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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
309.100 g/mol
XLogP3
4.300
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
372.000
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
Calculateurs de solution
Molarity Calculator
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Avis
Avis des clients
Application Protocols
No application protocols are provided in the Product Data for this item. As a synthetic building block, typical procedures align with standard organic synthesis protocols (e.g., coupling, deprotection, reduction) detailed under Reaction Conditions and Synthetic Utility.
If using in analytical contexts:
Prepare stock solutions in suitable organic solvents (e.g., DMSO, MeCN, DCM) at known concentrations.
Filter solutions (PTFE syringe filter, 0.2 µm) to remove particulates prior to HPLC/UPLC injections.
Protect from strong base/acid during sample prep to avoid ester hydrolysis (general guidance).
Biological Roles
This compound is a synthetic aromatic building block and is not known as a natural metabolite or a biochemical cofactor.
Benzophenone scaffolds can act as photoinitiators or photosensitizers due to n→π* transitions of the carbonyl conjugated to aromatics; any photochemical use should be validated for the specific substitution pattern.
Phenolic benzophenones (after deprotection of the acetoxy) may participate in hydrogen bonding and π–π interactions relevant to ligand–receptor studies in medicinal chemistry SAR campaigns. However, this product is sold strictly for research use, not for biological administration.
The presence of two aryl chlorides provides handles for late-stage diversification to generate analog libraries for in vitro screening (e.g., enzyme or receptor binding assays) conducted under appropriate laboratory safety and ethical guidelines.
No specific biological role, target, or pathway is assigned to this reagent in the Product Data. Any biological testing must be designed and interpreted by qualified researchers. Avoid any inference of pharmacological activity without dedicated experimental evidence.
Buffer Applications
Not typically applicable. 3-Acetoxy-2',3'-dichlorobenzophenone is a neutral, hydrophobic organic reagent with negligible aqueous solubility and no acid/base buffering capacity in the working biological pH range.
Practical note:
If used in aqueous biological assays (e.g., in vitro binding), dissolve first in a water-miscible organic cosolvent (e.g., DMSO, MeCN) and then dilute into buffer while keeping final organic content compatible with the assay. Determine solubility limits empirically. No item-specific solubility or buffer compatibility data are provided.
Green Alternatives
Greener choices pertain mainly to solvent and process design; the substrate itself is a halogenated aromatic, so end-of-life and EHS considerations should be addressed in waste handling.
Ethyl acetate for extractions and many reactions when polarity allows.
2-Methyltetrahydrofuran (2-MeTHF) as a bio-based ether for reductions, couplings, and organometallics (dry 2-MeTHF can substitute for THF in many cases).
Dimethyl carbonate (DMC) as an alternative medium or reagent where compatible.
Replace DMF/DMAc/NMP with:
Cyrene (dihydrolevoglucosenone) or propylene carbonate in certain polar-aprotic applications.
Reduce palladium loading in cross-couplings by employing highly active Pd precatalysts and tailored ligands; consider nickel catalysis for some aryl chloride couplings (with attention to scope and safety).
Comparison (general pros/cons):
2-MeTHF vs THF: greener, partially water-immiscible (simplifies workups), higher bp; may change reaction rates/selectivity.
EtOAc vs DCM: greener and less toxic; higher bp can lengthen concentration times; solvency different for highly polar solutes.
Aqueous ethanol/isopropanol: viable for NaBH4 reductions; reduces halogenated solvent waste.
Waste minimization:
Favor catalytic over stoichiometric halogen–metal exchange steps.
Implement in-process controls to avoid overreduction or hydrolysis, minimizing by-products.
Note: Validate substitutions with small-scale trials to confirm performance.
Pharmaceutical Uses
No pharmacopeial grade or excipient designation is provided for this product. It is supplied for research use only (Product Data: Research Use Note).
General R&D context (non-clinical, literature/general):
As a multifunctional benzophenone derivative, this compound can serve as a synthetic intermediate in medicinal chemistry for structure–activity relationship (SAR) exploration. Aryl chlorides allow cross-coupling to diverse functional groups; the acetoxy can be deprotected to a phenol for further derivatization (e.g., etherification, carbonate/urethane formation).
Potential roles in preclinical formulation screening are limited by low aqueous solubility; use organic vehicles or prodrug strategies in exploratory work. Any such use must remain within research settings and is not for human or veterinary administration.
