2,3-Dimethyl-3'-methoxybenzophenone - ≥95% , CAS No.750633-69-3

CAS: 750633-69-3 Cat. No.: D1262311 Formula: C₁₆H₁₆O₂ Peso molecolare: 240.302 PubChem CID: 19352291

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CC1=C(C(=CC=C1)C(=O)C2=CC(=CC=C2)OC)C
• IUPAC Name: (2,3-dimethylphenyl)-(3-methoxyphenyl)methanone
• InChIKey: MYDHKVSTQWMHSX-UHFFFAOYSA-N
• INCHI: 1S/C16H16O2/c1-11-6-4-9-15(12(11)2)16(17)13-7-5-8-14(10-13)18-3/h4-10H,1-3H3
• Isomeri SMILES: CC1=C(C(=CC=C1)C(=O)C2=CC(=CC=C2)OC)C
• PubChem CID: 19352291
• Peso molecolare: 240.302

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Benzophenones
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzophenones
• Alternative Parents: Diphenylmethanes Aryl-phenylketones o-Xylenes Phenoxy compounds Methoxybenzenes Benzoyl derivatives Anisoles Alkyl aryl ethers Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzophenone - Diphenylmethane - Aryl-phenylketone - Anisole - Phenoxy compound - Benzoyl - Phenol ether - Aryl ketone - Methoxybenzene - Xylene - O-xylene - Alkyl aryl ether - Ketone - Ether - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Descrizione: 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

Proprietà chimiche e fisiche

• Peso molecolare: 240.300 g/mol
• XLogP3: 4.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 240.115 Da
• Monoisotopic Mass: 240.115 Da
• Topological Polar Surface Area: 26.300 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 287.000
• 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 application protocols are provided in the Product Data for this item.

• General laboratory uses (examples; not item-specific claims):
  • As a substrate in carbonyl reductions or nucleophilic additions: dissolve in dry THF or DCM, add reagent under inert atmosphere, monitor by TLC/LC-MS.
  • For photochemical method development: prepare deoxygenated solutions (freeze–pump–thaw or sparge with N2) and irradiate with 365–405 nm LEDs, monitoring by HPLC.

Please develop and validate protocols appropriate to your equipment and regulatory context. Consult primary literature for methods involving substituted benzophenones.

Biological Roles

This item is a synthetic aryl ketone intended for research use. No biological role is specified for this product.

• General/literature context for benzophenone scaffolds (not specific to this item):
  • Benzophenone cores appear in various small molecules used as UV absorbers and photoinitiators; biological activity, if any, is highly structure-dependent and cannot be inferred for this compound without data.
  • The presence of a methoxy substituent can influence lipophilicity and membrane partitioning in small molecules, but no pharmacological or metabolic role is claimed or implied here.

For any biological testing, ensure appropriate approvals and controls. This product is provided strictly for research and laboratory use.

Buffer Applications

Not typically applicable. 2,3-Dimethyl-3'-methoxybenzophenone is a hydrophobic organic building block and is not used as a buffering agent or pH standard.

• Practical note: If preparing analytical samples in aqueous systems, dissolve first in a water-miscible organic co-solvent (e.g., acetonitrile, DMSO, or ethanol) and then dilute into buffer, keeping the organic content sufficiently high to prevent precipitation.

Green Alternatives

Because this product is a solid aryl ketone (reagent/building block), “green alternatives” considerations mainly concern solvents and reagents used with it, rather than replacing the compound itself.

• Greener solvent choices (literature/general):

  • Prefer EtOAc, 2-MeTHF, CPME, or toluene over chlorinated solvents when feasible. These often provide adequate solubility for benzophenone derivatives while reducing halogenated waste.
  • For chromatography, heptane/EtOAc gradients are greener than hexane/DCM systems.

• Greener reagents for typical transformations:

  • Reductions: replace LiAlH4 with catalytic hydrogenation (Pd/C, H2) or transfer hydrogenation (e.g., isopropanol/KOH with Ru- or Mn-based catalysts) where compatible.
  • Baeyer–Villiger: use H2O2-based systems (e.g., urea–H2O2 with organocatalysts) instead of mCPBA when possible.
  • Demethylation: consider catalytic hydrogenolysis routes (e.g., Pd/C under H2 for activated anisoles) instead of halogenated Lewis acids; feasibility depends on substrate electronics.

