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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
320.000 g/mol
XLogP3
6.000
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
319.914 Da
Monoisotopic Mass
317.917 Da
Topological Polar Surface Area
17.100 Ų
Heavy Atom Count
18
Formal Charge
0
Complexity
281.000
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
Lösungsrechner
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Application Protocols
Not applicable. No antibody or assay kit protocols are associated with this small-molecule building block.
For synthetic procedures, refer to the Reaction Conditions and Synthetic Utility sections for general, literature-based guidance.
For analytical methods, standard small-molecule protocols apply: NMR, IR (C=O stretch), LC–MS, HPLC/UPLC with UV detection (200–300 nm). Specific method validations are user- and project-dependent.
Biological Roles
This compound is a synthetic, halogenated diaryl ketone and does not have a known endogenous biological role.
Not a metabolite or cofactor in primary metabolism (literature/general).
Benzophenone cores can act as photochemical triplet sensitizers; while relevant to photochemistry, this is not a biological function and should not be conflated with bioactivity.
Due to hydrophobicity and halogenation, such compounds generally display low aqueous bioavailability and potential persistence; handling and disposal should therefore consider environmental stewardship rather than biological utility.
Researchers exploring interactions with biomacromolecules (e.g., photoaffinity labeling using benzophenone motifs) may use related scaffolds; however, any such use requires separate functionalization and rigorous safety/ethical approval. No specific biological targets or pathways are associated with Bis(3,4-dichlorophenyl)methanone in the provided Product Data.
Research use note: For research use only. Not for human or veterinary use. No clinical or diagnostic claims are made or implied.
Buffer Applications
Not typically applicable. Bis(3,4-dichlorophenyl)methanone is a hydrophobic organic building block, not a buffering agent.
It does not have acid/base functionality suitable for preparing aqueous buffer systems.
If used in any biochemical assay, dissolution would require organic co‑solvents (e.g., DMSO) at low percentages; buffer preparation itself should rely on standard buffering salts (phosphate, Tris, HEPES).
Green Alternatives
Greener considerations focus on solvent and reagent choices, since the substrate itself is a persistent, halogenated aromatic.
Prefer greener solvents where feasible:
Replace DCM/CHCl3 with EtOAc, MeTHF, CPME, or toluene when solubility and performance permit.
Use water/ethanol co‑solvent systems for reductions with NaBH4 if compatible (test solubility and chemoselectivity).
Catalysis and milder reagents:
For deoxygenation, consider catalytic transfer hydrogenation (e.g., Raney Ni or Pd/C with isopropanol/formate) instead of stoichiometric metal/acid when aryl chlorides must be retained.
For coupling at aryl chlorides, employ highly active Pd catalysts that operate in green solvents (e.g., aqueous micellar media) to reduce solvent impact.
Energy and waste:
Opt for flow photochemistry or LED sources if photochemical steps are used; avoid UV lamps with high energy consumption where possible.
Use solvent recycling and in‑process crystallizations to reduce chromatographic waste.
Compact comparison (literature/general):
DCM vs EtOAc: DCM has superior solvency but toxic/ozone‑depleting concerns (manufacture/disposal); EtOAc is biodegradable, lower toxicity.
THF vs 2‑MeTHF: Similar polarity; 2‑MeTHF is bio‑derived, forms fewer peroxides, higher boiling point enabling temperature flexibility; may solvate bases differently.
DMF/NMP vs Cyrene/PC: Dipolar aprotics like DMF/NMP are reproductive toxins; consider Cyrene or propylene carbonate for some coupling reactions if solubility and catalyst system allow.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided in the Product Data. This compound is offered for research use only.
Potential roles in a pharmaceutical R&D context (general): halogenated benzophenones can serve as synthetic intermediates en route to diarylmethanes, triarylmethanols, and extended aromatic frameworks used in medicinal chemistry SAR campaigns. Any application would be at the discovery/synthesis stage, not as a formulated excipient or API.
Regulatory/compendial: Not specified for this item; refer to CoA/Spec Sheet if any pharmacopoeia references exist for analogs.
