4'-(1,3-Dioxolan-2-YL)-2-methoxybenzophenone , CAS No.898759-86-9

CAS: 898759-86-9 Cat. No.: D975049 Summenformel: C₁₇H₁₆O₄ Molekulargewicht: 284.311 PubChem CID: 24726705

Storage

Room temperature

Specifications

Storage

Room temperature

Namen und Kennungen

Kanonisches Lächeln

COC1=CC=CC=C1C(=O)C2=CC=C(C=C2)C3OCCO3

IUPAC Name

[4-(1,3-dioxolan-2-yl)phenyl]-(2-methoxyphenyl)methanone

InChIKey

QWKBBDDAKFUSNW-UHFFFAOYSA-N

INCHI

1S/C17H16O4/c1-19-15-5-3-2-4-14(15)16(18)12-6-8-13(9-7-12)17-20-10-11-21-17/h2-9,17H,10-11H2,1H3

Isomere SMILES

COC1=CC=CC=C1C(=O)C2=CC=C(C=C2)C3OCCO3

PubChem CID

24726705

Molekulargewicht

284.311

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzophenones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzophenones
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzophenones
• Alternative Parents: Diphenylmethanes Aryl-phenylketones Phenoxy compounds Methoxybenzenes Benzoyl derivatives Anisoles Alkyl aryl ethers 1,3-dioxolanes Oxacyclic compounds Acetals Organic oxides Hydrocarbon derivatives Aldehydes
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzophenone - Aryl-phenylketone - Diphenylmethane - Phenoxy compound - Methoxybenzene - Aryl ketone - Phenol ether - Anisole - Benzoyl - Alkyl aryl ether - Meta-dioxolane - Ketone - Acetal - Oxacycle - Organoheterocyclic compound - Ether - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Aldehyde - Organic oxide - Aromatic heteromonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as benzophenones. These are organic compounds containing a ketone attached to two phenyl groups.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 284.310 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 284.105 Da
• Monoisotopic Mass: 284.105 Da
• Topological Polar Surface Area: 44.800 Ų
• Heavy Atom Count: 21
• Formal Charge: 0
• Complexity: 343.000
• 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

Application Protocols

No vendor-tested biological assay protocols are provided for this small-molecule reagent.

• General lab use suggestions (literature/general)
  • TLC monitoring under UV (254/365 nm) is effective due to the benzophenone chromophore.
  • Prepare stock solutions in dry, aprotic solvents (e.g., DCM, THF, MeCN, DMSO) and store under inert gas if long-term.
  • For acetal deprotection screens, perform small parallel trials varying acid type, solvent, and temperature to balance rate vs chemoselectivity.

For application-specific procedures, consult primary literature on benzophenone acetals and adapt conditions after small-scale optimization.

Biological Roles

This product is a small organic research chemical and not a biomolecule. No intrinsic biological function is indicated in the Product Data.

• General context (literature, not product-specific)
  • Benzophenone motifs can act as photo-crosslinkers in chemical biology probes due to their triplet-state reactivity, but such use requires specific derivatization and validation and is outside the scope of this catalog entry.
  • The 1,3-dioxolane is a protecting group and has no inherent biological role.

For laboratory biological studies, users typically derivatize benzophenone cores with bio-orthogonal handles; this item may serve as a synthetic intermediate toward such probes. Any biological testing must comply with institutional approvals and is strictly for research use only.

Buffer Applications

Not typically applicable. This compound is a hydrophobic aryl ketone/acetal and is not used to formulate aqueous buffer systems. For experimental work involving this reagent, prepare stock solutions in suitable organic solvents (e.g., DMSO, THF, MeCN, or DCM) and, if necessary, add to buffered systems at low percentages compatible with your assay. Always verify solubility and compatibility experimentally.

Green Alternatives

While the compound itself is a target molecule rather than a solvent, greener choices can be made around its use (solvents, reagents, and conditions). The behaviors below are literature/general and not product specifications.

• Solvent selection (greener options)

  • Replace DCM/CHCl3 with ethyl acetate, 2-MeTHF, CPME, or toluene where feasible.
  • For acetal hydrolysis, consider aqueous ethanol with catalytic organic acids (e.g., citric acid) instead of strong mineral acids when compatible.

• Reagent alternatives

  • Use solid acids (Amberlyst-15, Dowex 50) for acetal deprotection to reduce corrosive waste and simplify workup.
  • Employ catalytic hydrogenation with reusable catalysts for reduction steps rather than stoichiometric metal hydrides when the chemoselectivity permits.

