4-Acetoxy-3',5'-dichlorobenzophenone , CAS No.890100-15-9

CAS: 890100-15-9 Cat. No.: A936205 Formula: C₁₅H₁₀Cl₂O₃ Peso molecolare: 309.14 PubChem CID: 24723042

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

• Sorrisi canonici: CC(=O)OC1=CC=C(C=C1)C(=O)C2=CC(=CC(=C2)Cl)Cl
• IUPAC Name: [4-(3,5-dichlorobenzoyl)phenyl] acetate
• InChIKey: BQRPODSQINSLNZ-UHFFFAOYSA-N
• INCHI: 1S/C15H10Cl2O3/c1-9(18)20-14-4-2-10(3-5-14)15(19)11-6-12(16)8-13(17)7-11/h2-8H,1H3
• Isomeri SMILES: CC(=O)OC1=CC=C(C=C1)C(=O)C2=CC(=CC(=C2)Cl)Cl
• PubChem CID: 24723042
• Peso molecolare: 309.14

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 Phenol esters Phenoxy compounds Dichlorobenzenes Benzoyl derivatives Aryl chlorides Carboxylic acid esters Monocarboxylic acids and derivatives Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzophenone - Aryl-phenylketone - Diphenylmethane - Phenol ester - Phenoxy compound - Aryl ketone - Benzoyl - 1,3-dichlorobenzene - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Carboxylic acid ester - Ketone - Carboxylic acid derivative - Monocarboxylic acid or derivatives - Organohalogen compound - Organochloride - Carbonyl group - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - 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: 309.100 g/mol
• XLogP3: 4.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 308.001 Da
• Monoisotopic Mass: 308.001 Da
• Topological Polar Surface Area: 43.400 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 354.000
• 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

Not applicable. No validated bioassay or immunoassay protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for representative procedures and optimization tips.

Biological Roles

This product is a synthetic aromatic building block and does not have an established endogenous biological role.

• General/contextual information (literature; not product-specific activity claims)
  • Benzophenone motifs are widely used as photochemical probes in chemical biology because their triplet states can abstract hydrogen and form covalent adducts upon UV irradiation. Substituents modulate absorption and reactivity.
  • Aryl acetates are common protecting groups for phenols; the phenolic variants can participate in protein-labeling workflows after further derivatization (e.g., aryl azides, diazirines), but such applications require additional functionalization.

No medical, diagnostic, or therapeutic uses are claimed or supported for this item; it is supplied strictly for research and laboratory use.

Buffer Applications

Not typically applicable. 4-Acetoxy-3',5'-dichlorobenzophenone is a neutral, poorly water-soluble organic building block and is not used to prepare aqueous buffer systems. For work in aqueous environments, dissolve in a compatible co-solvent (e.g., DMSO or acetonitrile) before dilution into buffer, and verify solubility and stability of the acetate under the buffer’s pH.

Green Alternatives

While the compound itself is a solid reagent, greener choices can be made in the transformations it undergoes.

• Solvent alternatives (literature guidance)

  • Replace chlorinated solvents (DCM/CHCl3) with ethyl acetate, 2-MeTHF, CPME, or Me-THF/toluene blends when solubility permits.
  • For Pd-catalyzed couplings of aryl chlorides, aqueous micellar media (e.g., TPGS-750-M) or green ethers (CPME, 2-MeTHF) have shown efficacy, often at lower catalyst loadings.

• Bases and reagents

  • Deacetylation: favor mild inorganic bases (K2CO3) in MeOH/EtOH over stronger bases to reduce waste and side reactions.
  • Reductions: prefer catalytic hydrogenation (H2, Pd/C) or transfer hydrogenation (isopropanol, Ru/C) over stoichiometric hydrides where compatible.

• Small comparison (general)

  Solvent | Conventional choice | Greener alternative | Trade-offs --- | --- | --- | --- Cross-coupling | dioxane/DMF | 2-MeTHF or CPME | May require ligand/base optimization Extraction/workup | DCM | EtOAc | Slightly higher boiling point; generally safer Deprotection | THF/MeOH | EtOH/Water (if compatible) | Monitor for hydrolysis selectivity

Adopt in-process controls (IPC) to minimize repeats and waste; recover and recycle Pd where possible.