Formulation notes (research scale): due to hydrophobicity, dissolution for screening typically uses DMSO stock solutions with subsequent dilution into assay media with careful control of final solvent percentage. Stability in such stocks should be confirmed experimentally.
Physical Properties
Item-specific physico-chemical specifications are not provided in the Product Data; consult the CoA/Spec Sheet for definitive values. The following are general/literature characteristics for this structure class (3,4,3′,4′-tetrachlorobenzophenone):
Physical state/appearance: Typically a crystalline solid (literature, diaryl ketone analogs). Specific appearance for this item: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable for solids; Not specified for this item; refer to CoA/Spec Sheet if an oil.
LogP: High hydrophobicity expected for tetra‑chloro diaryl ketones (literature/estimated, qualitative only).
Solubility (qualitative, literature):
Water: very low.
Organic solvents: soluble to freely soluble in chlorinated solvents (CH2Cl2, CHCl3), aromatics (toluene), and moderately polar aprotics (THF, EtOAc, acetone). Solubility increases with warming and on addition of polar aprotics.
UV–Vis: Benzophenone chromophore expected to absorb in the near‑UV; exact UV cutoff/absorbance: Not specified for this item; refer to CoA/Spec Sheet.
Note: Chlorination deactivates the rings and lowers electron density, modestly shifting spectroscopic features compared with unsubstituted benzophenone (literature).
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for assay, impurity profile, and identification results.
Context for professional users:
Diaryl ketone building blocks are commonly offered in research grade (suitable for synthesis, screening, and method development). When purity is specified, it typically reflects GC/HPLC area % with structure confirmation by NMR/HRMS/IR. Because this listing does not state a purity, verify fitness-for-purpose via the CoA.
UV absorbance/background: For photochemical or analytical applications, low UV absorbance impurities are important. If you plan to use this ketone as a photosensitizer surrogate or in photoredox workflows, request a chromatographic trace and residual solvent data.
Stabilizers: None are indicated for this product. If a stabilizer or inhibitor is present in a future lot, it will be disclosed on the CoA/label; consider implications for photochemistry and for reductions.
Trace metals/ionic contaminants: Not specified for this item; refer to CoA/Spec Sheet. For cross-coupling on the aryl chlorides, upstream metal content is typically not critical, but downstream analyses may require ICP screening.
Recommended incoming QC (user-side): quick 1H/13C NMR in CDCl3 or DMSO‑d6; IR (C=O ~1650–1680 cm−1, literature); HRMS to confirm exact mass; melting point range if solid; HPLC purity with DAD at 210–300 nm to capture benzophenone chromophore.
Reaction and Applications
As a tetra‑chloro benzophenone, Bis(3,4-dichlorophenyl)methanone is a robust aryl ketone building block. Typical laboratory uses (literature/general):
Reductive transformations:
Hydride reduction (NaBH4, DIBAL‑H, LiAlH4) to the corresponding tetra‑chloro benzhydrol; subsequent dehydration or substitution expands access to diarylmethane scaffolds.
Deoxygenation to diarylmethane via Wolff–Kishner (NH2NH2/KOH, heat) or Clemmensen (Zn(Hg)/HCl) conditions, tolerating the aryl chlorides better under WK.
C–C bond construction:
McMurry coupling (Ti(0)/TiCl3 or TiCl4/Zn) to generate a tetra‑chloro tetraphenylethene analog (stilbene‑like) by coupling two carbonyl carbons.
Grignard/organolithium addition to form tertiary carbinols with introduction of a third carbon substituent at the carbonyl carbon.
Aryl chloride derivatization:
Cross-coupling (Suzuki–Miyaura, Buchwald–Hartwig, Kumada) at the 3‑ or 4‑chloro positions using Pd or Ni catalysts with tailored ligands (e.g., BrettPhos, SPhos, XPhos) enabling functional diversification on one or both rings.
Condensation/derivatization:
Oxime/hydrazone/semicarbazone formation for characterization or as intermediates.
Enolate chemistry is limited (no α‑hydrogens), but the carbonyl participates in acyl transfer under strong conditions and in photochemical H‑abstraction (benzophenone-like sensitizer behavior).