Item-specific notes:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Regulatory status: No pharmacopeial listing is indicated in the Product Data.
Physical Properties
Item-specific physicochemical specifications are not provided in the Product Data for this SKU. Do not use the following as specifications; consult the CoA/SDS for authoritative values.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point / Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density / Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (general/literature expectations for aryl ketone acetates):
Organic solvents: Typically soluble in dichloromethane, chloroform, THF, acetone, ethyl acetate, toluene; solubility often increases with gentle warming (literature/general guidance).
Water: Expected to be negligibly soluble due to hydrophobic aromatic framework (literature/general guidance).
LogP, pKa: Not specified for this item; refer to CoA/Spec Sheet. (Phenolic pKa is masked by acetyl protection; no acidic proton in the acetoxy form.)
UV–Vis (qualitative): Benzophenone chromophores commonly absorb in near-UV; exact maxima depend on substitution (literature/general guidance). Not specified for this item; refer to CoA/Spec Sheet for any UV cutoff/absorbance limits.
Practical handling notes (general):
Solid or viscous oil behavior varies among substituted benzophenones; if solid, mild heating (30–40 C) may aid dissolution; avoid prolonged heating to prevent hydrolysis of the acetoxy group (general guidance).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on interpreting grades (general):
Research or laboratory grade indicates suitability for routine synthetic and analytical laboratory use. If HPLC/LC–MS grade is indicated on a specific lot, it typically implies tighter control of nonvolatile residue and UV-absorbing impurities, which can be important when the reagent is used in photochemical studies or analytical sample preparation (general information).
Stabilizers/inhibitors: None are listed in the Product Data. If stabilizers are present on a specific lot, they will be declared on the CoA and may influence certain reactions (e.g., base-sensitive transformations).
Trace limits (water, metals, peroxides, UV): Not specified for this item; refer to CoA/Spec Sheet.
What is specific to this SKU:
Storage: Room temperature (Product Data).
Shipping: Shipped under normal conditions (Product Data).
Recommendations:
For moisture-sensitive transformations (e.g., base-promoted reactions that risk ester hydrolysis), consider drying the reagent under vacuum and handling under inert atmosphere.
Verify assay/purity, residual solvents, and identity (NMR/HRMS/UPLC) as needed for sensitive applications.
Reaction and Applications
As a substituted benzophenone with an acetoxy-protected phenol and two aryl chlorides, this molecule is a versatile intermediate. The points below are literature/general guidance to help plan synthetic use; they are not specifications for this item.
Key application families:
Protecting-group chemistry: The acetoxy serves as a removable protecting group for the corresponding 3-phenol. Base-mediated deacetylation (e.g., K2CO3/MeOH) or catalytic transesterification can unveil the phenol for further elaboration.
Cross-coupling on aryl chlorides: 2′,3′-dichloro positions can participate in Pd-catalyzed couplings (Suzuki–Miyaura, Buchwald–Hartwig) using chloride-competent catalysts/ligands (e.g., Pd2(dba)3 + XPhos/SPhos; or precatalysts). Site-selectivity may be influenced by sterics/electronics.
Carbonyl transformations: The benzophenone can be reduced to the corresponding benzhydrol (NaBH4, catalytic hydrogenation), converted to oximes/hydrazones (NH2OH, hydrazine), or engaged in Grignard/organolithium additions for tertiary alcohol formation.
Directed functionalization: After deprotection to the phenol, ortho-directing effects enable further C–H functionalization/metalation on that ring.
Photo-Fries rearrangement (general): Aryl acetates can undergo photo-Fries to yield hydroxyacylated phenols under UV irradiation; outcomes depend on substitution and conditions.
Use contexts:
Scaffold diversification in medicinal chemistry and agrochemical discovery.
Precursor to polyfunctional ligands, photosensitive materials, or UV-absorbing motifs (via the benzophenone chromophore).
Practical tips:
Protect the acetoxy group from strong base/acid if not meant to be removed.
For couplings at aryl chloride, ensure rigorous degassing, dry solvent, and an efficient Pd(0) catalyst system; consider microwave assistance for challenging sites.
Reaction Conditions
The following are literature/general conditions frequently used with related functionalities. They are not item-specific specifications; optimize for your substrate and scale.
