This compound belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy 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
261.070 g/mol
XLogP3
2.600
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
3
Exact Mass
259.968 Da
Monoisotopic Mass
259.968 Da
Topological Polar Surface Area
55.800 Ų
Heavy Atom Count
14
Formal Charge
0
Complexity
209.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
Not applicable. There are no WB/IHC/IF/FC or similar bioassay protocols associated with this small-molecule building block.
General laboratory use guidance (for synthetic applications):
Prepare stock solutions in dry DMSO, DMF, or an appropriate organic solvent for reaction setup or screening.
For parallel synthesis, dispense via positive-displacement tips; avoid prolonged exposure to ambient humidity when base-sensitive transformations are planned.
Monitor reactions by TLC (UV-active aromatic) or LC–MS; the salicylate chromophore typically provides strong UV absorbance (literature/general).
Biological Roles
This product is a synthetic aromatic ester and halogenated salicylate derivative intended for research and synthesis. It does not have a defined endogenous biological role.
General biochemical context (literature/general):
Salicylate frameworks appear in natural products and enzyme inhibitors; the 2-hydroxybenzoate (salicylate) motif can engage in metal chelation and H-bonding with protein active sites. However, the methyl ester and additional substituents here are designed for synthetic versatility, not for inherent bioactivity claims.
The phenolic OH can modulate acidity and binding modes; the ester serves as a pro-functional handle (hydrolyzable to the acid), useful in medicinal chemistry exploration of SAR rather than as a biological cofactor.
Use limitations:
For research use only (per Product Data). Not for human or veterinary use. No clinical or diagnostic applications are claimed or supported.
If biological evaluation is intended, users should determine purity, residual solvent/metal levels, and stability in relevant assay media; none of these parameters are specified for this catalog item and must be established experimentally.
Buffer Applications
Not typically applicable. This compound is a hydrophobic aromatic building block and does not function as a buffering agent. It lacks a conjugate acid/base pair with a suitable aqueous pKa window and has poor water solubility.
Guidance:
For aqueous assay work, dissolve in a compatible organic co-solvent (e.g., DMSO) and dilute into the buffer while keeping final organic content within assay tolerance.
Select established biological buffers (e.g., phosphate, HEPES, Tris) for pH control rather than using this compound.
Green Alternatives
Opportunities to improve sustainability when working with this aryl bromide salicylate focus on solvent and base choices, as the substrate itself is fixed.
Greener substitutions (literature/general):
Solvents:
Replace DMF/NMP with Cyrene, propylene carbonate, or dimethyl carbonate where solubility and catalyst compatibility permit.
Use 2-MeTHF or CPME in place of THF/dioxane for couplings; both are biorenewable and less prone to peroxide hazards (still test for peroxides as needed).
Employ aqueous micellar catalysis (e.g., TPGS-750-M, Savie) for Suzuki and Buchwald couplings at ppm Pd, reducing organic solvent usage.
Bases:
Swap inorganic carbonate bases in high-boiling polar aprotics for aqueous K2CO3/Na2CO3 in biphasic systems to simplify workup and reduce solvent burdens.
Catalysts:
Explore ligand-enabled low-Pd or Ni-catalyzed couplings to reduce precious metal loading.
Comparison snapshot (general guidance):
THF/dioxane: excellent solvating power for cross-coupling; petro-sourced, peroxide-forming (dioxane problematic for health/environment).
DMF/NMP: broad solubility; reproductive toxicity concerns and challenging removal; consider Cyrene/PC when feasible.
Implement in stages: start with greener solvent screens, then optimize base and catalyst loadings to balance EHS, cost, and performance.
Pharmaceutical Uses
No pharmacopeial or excipient status is provided for this item. It is supplied for research use only (per Product Data) as a synthetic building block.
General formulation/manufacturing context (literature/general):
Aromatic salicylate derivatives are commonly used as intermediates in medicinal chemistry programs to explore structure–activity relationships. The aryl bromide allows late-stage diversification via cross-coupling, while the phenolic OH and ester permit orthogonal protection and functional group interconversions.
If included in discovery screening libraries, dissolution is typically achieved in DMSO stock solutions (e.g., 10–50 mM), then aliquoted to assay plates with controlled final DMSO percentages.
