4-Ethyl-2'-methoxybenzophenone - ≥95% , CAS No.82520-38-5

CAS: 82520-38-5 Cat. No.: E992837 분자식: C₁₆H₁₆O₂ 분자량: 240.300

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

사양 및 순도

≥95%

보관 조건

Room temperature

순수함

≥95%

이름과 식별자

• 정식 스마일: CCC1=CC=C(C=C1)C(=O)C2=CC=CC=C2OC
• IUPAC Name: (4-ethylphenyl)-(2-methoxyphenyl)methanone
• InChIKey: WBDXHUKINUEBJE-UHFFFAOYSA-N
• INCHI: 1S/C16H16O2/c1-3-12-8-10-13(11-9-12)16(17)14-6-4-5-7-15(14)18-2/h4-11H,3H2,1-2H3
• 분자량: 240.300

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Benzenoids
• 분류: 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 Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzophenone - Aryl-phenylketone - Diphenylmethane - Phenoxy compound - Anisole - Methoxybenzene - Aryl ketone - Phenol ether - Benzoyl - Alkyl aryl ether - Ketone - Ether - Organic oxygen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• 설명: 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

화학 및 물리적 특성

• 분자량: 240.300 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• 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: 266.000
• 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-validated application protocols are provided for this item. Usage will depend on your synthetic or photochemical objective.

• General suggestions (non-binding, literature-informed):
  • Photochemistry: Dissolve in a UV-transparent solvent (e.g., acetonitrile or isopropanol), deoxygenate by sparging with N2/Ar, irradiate with 300–365 nm LEDs, and monitor by TLC/HPLC at 254 nm.
  • Carbonyl reduction: Dissolve in MeOH or EtOH, cool to 0 °C, add NaBH4 portionwise, stir until completion, quench with saturated NH4Cl, extract with EtOAc, dry, and purify by flash chromatography.
  • Grignard addition: Prepare RMgX in dry THF, cool the ketone solution to 0 °C under N2, add reagent dropwise, allow to warm to rt, then quench and work up as standard.

These are illustrative only. Optimize conditions for your specific system and consult primary literature. For GMP or regulated workflows, develop and validate formal SOPs.

Biological Roles

This product is a synthetic aromatic ketone intended for research and laboratory use; it does not have established endogenous biological roles.

• General context (not product-specific claims):

  • Benzophenone scaffolds are widely used as photoprobes in chemical biology due to their triplet-state reactivity, enabling covalent capture of nearby biomolecules upon UV irradiation. Substituents such as methoxy groups tune photophysical properties and binding interactions in designed probes.
  • In environmental and toxicological studies, certain benzophenone derivatives have been examined as UV absorbers or transformation products; however, such findings are compound-specific and should not be generalized without direct data on 4-ethyl-2'-methoxybenzophenone.

• Practical note:

  • If deploying this compound in photoaffinity labeling or materials interfacing with biological matrices, ensure thorough assessment of solvent, dose, and light exposure conditions. No biological activity or safety profile is specified for this item; consult primary literature and your institutional review processes before any bio-related experimentation.

Research Use Only: Not for diagnostic, therapeutic, or in vivo applications.

Buffer Applications

This compound is a hydrophobic organic building block and is not typically used to prepare aqueous buffer systems. If incorporated into experiments involving buffers (e.g., bioassays or photochemical studies in buffered media), dissolve first in a suitable co-solvent (e.g., DMSO, acetonitrile, or ethanol) and keep the final organic content low to maintain buffer capacity and compatibility.

For information on standard buffer systems (PBS, Tris, HEPES, phosphate–citrate), refer to dedicated buffer reagents.

Green Alternatives

Greener practices focus on solvent and reagent choices used with this compound rather than on the compound itself.

• Solvent optimization (general guidance):

  • Replace chlorinated solvents (DCM/CHCl3) with safer options where possible: 2-MeTHF, CPME, anisole, toluene, or ethyl acetate, balancing solubility and process needs.
  • For reductions, aqueous ethanol or isopropanol with catalytic hydrogenation can be greener than metal hydrides when compatible.

• Example comparisons (general; selection depends on reaction):

  | Use case | Conventional | Greener alternative | Trade-offs | |---|---|---|---| | Grignard addition | THF (petro) | 2-MeTHF (biorenewable) | Similar performance; 2-MeTHF more hydrophobic and higher bp aids workup; may change selectivity. | | Extraction/Workup | DCM | EtOAc or MTBE | Slightly lower density; may require larger volumes; improved EHS profile. | | Photochemistry | Acetonitrile | EtOAc, MeCN/H2O mixtures | Transparency and H-donor properties must be validated for target photoreaction. | | Column eluent | Hexanes | Heptane or cyclopentyl methyl ether blends | Reduced toxicity; may affect separation power. |

• Energy and light management:

  • Use LED UV sources with narrow bands to reduce energy consumption and byproducts vs broad-spectrum lamps.
  • Run reactions at ambient temperature when feasible; employ flow photochemistry for improved efficiency.

