This compound belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.
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
No assay-validated protocols are provided for this item. As a general laboratory building block, procedures will depend on the intended transformation.
General guidance
Prepare a concentrated stock solution in dry DMSO (e.g., 10–50 mM) for biological assays; filter if necessary (PTFE, 0.22 μm)
For synthetic use, dry solvents and glassware; for base-mediated steps, minimize moisture and CO2
Monitor reactions by TLC (UV active) or LC–MS; collect spectral data (1H/13C NMR, MS) for identity confirmation
Examples (literature-style outlines, not item-specific)
O-Alkylation: Dissolve substrate in dry DMF, add K2CO3 (2–3 eq) and alkyl bromide (1.2–1.5 eq). Stir 50°C for 4–12 h. Quench with water, extract with EtOAc, wash, dry, concentrate, and purify by flash chromatography
Aldol/Knoevenagel: Mix substrate with benzaldehyde derivative (1.1 eq) in EtOH with catalytic piperidine (10 mol%). Heat to reflux 4 h, remove solvent, and purify to obtain conjugated enone
Consult primary literature and the CoA/SDS for method selection and safety before scaling.
Biological Roles
Item-specific biological/biochemical roles are not provided. The following contextual notes describe general, literature-based properties of related benzofuran phenolic ketones; they are not claims for this specific product and do not imply suitability for any clinical use.
Chemical biology context (general)
Phenolic benzofurans offer H-bond donor/acceptor functionality (phenol, ketone) combined with an extended aromatic surface, making them useful scaffolds in probe development and fragment-based screening
The phenolic group can engage in reversible redox and hydrogen-bonding interactions; the aryl ketone can participate in polar recognition and, when conjugated (e.g., after condensation), in photophysical responses
ADME-relevant features (literature/general)
Moderate lipophilicity and polar surface area typical of aryl phenolic ketones may afford passive permeability while retaining opportunities for metabolic phase II conjugation (glucuronidation/sulfation of the phenol)
The acetyl moiety is a classical handle for metabolic transformations (reduction to alcohols, oxidation, or conjugation after derivatization)
Usage in research
Employed as a building block to synthesize candidate ligands or fluorescent/chromophoric reporters via chalcone formation
Suitable for in vitro assays after dissolution in DMSO; final DMSO content typically kept ≤1–2% in aqueous systems to avoid solvent effects
This product is for research use only and is not intended for diagnostic or therapeutic applications.
Buffer Applications
This compound is a hydrophobic organic building block and is not a buffering agent. It does not establish defined pH ranges like common buffer systems (e.g., phosphate, Tris, HEPES). For biological assays, dissolve in a suitable organic co-solvent (commonly DMSO) and dilute into the desired buffer while keeping the final organic fraction low.
Item-specific buffer data: Not applicable
Practical notes
Prepare concentrated DMSO stocks (e.g., 10–50 mM) and add to buffers with vigorous mixing to prevent precipitation
If higher aqueous solubility is needed, adjust pH to mildly basic to form the phenolate, recognizing this changes chemical state and may affect activity/readouts
Green Alternatives
While the compound itself is a solid building block rather than a solvent, greener choices can be made in the processes where it is used.
Prefer greener solvents (general guidance)
Replace DMF/NMP with safer polar aprotics when feasible: Cyrene (dihydrolevoglucosenone), propylene carbonate, or dimethyl carbonate for some base-mediated reactions
Use 2-MeTHF or CPME in place of THF/Et2O for condensations and extractions; both have higher boiling points and better peroxide profiles than ethers like THF
Favor ethyl acetate, IPA, or Me-THF over chlorinated solvents for workups and chromatography when resolution allows
Benign activation and catalysis
Employ organocatalysts (piperidine, proline derivatives) for Knoevenagel/aldol condensations instead of heavy-metal catalysts
Use aqueous base micellar catalysis (TPGS-750-M) for some O-alkylations to reduce organic solvent usage (literature-dependent feasibility)
Energy and waste minimization
Run reactions at ambient temperature where possible; leverage azeotropic water removal (Dean–Stark) rather than molecular sieves
Telescoping: Combine O-alkylation then condensation without isolation to reduce solvent cycles
Cyrene/propylene carbonate: Safer profiles, higher viscosity/boiling point; may require longer reaction times
DCM: Easy handling, volatile/chlorinated
EtOAc/2-MeTHF: Biobased options, good workup properties, sometimes lower solubility for highly polar intermediates
Pharmaceutical Uses
No pharmacopeial status, excipient role, or clinical use is specified for this item. The following pertains to research and development context only.
