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
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
274.700 g/mol
XLogP3
3.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
4
Exact Mass
274.04 Da
Monoisotopic Mass
274.04 Da
Topological Polar Surface Area
43.400 Ų
Heavy Atom Count
19
Formal Charge
0
Complexity
334.000
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule chemical.
For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for general literature-style procedures.
If preparing stock solutions for assays, typical practice is to dissolve in dry DMSO to 10–50 mM, filter if needed (PTFE syringe filter), and store aliquots at low temperature; validate concentration by UV or quantitative NMR as appropriate for your workflow.
Biological Roles
Item-specific: This product is provided for research use only; no biological role is assigned in the catalog entry.
General/literature context (no clinical claims)
Benzophenone scaffolds are widely used in chemical biology as photoaffinity labels due to their triplet-state reactivity under UV irradiation; substitution patterns tune photophysical properties. Whether this specific derivative is suitable depends on system-specific validation.
Aryl acetates can serve as protected phenols; phenolic derivatives of benzophenones appear in materials and photochemistry research. Any biological interaction would be context-dependent and requires empirical determination.
The presence of an aryl chloride provides a vector for late-stage diversification to libraries for target screening; however, target engagement and potency are not implied.
Environmental/biodegradation note (general): Polyaryl ketones tend to be hydrophobic with limited aqueous mobility; treat waste streams accordingly and avoid release to the environment.
Buffer Applications
This compound is a hydrophobic aryl ketone/aryl ester and is not a buffering agent. It does not define useful acid/base equilibria in water within physiological pH ranges.
Practical guidance
For aqueous work, dissolve in a co-solvent (DMSO, DMF, MeCN, or EtOH) before dilution into buffers if absolutely required, keeping final organic content compatible with your system.
If hydrolysis to the phenol is intended in aqueous media, use defined base (e.g., carbonate or hydroxide) rather than relying on buffer capacity.
No specific buffer systems are recommended for this item.
Green Alternatives
This SKU is a solid reagent; green considerations center on solvent and reagent choices during its use.
Greener solvent choices (literature guidance)
Replace DCM/CHCl3 with ethyl acetate, 2-MeTHF, CPME, or toluene where feasible.
For polar reactions, consider MeCN or propylene carbonate before DMF/DMAc/NMP (EHS concerns); water–alcohol mixtures for hydrolyses.
Base-promoted deacetylation: Employ K2CO3 in MeOH/EtOH (mild) before switching to strong bases.
Coupling chemistry: Modern Pd-ligand systems can reduce catalyst loading; consider recyclable catalysts or Ni catalysts where compatible.
Waste minimization
Plan telescoped sequences: hydrolysis → subsequent coupling on phenol as one-pot when appropriate.
Use in-process controls (TLC/UPLC) to avoid overreaction and reduce rework.
Pharmaceutical Uses
Item-specific: No pharmacopeial status or excipient role is specified for this SKU. For research use only.
General formulation/manufacturing context (no therapeutic claims)
Aromatic ketones such as benzophenone derivatives are sometimes used as synthetic intermediates in the preparation of more complex molecules. The acetoxy group can act as a protecting group for phenols during multistep synthesis.
Due to hydrophobicity, if used in discovery screening, compounds of this class are typically prepared as DMSO stock solutions and diluted into assay media with attention to final solvent percentage and potential adsorption to plastics.
No established role as a pharmaceutical excipient is indicated; any use in cGMP settings would require independent qualification and specification control.
For regulatory or excipient-related inquiries, consult appropriate pharmacopeial references and perform a formal risk assessment; this product is not supplied under GMP.
Physical Properties
Item-specific (Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet. (Calculated literature value provided below for reference.)
Literature/computed (non-spec; for planning only)
Formula: C15H11ClO3 (derived from the name)
Molecular weight: ~274.70 g/mol (calculated)
Physical state: likely solid at ambient temperature (typical for substituted benzophenones)
Solubility (qualitative): expected to be sparingly soluble in water; soluble in common organic solvents such as dichloromethane, chloroform, ethyl acetate, acetone, toluene; higher solubility in polar aprotics (DMF, DMSO) (literature trends for aryl esters/benzophenones)
UV/Vis: benzophenone chromophore typically shows strong absorption in the UV (near 250–260 nm and 320–350 nm regions) (literature, qualitative). Specific UV cutoff or extinction coefficients are Not specified for this item; refer to CoA/Spec Sheet.
Do not treat any values here as specifications. For exact MP/BP, density, refractive index, residuals, metals/UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet.
Quality and Grades
Item-specific (Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpretation
If provided as “research grade,” this denotes suitability for general laboratory synthesis and method development, not for clinical or GMP applications.
Where “≥98%” or higher purities are offered (not specified here), users can typically expect reduced levels of aromatic impurities and starting-material carryover; however, confirm via the CoA for the supplied lot.
For photochemical or analytical applications, low-UV-absorbing solvent residues and well-defined impurity profiles are important; verify via CoA (e.g., residual solvents by GC, HPLC purity, water by KF). Specific numeric limits for this SKU are Not specified for this item; refer to CoA/Spec Sheet.
