2,5-Dimethylbenzophenone , CAS No.13319-70-5

CAS: 13319-70-5 Cat. No.: D1350963 分子式: C₁₅H₁₄O 分子量: 210.27 EC番号: 653-980-2 PubChem CID: 77665

Storage

Room temperature

Shipped In

Normal

Specifications

保管条件

Room temperature

入荷

Normal

名前と識別子

• カノニカル・スマイル: CC1=CC(=CC(=C1)C(=O)C2=CC=CC=C2)C
• IUPAC Name: (3,5-dimethylphenyl)-phenylmethanone
• InChIKey: OLXZWWMXQRMOGP-UHFFFAOYSA-N
• INCHI: 1S/C15H14O/c1-11-8-12(2)10-14(9-11)15(16)13-6-4-3-5-7-13/h3-10H,1-2H3
• 異性体SMILES: CC1=CC(=CC(=C1)C(=O)C2=CC=CC=C2)C
• PubChem CID: 77665
• 分子量: 210.27

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 分類: Benzene and substituted derivatives
• Subclass: Benzophenones
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzophenones
• Alternative Parents: Diphenylmethanes Aryl-phenylketones m-Xylenes Benzoyl derivatives Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzophenone - Aryl-phenylketone - Diphenylmethane - M-xylene - Xylene - Aryl ketone - Benzoyl - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Aromatic homomonocyclic compound
• 説明: 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

化学的性質と物理的性質

• 分子量: 210.270 g/mol
• XLogP3: 4.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 210.104 Da
• Monoisotopic Mass: 210.104 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 230.000
• 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 manufacturer-tested bioassay or analytical protocols are specified for this item.

• Item-specific protocols/dilutions: Not specified for this item; refer to CoA/Spec Sheet.

• General lab usage examples (non-validated; literature-style guidance):

  • Preparation of a stock solution: dissolve an accurately weighed amount in dry acetonitrile, THF, or DCM to the desired concentration (e.g., 10–100 mM) under subdued light; store in amber vials.
  • Photochemical experiment setup: degas solution (freeze–pump–thaw or sparge with N2/Ar), irradiate at selected wavelength (e.g., 350–370 nm) while monitoring by TLC/HPLC.
  • Reduction to benzhydrol: stir with LiAlH4 in THF at 0 °C to rt; quench cautiously; purify by column chromatography using hexanes/EtOAc gradients.

Users should validate conditions for their specific systems; these are illustrative only.

Biological Roles

This product is a synthetic aromatic ketone and does not have established endogenous biological roles.

• Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general notes:

  • Benzophenone frameworks are widely used as photophysical probes and triplet sensitizers in biochemical photolabeling studies; 2,5-dimethyl substitution can modulate solubility and photoreactivity but does not confer any known native biochemical function.
  • Hydrophobic character suggests strong non-specific binding to lipidic or hydrophobic protein regions in vitro; care should be taken to avoid misinterpreting binding artifacts in biophysical assays.
  • No known role in metabolism, signaling, or structural biology has been assigned to this specific compound.

All uses should remain within research and analytical contexts; no clinical or diagnostic applications are implied.

Buffer Applications

This is a hydrophobic aromatic ketone and is not typically used to prepare aqueous buffer systems.

• Applicability:
  • Not commonly employed as a buffering agent or pH modifier.
  • Limited water solubility precludes standard biological buffer formulations.

For laboratory work involving this compound, select buffer systems only insofar as they are compatible with planned extractions or phase separations (e.g., adjusting aqueous pH to manipulate partitioning during workup).

Green Alternatives

While 2,5-dimethylbenzophenone is a solid building block rather than a solvent, greener choices arise in both its synthesis and its use environment.

• Greener solvent selection during use (general guidance):

  • Prefer ethyl acetate, 2-MeTHF, or IPA over chlorinated solvents when feasible for dissolving or crystallizing the ketone.
  • Replace benzene with toluene or greener aromatics (e.g., anisole) for photophysical studies when acceptable.

• Greener synthetic routes (literature context):

  • Friedel–Crafts acylations can be executed using reusable solid acids (zeolites, Nafion, montmorillonite K10) or with catalytic AlCl3 systems to reduce stoichiometric halide waste relative to classic AlCl3 routes.
  • Use of acyl transfer from carboxylic acids via mixed anhydrides under catalytic conditions (e.g., Pd/NHC) can minimize corrosive reagents.

• Tradeoffs (balanced perspective):

  • Chlorinated solvents often afford superior solubility and cleaner EAS profiles for benzophenones; greener replacements may require higher temperatures or longer reaction times.
  • 2-MeTHF is moisture-tolerant and derived from biomass, but can form peroxides and may change selectivity in organometallic reactions compared to THF.