Item-specific pharma/compendial information: Not specified for this item; refer to CoA/Spec Sheet.
R&D formulation and screening (general)
Commonly prepared as DMSO stock solutions for high-throughput screening or SAR exploration of benzofuran-derived libraries
The phenolic OH and aryl ketone enable rapid diversification to generate analog series for physicochemical optimization (logP, pKa, solubility)
Preformulation considerations (general)
Solubility limits in aqueous media may necessitate co-solvents (DMSO, PEG400) or cyclodextrin inclusion for in vitro use
Salt formation is not applicable to the neutral parent; ionization via deprotonation of the phenol is reversible and pH-dependent
This product is supplied strictly for research use only and is not intended for human or veterinary use.
Physical Properties
Item-specific physical constants are not provided in the Product Data for this SKU.
Item-specific values
Melting point, boiling point, density, refractive index, UV cutoff, water content: Not specified for this item; refer to CoA/Spec Sheet.
Literature/qualitative expectations (for context; not item specifications)
State: Typically an off-white to light yellow crystalline solid for many phenolic benzofuran ketones
Molecular weight (calc. from C10H8O3): ~176.17 g/mol (literature)
Polarity: Moderately polar due to phenol and ketone, with an overall aromatic character
Solubility profile: Expected to dissolve well in polar aprotic organic solvents (DMSO, DMF, acetone) and moderately in EtOAc, MeOH/EtOH; low aqueous solubility at neutral pH, improved in basic aqueous media via phenolate formation
Acid–base behavior: Phenolic pKa for related benzofurans commonly in the 9–10 range (literature, scaffold-dependent); ketone α-protons are enolizable
LogP: Aryl phenolic ketones often show logP ~1.5–2.5 (literature range; substitution dependent)
Practical handling notes (general)
Hygroscopicity: Phenolic solids are usually not strongly hygroscopic; however, moisture uptake can affect accurate weighing and base-sensitive reactions
Light sensitivity: Extended conjugation may lead to slow coloration on light/air exposure; protect from strong light for long-term storage
Always consult the CoA/SDS for authoritative, item-specific physical properties before use.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance)
Analytical/Reagent grade: Suitable for most synthetic applications; impurities at low levels but not necessarily controlled for trace metals
Purified/97–99%: Typical for building blocks; adequate for library synthesis, SAR, and routine transformations
HPLC grade (for solvents) or low-UV: Not applicable to this solid; for chromatography solvents only
Pharmaceutical/USP/EP: Not applicable unless explicitly stated; this product is supplied for research use only
Impurities of interest (general for aryl ketone phenols)
Residual starting materials or regioisomers (e.g., alternate hydroxy/acetyl substitution patterns)
Oxidation products (quinone-like tautomers) or minor oligomers from storage
Residual inorganic salts/solvents from synthesis and purification
Practical QC pointers
Confirm identity by 1H/13C NMR, HRMS, and, if necessary, 2D NMR to confirm substitution pattern on the benzofuran ring
HPLC/UPLC purity at multiple wavelengths (210–330 nm) is recommended due to extended conjugation
Water and residual solvent content may be measured by KF and GC-HS respectively if process-sensitive, but item-specific limits: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
This benzofuran derivative is a versatile building block leveraging two orthogonal handles: an enolizable acetyl at C-2 and a phenolic OH at C-7.
Transformations based on the acetyl group
Enolate chemistry: Aldol and Claisen-type condensations with aldehydes/esters to form benzofuranyl chalcones or β-dicarbonyl adducts (Knoevenagel with activated methylene partners). Typical bases: piperidine, pyrrolidine, DBU, or K2CO3; water removal drives equilibrium
Oxime/hydrazone formation: With hydroxylamine or hydrazines (useful for derivatization and characterization)
Reductions: NaBH4 or catalytic hydrogenation to secondary alcohols; selective over the aryl ring under mild conditions
Halogenation/α-functionalization: Via enol/enolate trapping (e.g., NBS for α-bromination) enabling subsequent substitution
Sulfonylation: Tosyl/mesyl activation for downstream substitutions
Metalation: Phenoxide-directed metalation can enable cross-coupling after conversion to suitable leaving groups (e.g., triflates)
Applications (general)
Scaffold for small-molecule libraries targeting redox-active or π-stacked binding sites
Precursor to conjugated systems (chalcones, styryl ketones) for photophysical probes and materials screening
Analytical derivatization standard due to strong UV chromophore
Manufacturer application specifics were not provided; the above reflects common literature uses of 2-acyl phenolic benzofurans.