Suitability notes
Aryl acetates can hydrolyze under basic moisture; if your application is base-sensitive, request recent CoA and consider verifying by NMR/LC to ensure integrity of the acetoxy group.
If coupling on the 2′-chloro position is planned, trace metal content may influence catalysis; metals limits for this SKU are Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
Functional handles present
Aryl chloride (2′-Cl) suitable for Pd-catalyzed cross-coupling (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira) under appropriately activated conditions.
Para-acetoxy aryl ester (4-OAc) that can undergo hydrolysis/deprotection to reveal the corresponding phenol, enabling further diversification (e.g., etherification, esterification, carbonate/urethane formation).
Benzophenone carbonyl enabling photochemical sensitization or further transformations (e.g., reduction to benzhydrols, oxime formation, imine/enamine chemistry with amines).
Typical synthetic uses (literature examples)
Saponolysis: 4-acetoxy → 4-hydroxy derivative under K2CO3/MeOH or NaOH/MeOH–H2O at rt–50 °C.
Fries rearrangement: Lewis-acid-mediated migration (e.g., AlCl3, BF3·Et2O) of the acyl group to ortho/para positions to access hydroxyacylated benzophenones.
Cross-coupling on Ar–Cl: Pd2(dba)3 or Pd(OAc)2 with bulky electron-rich ligands (XPhos, SPhos, BrettPhos) at 80–120 °C in toluene/dioxane/DMF for C–C/C–N bond formation.
Photochemistry: benzophenone triplet sensitization in UV-initiated processes; substitution pattern modulates triplet energy and H-abstraction ability (use only if compatible with your system).
Practical notes
Keep basic media dry if preserving the acetoxy group; adventitious base/water can partially hydrolyze.
For coupling, halide at the 2′-position may be more challenging (sterics); optimize ligand/base and temperature.
Purification generally straightforward by silica gel; avoid strong base in eluents to prevent transesterification/hydrolysis.
Manufacturer Applications: Not specified beyond “Research use only”; the above expands general synthetic opportunities consistent with the functional groups present.
Reaction Conditions
The following are literature-style general conditions to guide method planning; optimize for your substrate and scale.
Hydrolysis (deacetylation to phenol)
Base: K2CO3 (1–2 equiv) in MeOH or MeOH/H2O (9:1), rt–40 °C, 1–3 h. Alternative: NaOH (0.5–1.0 M aq) in MeOH/H2O at 0–25 °C for faster rates. Monitor by TLC/LC.
Fries rearrangement (aryl acetate migration)
Catalyst: AlCl3 (1–3 equiv); solvent: DCM, 1,2-DCE, or nitrobenzene; temp: 0 °C to reflux; time: 1–6 h. Work up cautiously to quench Lewis acid.
Cross-coupling at Ar–Cl (2′-position)
Suzuki–Miyaura: Pd2(dba)3 (1–2 mol%) + XPhos/SPhos (2–4 mol%); base: K3PO4 or Cs2CO3 (2–3 equiv); solvent: toluene/dioxane/DMF; 90–110 °C; 4–16 h.
Buchwald–Hartwig amination: Pd(OAc)2 (1–3 mol%) + BrettPhos or RuPhos ligand; base: NaOtBu or Cs2CO3; solvent: toluene/dioxane; 90–120 °C.
Sonogashira: Pd(PPh3)2Cl2 (1–3 mol%) + CuI (2–5 mol%); base: Et3N or i-Pr2NH; solvent: THF or DMF; 50–80 °C.
Carbonyl reduction
NaBH4 in MeOH/EtOH at 0–25 °C; or catalytic hydrogenation (Pd/C, H2 1–3 bar) in EtOAc/EtOH at rt–40 °C.
Photochemistry
UV irradiation (e.g., 300–365 nm) in appropriate solvent under inert atmosphere for triplet-sensitized processes; include actinometry and shielding as needed.
Yields, selectivities, and exact conditions are substrate- and scale-dependent; conduct small-scale optimization and maintain anhydrous, oxygen-controlled conditions where required.
Safety and Handling
Item-specific (Product Data)
Storage Conditions: Room temperature
GHS/Signal word/H-statements/Pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/analogous compounds; not a substitute for SDS)
Likely hazards: May cause skin/eye irritation; harmful if swallowed or inhaled. Aromatic ketones and aryl esters can be irritants. Avoid dust and aerosols.
PPE: Lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust/vapor.
Incompatibilities: Strong bases/acids can hydrolyze the acetoxy group; strong oxidizers may react with the aromatic system; strong reducing agents may affect the carbonyl. Avoid prolonged UV exposure if photoreactivity is a concern.
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; seek medical advice if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire safety: Use dry chemical, CO2, or foam. Combustion may produce CO/CO2/HCl-containing fumes.
Always consult the product’s SDS for authoritative, batch-specific hazard and response information.
Solvent Selection
This product is a solid building block/intermediate rather than a solvent. Solvent choice pertains to dissolving/processing it.