Always validate greener swaps by small-scale trials; maintain product quality and safety as primary criteria.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is specified for this item. 4-Ethyl-2'-methoxybenzophenone is primarily a research chemical and synthetic intermediate.

• Context (general, not specific to this item):

  • Aromatic ketones and benzophenone derivatives can serve as intermediates in the synthesis of APIs, ligands, or polymer additives. Their UV-absorbing properties are sometimes exploited in materials and packaging research.
  • Any use in pharmaceutical development would require stringent control of purity, residual solvents, and photochemical stability, along with toxicological evaluation.

• Documentation:

  • No USP/Ph. Eur. monograph or excipient status is indicated. For any regulated application, obtain full analytical characterization, impurity profile, and stability data for your specific lot.

Research Use Only: Not for clinical or therapeutic use.

Physical Properties

• Item-specific specs (from 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.

• Literature/computed information (for context; not specifications):

  • Estimated molecular formula: C16H16O2 (computed from structure rationale).
  • Estimated molecular weight: ~240.30 g/mol (computed).
  • Physical state: Benzophenone derivatives of this substitution pattern are typically crystalline solids at ambient temperature (literature trend).
  • Solubility profile: Generally sparingly soluble in water; soluble in common organic solvents such as dichloromethane, chloroform, toluene, THF, acetone, and ethyl acetate (literature, typical for substituted benzophenones).
  • UV–Vis: Benzophenone chromophores typically show strong absorption in the UV-B/UV-C with n→π* and π→π* transitions; substituents (–OMe) red-shift bands relative to unsubstituted benzophenone (literature trend; exact λmax not specified for this item).
  • LogP: Substituted benzophenones with alkyl and methoxy groups are typically lipophilic (positive logP; literature trend). Specific value not located for this compound.
  • Melting/Boiling points, density, refractive index: Not specified for this item; consult CoA/Spec Sheet or primary literature for exact values.

Note: Use the item’s Certificate of Analysis for definitive specifications for your lot.

Quality and Grades

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

• Guidance on grades (general; for context):

  • Research grade: Suitable for most synthetic and analytical workflows; purity typically ≥95%, but refer to CoA for exact assay and impurity profile.
  • High-purity/analytical grades: When available, these emphasize low non-volatile residue, narrow melting range, and minimized UV-absorbing impurities—useful for photochemical studies or spectroscopic assays involving benzophenone chromophores.
  • Stabilizers: Not indicated for this item. Substituted benzophenones are generally shelf-stable without added stabilizers; if any are used, they will be listed on the CoA, and may affect downstream photochemistry.

• What to check on receipt:

  • Assay (HPLC/GC), identity (NMR/IR/MS), and residual solvents.
  • Water content (Karl Fischer) if moisture-sensitive steps are planned; while aromatic ketones are not typically hygroscopic, water can affect some reactions (e.g., Grignard additions).
  • Trace metals are usually not critical for neutral organic building blocks, but verify if the compound is destined for catalysis-sensitive transformations.

For definitive grade definitions, UV cutoff, impurity limits, and exact purity, consult the product’s CoA/Specification Sheet for your lot.

Reaction and Applications

As a substituted benzophenone, 4-ethyl-2'-methoxybenzophenone functions both as a photochemical handle and as a versatile aryl ketone building block.

• Photochemistry (general knowledge):

  • The benzophenone unit efficiently populates a long-lived triplet n→π* state, enabling hydrogen abstraction (Norrish type II-like processes) and energy transfer. The ortho-methoxy group can modulate triplet energy, facilitating photosensitization or intramolecular H-abstraction depending on context.
  • Applications include polymer crosslinking studies, photoinduced radical generation, and synthesis of pinned aryl frameworks via photoreactions.

• Carbonyl transformations:

  • Nucleophilic additions (Grignard/organolithium) to form tertiary/secondary benzhydrols; subsequent dehydrations yield diaryl alkenes.
  • Reductions: NaBH4 or catalytic hydrogenation to the corresponding diaryl carbinol; Clemmensen or Wolff–Kishner conditions access the diaryl methane (decarbonylation equivalents in multistep sequences).
  • Oxime/hydrazone formation for derivatization or as precursors to Beckmann or Wolff rearrangements (with appropriate conditions).

