2,4'-Dichloro-3'-methylbenzophenone - ≥95% , CAS No.74617-45-1

CAS: 74617-45-1 Cat. No.: D1253129 Fórmula: C₁₄H₁₀Cl₂O Peso molecular: 265.13 PubChem CID: 12614591

GRAU & PUREZA ≥95%

Storage

Room temperature

Shipped In

Normal

Especificações

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Enviado em

Normal

Pureza

≥95%

Nomes e identificadores

Sorrisos canónicos

CC1=C(C=CC(=C1)C(=O)C2=CC=CC=C2Cl)Cl

IUPAC Name

(4-chloro-3-methylphenyl)-(2-chlorophenyl)methanone

InChIKey

MQAAOMKDVIWSHC-UHFFFAOYSA-N

INCHI

1S/C14H10Cl2O/c1-9-8-10(6-7-12(9)15)14(17)11-4-2-3-5-13(11)16/h2-8H,1H3

SMILES isoméricas

CC1=C(C=CC(=C1)C(=O)C2=CC=CC=C2Cl)Cl

PubChem CID

12614591

Peso molecular

265.13

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 Benzoyl derivatives Toluenes Chlorobenzenes Aryl chlorides Vinylogous halides Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzophenone - Diphenylmethane - Aryl-phenylketone - Benzoyl - Aryl ketone - Toluene - Halobenzene - Chlorobenzene - Aryl chloride - Aryl halide - Vinylogous halide - Ketone - Organooxygen compound - Organochloride - Organohalogen compound - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Descrição: 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

Propriedades químicas e físicas

• Peso molecular: 265.100 g/mol
• XLogP3: 4.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 264.011 Da
• Monoisotopic Mass: 264.011 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 279.000
• 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 assay or bioanalytical application protocols are provided for this small-molecule reagent. Typical use is in synthetic organic chemistry as described in the Reaction & Applications and Synthetic Utility sections. For any analytical deployment (e.g., HPLC reference), establish internal SOPs and validate performance (linearity, purity, stability) with your instrumentation.

Biological Roles

• This product is a synthetic, chlorinated aryl ketone and is not a natural metabolite or typical biochemical reagent.
• General chemistry knowledge (not product-specific claims)
  • Benzophenone motifs can act as triplet sensitizers and UV absorbers in materials contexts; however, such photophysical behavior does not imply a biological role.
  • Aryl ketones of this type typically show high hydrophobicity and low aqueous solubility, limiting direct participation in aqueous biological pathways.
• Research context
  • May serve as a model substrate for enzymatic or biomimetic reductions/oxidations of aryl ketones in methodological studies.

Note: No biological activity or role is claimed for this item. For research use only (per Product Data).

Buffer Applications

This compound is a hydrophobic aryl ketone and is not used to prepare laboratory buffers or biological buffer systems. If your work involves aqueous systems, focus on extraction/solubilization strategies (e.g., co-solvents, cyclodextrins, micelles) rather than buffering considerations.

Green Alternatives

• Solvent choices (general green chemistry perspective)

  • Prefer greener solvents where feasible:
    • Use toluene or ethyl acetate instead of chlorinated solvents (DCM, CHCl3) for dissolution and extraction when compatible with the reaction/purification.
    • Consider 2-MeTHF or CPME in place of THF/MTBE for reductions and organometallic steps; both offer better sustainability and lower peroxide concerns (still monitor peroxides routinely).
    • For Pd-catalyzed couplings, ethanol/water or 2-MeTHF have reported success with appropriate ligands and bases; this reduces reliance on high-boiling polar aprotics (NMP/DMAc), which pose reproductive toxicity concerns.

• Reagent selection (general)

  • Reductions: Catalytic hydrogenation (H2, Pd/C) can replace stoichiometric hydrides when the substrate tolerates hydrogenolysis risk on aryl chlorides (often acceptable under mild conditions).
  • Oxidations: Use Oxone or H2O2-based systems (with organocatalysts) where selectivity allows, minimizing halogenated oxidants or peracids.

• Mini comparison (general guidance)

  • THF vs. 2-MeTHF: Similar polarity and performance; 2-MeTHF has bio-based sourcing and easier phase splits. Downside: higher boiling point and occasional odor.
  • DCM vs. EtOAc: DCM offers rapid dissolution and low boiling but has higher toxicity; EtOAc is biodegradable with a benign safety profile yet may dissolve more slowly and can hydrolyze under strong base/acid.