Polarity and solubility (literature-based expectations)
Poor: water and very protic, highly hydrogen-bonding media at neutral pH.
Selection tips by task
Hydrolysis/deprotection of the acetoxy group: MeOH/H2O with base (K2CO3, NaOH); EtOH/H2O also common.
Electrophilic acyl transfer or Fries rearrangement: non-nucleophilic chlorinated aromatics (DCM, 1,2-DCE) or nitrobenzene are often used with Lewis acids.
Cross-coupling at the aryl chloride: polar aprotics with high boiling points (DMF, DMAc, NMP, dioxane) or toluene/tert-amyl alcohol mixtures under Pd catalysis.
Chromatography: silica gel eluted with hexanes/EtOAc or toluene/EtOAc gradients.
Small comparison (literature)
DCM vs EtOAc: DCM dissolves faster and allows low-temperature operations but is less green; EtOAc is greener and often adequate for workups/purifications.
DMF/DMSO vs MeCN: DMF/DMSO give superior solubility for polar reactions but are harder to remove; MeCN is more volatile and sometimes sufficient if solubility allows.
Storage and Reconstitution
Item-specific (Product Data)
Storage Conditions: Room temperature
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance
Store tightly closed in a dry place, protected from excessive heat and direct light.
Avoid prolonged exposure to basic vapors or moisture to minimize hydrolysis of the acetoxy group.
If long-term storage is planned, consider an inert atmosphere (argon/nitrogen) and desiccant.
Preparation of solutions (literature practice)
Stock solutions: Dissolve in anhydrous DCM, THF, toluene, DMF, or DMSO as needed. For bioassay stocks, dry DMSO (10–50 mM) is common.
Filtration: If particulate is present, filter through a PTFE (or PES for polar solvents) 0.2–0.45 µm membrane.
Storage of solutions: Refrigerate (2–8 °C) or freeze (−20 °C) in amber vials; minimize freeze–thaw by aliquoting. Assess stability before use; hydrolysis may occur in basic or wet solvents.
Reconstitution
No aqueous reconstitution is recommended due to low water solubility; use an organic solvent first, then dilute into aqueous systems with surfactant or co-solvent if necessary.
Always consult the CoA/SDS for lot-specific storage and handling instructions. Research use only.
Structure and Identity
Item-specific (Product Data)
SKU: A988855
Product Name: 4-Acetoxy-2'-chlorobenzophenone
CAS: 185606-03-5
InChIKey: 191221 (as provided)
Storage Conditions: Room temperature
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (identity and structure; non-spec):
Structural features: diaryl ketone (benzophenone core), one ring bearing an ortho-chloro substituent (2′-Cl) and the other ring bearing a para-acetoxy substituent (4-OAc). Contains an aryl chloride, an aryl ester, and a conjugated benzophenone carbonyl.
2D description: Two phenyl rings connected via a central carbonyl (C=O). On ring A, the carbonyl is flanked by a chlorine at the ortho position. On ring B, the para position relative to the carbonyl bears an acetoxy group (–O–C(=O)–CH3). No stereocenters; planar conjugated system is expected around the benzophenone core.
Notes
Any structural depictions above are for general reference; for release-specific identity attributes consult the CoA/SDS.
Synthetic Utility
Retrosynthetic value
The 4-acetoxy group masks a phenol: facile unmasking provides 4-hydroxy-2′-chlorobenzophenone, a versatile handle for etherification (Williamson), esterification, carbonate/urethane formation, and metal–phenoxide-mediated couplings.
The 2′-chloro substituent enables cross-coupling diversification to biaryl, aryl-alkynyl, or aryl-amine derivatives using Pd catalysis and appropriate ligands.
Transformations (literature precedents)
Deprotection: K2CO3/MeOH or Na2CO3/MeOH–H2O, rt–50 °C, 0.5–4 h, to phenol in good yields.
Reduction of the benzophenone carbonyl: NaBH4 or catalytic hydrogenation (e.g., Pd/C under H2) to the corresponding benzhydrol, followed by further functionalization.
Oxime/hydrazone formation: reaction with hydroxylamine or hydrazines for derivatization or purification handles.
Fries rearrangement: AlCl3 (1–3 equiv), 0 °C to reflux, to generate acylphenols regioselectively (conditions dictate ortho/para ratio).
Cross-coupling: Suzuki–Miyaura with aryl/alkenyl boron species (Pd/XPhos or SPhos, base K3PO4 or Cs2CO3, 80–120 °C). Buchwald–Hartwig amination to install anilines under BrettPhos-type ligands.
Strategic notes
Orthogonal handles (Ar–Cl and Ar–OAc) allow stepwise diversification; sequence planning can exploit chemoselectivity (e.g., couple at Ar–Cl first, then deprotect phenol).
Protecting-group stability: the acetoxy survives many neutral/acidic couplings but is labile to base and nucleophiles.
Target Specificity
This product is a small-molecule chemical and is not an antibody, enzyme, or biological probe with defined target specificity.
Item-specific data such as antigen/epitope, species reactivity, clone, or isotype: Not applicable to this compound and not provided in the Product Data.
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