• Quick comparison (use-phase solvents; literature):

  • DCM: excellent solvency, poor EHS profile.
  • EtOAc: good EHS, moderate solvency; may need heating.
  • 2-MeTHF: greener ether, good for Grignard; distinct coordination vs THF can alter rates/selectivity.

Pharmaceutical Uses

• Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet.

• General context (non-clinical):

  • 2,5-Dimethylbenzophenone is primarily a research intermediate. While benzophenone cores appear in some UV-absorbing additives and process reagents, this specific isomer is not a standard pharmacopeial excipient to the best of general literature knowledge.
  • Potential roles in pharmaceutical process development include:
    • Synthetic intermediate toward diarylmethanols/diarylmethanes that may serve as advanced intermediates.
    • Photochemical probe in formulation research (e.g., studying photostability of dosage forms), strictly in laboratory studies.

No therapeutic or clinical claims are made; product is for research use only, as noted in the Product Data.

Physical Properties

• Item-specific specs: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties for 2,5-dimethyl-substituted benzophenones (for context; not item specifications):

  • Physical state: typically a white to off-white crystalline solid (aromatic diaryl ketone class).
  • Molecular weight (calculated from C15H14O): ~210.27 g/mol (literature).
  • Polarity/partitioning: hydrophobic; expected high logP relative to benzophenone due to two additional methyl groups (literature trend).
  • Solubility profile: sparingly soluble in water; soluble in common organic solvents such as dichloromethane, chloroform, toluene, THF, acetone, and hot alcohols (literature, class behavior).
  • UV–Vis: aromatic ketones show π→π* bands ~240–260 nm and n→π* around 330–360 nm; methyl substitution can slightly red-shift/alter intensities (literature, benzophenone family).
  • Melting/boiling: specific MP/BP for the 2,5-dimethyl isomer are not cited here; diaryl ketones of this mass typically have melting points in the solid range and high boiling points with potential for thermal decomposition before distillation (literature, qualitative).
  • Refractive index, density, pKa: not typically defined for solids (pKa not applicable; no acidic/basic centers). Specific values: Not specified for this item; refer to CoA/Spec Sheet.

Note: Use the product’s CoA for precise batch-specific physical constants needed for QC or method development.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Interpreting common grades (general guidance):

  • Research/technical grade: suitable for most synthetic applications; typical organic and elemental impurity levels are controlled for lab use but may not meet stringent analytical baselines.
  • High-purity or ≥98–99% grades (if specified on CoA) reduce byproducts in reactions sensitive to electrophiles, bases, or photochemical behavior.
  • Chromatography/HPLC grade is generally reserved for solvents; for solids like diaryl ketones, low UV-absorbing impurities are desirable when using as an internal standard or UV probe.

• Stabilizers/inhibitors: Not typically required for benzophenone derivatives; none are stated for this item. If stabilizers are present, they will be listed on the CoA; their presence may influence downstream photochemistry.

• What to check on receipt (best practices):

  • Appearance and consistency of solid; absence of discoloration (yellowing can indicate adventitious photoproducts).
  • Verify assay/purity by NMR/GC/LC as needed for critical applications.
  • Confirm identity by HRMS or melting point against literature if new to your process.

Use the batch-specific Certificate of Analysis for definitive grade, assay, and impurity profile.

Reaction and Applications

• Typical research uses (general for 2,5-dimethylbenzophenone and related diaryl ketones):

  • Intermediate in fine-chemical and materials synthesis where a sterically biased benzophenone scaffold is desired (e.g., for ligand, photoinitiator, or dye precursor development).
  • Photochemistry: benzophenone cores act as triplet sensitizers; 2,5-dimethyl substitution tunes triplet energy and solubility, enabling Paternò–Büchi, Norrish type I/II studies, and energy-transfer catalysis (literature context).

• Transformations of the carbonyl group:

  • Nucleophilic additions: Grignard/organolithium reagents provide tertiary benzhydrols; cyanide addition gives cyanohydrins (under controlled conditions).
  • Reductions: hydride reagents (NaBH4 typically sluggish for ketones; LiAlH4, BH3·THF, or catalytic hydrogenation) convert to diarylmethanols; Wolff–Kishner or Clemmensen conditions yield the corresponding diarylmethane (if needed).
  • Oxime/hydrazone formation with hydroxylamine/hydrazines enables subsequent Beckmann- or Wolff–Kishner-type chemistry.