No therapeutic, diagnostic, or clinical claims are made. Any progression toward regulated use would require independent qualification (impurity profile, residual solvents/metals, stability, solid-state form) not specified for this item.
Physical Properties
Item-specific physical constants are not provided in the Product Data. The following are general/literature-based expectations for this scaffold; treat as guidance only, not specifications.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet. (Aryl-salicylate esters of comparable substitution typically crystallize with mp in the 100–180 °C range; literature/general.)
Boiling point: Not practical (may decompose before boiling under ambient pressure; literature/general for polyfunctional aromatics).
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable/typically not reported for solids; Not specified for this item.
Solubility (qualitative, literature/general):
Water: expected very low due to hydrophobic aryl and ester; phenolic OH confers only weak aqueous solubility.
Organic: soluble in polar aprotic solvents (DMSO, DMF, acetonitrile), chlorinated solvents (DCM, CHCl3), esters (EtOAc); moderate in alcohols (MeOH, EtOH).
LogP: Likely in the moderate hydrophobic range given aryl bromide and dual aryl ethers (literature/general trend); Not specified for this item.
pKa (phenolic OH): salicylate phenols typically pKa ~9–11 depending on substitution (literature/general); Not specified for this item.
For precise values (mp, water content, assay), consult the item’s CoA/Spec Sheet for the supplied lot.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting common grades (general information):
Research grade/technical grade: Suitable for most synthetic applications; may have broader impurity profiles. Verify assay on CoA.
≥98–99% (typical for building blocks): Facilitates high-yield cross-couplings and minimized purification burdens. UV purity may matter for photophysical studies.
HPLC-assayed materials: Provide chromatographic purity trace; does not guarantee trace-metal levels unless specified.
Impurity considerations for this scaffold (general):
Potential related substances: dehalogenated analogs, O-demethylated phenols, hydrolysis products (free acid), and O-methylation byproducts.
Residual halides/solvents: DMF, DCM, EtOAc or others from synthesis/purification may be present unless specifically controlled.
Metal content: Catalytic Pd/Ni residues can be present when prepared via cross-coupling; trace-metal limits are item-specific. Not specified for this item; refer to CoA/Spec Sheet.
What to verify on receipt:
Assay (HPLC/GC), identity (1H/13C NMR, MS), water (KF), and residual solvents (GC) as required by your workflow.
If using in metal-catalyzed reactions, consider a brief pre-dry (vacuum, ambient T) and, where critical, re-purify by recrystallization or flash chromatography.
Reaction and Applications
As an electron-rich aryl bromide bearing a salicylate motif, this compound is a versatile intermediate for assembling substituted salicylates, biaryl ethers, anilides, and heteroaryl analogs.
Key application families (literature/general):
Cross-coupling at C5–Br:
Suzuki–Miyaura to install aryl/heteroaryl boronates, enabling SAR sweeps on the salicylate scaffold.
Buchwald–Hartwig amination to form 5-arylamino derivatives; phenolic OH and ester typically tolerated with appropriate ligands/bases.
Sonogashira/Heck to introduce alkynyl/vinyl fragments (protect OH if necessary to suppress side reactions).
Phenolic OH transformations:
O-alkylation/acylation (Williamson ether synthesis; Steglich acylation) to tune polarity and H-bonding.
Directed metalation/chelation-assisted functionalization ortho to OH/ester (salicylate chelation effects can guide reactivity).
Ester chemistry:
Hydrolysis (saponification) to the corresponding acid; re-esterification to other alcohols (Fischer or DCC/DMAP methods).
Curtius/amide couplings following conversion to acid chloride (after hydrolysis) for amide libraries.
Intramolecular strategies:
Leveraging the salicylate OH for intramolecular H-bonding to influence conformation and NMR behavior; can assist in selective transformations.
Practical tips:
Use base/ligand systems that minimize phenol deprotonation when undesired (e.g., weaker bases or protection as methyl/benzyl ether).
Protect the phenolic OH (e.g., MOM/Bn) for aggressive cross-coupling conditions; deprotect post-coupling under mild conditions.