• Energy and safety:

  • Conduct photochemical reactions with LED sources at appropriate wavelengths to minimize energy consumption and heat load compared to mercury lamps.
  • Apply solvent-recycling and minimize high-boiling solvent use.

Trade-offs: Greener solvents may reduce solubility and reaction rates; re-optimize concentrations, temperatures, and catalysts accordingly.

Pharmaceutical Uses

No pharmaceutical or clinical use is specified for this item. It is supplied for research use only.

• General formulation context (literature/general):
  • Aromatic ketones like benzophenone derivatives are occasionally used as intermediates in the synthesis of API candidates or as photoinitiators in certain manufacturing processes; such use is highly structure- and process-specific.
  • This product is not accompanied by pharmacopeial monographs or GMP documentation in the provided data; therefore, it should not be used in drug product manufacturing without appropriate qualification.

For any regulated application, obtain full quality documentation (CoA, impurity profile, residual solvents, elemental impurities) and perform internal qualification per your quality system.

Physical Properties

• Item-specific (Product Data):

  • Appearance: 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.

• Computed/literature values (informational; not item-specific specifications):

  • Estimated molecular formula (from structure): C16H16O2
  • Estimated molecular weight: ~240.30 g/mol
  • Physical state: likely crystalline solid at ambient conditions (literature expectation for substituted benzophenones of similar size)
  • Solubility: typically low in water; soluble in common organic solvents (e.g., dichloromethane, THF, toluene, acetone) — literature/general for benzophenone derivatives.
  • UV–Vis: benzophenone chromophore usually shows strong absorption in the UV region (ca. 240–260 nm and 320–350 nm), substituents may shift bands (literature/general).
  • LogP: benzophenone derivatives with alkyl/methoxy substitution are generally hydrophobic (literature/general), but an exact value for this compound is not available here.
  • Melting/boiling point, density, refractive index, pKa: Not specified for this item; consult primary literature or the CoA/Spec Sheet if available.

• Practical note:

  • If precise purity limits, residual solvent content, water content, or UV cutoff are critical for your method, please refer to the lot-specific CoA/Spec Sheet; do not infer performance from literature expectations.

Quality and Grades

• Item-specific (Product Data):

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

• Guidance for interpreting grade (general):

  • Research grade materials are intended for laboratory R&D use and are not certified for food, drug, or household use. If HPLC or UV-grade specifications are required (e.g., low UV background, stringent metal limits), confirm that on the CoA; do not assume such properties for an unspecified grade.
  • Stabilizers/inhibitors: None indicated for this item. If a stabilizer were present (e.g., for photosensitive materials), it would be listed on the CoA/label. Absence of such a note here does not guarantee stabilizer-free material; verify per lot documentation if critical.
  • Identity/purity confirmation: For aryl ketones, NMR (1H/13C), GC/LC purity, and HRMS are standard. Trace isomers (positional) may occur if synthetic routes are not fully regioselective; CoA should specify identity tests.

• Practical recommendations:

  • If using this compound as a photochemical standard, polymerization additive, or in sensitive catalysis, request UV absorbance profile, water content, and any residual solvent/metal analyses from the CoA.
  • For chromatography-critical applications, pre-screen the lot by LC-UV at your analytical wavelength of interest to ensure baseline performance.

Reaction and Applications

• General reactivity of this class (benzophenone derivatives; literature/general):

  • Carbonyl transformations: reducible to benzhydrols (e.g., NaBH4, LiAlH4, catalytic hydrogenation); oxidatively cleavable under strong conditions; undergoes imine/enamine formation with amines under dehydrating conditions if converted to oximes first.
  • Nucleophilic additions: organolithium/Grignard reagents add to form tertiary alcohols; methoxy/methyl substituents influence regioselectivity in subsequent electrophilic substitutions.
  • Photochemistry: benzophenones are efficient triplet sensitizers and hydrogen abstractors; substitution affects triplet energies and photoreactivity. Derivatives can be used as photosensitizers in polymerization/photoreactions; validate suitability experimentally for this specific isomer.
  • Baeyer–Villiger oxidation: aryl ketones convert to aryl esters under peracid or catalytic systems; methoxy substitution may direct migratory aptitude.

• Synthetic applications:

  • Building block for substituted diphenylmethanols via carbonyl reduction.
  • Starting point for ether cleavage (anisole-type demethylation) to yield phenolic derivatives using BBr3/AlCl3 (method development required to avoid affecting the ketone).
  • Friedel–Crafts on the aryl rings is deactivated by the carbonyl but can proceed with strong Lewis acids; directing effects from methoxy/methyl groups modulate outcomes.