• Arene functionalization:

  • Directed ortho metalation adjacent to the carbonyl on the unsubstituted ring (with strong bases) can install additional substituents; note the 2-methyl on the other ring raises steric hindrance near the carbonyl.
  • Electrophilic aromatic substitution is deactivated meta to the carbonyl yet activated by the methyl groups on their ring; regiocontrol must be considered in mixed EAS.

• Practical tips:

  • Dry, oxygen-free conditions improve reproducibility in organometallic additions.
  • Control light exposure to prevent unintended photoreactions during synthesis or storage.
  • Monitor by TLC/LC–MS; UV at ~254–280 nm is effective for benzophenone cores (literature).

Reaction Conditions

General literature guidance for transformations of 2,5-dimethylbenzophenone (adapt to your substrate and safety protocols):

• Nucleophilic additions to the ketone:

  • Grignard (RMgX) or organolithium (RLi): THF or Et2O; −78 to 0 °C for sensitive additions, 0 to rt for robust reagents; quench with NH4Cl; typical tertiary alcohol formation in good to excellent yields for unhindered reagents.
  • Cyanohydrin formation: HCN equivalents or TMSCN with Lewis acids (e.g., ZnI2) in MeCN/DCM at 0–25 °C; strictly control cyanide safety.

• Reductions:

  • Catalytic hydrogenation (Pd/C) in EtOH/EtOAc at 1–5 bar H2, rt–50 °C; furnishes benzhydrol. Monitor for over-reduction (diarylmethane) under forcing conditions.
  • LiAlH4 in THF, 0 °C to reflux; work up carefully with water/NaOH.

• Deoxygenation:

  • Wolff–Kishner (NH2NH2, KOH, high-boiling solvent like diethylene glycol, 180–200 °C) or Clemmensen (Zn(Hg)/HCl, refluxing toluene/DCM biphasic) to diarylmethane.

• Electrophilic aromatic substitution on the methylated ring:

  • Bromination/chlorination: Br2/FeBr3 or NBS with radical initiators; control to avoid benzylic halogenation unless desired.

• Photochemistry (benzophenone core):

  • UV irradiation (e.g., 365 nm) in degassed solvents (acetonitrile, benzene/toluene) for Norrish/Paternò–Büchi studies; inert atmosphere recommended to suppress triplet quenching by O2.

Note: Specific temperatures, times, and yields depend on reagent set and substrate; optimize empirically.

Safety and Handling

• Item-specific GHS details: Not specified for this item; refer to SDS for authoritative hazard classification, H-statements, and pictograms.

• General hazards for aromatic ketones (literature/general):

  • May cause skin and eye irritation; avoid contact. Some benzophenone derivatives can act as photosensitizers under UV exposure.
  • Combustible organic solid; avoid ignition sources and dust formation.

• Handling recommendations (good laboratory practice):

  • Wear appropriate PPE: lab coat, safety glasses, and suitable gloves (e.g., nitrile). Work in a fume hood to avoid inhalation of dust or solvent vapors during dissolution.
  • Avoid prolonged UV exposure of material and solutions to minimize undesired photochemical reactions.
  • Incompatibilities: strong oxidizers (risk of exothermic reactions); strong reducing agents may reduce the carbonyl. Store away from reactive metals and bases that might catalyze aldol-like side reactions with other components.

• First aid (overview; defer to SDS):

  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: move to fresh air; obtain medical advice if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product-specific SDS before use and implement institutional risk assessments.

Solvent Selection

This compound is a nonpolar/aromatic ketone solid; solvent choice typically centers on dissolving capacity, stability to light/oxygen, and compatibility with planned transformations.

• Polarity class and miscibility (general):

  • Hydrophobic aromatic; poorly soluble in water. Readily soluble in moderately polar aprotic and nonpolar organic solvents (e.g., DCM, CHCl3, toluene, THF, acetone, ethyl acetate). Solubility increases with temperature.

• Selection by application:

  • Spectroscopy/photochemistry: use spectroscopic-grade acetonitrile, benzene/toluene, or isooctane depending on target absorption/emission; minimize protic solvents that may quench excited states.
  • Reductions (e.g., to benzhydrols) or Grignard additions: ethereal solvents (THF, diethyl ether) or toluene are common; ensure water-free conditions.
  • Friedel–Crafts-type transformations on the aryl rings: chlorinated solvents (DCM) or nitrobenzene/1,2-dichloroethane are typical with Lewis acids; ensure temperature control.

• Practical notes:

  • Avoid neat highly basic media that might induce side reactions on methylated rings via benzylic deprotonation under forcing conditions.
  • For crystallizations, pairs such as toluene/hexanes or EtOAc/hexanes often provide tunable solubility.

