This compound belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.
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
180.200 g/mol
XLogP3
1.100
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
180.079 Da
Monoisotopic Mass
180.079 Da
Topological Polar Surface Area
38.700 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
172.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
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
Recensioni dei clienti
Application Protocols
No biological assay or immunoassay protocols are associated with this small‑molecule building block. For synthetic use, consider the general procedures outlined under Reaction Conditions and Synthetic Utility. If you require a detailed step‑by‑step protocol for a specific transformation (e.g., Dess–Martin oxidation or Mitsunobu substitution), contact us for a literature‑backed method sheet.
Biological Roles
No biological attributes are specified for this catalog item. The following is general biochemical context for chroman scaffolds and methoxy‑substituted aromatics (literature; not a claim for this product’s biological activity):
Structural motif: The chroman (2H‑benzopyran) ring system is a core structural element in numerous natural products, including tocopherols and related phenolic antioxidants. In those systems, the chroman oxygen and benzylic positions influence redox behavior and membrane association.
Functional groups and interactions: A benzylic secondary alcohol can participate in hydrogen bonding as a donor/acceptor, potentially affecting ligand binding in discovery screening. Anisole‑type methoxy groups modulate electron density, often enhancing π–π and cation–π interactions in protein pockets.
Metabolic considerations: In xenobiotic metabolism (general), aryl methoxy groups may undergo O‑demethylation (CYP450‑mediated) to phenols; benzylic alcohols can be oxidized to ketones and conjugated (glucuronidation/sulfation). The embedded ether may resist hydrolysis under physiological pH but can be metabolically oxidized.
Physicochemical profile: Compounds combining an aryl methoxy and a benzylic alcohol typically have moderate polarity and logP suitable for crossing organic phases, making them useful probes for ADME method development (no application data provided for this item).
Research use reminder: For research use only. No testing has been performed by us regarding biological activity, safety, or suitability in vivo or for diagnostic use.
Buffer Applications
This compound is an organic building block and is not used as a buffering agent. It lacks the acid/base pairs and pKa profile suited for preparing laboratory buffers.
Practical note: When handling this material in aqueous workups or biochemistry contexts, choose a buffer system compatible with your transformation or assay (e.g., phosphate, acetate, Tris), but the compound itself is not typically incorporated into buffer formulations.
Green Alternatives
This product is a target/intermediate, not a process solvent. Green considerations therefore center on choosing safer reagents and solvents for its transformations and purification.
Greener choices (general, literature‑based):
Oxidation of the benzylic alcohol:
Prefer TEMPO/NaClO (aqueous bleach) or catalytic TEMPO with Oxone in MeCN/H2O over chromium(VI) reagents (PCC/PDC), which are toxic and generate hazardous waste.
Dess–Martin affords cleaner reactions than Swern with less cryogenic waste but remains an iodine oxidant; ensure proper waste handling.
Solvent selection:
Replace DCM with EtOAc, 2‑MeTHF, CPME, or toluene where performance allows. For Mitsunobu reactions, 2‑MeTHF can substitute for THF in many cases.
For chromatographic purification, heptane/EtOAc or EtOAc/IPA mixtures reduce chlorinated solvent usage.
Demethylation of aryl methoxy:
Consider AlCl3/thiol or oxidative demethylation approaches where compatible, to avoid BBr3 (corrosive, moisture sensitive). However, reactivity/selectivity often necessitates BBr3—balance EHS with performance.
Workup/waste minimization:
Employ aqueous‑biphasic oxidations/reductions where possible; use in‑process crystallizations to avoid extensive silica gel usage.
Illustrative comparison (general):
DCM vs EtOAc/2‑MeTHF: lower toxicity and better environmental profile for EtOAc/2‑MeTHF; tradeoffs include different polarity and sometimes lower substrate solubility.
Cr(VI) vs TEMPO/NaClO: dramatically improved EHS with catalytic TEMPO; tradeoff can be chemoselectivity and need for careful pH control.
Always validate greener substitutions at small scale to confirm chemoselectivity on the chroman scaffold.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or formulation grade is specified for this item; refer to the CoA/Spec Sheet if required. The following information is general to aromatic benzylic alcohol intermediates and is not specific to this SKU:
Role in development chemistry: Chroman derivatives are common scaffolds in medicinal chemistry campaigns. 5‑Methoxychroman‑4‑ol can serve as a synthetic intermediate en route to analogs explored in SAR studies.
Process considerations: If used in route scouting, the secondary alcohol can be converted to more robust handles (e.g., ketone, mesylate) to facilitate telescoped sequences. Polymorph control may be relevant if crystalline derivatives are advanced.