Deacetylation to phenol:
K2CO3 (1–2 equiv) in MeOH or MeOH/THF at rt to 40 C, 0.5–4 h; monitor by TLC/HPLC. Acidic workup to neutralize. Alternatively, NaOMe/MeOH (0.1–0.5 M) at 0–25 C for rapid deprotection.
Suzuki–Miyaura coupling at aryl chloride:
Pd2(dba)3 (1–2 mol%) + XPhos/SPhos (2–4 mol%) or Pd-PEPPSI precatalyst; base K3PO4 or Cs2CO3 (2–3 equiv); solvent dioxane/water (10:1) or toluene/EtOH/H2O; 80–110 C, 2–16 h. For challenging sites, use BrettPhos/RuPhos systems or microwave heating.
Buchwald–Hartwig amination:
Pd(OAc)2 (1–3 mol%) + BrettPhos/RuPhos (2–6 mol%); base NaOtBu or Cs2CO3; solvent toluene or dioxane; 90–120 C. For hindered amines, consider AlPhos/BippyPhos ligands.
Sonogashira coupling:
Pd(PPh3)2Cl2 (1–2 mol%) + CuI (1–5 mol%); base Et3N or i-Pr2NH; solvent THF or DMF; 25–70 C; copper-free protocols available with specialized ligands.
Carbonyl reduction:
NaBH4 (1.2–2.0 equiv) in MeOH/THF at 0–25 C, 0.5–2 h to benzhydrol. For chemoselectivity in presence of aryl chlorides/acetate, use milder hydride donors (NaBH(OAc)3 not effective for ketones; consider catecholborane with Lewis acid, or catalytic hydrogenation 1–5 bar H2, Pd/C in EtOH).
Oxime formation:
NH2OH·HCl (1.2–1.5 equiv) + pyridine or NaOAc buffer; EtOH or MeOH; rt–60 C, 1–6 h.
Monitor for ester hydrolysis under strong base; if undesired, protect conditions or reverse sequence (couple first, deprotect later).
Safety and Handling
GHS classification and hazard statements are not specified in the Product Data for this item. Always consult the product’s SDS for definitive safety information.
General safety guidance for aryl ketone/aryl ester compounds (literature/general):
Likely hazards: May cause skin/eye irritation and respiratory tract irritation if dust or vapor is generated. Avoid inhalation of dust and contact with skin/eyes.
PPE: Use lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a chemical fume hood to minimize exposure.
Storage incompatibilities: Avoid strong bases (risk of ester saponification), strong acids (acid-catalyzed hydrolysis), strong oxidizers, and strong reducing agents. Avoid prolonged UV exposure if photoreactivity is a concern for benzophenone cores.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation persists.
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
Spill/cleanup: Avoid dust generation. Collect mechanically; place in suitable container for disposal according to local regulations. Ventilate area.
Thermal/chemical stability: Esters can hydrolyze under acidic/basic conditions; aryl chlorides are generally stable but can undergo substitution under forcing conditions (general note).
Signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
Solvent Selection
This compound is a moderately lipophilic aryl ketone bearing an acetoxy group and two aryl chlorides. It behaves as a neutral, nonionic organic molecule.
General solubility/miscibility guidance (literature/general):
Preferred solvents for dissolution and reactions: dichloromethane (DCM), chloroform, THF, acetone, ethyl acetate (EtOAc), acetonitrile (MeCN), and toluene/xylene. Solubility often improves with mild warming.
Poorly soluble in water; biphasic systems may require a phase-transfer strategy if aqueous reagents are used.
Selection tips:
For base-sensitive steps (avoid ester hydrolysis): choose aprotic, non-basic solvents (DCM, toluene) or weakly basic polar aprotics (THF, MeCN) with controlled base equivalents.
For cross-coupling at aryl chlorides: 1,4-dioxane, toluene, or DMAc/DMF are commonly used (literature) with palladium catalysts; ensure the acetoxy group is compatible with conditions.
For reductions of the benzophenone carbonyl: protic (i-PrOH, MeOH) or mixed MeOH/THF with NaBH4; or EtOH/THF under catalytic hydrogenation (literature guidance).
Quick comparison (general):
DCM: excellent solvation, easy removal; not green; good for chromatography and functional group tolerance.
EtOAc/2-MeTHF: greener; good for extractions and many reactions; boiling point higher than DCM.
THF: versatile and coordinating; forms peroxides; dry grade recommended for air-/moisture-sensitive reactions.