• Waste management

  • Chlorinated aromatic residues should be segregated and sent for appropriate incineration. Capture Pd residues for metal recovery.

Pharmaceutical Uses

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

• General context

  • Substituted benzophenones may appear as intermediates in the synthesis of active pharmaceutical ingredients or advanced intermediates. Their roles are typically confined to chemical manufacturing steps (e.g., cross-coupling platforms, carbonyl chemistry) rather than as excipients.
  • Due to hydrophobicity and halogenation, these structures are more aligned with intermediate chemistry than with formulation roles.

No therapeutic or clinical claims are made. For research and laboratory use only.

Physical Properties

• Item-specific properties

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

• Literature/general expectations for this structural class (for guidance only; not product specifications)

  • Phase at ambient conditions: Typically a crystalline solid for mono-/di-substituted benzophenones.
  • Molecular weight (literature for this structure): ~267.15 g/mol.
  • Polarity: Moderately lipophilic aryl ketone; strong UV absorption in near-UV due to aryl–carbonyl conjugation.
  • Solubility profile (qualitative):
    • Likely soluble in common organic solvents (e.g., dichloromethane, chloroform, THF, acetone, ethyl acetate, toluene).
    • Poorly soluble in water (typical for chlorinated benzophenones).
  • Volatility: Low (solid aryl ketones generally have low vapor pressures at room temperature).

• Not provided for this item (consult CoA/Spec Sheet or SDS if required for your process)

  • Melting point, boiling point, density, refractive index, pKa, logP, UV–Vis cutoffs, elemental limits: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

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

• Guidance on grades (general information)

  • Research-grade vs. analytical/HPLC grades: Analytical or HPLC grades prioritize low non-volatile residue and low UV background—relevant if using this compound as a chromatographic standard or in photochemical studies. Research-grade material is typically suitable for synthetic transformations and general laboratory use.
  • Stabilizers: None specified for this item. Substituted benzophenones generally do not require stabilizers; however, trace inhibitors are sometimes used for highly photoreactive analogs. Absence/presence of stabilizer should be confirmed on the CoA if critical.
  • Verification: For structure-sensitive applications (e.g., cross-coupling where aryl chloride count matters), confirm identity and substitution pattern via NMR (1H, 13C, DEPT), HRMS, and possibly GC/LC purity. Halogen content can be corroborated by HRMS isotopic patterns.
  • Impurities to be mindful of (general): Unsubstituted benzophenone, mono-chloro or positional isomers, and residual halogenated starting materials. If photochemical background is a concern, verify low levels of UV-active impurities by HPLC-UV.

• Documentation

  • For exact specifications (purity %, residual solvents, metals, water content, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

• General roles for substituted benzophenones (expanding on typical research uses)

  • Building block for further functionalization: The aryl chloride positions provide handles for cross-coupling (Suzuki–Miyaura, Buchwald–Hartwig amination, Sonogashira), though aryl chlorides require more active Pd catalysts/ligands (e.g., XPhos, BrettPhos, SPhos) and elevated temperatures.
  • Carbonyl transformations:
    • Reductions to benzhydrol derivatives (NaBH4, catalytic hydrogenation, or borane reagents). Electron-withdrawing chloro substituents can moderate reduction rate; protic/ Lewis acid activation may help.
    • Oxime/hydrazone formation enabling Wolff–Kishner or Clemmensen-type deoxygenation to the corresponding diarylmethane.
    • Baeyer–Villiger oxidation (e.g., mCPBA) to give aryl benzoate esters; substituent effects influence migration selectivity.
  • Photochemistry: Benzophenone cores are prototypical triplet sensitizers; substitution can alter absorption/emission and intersystem crossing efficiency. If used photochemically, verify purity and UV profile.

• Practical tips

  • Cross-coupling on aryl chlorides: Employ Pd2(dba)3 or Pd(OAc)2 with bulky biaryl phosphines (BrettPhos, tBuXPhos) in toluene/dioxane/DMAc at 80–120 °C; add base (K3PO4, Cs2CO3) and strict exclusion of moisture/air for amination.
  • Reduction to alcohol: NaBH4 in MeOH/THF at 0–25 °C often proceeds cleanly; for sluggish substrates, add CeCl3 (Luche conditions) or switch to BH3·THF.
  • Oxidation: For Baeyer–Villiger, 1.2–2.0 equiv mCPBA in DCM at 0–25 °C, with buffering (NaHCO3) to manage acids.
  • Regioselectivity/sterics: The ortho-chloro on one ring can twist the C(=O)–aryl dihedral, influencing reactivity and NMR chemical shifts.