Impurity control: Benzylic oxidation byproducts (ketone, over‑oxidation) and O‑demethylated aromatics are typical related substances to monitor by HPLC/LC–MS.
Important: This product is offered strictly for research use only and is not intended for human or veterinary use, clinical applications, or as an active pharmaceutical ingredient or excipient.
Physical Properties
Item-specific values (this product):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature- and computation-based general expectations for chroman‑4‑ols with aryl methoxy substitution (for context only; not item specifications):
Physical state: low‑melting solid or viscous oil depending on substitution pattern; benzylic alcohols in this class can crystallize upon standing.
Polarity/solubility: moderately polar due to one ether oxygen and one secondary alcohol; typically soluble in common organic solvents (EtOAc, DCM, THF, MeOH) and sparingly soluble in water.
Hydrogen bonding: can act as H‑bond donor (–OH) and acceptor (two ring/alkoxy oxygens), leading to elevated polarity relative to simple arenes.
UV characteristics: aromatic chromophore with a methoxy donor generally shows UV absorbance in the 200–300 nm region (literature), enabling HPLC/UV detection.
Volatility: reduced volatility compared to simple ethers; benzylic alcohols generally show low vapor pressure at ambient conditions (literature).
Measurement notes:
If exact BP/MP, refractive index, or logP are needed for method development or scale‑up, please consult the lot‑specific CoA/Spec Sheet or measure under controlled conditions. Avoid relying on generic values for quantitative process design.
Quality and Grades
Item-specific quality attributes provided:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting typical grades (general information):
Research grade: suitable for most synthetic and analytical laboratory uses. Impurity profiles typically controlled by NMR/LC‑MS/GC but not necessarily by pharmacopeial monograph.
Purified/98–99%: indicates high assay by quantitative NMR/GC/HPLC; trace residual solvents and related substances may still be present.
Stabilizers/inhibitors: none are indicated for this item. If present in a specific lot, they will be disclosed on the CoA and may need to be removed (e.g., by flash chromatography or washing) before sensitive reactions.
Verification and documentation:
Always consult the lot‑specific CoA for assay, residual solvent content, water content, and identification data (NMR/IR/MS). If you require enhanced purity (e.g., chiral enrichment or metal screening), contact us for available grades or custom purification.
Use implications:
For oxidation‑sensitive transformations or chiral applications at C‑4, tighter specifications (enantiomeric ratio, peroxide content, metal screening) may be necessary. None of these parameters are specified for this catalog item unless stated on the CoA.
Reaction and Applications
5‑Methoxychroman‑4‑ol is a versatile intermediate for assembling chroman‑based scaffolds prevalent in natural products (e.g., tocopherol‑like motifs) and in medicinal chemistry libraries. Typical synthetic roles include:
Oxidation to chroman‑4‑ones: The secondary benzylic alcohol is readily oxidized (literature) using PCC, Dess–Martin periodinane, Swern, or TEMPO/bleach systems to give the corresponding 4‑one, a valuable electrophile for further elaboration (e.g., enolate chemistry, reductive amination at C‑4).
Nucleophilic substitution at C‑4: Under Mitsunobu conditions (PPh3/DIAD or DEAD), the –OH can be inverted and displaced by O‑, N‑, or S‑nucleophiles to furnish 4‑substituted chroman derivatives. Alternatively, activation as mesylate/tosylate enables SN1/SN2 pathways depending on substrate/control.
Reductive transformations: Conversion to the corresponding 4‑deoxy chromane can proceed via tosylate formation followed by reduction (LiAlH4 or catalytic hydrogenation) or via dehydration to a chromene followed by hydrogenation (literature).
Aromatic functionalization: The 5‑methoxy group directs electrophilic substitution ortho/para. Halogenation, nitration (mild), or Friedel–Crafts acylation at positions activated by –OMe enables subsequent cross‑couplings.
Demethylation gateway: Selective demethylation of the 5‑methoxy group with BBr3 or AlCl3 produces 5‑hydroxychroman‑4‑ols, diversifying H‑bonding patterns for SAR studies.
Protecting group strategies: The benzylic –OH can be protected (TBDMS, MOM, benzyl) to mask reactivity during harsh aromatic transformations; deprotection under standard conditions restores the alcohol.
Applications span building of antioxidant‑like motifs, ligand frameworks, and conformationally constrained scaffolds where the chroman oxygen preorganizes substituents (general/literature).