• Aromatic substitutions and modifications:

  • Electrophilic substitution on the ethyl-substituted ring (the methoxy-bearing ring is less reactive due to proximity to the carbonyl and ortho substitution).
  • O-Demethylation (e.g., BBr3) to give the corresponding 2'-hydroxybenzophenone, a useful ligand/intermediate.
  • Directed ortho-metalation adjacent to the methoxy substituent can enable further functionalization under carefully controlled conditions.

• Purification/analysis tips:

  • Monitor by UV-active TLC/HPLC; benzophenone chromophores respond strongly at ~254 nm (literature). Protect from intense UV during handling to minimize unintended photoreactions.

Reaction Conditions

General literature guidance for reactions of substituted benzophenones (adapt to your system; optimize experimentally):

• Nucleophilic additions to the carbonyl:

  • Grignard (RMgX) in dry THF or Et2O, 0 °C to room temperature, 1–4 h, then standard aqueous workup; benzhydrols typically form in good yields with appropriate stoichiometry and quench control (literature generality).
  • Organolithium reagents at −78 to 0 °C in THF or toluene; lower temperatures improve chemoselectivity when other electrophiles are present.

• Reductions:

  • NaBH4 in MeOH/EtOH at 0–25 °C, 0.5–2 h; carbonyl reduces to alcohol. Avoid excess base/heat to minimize O-demethylation.
  • Catalytic hydrogenation (Pd/C) in EtOH/EtOAc at ambient temperature and 1–5 bar H2 can reduce the carbonyl in the presence of some substituents; verify selectivity with methoxy and aryl rings.

• O-Demethylation (to phenol):

  • BBr3 (1–3 equiv) in DCM at −78 to 0 °C, then warm to rt; quench cautiously. Alternatively, AlCl3/thiol systems under Friedel–Crafts-type conditions.

• Electrophilic aromatic substitution:

  • Halogenation (Br2/FeBr3) or nitration (HNO3/H2SO4) at 0–25 °C; regioselectivity favors the ethyl-bearing ring. Monitor closely to avoid overreaction.

• Photochemical operations:

  • UV irradiation at 300–365 nm in oxygen-free solvents (degassed MeCN, toluene, or iPrOH) for hydrogen abstraction or energy transfer; inert atmosphere improves reproducibility. LED sources enhance control.

Note: Temperatures, times, and yields are general literature guidance for benzophenone derivatives and not item-specific specifications. Validate on small scale.

Safety and Handling

• Item-specific hazard designations (from Product Data):

  • 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 safety considerations for aromatic ketones and substituted benzophenones (general knowledge; not a substitute for SDS):

  • May cause skin and eye irritation; avoid inhalation of dust/particulates and contact with skin or eyes. Handle in a chemical fume hood.
  • Photoreactivity: Benzophenone cores readily access triplet states under UV irradiation and can participate in hydrogen abstraction; minimize unnecessary UV/strong light exposure if photochemical side reactions are a concern.
  • Incompatibilities: Strong oxidizers (risk of exotherm), strong reducing agents (may reduce the carbonyl), strong bases/acids can promote side reactions (e.g., demethylation under harsh conditions). Store away from such reagents.
  • Combustible organic solid: Keep away from ignition sources. Ground and bond when transferring fine powders.

• Recommended PPE and hygiene:

  • Wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use a particulate respirator if dust cannot be controlled (per risk assessment).
  • Wash thoroughly after handling; avoid eating or drinking in the lab.

• First-aid overview (consult SDS for full procedures):

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

Always consult the product SDS for authoritative and item-specific safety information.

Solvent Selection

4-Ethyl-2'-methoxybenzophenone is a neutral, hydrophobic aromatic ketone. Solvent choice is driven by its lipophilicity, benzophenone chromophore, and planned reactivity.

• Polarity/miscibility profile (general trends):

  • Poorly soluble in water; readily soluble in mid- to non-polar organic solvents (e.g., dichloromethane, chloroform, toluene, THF, acetone, ethyl acetate). Alcohols (MeOH/EtOH) may dissolve it moderately when warmed.
  • For chromatography, hexanes/EtOAc or toluene/EtOAc gradients typically provide good separations for benzophenone derivatives.

• Typical solvent choices by task:

  • Photochemistry: Acetonitrile, isopropanol, or benzene/toluene are commonly used for benzophenone-sensitized reactions; choose based on hydrogen-donor propensity if triplet H-abstraction is intended.
  • Nucleophilic additions to the carbonyl (e.g., Grignard): Use strictly anhydrous ethereal solvents (THF/Et2O) under inert atmosphere.
  • Reductions (NaBH4): Alcoholic solvents (MeOH/EtOH) or protic mixtures with THF; control temperature to avoid over-reduction.
  • Electrophilic aromatic substitution on the ethyl-bearing ring: Nonpolar aromatics (toluene, chlorobenzene) with Lewis/Brønsted acids, as appropriate.