Pharmaceutical Uses

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

• General context (no therapeutic claims)

  • Benzophenone derivatives can serve as synthetic intermediates during API route development (e.g., diversification by cross-coupling or reduction). The para-acetoxy handle enables late-stage unmasking of phenols, and the two aryl chlorides permit modular assembly.
  • This compound is not indicated as a pharmacopeial excipient. Any use in pharmaceutical manufacturing would be as a process intermediate in non-GMP research phases unless explicitly qualified.

• Practical considerations for formulation R&D

  • For screening or photochemical studies, prepare analytical stock solutions in DMSO or acetonitrile; evaluate stability against hydrolysis and photolysis.
  • If used in photolabeling tool synthesis, document photoreactivity and residual UV absorbers to ensure analytical specificity.

Physical Properties

• Item-specific (from Product Data)

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

• Literature/computed (general guidance; not item-specific specifications)

  • State: typically an aromatic, nonvolatile organic solid for benzophenone derivatives of this mass
  • Molecular formula (computed): C15H10Cl2O3
  • Molecular weight (computed): ~309.14 g/mol
  • Polarity: moderately lipophilic aryl ketone bearing weakly polar acetate; overall nonionic
  • Solubility (qualitative, literature):
    • Poorly soluble in water
    • Soluble in common organic solvents such as dichloromethane, chloroform, THF, acetone, acetonitrile, ethyl acetate, toluene; variable in alcohols; limited in aliphatic hexanes
  • UV/Vis: aromatic benzophenone chromophore typically absorbs in near-UV; exact λmax/UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
  • Melting point, boiling point, density, refractive index, logP, pKa: Not specified for this item; refer to CoA/Spec Sheet.

Notes for practitioners

• The benzophenone chromophore can interfere with UV detection in analytical HPLC (strong UV absorbance); adjust wavelengths accordingly.
• For preparative handling, solubility is often best in chlorinated solvents or polar aprotics (DCM, THF, MeCN).

Quality and Grades

• Item-specific information

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

• Guidance on grades (general)

  • Research-grade aryl ketones are typically supplied at high chemical purity suitable for synthetic and analytical work. When stated, “95%+” or “98%+” refers to assay by HPLC/GC/NMR; residual solvents, moisture, or inorganic residues are controlled per internal specifications.
  • If an HPLC or LC–MS grade is offered, it emphasizes low UV background/particulate for chromatographic applications; not generally necessary for routine synthesis.
  • Stabilizers: none are commonly used for benzophenone solids; if a stabilizer or inhibitor were present, it would be declared on the label/CoA as it can affect reactivity and purification.

• What to check on receipt

  • CoA for batch-specific assay, identity (NMR/HRMS), and residual solvent/water content. If application is moisture-sensitive (e.g., selective acetyl migrations), verify KF or water content where relevant.
  • For photochemical studies, confirm UV–Vis profile and any fluorescent impurities if necessary.

Note: Where a specific numerical specification is needed (water, metals, UV cutoff), this information is not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

• Functional handles

  • Aryl ketone (benzophenone): engages in photochemistry (triplet sensitizer), reductions to benzhydrols, and further acyl/alkyl manipulations at the carbonyl (e.g., Grignard addition to form tertiary alcohols).
  • Aryl acetate (para-acetoxy): protected phenol equivalent; readily deacetylated to the phenol, which can undergo etherification, esterification, or cross-coupling after conversion to aryl triflate.
  • 3′,5′-Aryl chlorides: serve as cross-coupling sites (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira) under Pd catalysis; can also participate in SNAr only under strongly activating conditions, which are less favored here.

• Typical synthetic uses (literature examples)

  • Selective deprotection to 4-hydroxy-3′,5′-dichlorobenzophenone with K2CO3/MeOH at ambient temperature.
  • Pd-catalyzed Suzuki coupling at aryl–Cl with aryl/alkenyl boron reagents using Pd(dppf)Cl2 or Pd-PEPPSI-type catalysts, elevated temperatures (90–120 °C).
  • Buchwald–Hartwig amination of the aryl chlorides with amines using BrettPhos/SPhos ligands under basic conditions.
  • NaBH4 or catalytic hydrogenation reduces the benzophenone carbonyl to the corresponding benzhydrol; subsequent acyl migrations should be monitored to preserve the acetate.
  • Photochemical applications leveraging the benzophenone triplet for H-abstraction or as a photolabeling handle (substituent pattern modulates photoreactivity).