Reaction Conditions
General literature conditions relevant to 5‑methoxychroman‑4‑ol (guidance only; optimize for your substrate and scale):
Oxidation (4‑ol → 4‑one):
Dess–Martin periodinane (1.3–1.5 equiv), DCM, 0 °C to rt, 1–3 h; typical isolated yields 70–90% for benzylic alcohols. Work up with aq. NaHCO3 and thiosulfate.
TEMPO (5–10 mol%), NaClO (1.5–2.0 equiv active chlorine), KBr (cat.), pH 8.6 buffer, EtOAc/MeCN/H2O biphasic, 0–10 °C; 60–85% typical.
Swern (oxalyl chloride/DMSO, –78 °C → Et3N) in DCM for sensitive substrates.
Mitsunobu substitution (inversion at C‑4):
Alcohol (1.0 equiv), PPh3 (1.2 equiv), DIAD (1.2 equiv), nucleophile (1.5–2.0 equiv), THF or toluene, 0 °C to rt, 2–16 h. Minimize elimination by keeping temperature low and using less basic nucleophiles.
Activation as sulfonate and displacement:
MsCl or TsCl (1.2–1.5 equiv), Et3N or pyridine, DCM/DMAP (cat.), 0 °C to rt; then SN2 with NaN3, halides, or O/N nucleophiles in DMF/MeCN at 0–60 °C.
Demethylation of aryl –OMe:
BBr3 (1.2–3.0 equiv), anhydrous DCM, –78 to 0 °C, 1–4 h; quench with MeOH/H2O; often 60–90% to phenol (avoid in presence of base‑labile protections).
Dehydration/hydrogenation:
Acid‑catalyzed dehydration (p‑TsOH, toluene, reflux, Dean–Stark) to chromene; subsequent Pd/C hydrogenation (H2, 1–3 bar, EtOH) affords deoxy chromane.
Analytics and handling:
Monitor by TLC (UV 254 nm; stains), GC or HPLC (UV 220–280 nm typical for anisoles). Maintain anhydrous conditions for Lewis acid steps; pre‑dry solvents and glassware.
Safety and Handling
Authoritative safety information must be taken from the SDS for this product/lot. The following guidance is general for benzylic secondary alcohols and methoxy‑substituted chromans.
Item-specific hazard details (as provided):
Signal word: Not specified for this item; refer to SDS.
H‑statements: Not specified for this item; refer to SDS.
GHS classification/pictograms: Not specified for this item; refer to SDS.
General handling recommendations (good laboratory practice):
PPE: wear appropriate lab coat, safety glasses/goggles, and nitrile gloves. Use in a fume hood when weighing, transferring, or heating.
Incompatibilities: avoid strong oxidizers (can oxidize the benzylic alcohol), strong acids or bases (may induce ring‑opening/solvolysis or demethylation under forcing conditions), and dehydrating agents (may promote elimination to chromenes).
Stability considerations: benzylic alcohols are typically stable at room temperature under dry, dark storage. Limit exposure to strong light/air if long‑term purity is critical; keep container tightly closed to prevent moisture uptake or contamination.
First aid overview: eye/skin contact—rinse with water for at least 15 minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth and seek medical attention. Always follow SDS instructions.
Fire safety: treat as an organic combustible. Use CO2, dry chemical, or foam for small fires. Combustion may produce CO/CO2 and irritating fumes.
Spill response: absorb small spills with inert material (vermiculite), collect in suitable waste; wash area with mild detergent. Prevent release to drains.
Transportation/storage notes for this SKU:
Storage: Room temperature (as provided). Keep in original, well‑closed container.
Shipping: Normal (as provided).
Solvent Selection
This product is a heteroaromatic building block/secondary alcohol, not a solvent. The Solvent Selection topic here addresses suitable media for dissolving and reacting 5‑methoxychroman‑4‑ol.
Solubility profile (general): typically soluble in polar aprotic (DCM, THF, EtOAc, MeCN) and polar protic (MeOH, EtOH) solvents; limited solubility in water. For crystallization, EtOAc/hexanes or toluene/hexanes mixtures often provide good control for benzylic alcohols (literature guidance).
Choosing reaction media:
Oxidations to chroman‑4‑one: DCM, EtOAc, or MeCN with PCC, Dess–Martin, or Swern conditions (literature) are commonly used.
Mitsunobu substitution at C‑4: THF or toluene provide good solubility for PPh3/DIAD systems (literature).
Electrophilic aromatic substitution on the methoxy‑activated ring: non‑nucleophilic solvents (DCM, nitrobenzene, or acetic acid depending on electrophile) help control regioselectivity.
Demethylation (Ar–OMe → Ar–OH): anhydrous DCM or toluene for BBr3/BCl3 protocols at low temperature (literature).