Reaction Conditions
General literature guidance for common transformations of 2-acyl phenolic benzofurans; optimize for your substrate set. Values below are typical ranges and not item specifications.
O-Alkylation (Williamson ether synthesis)
Conditions: Alkyl halide (1.2–2.0 eq), K2CO3 or Cs2CO3 (2.0–3.0 eq)
Solvent: DMF or acetone; 0.05–0.2 M
Temperature/time: 25–60°C, 2–18 h
Notes: Minimize water; phase-transfer catalysts (TBAB) can accelerate in acetone/MeCN
Aldol/Knoevenagel condensation at the acetyl
Conditions: Aldehyde (1.0–1.5 eq), catalytic piperidine or ammonium acetate; or K2CO3/EtOH
Solvent: EtOH, i-PrOH, toluene (Dean–Stark for water removal)
Temperature/time: RT–110°C, 2–24 h
Outcome: Conjugated enones (benzofuranyl chalcones); E-selectivity common
Oxime formation
Conditions: Hydroxylamine·HCl (1.2–2.0 eq), pyridine or NaOAc as base
Solvent: EtOH/MeOH or aqueous ethanol
Temperature/time: 25–60°C, 1–6 h
Carbonyl reduction
Conditions: NaBH4 (1.1–1.5 eq) in MeOH/EtOH at 0–25°C
Notes: Typically chemoselective for the aryl ketone; monitor to avoid over-reduction
α-Halogenation
Conditions: NBS (1.1 eq) with acid or radical initiator; or Br2 under controlled conditions
Cross-coupling after O-triflation
Triflation: Tf2O, pyridine or 2,6-lutidine, DCM, 0°C→RT
Suzuki coupling: Pd(0/II), base (K2CO3/K3PO4), dioxane/H2O, 60–100°C
Always run small-scale trials and monitor by TLC/HPLC/LC–MS.
Safety and Handling
Item-specific hazard classification is not provided in the Product Data.
Item-specific hazard statements, pictograms, GHS class, signal word: Not specified for this item; refer to SDS.
General safety guidance for phenolic aryl ketones (informational)
Likely hazards: Eye/skin irritation and respiratory tract irritation as dust; avoid inhalation/ingestion
PPE: Wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle solids in a fume hood to minimize dust exposure
First aid (general): If on skin/eyes, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical advice. Always follow institutional protocols
Incompatibilities: Strong oxidizers; strong bases/acids may cause hydrolysis or promote side reactions (e.g., base-induced O-alkylation reactivity). Avoid reactive acylating/alkylating agents unless intended
Thermal/photochemical stability: Aromatic conjugates may discolor on prolonged light/air exposure; store in tightly closed containers, protected from excessive heat and light
Waste disposal
Collect organic solid waste according to local regulations. Avoid release to the environment. Phenolic compounds may require controlled incineration per facility guidelines
This product is for research use only. Always consult the SDS for definitive hazard, handling, and first-aid information.
Solvent Selection
As a moderately polar, aromatic heterocycle bearing a phenol and a ketone, 2-acetyl-7-hydroxybenzofuran dissolves best in polar organic media.
Solubility/miscibility tendencies (general)
Excellent: DMSO, DMF, NMP, acetone
Good: Ethyl acetate, acetonitrile, methanol/ethanol (warming may help)
Limited: Toluene, dichloromethane (improves with heating or small alcohol co-solvent)
Poor: Water at neutral pH; solubility improves under basic conditions via phenolate formation
Selection by use case
Stock solutions for screening/biology: DMSO (10–50 mM typical), then dilute into assay buffers with ≤1–2% final DMSO
Nucleophilic substitutions/O-alkylations: DMF or acetone with K2CO3/Cs2CO3; avoid protic solvents that quench base
Aldol/Knoevenagel condensations: EtOH, i-PrOH, or toluene with catalytic base/amine; remove water (Dean–Stark) for equilibrium-driven condensations
Chromatography: EtOAc/hexanes or DCM/MeOH gradients; aromatic polarity enables UV detection at 254–320 nm
Comparison (general)
DMSO vs DMF: DMSO affords highest solubility for stocks; DMF is easier to remove but may leave odor; both are hygroscopic
EtOAc vs MeOH: EtOAc balances polarity and volatility; MeOH enhances solubility of phenols but can participate in acetal/transester equilibria
Item-specific solubility constants and UV cutoffs are not provided; consult the CoA/Spec Sheet or determine empirically for your application.