Reaction Conditions
Representative literature-style conditions for transformations of aryl bromides bearing salicylate motifs. These are general guidelines, not item-specific specifications.
Suzuki–Miyaura coupling (biaryl formation):
Substrate + aryl/heteroaryl boronic acid (1.2–1.5 eq), Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (1–2 mol%) with XPhos/SPhos (2–4 mol%), K2CO3 or K3PO4 (2–3 eq), 1,4-dioxane/H2O (4:1) or 2-MeTHF/H2O, 80–100 °C, 4–16 h. Protect phenol if base-sensitive selectivity is an issue.
Buchwald–Hartwig amination:
Substrate + amine (1.2–1.5 eq), Pd2(dba)3 (1–2 mol%) with BrettPhos or RuPhos (3–5 mol%), NaOtBu or Cs2CO3 (2 eq), toluene or CPME, 90–110 °C, 6–18 h. Phenol protection may improve yields.
Sonogashira coupling (alkynylation):
Substrate + terminal alkyne (1.2 eq), Pd(PPh3)2Cl2 (1–2 mol%), CuI (5–10 mol%), Et3N or i-Pr2NH, THF or 2-MeTHF, rt–60 °C, 4–12 h.
O-Alkylation (Williamson ether):
Substrate (phenol) + alkyl halide (1.2–1.5 eq), K2CO3 or Cs2CO3 (2 eq), acetone/DMF/MeCN, 25–60 °C, 2–16 h. Avoid competing C-arylation by choosing non-copper conditions.
Ester hydrolysis (saponification):
Substrate (1.0 eq), NaOH or K2CO3 (1.5–3 eq), MeOH/H2O or THF/H2O (1:1), 25–50 °C, 1–6 h; acidify to pH ~2 to isolate the acid.
Demethylation of aryl OMe (if needed):
BBr3 (1–3 eq), DCM, −78 to 0 °C, 1–4 h; quench cautiously. Phenolic OH should be protected if selective demethylation is required.
Note: Salicylate OH can coordinate metals; ligand choice and base strength strongly influence outcomes. Conduct small-scale screens to optimize.
Safety and Handling
Safety details specific to this catalog item are not provided. Use prudent practices for halogenated aromatic esters and phenols.
GHS classification, pictograms, signal word, and H-statements: Not specified for this item; refer to SDS.
Likely hazards (general): May cause skin/eye irritation; dust may irritate respiratory tract. Phenolic OH may increase local irritation. Avoid inhalation of dust and contact with skin/eyes.
Personal protective equipment (PPE):
Safety glasses or chemical splash goggles
Lab coat; nitrile gloves (change regularly)
Handle powders in a fume hood to minimize inhalation exposure
Aryl bromides are generally stable; no peroxide formation risk typical of ethers.
Incompatibilities: strong bases (will hydrolyze the methyl ester), strong oxidizers; strong acids/bases may cause degradation.
First aid (overview; defer to SDS):
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; 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 advice.
Fire safety: Combustible organic solid. Use CO2, dry chemical, or foam. Combustion may release HBr and other irritants.
Always consult the SDS for authoritative hazard classifications and response procedures.
Solvent Selection
This product is a solid aromatic building block rather than a solvent. The following guidance addresses solvent choice for its dissolution and use in reactions.
Polarity/solubility profile (general):
Readily dissolves in polar aprotic media: DMSO, DMF, NMP, acetonitrile
Good solubility in moderately polar organics: THF, 1,4-dioxane, ethyl acetate
Soluble in chlorinated solvents: DCM, chloroform
Sparingly soluble in water; modest in alcohols (MeOH, EtOH)
Selection by application:
Pd-catalyzed cross-coupling (Suzuki, Buchwald–Hartwig): 1,4-dioxane, toluene, or THF often with H2O or alcohol co-solvent; DMF/NMP for challenging substrates.
Nucleophilic O-alkylation (phenol): acetone, acetonitrile, or DMF with K2CO3/CS2CO3.
Hydrolysis of methyl ester: MeOH/H2O or THF/H2O with base (NaOH, K2CO3); or MeOH with catalytic acid.
Crystallization/purification: EtOAc/hexanes or toluene/hexanes systems are often effective.