Application domains (non-clinical): synthesis of halogenated polyaromatic intermediates for materials, pigments, and SAR exploration in agrochemical discovery, where chloro patterns and diaryl methanol/alkane derivatives are frequently probed.
Reaction Conditions
General literature guidance for typical transformations of tetra‑chloro benzophenones; optimize per substrate/scope.
Hydride reduction to benzhydrol:
Reagents: NaBH4 (1.5–3.0 eq) in MeOH, EtOH, or THF/MeOH at 0–25 °C; or LiAlH4 (1.2–2.0 eq) in dry THF/Et2O at 0–25 °C.
Workup: cautious aqueous quench; extract into EtOAc/DCM; purify by crystallization or silica (avoid strong UV during workup).
Deoxygenation to diarylmethane:
Wolff–Kishner: hydrazine/KOH in high-boiling solvent (DEG, DMSO) at 160–200 °C; aryl chlorides are typically tolerated.
McMurry: TiCl4/Zn or TiCl3/Zn in THF/toluene, 0–80 °C then reflux; inert atmosphere, strictly anhydrous. Forms alkene by dimerization; yields depend on sterics/electronics.
Cross-coupling at aryl chlorides:
Suzuki–Miyaura: Pd2(dba)3 or Pd(OAc)2 (1–3 mol%), SPhos/XPhos/Buchwald ligands, K3PO4/K2CO3 base, toluene/dioxane/H2O or CPME/H2O, 80–110 °C, 6–24 h.
Buchwald–Hartwig amination: Pd2(dba)3 + BrettPhos or RuPhos, NaOtBu or Cs2CO3, dioxane/toluene, 90–120 °C.
Sonogashira (copper-free): Pd(PtBu3)2, DBU, toluene or DMAc, 60–100 °C.
Photochemistry:
Triplet sensitization under 350–365 nm LEDs with H‑donors (iPrOH, amines), oxygen exclusion to favor ketyl formation; monitor to avoid overreduction.
Notes:
This substrate is electron-poor; aryl chloride activation still requires optimized ligands/catalysts.
Provide rigorous drying (oven-dried glassware, anhydrous solvents) for organometallics and Ti-mediated couplings.
Expected yields are highly protocol-dependent; consult primary literature for closely related chloro‑benzophenone examples.
Safety and Handling
GHS/SDS details are product- and lot-specific and are not provided here. Always consult the Aladdin Scientific SDS for SKU B1038787 prior to use.
GHS classification, signal word, pictograms, H‑statements: Not specified for this item; refer to SDS.
Anticipated hazards (general for chlorinated diaryl ketones; not a specification): may cause skin/eye irritation; harmful if swallowed or inhaled; environmentally hazardous to aquatic life due to persistence/hydrophobicity.
PPE: laboratory coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control dust/vapor and potential photochemical byproducts.
Handling notes:
Avoid dust generation; prevent inhalation and skin contact.
Diaryl ketones can undergo photochemical reactions; minimize strong UV exposure during handling and storage.
Keep away from strong bases and strong reducing agents when not intended—these may reduce the ketone to benzhydrols/diarylmethanes.
Avoid contact with strong oxidizers.
First aid (general):
Skin/eye: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention as needed.
Inhalation: move to fresh air; obtain medical attention if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Use CO2, dry chemical, or foam. Combustion may produce HCl, CO/CO2, and chlorinated aromatics—wear SCBA.
Spills/waste: Collect solids by inert absorbent; place in labeled container. Dispose according to local regulations; avoid release to the environment.
Solvent Selection
This compound is a hydrophobic, chlorinated diaryl ketone. Practical solvent guidance (literature/general):
Polarity/miscibility class: nonpolar to moderately polar aprotic solute; very low water solubility.
Good solvents for dissolution, recrystallization, and reactions:
Aromatic: toluene, chlorobenzene (useful for higher-temperature reactions and cross-couplings on the aryl chlorides).
Polar aprotics: THF, 1,4-dioxane, acetone, ethyl acetate, acetonitrile (often adequate; choose by reaction needs and temperature).