• Practical notes:

  • Moisture is generally not critical for handling, but strictly anhydrous conditions are required for organometallic additions.
  • Positional isomerism matters; confirm substitution pattern by 2D NMR before using in structure–property studies.

Reaction Conditions

General literature guidance for reactions of substituted benzophenones; adjust to your system and confirm with small-scale trials.

• Reductions to benzhydrols:

  • NaBH4 in MeOH/THF at 0–25°C, 1–4 h; or catalytic hydrogenation (Pd/C, H2, 1–5 bar) in EtOH/EtOAc at RT–50°C. Monitor by TLC/LC.

• Grignard/organolithium additions:

  • RMgX or RLi (1.2–2.0 equiv) in anhydrous THF or Et2O at −78 to 0°C, 0.5–3 h; quench with NH4Cl. Tertiary carbinol expected. Protect methoxy group if conditions are strongly basic/prolonged.

• Baeyer–Villiger oxidations:

  • mCPBA (1.2–1.5 equiv) in DCM at 0–25°C, 2–16 h; or H2O2 (30%) with catalytic acids in MeCN at 25–50°C. Product distribution (which aryl migrates) can be affected by substituents.

• Demethylation (anisole O–Me):

  • BBr3 (1–3 equiv) in DCM at −78 to 0°C, 1–4 h, then warm to RT; or AlCl3/thiols under non-aqueous conditions. Consider carbonyl protection (ketal) to avoid side reactions.

• Electrophilic substitutions on the rings:

  • Strong Lewis or Brønsted acid catalysis (e.g., AlCl3, TfOH) in inert solvents (DCM, nitrobenzene, HFIP) at −20 to 50°C; regioselectivity guided by methoxy/methyl activation.

• Photochemistry:

  • LED 365–405 nm, acetonitrile or acetone as solvent, O2 exclusion if radical side reactions undesired. Validate triplet sensitization efficiency for this derivative.

All values above are literature-style general conditions; optimize for your substrate and scale.

Safety and Handling

• Item-specific (Product Data):

  • Storage Conditions: Room temperature
  • Shipped In: Normal
  • GHS Classification / Signal Word / H-Statements / Pictograms: Not specified for this item; refer to SDS.

• General safety (literature/general for aromatic ketones and benzophenone derivatives):

  • Hazards: Many benzophenones can cause skin/eye irritation and may be harmful if swallowed; dusts may irritate the respiratory tract. Some substituted benzophenones are hazardous to aquatic life. Actual classification must be confirmed on the SDS for this item.
  • PPE: Use laboratory coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust or vapors during heating.
  • Incompatibilities: Strong oxidizers may react with aryl ketones; strong reducing agents can reduce the carbonyl to the corresponding benzhydrol. Avoid strong bases under heating if aldol-type condensations or demethylation could occur in complex mixtures.
  • Thermal/photochemical behavior: Benzophenones are photoactive; exposure to strong UV can generate excited triplet states and potentially radicals. Store in closed containers away from intense UV sources to prevent unintended photochemistry.
  • First aid (overview; consult SDS): Move to fresh air after inhalation; rinse skin/eyes with water for at least 15 minutes after contact; seek medical attention if symptoms persist. If ingested, rinse mouth and seek medical advice; do not induce vomiting unless directed by medical personnel.

Always consult the product-specific SDS for authoritative hazard, exposure limits, and emergency measures.

Solvent Selection

This product is a solid aryl ketone, not a solvent. Solvent selection considerations therefore focus on dissolving and processing the compound for synthesis, purification, or analysis.

• General solubility profile (literature/general for substituted benzophenones):

  • Good solubility: dichloromethane, chloroform, THF, acetone, acetonitrile, toluene, hot ethanol/isopropanol, ethyl acetate.
  • Limited solubility: aliphatic hydrocarbons at room temperature (hexanes/heptane), water.

• Polarity and handling:

  • The benzophenone core plus methoxy substitution imparts moderate polarity in polar aprotic media, while remaining hydrophobic overall. Choose medium-polarity organic solvents for reactions and recrystallizations.

• Comparison guidance:

  • DCM vs. EtOAc: DCM typically gives higher solubility and faster evaporation; EtOAc is a greener option but may show lower solubility at RT.
  • THF vs. Me-THF: THF often dissolves aryl ketones well; 2-MeTHF may be a greener alternative with similar solvency and better water immiscibility.