• Mini comparison (general)

  • DCM vs 2-MeTHF
    • Health/environment: DCM is a chlorinated solvent with higher health concerns; 2-MeTHF is bio-based and has better environmental metrics.
    • Performance: Both dissolve benzophenone derivatives; 2-MeTHF is water-immiscible, easing separations.
  • Mineral acid (HCl/H2SO4) vs solid acid resin
    • Waste: Aqueous salt/acid waste vs regenerable solid; solids reduce neutralization steps.

• Process considerations

  • Run reactions at higher substrate concentration to reduce solvent volumes.
  • Optimize crystallizations rather than chromatography where possible to lower solvent consumption.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided in the Product Data.

• General context (literature/general)
  • Compounds of this class may serve as synthetic intermediates in the preparation of active pharmaceutical ingredients (APIs) where a benzophenone core and a temporarily masked aldehyde are required. The acetal provides stability during multi-step sequences and can be unveiled late-stage under mild acidic conditions.
  • Photostability considerations: Benzophenone chromophores can absorb UV; in formulation chemistry, analogous motifs are sometimes leveraged as UV absorbers. Any such use would require dedicated toxicological and regulatory assessment and is outside the scope of this listing.

Research use only: not for human or veterinary use, diagnostic procedures, or as a drug substance. For regulated applications, consult your QA unit and the item’s CoA/Spec Sheet for purity, residual solvents, and elemental impurities where applicable.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general expectations for analogous benzophenone acetals (not specifications)

  • Physical state: typically a crystalline solid for diaryl ketone acetals; color often off-white to pale yellow depending on purity.
  • Solubility (qualitative): low in water; good solubility in common organic solvents (e.g., dichloromethane, chloroform, THF, acetone, ethyl acetate, toluene, acetonitrile); limited in alkanes.
  • UV–Vis: benzophenone chromophore usually shows strong absorption in near-UV (ca. 240–260 nm, 320–350 nm; literature, non-item-specific), useful for TLC/UV tracking.
  • Acetal stability: stable under neutral/basic conditions and dry media; hydrolyzes under aqueous acid to the corresponding aldehyde (literature behavior of 1,3-dioxolanes).

• Not specified for this item; refer to CoA/Spec Sheet

  • Melting point
  • Boiling point / decomposition
  • Density
  • Refractive index
  • LogP, pKa, dielectric properties

Note: All numerical property values should be taken from the item’s CoA/Spec Sheet when required for regulated or quantitative work.

Quality and Grades

• Item-specific (from Product Data)

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grade (general guidance)

  • If provided, a research-grade small molecule typically indicates suitability for synthetic and analytical laboratory work. Higher designations (e.g., ≥98% purity, HPLC-verified) support sensitive transformations, photochemical work, or materials studies.
  • For chromatography-sensitive uses (UV detection), low UV-absorbing impurities are preferred; HPLC area% and NMR integrals are commonly used acceptance criteria.

• Stabilizers/inhibitors

  • No stabilizers are indicated in the Product Data. If present in specific lots, they will be listed on the CoA; implications include possible removal prior to certain reactions (e.g., alumina plug).

• What to check on receipt

  • Identity confirmation: 1H/13C NMR should show benzophenone aromatic resonances, a methoxy singlet (~3.7–3.9 ppm, literature), and 1,3-dioxolane methylene multiplets (~3.8–4.2 ppm; literature). IR shows strong C=O (benzophenone) near ~1650–1680 cm−1 (literature).
  • Purity: HPLC or GC (if thermally stable) and melting range. Water content by Karl Fischer only if needed; not specified for this item.

Refer to the CoA/Spec Sheet for lot-specific specifications and analytical results.

Reaction and Applications

• Role in synthesis (literature/general, expanded)

  • Protected aldehyde equivalent: The 1,3-dioxolane masks a 4'-formyl group. This allows multi-step sequences on the benzophenone core without aldehyde reactivity (e.g., avoiding aldol/oxidation). Subsequent acid-catalyzed hydrolysis liberates 4'-formyl-2-methoxybenzophenone.
  • Photochemical utility: Benzophenone is a robust triplet photosensitizer and H-abstractor. Substitution patterns modulate triplet energies; the methoxy group slightly red-shifts absorption (literature). Can be used to study photochemical processes or initiate radical pathways in model systems.
  • Electrophilic aromatic substitution: The methoxy group activates the adjacent ring (ortho/para directing) enabling further functionalization (e.g., iodination, nitration under controlled conditions). The acetal-bearing ring is deactivated by the ketone but para already occupied.
  • Cross-coupling precursor: With prior halogenation, Suzuki/Negishi couplings can elaborate the scaffold; the acetal is generally stable to many Pd-catalyzed conditions if base/water are controlled.