• Quick comparison (literature trends):

  • DCM: excellent solubility, easy removal; not green.
  • Toluene: good solubility; higher bp enables elevated-temperature reactions.
  • THF: coordinates metals (useful for organometallics); peroxide formation risk—monitor and inhibit as needed (solvent-specific caution).

Storage and Reconstitution

• Item-specific storage and shipping (from Product Data):

  • Storage Conditions: Room temperature.
  • Shipped In: Normal.

• General storage guidance for aromatic ketone solids:

  • Keep container tightly closed in a dry, well-ventilated place. Protect from light (use amber glass) to minimize photochemical degradation.
  • Avoid prolonged exposure to heat; store away from oxidizing agents.

• Reconstitution/preparation of solutions (general):

  • Solvents: dissolve in common organic solvents such as dichloromethane, chloroform, toluene, THF, acetone, or ethyl acetate. Water solubility is expected to be very low.
  • Concentration: prepare concentrated stocks (e.g., 0.05–0.5 M) as needed for synthesis; filter if particulates persist.
  • Storage of solutions: store in amber vials under inert gas at 2–8 °C for short-term use; assess stability by LC/UV before critical experiments. For long-term storage, prefer solid state.

• Freeze–thaw: Not typically applicable to solids. For solutions, minimize freeze–thaw cycling by aliquoting.

Refer to the product SDS and CoA for any additional, batch-specific handling instructions. For research use only (per Product Data).

Structure and Identity

Brief description: 2,5-Dimethylbenzophenone is a diaryl ketone (benzophenone core) bearing two methyl substituents at the 2- and 5-positions of one phenyl ring. It is a useful hydrophobic aryl ketone building block.

• Item-specific (Product Data):

  • SKU: D1350963
  • CAS: 13319-70-5
  • InChIKey: 261466 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (general reference information):

  • Common name: 2,5-Dimethylbenzophenone (a.k.a. 2,5-xylyl phenyl ketone)
  • Molecular formula (literature): C15H14O
  • Molecular weight (literature): ~210.27 g/mol
  • Core functional group: aromatic ketone (benzophenone)
  • Substitution pattern: one phenyl ring is 2,5-dimethyl-substituted; the other ring is unsubstituted phenyl.
  • 2D structure in words: a central carbonyl carbon double-bonded to oxygen; the carbonyl carbon is bonded to two sp2 carbons, each part of a benzene ring. On one ring, methyl groups occupy the ortho (2-) and meta (5-) positions relative to the carbonyl-bearing carbon.

• Structural features and implications (general):

  • Conjugated aryl–CO–aryl system supports n→π* and π→π* transitions (benzophenone photochemistry).
  • Ortho-methyl increases steric hindrance near the carbonyl, subtly affecting reactivity and rotational conformers.
  • Hydrophobic, non-ionizable under neutral conditions; weak H-bond acceptor at the carbonyl oxygen.

Synthetic Utility

• Functional group behavior:

  • The carbonyl of 2,5-dimethylbenzophenone is a versatile electrophile that tolerates a wide range of conditions. It undergoes nucleophilic addition, reductions, imine/oxime formation, and serves as a handle for further diversification.

• Strategic uses in synthesis (literature/general):

  • Access to tertiary benzhydrols via organometallic addition enables downstream dehydrations to alkenes or conversions to halides/ethers.
  • Reductive deoxygenation (Clemmensen/Wolff–Kishner) provides the diarylmethane skeleton retaining the 2,5-dimethyl pattern—useful in materials and ligand synthesis.
  • Photochemical transformations of benzophenone cores (e.g., Norrish Type I/II) can install radicals or rearranged frameworks; methyl substitution influences conformer populations and radical pathways.
  • As a directing/activating element, the carbonyl can guide ortho metallation on the unsubstituted ring for regioselective functionalization (e.g., halogenation, formylation after quench).

• Retrosynthetic note:

  • Forward routes often arise from Friedel–Crafts acylation of 1,4-dimethylbenzene (p-xylene) using benzoyl chloride or via benzoylation of 2,5-dimethyl-substituted aromatics followed by coupling. Alternative routes include acylation followed by Suzuki/Negishi cross-couplings to assemble the diaryl motif.

Target Specificity

Not applicable. This product is a small-molecule aromatic ketone, not a biological targeting reagent or antibody.

• Item-specific targeting data: Not specified for this item; refer to CoA/Spec Sheet if any assay-related details are provided.

For applications requiring biochemical target engagement, complementary assays or derivatization (e.g., photolabeling handles) would be necessary.