• Practical tips:

  • For analytical HPLC, acetonitrile/water with 0.1% acid modifier is common; the compound will elute at relatively high organic content due to hydrophobicity.
  • For recrystallization, toluene or EtOAc/hexanes mixtures are typical starting points; adjust based on trial solubility tests.

Storage and Reconstitution

• Item-specific (Product Data):

  • Storage Conditions: Room temperature
  • Shipped In: Normal

• General storage guidance for aryl ketones (literature/general):

  • Store tightly closed in a dry, well-ventilated place away from strong light sources (benzophenone cores are photoactive). Amber bottles or secondary light protection are prudent for long-term storage.
  • Avoid strong oxidizers and strong reducing agents in nearby storage.
  • If the material cakes or compacts, gently loosen before weighing; minimize exposure to ambient moisture even though aryl ketones are typically not hygroscopic.

• Reconstitution/solution preparation:

  • Not applicable for a dry solid. For stock solutions, dissolve in a suitable organic solvent (e.g., DCM, THF, acetonitrile, toluene, or ethanol) to the desired concentration. Filter through a PTFE syringe filter (0.45 µm) if particulates are present.
  • For analytical stocks intended for LC, use HPLC-grade solvents and record solvent lot and concentration; store solutions at 2–8°C protected from light and use within a defined period (e.g., 1–4 weeks), based on internal stability studies.

• Research Use Note: For research use only.

Structure and Identity

Brief overview: 2,3-Dimethyl-3'-methoxybenzophenone is a substituted benzophenone bearing two methyl groups on one ring (positions 2,3) and a methoxy substituent at the 3' position on the other ring, linked by a central benzoyl (diphenyl ketone) moiety.

• Item-specific (Product Data):

  • CAS: 750633-69-3
  • CID: 19352291
  • InChIKey: 231615 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Synonyms: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity (for context; not item-specific specifications):

  • Expected molecular formula (from name): C16H16O2
  • Approx. molecular weight (calculated): ~240.30 g/mol; exact mass ~240.1150 (literature calculation)
  • Core functional group: aryl–aryl ketone (benzophenone carbonyl, Ar–C(=O)–Ar')
  • Substituents: one ring bears 2,3-dimethyl (ortho/meta methyls); the other ring bears a 3'-methoxy (meta-methoxy) substituent.
  • 2D structural description: two phenyl rings connected via a central carbonyl carbon; electron-donating methoxy group meta to the carbonyl on ring A; two methyl groups ortho and meta to the carbonyl on ring B.

• General notes:

  • Structural features suggest a moderately electron-rich/neutral benzophenone, with potential for photophysical activity typical of benzophenones and altered by methoxy substitution.
  • No stereocenters; achiral, conformationally flexible about the aryl–C(=O) bonds.

Synthetic Utility

• Functional group leverage:

  • The benzophenone carbonyl (Ar–C(=O)–Ar') enables classic carbonyl chemistry: reductions to benzhydrols, Grignard/organolithium additions to tertiary alcohols, formation of oximes/hydrazones, and Baeyer–Villiger oxidation to aryl esters.
  • The 3'-methoxy group is an electron-donating substituent that can direct electrophilic aromatic substitution ortho/para on its ring and can be demethylated to a phenol to diversify functionality.
  • The 2,3-dimethyl pattern provides steric modulation and weak activation, useful for tuning reactivity and physical properties.

• Retrosynthetic value (literature/general):

  • Accessible via Friedel–Crafts acylation of appropriately substituted anisoles/toluenes with benzoyl chlorides or via carboxyl activation/cross-coupling strategies (e.g., acyl Suzuki with arylboronic acids and acid chlorides/anhydrides).
  • Methoxy-bearing rings can be introduced through ligand-controlled acylative cross-coupling to manage regioselectivity and minimize isomers.

• Diversification routes:

  • Convert carbonyl to imines/enamines then to amines via reduction (Reductive amination after prior functionalization).
  • Ortho-metalation adjacent to methoxy or methyl substituents (with strong bases, low temperature) can enable directed lithiation–functionalization; protect carbonyl as ketal if required.
  • Photochemical use as a triplet sensitizer or H-abstractor in method development, subject to experimental validation for this specific substitution pattern.

Target Specificity

Not applicable. This product is a small-molecule aromatic ketone and not a biological macromolecule or affinity reagent. No target, antigen, epitope, or species reactivity is defined in the Product Data.