Comparison (general):
DMF vs 2-MeTHF: DMF maximizes solubility; 2-MeTHF is greener and aids workup but may require heating.
Dioxane vs Toluene: dioxane improves polar solubility; toluene offers higher bp and easier removal of coordinating solvent effects.
Drying: For moisture-sensitive couplings, dry solvents (molecular sieves or distillation) improve reproducibility, especially when strong bases are employed.
Storage and Reconstitution
Storage conditions (from Product Data): Store at room temperature. Ship normal.
Container: Keep tightly closed in a dry, well-ventilated place. Use amber glass if long-term storage under light-sensitive conditions is a concern (general good practice for aromatics).
Stability considerations (general):
Stable under ambient lab conditions when dry. Prolonged exposure to strong bases can hydrolyze the methyl ester; moisture and base together accelerate saponification.
Phenolic OH may slowly oxidize/discolor upon extended exposure to air/light; minimize by protecting from light and air when possible.
Reconstitution/dissolution:
For stock solutions: dissolve in dry DMSO, DMF, acetonitrile, THF, or ethyl acetate to the desired concentration (e.g., 10–100 mM for screening). Filter if particulates remain.
For aqueous assays: prepare a concentrated DMSO stock and dilute into buffer, keeping final DMSO typically ≤1–2% v/v as assay permits.
Freeze–thaw: Not applicable to solids. For solution stocks, aliquot and store at low temperature (e.g., −20 °C) to avoid repeated freeze–thaw; check for precipitation or degradation before use.
For any item-specific shelf life, assay, water content, or stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Structure and Identity
A halogenated salicylate building block combining an aryl bromide, a phenolic OH, an anisole (methoxy) substituent, and a methyl benzoate ester.
Aromatic benzene core bearing four substituents: (1) a methyl ester (–CO2Me) as the benzoate; (2) an ortho phenolic hydroxyl at C2 relative to the ester (salicylate motif); (3) a para-to-OH methoxy group at C4; (4) a bromine at C5.
Conjugation: fully aromatic ring with electron-donating OMe and OH substituents activating the ring toward electrophilic substitution; bromide positioned for Pd-catalyzed cross-coupling.
Stereochemistry: achiral; no stereocenters.
Note: Exact identifiers (SMILES/InChI) and any tautomeric annotations should be verified on the item’s CoA/Spec Sheet for this specific lot.
Synthetic Utility
Functional handles and their reactivity (literature/general):
Aryl bromide (C5–Br):
Cross-coupling platform for biaryl, aryl–N, aryl–O, and aryl–C(sp) linkages (Suzuki, Buchwald–Hartwig, Ullmann-type, Sonogashira).
Halogen–lithium exchange possible at low temperature (e.g., n-BuLi, −78 °C) but exercise caution due to competing deprotonation/coordination by the salicylate motif.
Phenolic OH (C2):
O-alkylation/acylation (Williamson; Steglich) to tune electronics and solubility.
Can be protected (Bn, MOM, SEM) prior to harsh cross-couplings; intramolecular H-bonding to the ester influences conformation and reactivity.
Methyl ester:
Hydrolyze to the acid for amide couplings (EDC/HATU/DIC) or to make acid chlorides (SOCl2, oxalyl chloride) for further derivatization.
Transesterification to alternative alcohols (Fischer with acid catalyst or via DCC/DMAP conditions).
Methoxy (C4–OMe):
Electron-donating; activates ring toward EAS. Can be demethylated (e.g., BBr3) to access catechol-like motifs if desired.
Strategic value:
Enables rapid library synthesis where C5 is diversified via Pd-catalysis, while O-2 and CO2Me serve as orthogonal tuning elements for polarity and binding interactions.
The salicylate OH and carbonyl provide a bidentate chelation site that can direct ortho-functionalization or stabilize transition states in metalation chemistry.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (e.g., antibody, ligand with defined target profile). No antigen/epitope, clone, isotype, or species reactivity data are relevant to this item.
Domande frequenti
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 39503-52-1, the molecular formula is C9H9BrO4, and the molecular weight is 261.074 g/mol. InChIKey WLCVGKZBHDBQJN-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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