Workup/purification tips:
Avoid highly basic aqueous washes early in workup when retention of the benzylic –OH is desired; strong base can promote elimination.
Silica gel chromatography is typically effective; pre‑neutralize silica (1–2% Et3N) if acid‑sensitive intermediates are present.
Note: Select solvents to match downstream analytics (HPLC/GC/LC–MS compatibility) and EHS objectives; confirm actual solubility for your lot experimentally.
Storage and Reconstitution
Storage condition (item-specific): Room temperature (as provided). Store in a tightly closed container in a dry, well‑ventilated place. Protect from excessive heat and direct light to maintain purity.
Shipping (item-specific): Normal (as provided).
Stability: Benzylic alcohols of this type are generally stable under ambient conditions. If long‑term storage is planned, consider storing under inert atmosphere and desiccation to minimize slow oxidation or moisture‑assisted degradation (general guidance; check CoA for any stabilizer note—none specified here).
Reconstitution: Not applicable; this is supplied as a neat small molecule. If preparing stock solutions, use dry, oxygen‑free solvents when required by your application (e.g., for air‑sensitive transformations), and store solutions at 2–8 °C in sealed vials. Label with solvent, concentration, and preparation date.
Freeze–thaw: Not relevant for neat solids/oils. If stored in solution, minimize freeze–thaw cycles to avoid concentration drifts or precipitation; prepare aliquots as needed.
Always refer to the lot‑specific CoA and SDS for authoritative guidance on storage, stability, and handling.
Structure and Identity
Short description: 5‑Methoxychroman‑4‑ol is a methoxy‑substituted chroman bearing a secondary alcohol at C‑4 on the dihydrobenzopyran ring system.
Product identifiers (item-specific):
CAS: 1616526-84-1 (as provided)
InChIKey: 70927 (as provided; note: appears non-standard/truncated—verify on CoA/SDS)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (general chemistry description):
Core scaffold: chroman (3,4‑dihydro‑2H‑1‑benzopyran), a bicyclic system consisting of a benzene ring fused to a saturated tetrahydropyran.
Functional groups: an aryl methoxy substituent at the 5‑position of the benzene ring; a benzylic secondary alcohol at the 4‑position of the chroman ring; an internal ether (the chroman oxygen).
Stereochemistry: the 4‑position alcohol center is stereogenic in the chroman series; commercial materials may be racemic unless otherwise specified (no stereochemical specification provided for this item).
Electronic effects: the 5‑methoxy group is a strong ortho/para director, activating the aromatic ring; the 4‑ol is benzylic and readily oxidized to the corresponding chroman‑4‑one under typical conditions (literature).
2D structure (verbal depiction): a benzene ring bearing an –OCH3 at C‑5, fused to a six‑membered oxygen heterocycle; the saturated ring bears an –OH at C‑4 (adjacent to the ring oxygen).
Synthetic Utility
Key reactivity elements of 5‑methoxychroman‑4‑ol that underpin its value in synthesis (general literature guidance):
Benzylic secondary alcohol at C‑4:
Oxidation to chroman‑4‑one enables enolate chemistry (alkylation/acylation), conjugate addition (if unsaturation introduced), and reductive amination to install 4‑aminomethyl or 4‑alkylamino derivatives.
Activation as sulfonate (Ms/Ts) or via Mitsunobu enables O‑, N‑, S‑substitution at C‑4 with inversion (Mitsunobu) or substitution pathways tuned by conditions.
Protection (e.g., TBDMS, MOM, benzyl) to mask reactivity during electrophilic aromatic substitutions or demethylation steps.
Aryl methoxy at C‑5:
Powerful ortho/para director enhancing EAS; selective halogenation, nitration, or Friedel–Crafts acylation expands handles for cross‑coupling (Suzuki, Buchwald–Hartwig after halogenation).
Demethylation with BBr3/BCl3 generates a phenolic handle for ether/ester formation or as an H‑bond donor in targets.
Embedded ether (chroman oxygen):
Confers conformational bias and can stabilize benzylic cations under activating conditions, facilitating substitution/elimination sequences (e.g., dehydration to chromenes followed by hydrogenation or hydrofunctionalization).
Retrosynthetic value: The scaffold can arise from intramolecular O‑alkylation of 2‑(2‑hydroxy)aryl alcohols, Prins‑type cyclizations, or hydrogenation of chromenes—allowing late‑stage installation of the benzylic hydroxyl for diversity‑oriented synthesis.
Target Specificity
Not applicable. This product is a small‑molecule chemical reagent, not a biological affinity reagent. No antigen/epitope, clone, isotype, or species reactivity information applies.
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