Reaction Conditions

The following are literature-style, general conditions for typical transformations of chlorinated benzophenones. They are guidance only and not product specifications.

• Suzuki–Miyaura coupling (aryl chloride site)

  • Catalyst: Pd2(dba)3 (1–2 mol%) + BrettPhos (2–4 mol%) or Pd-PEPPSI-type precatalyst.
  • Base: K3PO4 (2–3 equiv) or Cs2CO3.
  • Solvent: Toluene, dioxane, or DMAc; 80–110 °C.
  • Time/Yield: 4–16 h; often 60–90% with suitable partners.

• Buchwald–Hartwig amination

  • Catalyst: Pd(OAc)2 (1–3 mol%) with tBuXPhos or XPhos; or precatalysts (e.g., XPhos Pd G3).
  • Base: NaOtBu or Cs2CO3.
  • Solvent: Toluene, dioxane, or CPME; 80–110 °C.

• Reduction to benzhydrol

  • Reagent: NaBH4 (2–4 equiv) in MeOH, EtOH, or THF; 0–25 °C.
  • Additive: CeCl3·7H2O (Luche reduction) can accelerate and increase chemoselectivity.
  • Workup: Quench with aqueous NH4Cl; extract with EtOAc.

• Baeyer–Villiger oxidation

  • Oxidant: mCPBA (1.5–2.0 equiv, 77% grade) in DCM.
  • Conditions: 0–25 °C, 2–12 h; buffer acid with NaHCO3 to mitigate chlorinated byproducts.

• Photochemistry (sensitization)

  • Solvent: Acetonitrile, toluene, or isooctane depending on substrate.
  • Light: 300–365 nm; inert atmosphere recommended.

Always verify compatibility of chloro substituents and avoid conditions that promote dehalogenation if those positions are required for downstream steps.

Safety and Handling

• Item-specific hazard 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 aryl ketones and chlorinated aromatics (informational; defer to SDS)

  • Potential hazards: Eye/skin irritation and respiratory irritation from dusts; harmful if swallowed/inhaled is common for related compounds. Chlorinated aromatics may exhibit aquatic toxicity—manage waste accordingly.
  • PPE: Use lab coat, safety glasses or splash goggles, and suitable chemical-resistant gloves (e.g., nitrile). Handle solids in a fume hood to avoid inhalation of dust or solvent vapors from solutions.
  • Incompatibilities: Strong oxidizing agents (risk of exotherm); strong reducing agents (may reduce the carbonyl); strong bases in combination with halide-bearing aromatics under forcing conditions may cause side reactions.
  • Fire safety: Organic solid; may burn releasing HCl/Cl-containing fumes. Use CO2, dry chemical, or foam. Avoid water jets on solvent-containing fires.
  • First aid (overview):
    • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
    • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical advice if irritation persists.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Handling tips: Minimize dust generation; weigh in a ventilated enclosure. Use sealed containers for storage and transport in the lab.

• Storage and shipping (from Product Data)

  • Storage: Room temperature.
  • Shipped in: Normal conditions.

Solvent Selection

• Polarity and miscibility (general guidance for chlorinated benzophenones)

  • Polarity class: Moderately nonpolar aromatic ketone; capable of dipolar interactions via the carbonyl.
  • Expected solubility: Good solubility in chlorinated solvents (DCM, chloroform), ethers (THF, MTBE), esters (EtOAc), ketones (acetone, MEK), and aromatics (toluene). Low water solubility.

• Choosing solvents by application

  • Purification: Recrystallization frequently succeeds from ethanol/IPA–water mixtures, ethyl acetate/hexanes, or toluene/hexanes, depending on impurity profile. Optimize empirically.
  • Synthesis: For cross-coupling on aryl chlorides, high-boiling polar aprotics (DMAc, NMP, dioxane) or toluene with tailored ligands are common. For reductions/oxidations, THF, MeOH, DCM, or acetonitrile are typical depending on reagent compatibility.
  • Spectroscopy: CDCl3 or DMSO-d6 for NMR; ACN or MeOH for LC–MS sample prep if ionization is needed (consider adduct formation and solubility limits).