• Application domains

  • Advanced intermediates for functional materials, UV-absorbing scaffolds, and photo-crosslinkers; structure enables subsequent diversification on both rings.

Reaction Conditions

General literature conditions for common transformations of this scaffold (guidance only; optimize per substrate and scale):

• Deacetylation to phenol

  • Conditions: K2CO3 (1–2 eq), MeOH or MeOH/THF, rt to 40 °C
  • Time: 0.5–6 h; monitor by TLC/HPLC
  • Notes: Avoid strong base if benzylic reduction or acyl migration is a concern.

• Suzuki–Miyaura coupling on aryl chlorides (3′,5′)

  • Catalyst: Pd(dppf)Cl2·DCM (1–3 mol%) or Pd-PEPPSI-type catalysts (0.5–1 mol%)
  • Ligand: dppf, XPhos, SPhos (if using Pd(OAc)2 precursor)
  • Base: K3PO4 or Cs2CO3 (2–3 eq)
  • Solvent: toluene/dioxane, 2-MeTHF, or CPME; H2O co-solvent (5–20%) can help
  • Temp: 90–120 °C; 4–16 h

• Buchwald–Hartwig amination

  • Catalyst/ligand: Pd2(dba)3 (0.5–1 mol% Pd) with BrettPhos or tBu-XPhos
  • Base: NaOtBu or Cs2CO3
  • Solvent: toluene or 1,4-dioxane
  • Temp: 80–110 °C

• Carbonyl reduction

  • NaBH4 (1.5–3 eq) in MeOH or EtOH, 0–25 °C, 0.5–2 h; or H2 (1–5 bar), Pd/C (5–10 wt%), EtOAc/EtOH, rt–40 °C

• Workup/purification

  • Quench into water/brine; extract with EtOAc or toluene; dry (Na2SO4). Purify by silica gel using hexanes/EtOAc gradients.

Note: Yields and exact conditions vary; consult primary literature and run small-scale scouts.

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 guidance for aryl ketone/aryl acetate solids (literature/industry practice)

  • Likely hazards: organic solids of this class may cause skin/eye irritation and respiratory irritation as dust. Avoid dust formation and inhalation.
  • PPE: lab coat, safety glasses or face shield, and chemical-resistant gloves (e.g., nitrile). Handle in a fume hood.
  • Storage incompatibilities: keep away from strong oxidizers and strong bases/acids that can promote hydrolysis/transesterification. Avoid prolonged exposure to strong UV light due to benzophenone photoreactivity.
  • Handling tips: minimize moisture if acetate integrity is critical; cap tightly after use. Use amber glass for long-term storage to limit photolysis.
  • First aid (overview; defer to SDS):
    • Skin/eyes: rinse with water for at least 15 minutes; remove contaminated clothing.
    • Inhalation: move to fresh air; seek medical attention if symptoms persist.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.

Always consult the product’s SDS for authoritative hazard, exposure limits, and emergency procedures.

Solvent Selection

This product is a functionalized benzophenone solid, not a solvent. Solvent choice is primarily to ensure dissolution for reactions or analytics.

• Solubility/miscibility profile (literature/general)

  • Good: dichloromethane, chloroform, THF, acetone, acetonitrile, ethyl acetate, toluene
  • Moderate/variable: methanol, ethanol, isopropanol (risk of slow acetate hydrolysis in basic alcohols)
  • Poor: water; aliphatic hydrocarbons (e.g., hexanes) unless mixed with more polar co-solvent

• Selection tips by use case

  • Nucleophilic substitutions/cross-couplings on aryl chlorides: toluene, dioxane, or CPME with polar co-solvent (e.g., t-BuOH, DMAc) can be effective; ensure ligand/base compatibility.
  • Deprotection of the acetate: MeOH or MeOH/THF with mild base (K2CO3) are common.
  • Preparative chromatography: elute on silica with gradients of hexanes/ethyl acetate or toluene/EtOAc; avoid strong basic modifiers that could hydrolyze acetate.