Storage and Reconstitution
Item-specific storage and shipping
Storage: Room temperature (per Product Data). Protect from prolonged light and moisture; keep tightly closed
Shipped in: Normal conditions (per Product Data)
Stability considerations (general)
Phenolic aryl ketones are typically stable at ambient conditions. Minor discoloration over time may occur due to slow oxidation; this rarely affects performance in synthesis but check purity before critical work
Reconstitution and stock solutions (general)
For synthetic use: Dissolve in a suitable dry organic solvent (e.g., DCM, EtOAc, acetone, THF, DMF, or DMSO) as needed
For assay stocks: Prepare 10–50 mM in anhydrous DMSO; store aliquots at −20°C to minimize freeze–thaw cycles. Allow to reach room temperature before opening to avoid condensation
Aqueous use: Limited solubility at neutral pH; if required, dissolve in DMSO then dilute into buffer, keeping final DMSO ≤1–2%. Mild basification can increase solubility via phenolate formation
Shelf-life documentation
Item-specific retest/expiry and analytical acceptance criteria: Not specified for this item; refer to CoA/Spec Sheet.
Research use only. Always consult the SDS for detailed handling and storage guidance.
Structure and Identity
A heteroaromatic building block featuring a benzofuran core bearing an acetyl group at C-2 and a phenolic hydroxy at C-7. The 2D structure is a fused benzene–furan system (benzofuran); the furan carbon at position 2 carries an acetyl (–COCH3), while the benzene ring position para to the fusion oxygen (position 7) bears –OH.
Item-specific identifiers (from Product Data)
CAS: 40020-87-9
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers (informational; not item specifications)
Conjugation: Extended π-system across benzofuran and aryl–carbonyl
Tautomerism: Phenol can form minor keto–enol resonance with adjacent positions; the acetyl group forms classical enol/enolate under base
H-bonding: Intramolecular and intermolecular H-bonding possible via the 7–OH and carbonyl oxygen
Note: Exact structural descriptors for this specific catalogue item (SMILES, InChI, MF, MW) should be confirmed against the product CoA/Spec Sheet.
Synthetic Utility
2-Acetyl-7-hydroxybenzofuran is strategically valuable because it carries two orthogonal, chemoselectively addressable handles embedded in a rigid, π-rich heteroaromatic framework.
Handles and reactivity
7-Phenol: Enables O-alkylation (ethers), O-acylation (esters), O-sulfonylation (tosylates/mesylates), and conversion to aryl triflates for cross-coupling (Suzuki, Heck, Buchwald–Hartwig after suitable transformation)
2-Acetyl: Enolizable; supports aldol, Claisen, Knoevenagel, and Henry-type couplings with aldehydes/activated methylenes to yield conjugated enones (benzofuranyl chalcones). Also amenable to oxime/hydrazone formation and selective reductions to benzylic alcohols
Divergent synthesis opportunities
Build donor–acceptor systems by condensing with electron-poor aldehydes, tuning photophysics
Form bidentate ligands by O-alkylating with functionalized arms, followed by condensation at the acetyl to introduce a second coordination site
Generate leaving groups at O-7 (triflate) to install C–C/C–N/C–S bonds via Pd-catalyzed cross-couplings on the benzofuran ring
Retrosynthetic value
Serves as a linchpin to access 2-substituted and 7-substituted benzofurans in orthogonal sequences (protect phenol, functionalize acetyl, then deprotect; or vice versa)
Purification/analysis
Strong UV chromophore facilitates HPLC monitoring; conjugated derivatives often show bathochromic shifts enabling multiwavelength tracking
These features make it a robust scaffold for library generation in medicinal and materials chemistry.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope specificity, clone, isotype, or species reactivity applies.
Häufig gestellte Fragen
How should this product be stored?
Store at room temperature.
What is the purity of this product, and how is it determined?
This product is supplied at ≥98% purity, determined by gas chromatography (GC). Lot-specific values are stated on the Certificate of Analysis.
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 40020-87-9, the molecular formula is C10H8O3, and the molecular weight is 176.17 g/mol. InChIKey HRIVIHCUSKDPNK-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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