• Comparison snapshot (general)

  • DCM vs. THF: DCM often gives rapid dissolution and easy workup; THF offers broader reagent compatibility and is preferred for organometallic reductions.
  • Toluene vs. dioxane: Toluene is greener and less coordinating; dioxane offers superior Pd-catalysis solvation at the cost of higher hazard classification.

Storage and Reconstitution

• Storage (from Product Data)

  • Store at room temperature in a tightly closed, inert container. Protect from light if photochemical work is anticipated (benzophenone cores are UV-active).
  • Shipped under normal conditions.

• Reconstitution/Preparation

  • Solid handling: If provided as a solid, dissolve in an appropriate dry organic solvent (e.g., DCM, THF, toluene, acetone, or EtOAc) to prepare stock solutions. Filter if particulates are present.
  • Concentrated stocks: For stability, prepare single-use aliquots and store in amber vials when light sensitivity is a concern.

• Stability considerations (general)

  • Substituted benzophenones are typically stable under ambient dry conditions. Avoid prolonged exposure to strong light/UV and strong acids/bases.
  • Water content, residual solvents, and assay purity: Not specified for this item; refer to CoA/Spec Sheet.

• Freeze–thaw

  • Not applicable unless solutions are prepared. If freezing solutions, ensure solvent suitability and headspace to accommodate expansion.

For exact shelf-life and retest periods, consult the product’s CoA/Spec Sheet and SDS.

Structure and Identity

Brief description: 2,4'-Dichloro-3'-methylbenzophenone is a substituted benzophenone featuring two chloro substituents and one methyl substituent distributed across the two aromatic rings of the benzophenone core.

• Item-specific identifiers (from Product Data)

  • CAS: 74617-45-1
  • InChIKey: 225594 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity (informational; not item-specific specs)

  • Common name parsing: “2,4′-dichloro-3′-methylbenzophenone” denotes a benzophenone (diphenyl ketone) where the unprimed ring bears a chloro at C-2, and the primed ring bears a chloro at C-4′ and a methyl at C-3′.
  • Molecular formula (literature, derived from substitution pattern): C14H12Cl2O
  • Molecular weight (literature): ~267.15 g/mol
  • Core functional group: aryl ketone (benzophenone)
  • Structural features: two fused phenyl rings linked via a carbonyl carbon; one ring electron-withdrawing (chloro), the other bearing both electron-withdrawing (chloro) and electron-donating (methyl) substituents.

• 2D structural description (general): The molecule consists of a central carbonyl (C=O) flanked by two phenyl rings. On ring A (unprimed), a chlorine is ortho (2-position) to the carbonyl linkage. On ring B (primed), a methyl is meta (3′) and a chlorine is para (4′) to the carbonyl connection. No stereocenters; planarity is partially disrupted by ortho substitution, reducing conjugation between rings.

Synthetic Utility

• Functional handles present

  • Aryl ketone (benzophenone): amenable to reductions (benzhydrols), imine/oxime formation, hydrazone chemistry, Baeyer–Villiger oxidation, and enolate-related reactivity under strong base (though aryl ketones have limited alpha-acidity when diaryl-substituted).
  • Two aryl chlorides: cross-coupling nodes for C–C (Suzuki, Negishi, Kumada under optimized conditions for aryl chlorides), C–N (Buchwald–Hartwig), and C–O couplings. Chlorides typically require more active catalyst systems than bromides/iodides.
  • Aryl methyl group (meta to carbonyl on one ring): potential site for directed metalation under strong base with appropriate directing groups, or benzylic oxidation under harsh conditions, though deactivation by adjacent chloro/ketone must be considered.

• Retrosynthetic value

  • Disconnection through the carbonyl suggests routes via Friedel–Crafts acylation of substituted arenes with the corresponding acid chloride/anhydride, or by nucleophilic acyl substitution using lithium/Grignard reagents to forge the diaryl ketone.
  • Halide positions enable late-stage diversification: install heteroaryl/alkyl substituents by Pd-catalysis to build small libraries around a conserved benzophenone core.

• Practical notes

  • Ortho-chloro substituent can twist the aryl–carbonyl bond, affecting reactivity and chromatographic behavior; anticipate slightly broadened aromatic signals in NMR.
  • Protect aryl chlorides during hydrogenation; use mild conditions and monitor for dehalogenation.

Target Specificity

Not applicable. This product is a small-molecule organic reagent and is not an antibody, enzyme, or affinity reagent. No antigen/epitope specificity applies.