• Practical tips

  • Keep the medium neutral/basic and anhydrous to preserve the acetal during steps; include molecular sieves when necessary.
  • For photochemistry, degas solutions (freeze–pump–thaw or sparge with N2/Ar) to minimize oxygen quenching of excited states.
  • Monitor acetal integrity by 1H NMR: disappearance of dioxolane signals indicates deprotection.

• Manufacturer Applications (from catalog)

  • Not specified beyond “For research use only.” This item is suited to general synthetic and photochemical research as outlined above.

Reaction Conditions

Literature/general guidance for functional groups present (not product specifications):

• Acetal deprotection (to 4'-formyl-2-methoxybenzophenone)

  • Conditions: Aqueous acid (e.g., 0.5–1.0 M HCl, H2SO4, or p-TsOH in acetone/water, THF/water, or MeOH/water), 20–60 °C.
  • Workup: Neutralize, extract into DCM/EtOAc, dry, and purify by flash. Monitor by TLC/1H NMR (loss of dioxolane signals; appearance of aldehyde ~9.8–10.1 ppm, literature).

• Preservation of acetal during other steps

  • Use neutral or basic conditions (e.g., Na2CO3, K2CO3) and anhydrous solvents. Avoid protic acids and prolonged exposure to water at elevated temperature.

• Benzophenone photochemistry

  • Typical: UV irradiation (e.g., 300–365 nm), degassed solvents (acetonitrile, benzene/toluene, or isopropanol for H-donor studies). Oxygen quenches triplets; keep under N2/Ar.

• O-Demethylation of the anisole (if phenol is desired)

  • Reagents: BBr3 (1–3 equiv) in DCM, −78 to 0 °C; quench carefully. Alternatives: AlCl3/thiols or TMSI.

• Reductions of the benzophenone carbonyl

  • NaBH4 or NaBH(OAc)3 typically reduce diaryl ketones slowly; stronger hydrides (e.g., LiAlH4) or catalytic hydrogenation may be employed, with attention to chemoselectivity vs acetal.

Note: Reaction temperatures, times, and yields depend on scale, substrate purity, and setup. Optimize on small scale and consult primary literature for closely related substrates.

Safety and Handling

• Item-specific (from Product Data)

  • Storage conditions: Room temperature
  • GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.

• General safety guidance for aromatic ketones and acetals (literature/general; defer to SDS for authority)

  • Likely hazards: May cause skin/eye irritation and respiratory tract irritation if dust is generated. Avoid inhalation of dust and contact with eyes/skin.
  • PPE: Use lab coat, safety glasses or goggles, and suitable gloves (e.g., nitrile). Employ a fume hood for weighing/handling to minimize dust/vapor exposure.
  • Incompatibilities: Avoid strong acids (risk of acetal hydrolysis), strong oxidizers (potential exotherm/oxidation), and strong bases at elevated temperature (possible side reactions). Keep dry; moisture and acid accelerate deprotection.
  • First aid (overview):
    • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
    • Skin: Wash with soap and water; remove contaminated clothing.
    • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation persists.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
  • Fire safety: Treat as combustible organic solid. Use CO2, dry chemical, or foam. Thermal decomposition may generate irritating fumes; firefighters should wear SCBA.

Always consult the product-specific SDS before use for authoritative hazard and response information.

Solvent Selection

• Polarity and miscibility (literature/general for benzophenone acetals)

  • Non-ionic, moderately lipophilic aryl ketone with an acetal; poor water solubility; good solubility in medium-polarity organic solvents (DCM, THF, acetone, EtOAc, toluene, MeCN). Typically less soluble in hexanes unless warmed or with a co-solvent.

• Typical use scenarios

  • Reaction medium: DCM or toluene for acetal manipulations; THF for organometallic steps; MeCN or DMF for coupling chemistry on the aryl rings (if further derivatization is planned).
  • Workup/purification: EtOAc/hexanes or DCM/MeOH gradients in flash chromatography; compound is UV-active, simplifying TLC visualization.

• When to choose vs alternatives

  • Choose polar aprotic solvents (THF, MeCN, DCM) to dissolve both the aryl ketone and reagents for acetal hydrolysis/protection or electrophilic aromatic substitutions.
  • Avoid prolonged exposure to aqueous alcoholic acids if the acetal should remain intact; use strictly anhydrous aprotic systems.