Note: No item-specific solubility data are provided; confirm experimentally for your application.
Storage and Reconstitution
Storage conditions (Product Data): Store at room temperature. Protect from moisture and strong light; keep container tightly closed. Store in a dry, well-ventilated place.
Shipping (Product Data): Shipped under normal conditions.
Additional handling guidance (general):
Moisture sensitivity: The acetoxy group can hydrolyze under humid, basic, or acidic conditions. Use desiccation for long-term storage. Purge headspace with inert gas if frequently opened.
Reconstitution/solution preparation: If supplied as a solid, dissolve in an appropriate organic solvent such as DCM, THF, acetone, EtOAc, toluene, or MeCN. If supplied as an oil, handle with positive displacement pipettes and prepare solutions gravimetrically for accuracy.
Stock solutions: For biological assay development, DMSO stocks (10–100 mM) can be prepared; store aliquots at 2–8 C or −20 C to minimize repeated freeze–thaw. Confirm stability experimentally; no item-specific stability data are provided.
Stability: Item-specific limits (peroxides, water content, UV cutoff) are not specified; refer to the CoA/SDS. Avoid prolonged exposure to strong UV if photoreactivity could be problematic for benzophenone motifs.
Research Use Note: For research use only (Product Data).
Structure and Identity
Brief description: 3-Acetoxy-2',3'-dichlorobenzophenone is an aryl–aryl ketone (benzophenone core) bearing a phenyl acetate (acetoxy) substituent and two chloro substituents on the opposite ring.
InChIKey: 333351 (as provided; atypical format in Product Data)
SMILES: 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.
Synonyms (general/literature): 3-(Acetoxy)benzophenone bearing 2′,3′-dichloro substitution on the distal ring (literature description).
Structural features (general description):
Core: Benzophenone (diphenyl ketone) framework with a central carbonyl (Ph–CO–Ph').
Substituents: One ring carries an acetoxy group at the meta (3-) position; the opposite ring carries two chloro substituents at the 2′- and 3′-positions.
Stereochemistry: None (achiral); all substituents are on sp2 carbons in aromatic rings.
2D structure in words: Two benzene rings linked by a carbonyl carbon; on ring A, an –OAc group resides meta to the carbonyl-bearing ipso carbon; on ring B, chlorine atoms occupy the ortho and meta positions relative to the carbonyl-bearing ipso carbon.
Synthetic Utility
Functional handles and their strategic value (literature/general guidance):
Benzophenone carbonyl (Ph–CO–Ph′):
Reductions to benzhydrols (NaBH4, DIBAL-H, catalytic hydrogenation).
Carbon–carbon bond formation via nucleophilic addition (RMgX/RLi) to give tertiary carbinols; subsequent dehydration or further elaboration.
Formation of imines/enamines/oximes/hydrazones for derivatization or as UPLC/GC derivs.
Acetoxy group (Ar–OAc):
Protecting group for phenol; removable under mild basic conditions (K2CO3/MeOH, NaOMe/MeOH) or catalytic transesterification.
Entry to phenoxide-driven reactions (etherification with alkyl halides/activated sulfates; carbonate/carbamate formation).
Potential photo-Fries rearrangement to ortho/para acylphenols under UV.
Aryl chlorides (2′,3′-):
Cross-coupling (Suzuki–Miyaura, Buchwald–Hartwig, Sonogashira) using chloride-competent Pd or Ni catalysts/ligands; sequential or selective activation possible.
SNAr is unlikely without additional activation but may proceed under forcing conditions with strong nucleophiles if the ketone exerts sufficient deactivation.
Retrosynthetic perspective:
The target can arise from acylation of a substituted anilide/phenylmagnesium with the complementary acid chloride, or via Friedel–Crafts acylation on a protected phenol ring followed by selective chlorination/acetylation.
Orthogonality:
Many carbonyl chemistries tolerate aryl chlorides and acetates; plan sequences to avoid premature deprotection or undesired coupling.
Target Specificity
Not applicable. This product is a small-molecule reagent, not a biological antibody, enzyme, or affinity reagent. No target, antigen, clone, or species reactivity information is provided or relevant for this item.
We use cookies to ensure the website functions properly and, where permitted, to improve your experience. You can manage your preferences at any time in Settings. Learn more in our Cookie Policy.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
