor in water at neutral pH; solubility increases in basic aqueous media via phenolate formation (not recommended unless deprotonation is desired).
Selection by application:
Cross-coupling (Suzuki/Heck/Buchwald–Hartwig on Ar–Br): 2-MeTHF, CPME, toluene, dioxane, or Me-THF/water biphasic systems are popular; DMF/MeCN/1,4-dioxane remain common.
Carbonyl chemistry (Knoevenagel, Wittig, HWE): THF, toluene, MeCN, or green ethers (2-MeTHF/CPME). Avoid strongly basic aqueous media if you need to preserve the aldehyde from side reactions.
O-alkylation of the phenol: Polar aprotic solvents (DMF, DMSO, MeCN) with base (K2CO3, Cs2CO3) to maximize SN2 rates.
2-MeTHF/CPME: greener ether choices; good for couplings/olefinations; water-tolerant.
MeCN: polar, low viscosity; good for base-mediated condensations.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per Product Data). Store tightly sealed in a dry, well-ventilated area.
Light/air sensitivity (general for aldehydes): Protect from light and prolonged air exposure to minimize oxidation to the corresponding acid and polymerization; consider inert gas backfill for long-term storage.
Moisture: Keep desiccated; phenolic OH is hygroscopic to a minor degree and the aldehyde can hydrate under strongly aqueous conditions.
Container: Amber glass vial with PTFE-lined cap recommended.
Reconstitution/dissolution:
Prepare stock solutions in DMSO, MeCN, THF, or DCM depending on downstream use. Filter if particulates are present.
For assay work, dilute organic stocks into buffered media with vigorous mixing; monitor for precipitation.
Shipping (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Always follow your institution’s chemical storage and waste policies. This product is for research use only.
Structure and Identity
A brominated, phenolic anisaldehyde derivative bearing an aldehyde, a phenol, and a methoxy group on a 1,2,4,6-substituted benzene ring.
2D description: A 1,2,4,6-tetrasubstituted benzene where the ring bears, clockwise from the formyl carbon: 2-bromo, 4-methoxy, and 6-hydroxy groups; two remaining ring positions hold hydrogens.
Notes:
The combination of an aryl bromide and an aldehyde makes this a versatile bifunctional building block for cross-coupling and carbonyl chemistry.
Synthetic Utility
Key functional handles and their reactivity (literature/general):
Aryl bromide (C2):
Entry point for Suzuki, Heck, Sonogashira, and Buchwald–Hartwig couplings.
Orthogonality: can couple first, then exploit –CHO/–OH; or protect –CHO (as acetal/oxime) depending on catalyst/base.
Aldehyde (C1):
Wittig/HWE to elaborate vinyl/alkenyl linkers.
Imine/oxime/hydrazone formation for protection or fragment elaboration.
Selective reduction to benzyl alcohol for subsequent derivatization.
Phenol (C6) and Methoxy (C4):
O-alkylation/acylation of phenol; demethylation of anisole to access catechol motifs (manage regioselectivity/protection).
Retrosynthetic value:
Target motifs derived from this scaffold are accessible via C2 diversification first (cross-coupling), followed by aldehyde condensation, and final-stage phenol functionalization—often avoiding protecting groups when mild catalysts/bases are used.
Selectivity notes:
Electron-withdrawing CHO and Br slightly deactivate the ring toward EAS; cross-coupling is therefore typically preferred over direct substitution for installing new C–C/C–N/C–O bonds.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or biological targeting agent. No antigen/epitope or species reactivity information applies.
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