• Small comparison (literature/general)

  • DCM vs toluene: DCM offers better solubility and lower temperatures; toluene allows higher reflux temperatures and reduced polarity.
  • THF vs 2-MeTHF: 2-MeTHF provides greener profile and water immiscibility; both dissolve benzophenone derivatives well.

Storage and Reconstitution

• Item-specific (from Product Data)

  • Storage conditions: Room temperature
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Practical storage guidance (literature/general)

  • Keep container tightly closed in a dry, well-ventilated place. Protect from moisture and acidic vapors to preserve the acetal. If feasible, store under inert atmosphere (N2/Ar) after opening to minimize hydrolysis and oxidation of trace impurities.
  • Avoid prolonged exposure to strong light/UV, which can induce benzophenone photochemistry in solution; solid is typically stable in the dark.

• Reconstitution/solution preparation

  • Dissolve in dry organic solvents (DCM, THF, EtOAc, toluene, MeCN, or DMSO) to prepare stock solutions. Use 3Å molecular sieves for strictly anhydrous work.
  • For long-term solution storage, prefer amber glass, inert atmosphere, and low temperature (e.g., 2–8 °C) to slow any degradation. Verify stability by TLC/NMR before use.

Always refer to the product’s SDS and CoA/Spec Sheet for lot-specific handling and stability details. Research use only.

Structure and Identity

Brief overview: 4'-(1,3-Dioxolan-2-yl)-2-methoxybenzophenone is an aryl ketone (benzophenone scaffold) bearing a para-acetal protecting group (1,3-dioxolane) on one ring and an ortho-methoxy substituent on the other. It functions as a masked 4'-formylbenzophenone equivalent.

• Item-specific (from Product Data)

  • SKU: D975049
  • Product name: 4'-(1,3-Dioxolan-2-YL)-2-methoxybenzophenone
  • CAS: 898759-86-9
  • PubChem CID: 24726705
  • InChIKey: 308267 (as provided)
  • 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.

• Literature/structure notes (general chemistry)

  • Core features: benzophenone carbonyl (diaryl ketone), 2-methoxy substituent on one phenyl, and 4'-(1,3-dioxolan-2-yl) substituent on the other phenyl.
  • The 1,3-dioxolane ring (five-membered acetal) is typically derived from an aldehyde protected with ethylene glycol; thus this compound is the acetal of 4'-formyl-2-methoxybenzophenone.
  • 2D description in words: a benzophenone with one ring bearing an ortho-methoxy group; the opposite ring bears, at its para position, a 1,3-dioxolane fused via C-2 of the dioxolane to the aromatic carbon.

• Stereochemistry

  • No stereogenic centers; the molecule is achiral. The 1,3-dioxolane is substituted at C-2, but with two ring oxygens there is no fixed stereocenter in this acetal context.

Synthetic Utility

• Functional group portfolio

  • Benzophenone carbonyl (diaryl ketone): amenable to photochemical activation, reductions to benzhydrols, or further derivatization (e.g., oxime formation).
  • 1,3-Dioxolane (acetal): a protecting group for an underlying aldehyde at the 4' position; stable to bases and many nucleophiles, cleavable under aqueous acid.
  • 2-Methoxy (anisole) substituent: electron-donating; activates its ring toward electrophilic aromatic substitution and can be demethylated (e.g., BBr3) to a phenol for further diversification.

• Strategic uses (literature/general)

  • Masked-aldehyde strategy: conduct metalations/couplings on the anisole ring or modifications on the ketone without side reactions at the aldehyde; then deprotect to unveil the aldehyde for formyl-based couplings (e.g., Wittig, Knoevenagel, reductive amination after oxidation/reduction as needed).
  • Photochemistry: leverage benzophenone’s triplet to perform intramolecular H-abstraction or to initiate polymerizations in model systems; substitution modulates reactivity.
  • Late-stage diversification: Demethylation → phenol → O-alkylation/O-acylation; acetal hydrolysis → aldehyde → imine/crystal engineering derivatives.

• Protection/deprotection orthogonality

  • The acetal typically survives many Pd-catalyzed couplings, organometallic additions away from the acetal, and mild bases; choose acid-labile conditions only when ready to reveal the aldehyde.

Target Specificity

Not applicable. This product is a small organic compound, not a biological macromolecule or antibody. No antigen/epitope, species reactivity, clone, or isotype information applies.