• Analytical

  • Prepare stock solutions in acetonitrile, DMSO, or dichloromethane for LC/UV. Filter (0.2 µm PTFE) before injections to protect columns.

Note: Exact solubility values are not specified for this item; verify experimentally at the working temperature/concentration.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions: Room temperature (per Product Data). Protect from light and moisture to preserve the aryl acetate and minimize photochemical changes.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General handling

  • Keep container tightly closed in a dry place. Use amber vials for long-term storage. Under typical lab conditions, the aryl acetate is stable, but prolonged exposure to strong base or high humidity can promote hydrolysis.

• Solution preparation (for research use)

  • Prepare concentrated stock solutions in dry DMSO, acetonitrile, dichloromethane, or THF. For biological assays requiring aqueous media, dissolve first in DMSO/MeCN and dilute into buffer while monitoring for precipitation.
  • Filter sterile stocks through 0.2 µm PTFE if needed. Avoid repeated freeze–thaw of solutions; aliquot and store at 2–8 °C or −20 °C as appropriate to the solvent used.

• Stability

  • Long-term solution stability depends on solvent and light exposure; assess by HPLC/LC–MS at intervals. Solid-state stability is typically good at room temperature when protected from light and humidity.

Research Use Note: For research use only.

Structure and Identity

Brief description: 4-Acetoxy-3',5'-dichlorobenzophenone is an aryl ketone bearing a para-acetoxy group on one ring and two chloro substituents (3′,5′) on the other, making it a versatile, functionalized benzophenone building block.

• Item-specific (from Product Data)

  • Product Name: 4-Acetoxy-3',5'-dichlorobenzophenone
  • CAS: 890100-15-9
  • CID: 24723042
  • InChIKey: 31884 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature structural information (not item-specific specs)

  • Core scaffold: benzophenone (diphenyl ketone)
  • Substituents: para-acetoxy (–O–C(O)CH3) on ring A; 3′,5′-dichloro on ring B
  • Functional groups: aromatic rings, aryl ketone (benzophenone carbonyl), aryl acetate (phenyl O-acetate), aryl chlorides
  • Stereochemistry: none (achiral)
  • Molecular formula (computed from structure): C15H10Cl2O3
  • Molecular weight (computed): ~309.14 g/mol

• 2D structure in words

  • A central ketone carbonyl links two phenyl rings. One phenyl bears a para-oxygen substituent further acylated with an acetyl group (acetoxy). The other phenyl ring carries two chlorine atoms at positions 3′ and 5′ (meta to the carbonyl linkage).

Synthetic Utility

• Strategic features

  • Orthogonal reactivity: aryl chlorides (cross-coupling), aryl acetate (protecting group chemistry), and benzophenone carbonyl (reduction/addition) allow stepwise functionalization.
  • Para-acetoxy as a traceless protecting group: deprotect to a phenol, convert to aryl triflate, then effect C–C or C–N coupling at the para position.

• Representative transformations (literature)

  • Deacetylation: K2CO3, MeOH, rt → phenol (high conversion, typically minutes–hours).
  • Triflation of phenol: Tf2O, pyridine/DCM, 0–25 °C → aryl triflate, then Suzuki–Miyaura coupling.
  • Cross-coupling on aryl–Cl: Pd(dppf)Cl2 or Pd/XPhos, base (K3PO4, Cs2CO3), 90–120 °C in toluene/dioxane/2-MeTHF.
  • Carbonyl manipulation: NaBH4 or catalytic hydrogenation to benzhydrol; Grignard addition (RMgX) or organolithium (RLi) to form tertiary benzhydrols; subsequent oxidations as needed.
  • Photochemistry: benzophenone triplet sensitization for intramolecular cyclization or intermolecular H-abstraction (requires UV irradiation; monitor to avoid acetate cleavage).

• Retrosynthetic value

  • Can be accessed from 4-hydroxy-3′,5′-dichlorobenzophenone via acetylation (Ac2O, DMAP). The dichloro ring offers two points for diversification, facilitating library synthesis.

Target Specificity

Not applicable. This product is a small-molecule building block and not a biological macromolecule or affinity reagent. No antigen/epitope or species selectivity applies.