• Comparison (general):

  • DCM vs toluene: DCM provides faster dissolution and easier removal; toluene is higher-boiling and better for elevated-temperature operations.
  • THF vs Et2O: THF offers improved solvation of organometallic reagents; Et2O lowers polarity and may suppress side reactions in some cases.

Always match solvent dryness and UV transparency to your application needs.

Storage and Reconstitution

• Item-specific storage from Product Data:

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

• General storage guidance for substituted benzophenones:

  • Store tightly closed in a cool, dry, well-ventilated place, away from strong light (especially UV) to minimize unintended photochemical changes.
  • Protect from strong oxidizers and strong acids/bases.
  • If long-term storage is planned, consider amber glass and desiccation; inert gas backfill is optional but can help for highly light-sensitive operations.

• Reconstitution/dissolution:

  • The compound dissolves readily in organic solvents such as DCM, THF, acetone, EtOAc, toluene, and acetonitrile (general trend). Warm gently and sonicate if needed. For aqueous systems, use a miscible co-solvent (e.g., DMSO or MeCN) and add slowly to the aqueous phase with stirring.
  • Filter solutions through PTFE (0.2–0.45 µm) before sensitive applications.

Always follow your institution’s chemical hygiene plan. For container/closure compatibility and any lot-specific notes, consult the product label and CoA.

Structure and Identity

4-Ethyl-2'-methoxybenzophenone is a monosubstituted benzophenone bearing a para-ethyl group on one ring and an ortho-methoxy group on the other. The core is a diaryl ketone (benzophenone) with one carbonyl linking two substituted phenyl rings.

• Item-specific identifiers from Product Data:

  • CAS: 82520-38-5
  • CID: 24722759
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists a placeholder.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identifiers and composition (informational):

  • Functional groups: aromatic ketone (benzophenone carbonyl), anisole ether (methoxy aryl), ethyl-substituted arene.
  • Molecular formula (computed from substitution pattern): C16H16O2.
  • Molecular weight (computed): ~240.30 g/mol.

• 2D structural description (general):

  • Ring A: phenyl ring bearing a para-ethyl (–CH2CH3) substituent relative to the carbonyl connection.
  • Carbonyl: benzophenone C=O linking the two aryl rings.
  • Ring B: phenyl ring bearing an ortho-methoxy (–OCH3) substituent relative to the carbonyl.
  • No stereocenters; planarity is disrupted slightly by the carbonyl and ortho-methoxy, leading to a non-coplanar aryl arrangement typical for benzophenones.

• Structural features of interest (general knowledge):

  • The methoxy substituent is ortho/para-directing and can modulate the triplet energy and photoreactivity of the benzophenone core.
  • The ethyl group increases lipophilicity versus benzophenone and can affect solubility and crystallinity.

Synthetic Utility

4-Ethyl-2'-methoxybenzophenone is a versatile diaryl ketone that can participate in a wide range of transformations.

• As a carbonyl electrophile:

  • Addition of organometallic reagents (RMgX, RLi) yields tertiary/secondary benzhydrols; these can be leveraged for subsequent dehydrations or rearrangements.
  • Reductions (NaBH4, DIBAL-H, catalytic hydrogenation) furnish the corresponding alcohol; selective conditions avoid ether cleavage.
  • Formation of imines/oximes/hydrazones enables protection/derivatization or downstream rearrangements (e.g., Beckmann under activating conditions).

• Arene functionalization:

  • The para-ethyl ring remains activated toward electrophilic substitution relative to electron-withdrawing analogues; halogenation, nitration, or Friedel–Crafts alkylations/acylations can be directed there under controlled conditions.
  • The methoxy-bearing ring supports directed ortho-metalation adjacent to –OMe; however, sterics from the ortho-OMe and the carbonyl should be considered. O-Demethylation (BBr3, AlCl3/thiolates) gives the phenolic derivative.

• Photochemical utility:

  • Benzophenone triplet sensitization under UV (≈300–365 nm, literature) enables hydrogen abstraction, Paterno–Büchi with alkenes (via excited carbonyls), and crosslinking chemistry in polymers or surface science.

• Retrosynthetic/value:

  • Serves as a branching point to phenolic benzophenones, diaryl methanes (through stepwise reduction/deoxygenation), and elaborated triarylmethanes after nucleophilic additions.

Careful choice of solvent, light source, and protecting groups ensures high selectivity and yield.

Target Specificity

Not applicable. This product is a small-molecule organic compound, not a biological reagent (e.g., antibody, enzyme, ligand with defined biomolecular target) with specified target specificity. If used as a photoaffinity probe precursor, any target engagement will depend on the appended recognition element, which is outside the scope of this listing.