Poor solvents: water, very nonpolar alkanes (heptane/hexane) unless hot or with co‑solvent.
Selection tips:
For reductions (NaBH4, DIBAL, LAH): THF, Et2O, or MeOH/THF mixtures (NaBH4) are common; control exotherm and quench carefully.
For McMurry couplings or deoxygenations: THF, dioxane, or toluene under rigorously anhydrous, inert conditions.
For Pd-catalyzed cross-coupling at the aryl chloride positions: toluene, dioxane, or DMF/NMP with tailored ligands; add water to promote base solubility if needed.
Comparison (literature/general):
DCM vs EtOAc: DCM offers superior solubility and fast evaporation; EtOAc is greener and suitable for chromatography and some recrystallizations.
Toluene vs THF: Toluene allows higher temperatures for sluggish substitutions; THF supports organometallics and hydride reductions but requires peroxide control and water exclusion.
Light/moisture: Store tightly closed in a dry place; minimize exposure to strong light/UV to limit photochemical reactions typical of benzophenones.
Container: Use amber glass with PTFE-lined cap where possible; purge headspace with inert gas for long-term storage if frequent photochemical applications are planned.
Stability: Item-specific stability data are not provided; for long projects, verify by periodic NMR/HPLC.
Reconstitution/dissolution (general):
Readily dissolves in DCM, CHCl3, toluene, THF, acetone, and EtOAc (literature/qualitative). Warm gently and sonicate if needed.
Prepare concentrated stock solutions in dry solvents for moisture-sensitive reactions; filter if particulates remain.
Shipping: Not specified for this item; refer to CoA/Spec Sheet. Given ambient stability, standard ambient shipment is typical unless local regulations dictate otherwise.
Research use note: For research use only. Not for human or veterinary use.
Before use, allow any shipped container to equilibrate to room temperature to avoid condensation ingress on opening. Re-close promptly after dispensing to maintain material quality.
Structure and Identity
Bis(3,4-dichlorophenyl)methanone is a diaryl ketone (a tetra‑chlorinated benzophenone) featuring two 3,4‑dichloro‑substituted phenyl rings flanking a central carbonyl.
CAS: 75795-07-2 (Product-specific)
PubChem CID: 2760559 (Product-specific)
InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: C13H6Cl4O (literature)
Molecular weight: ~320.00 g/mol (literature, calculated from formula)
Structural features (descriptive):
Core scaffold: benzophenone (diphenyl ketone) bearing a single carbonyl (C=O) conjugated with two aryl rings.
Substitution pattern: each ring is dichloro at the 3- and 4-positions (meta- and para- relative to the carbonyl-bearing carbon), giving a 3,4,3′,4′-tetrachloro substitution overall.
Functional groups: one ketone (aryl–CO–aryl); four aryl chlorides (deactivated rings, potential for cross-coupling under suitable Pd/Ni catalysis).
Stereochemistry: none (achiral, planar conjugated ketone with restricted rotation relative to the carbonyl).
2D description in words: a central carbonyl carbon double‑bonded to oxygen, single‑bonded to two ipso carbons of chlorinated phenyl rings. On each phenyl ring, chlorine atoms occupy adjacent positions (3 and 4) distal from the carbonyl, creating a deactivated, electron-poor aryl system due to both the carbonyl and chloro substituents.
Synthetic Utility
Key reactivity derives from the aryl–CO–aryl ketone and from the four aryl chlorides.
Cross-couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Kumada) enable late-stage diversification at 3/4‑positions. Aryl chlorides demand more active catalysts/ligands (e.g., Pd(0) with biaryl phosphines or Ni with NHCs). Orthogonal reactivity can allow mono‑ vs di‑functionalization.
SNAr is possible only under forcing conditions due to modest activation; 4‑Cl positions para to the carbonyl may be more reactive.
Photochemistry:
Benzophenone-like triplet sensitization enables hydrogen abstraction from suitable donors to form ketyl radicals; this can be leveraged in polymer/photo-crosslinking studies or in synthetic photoreductions (literature/general), subject to solubility and substitution effects.
Retrosynthetic value:
Accessible via double Friedel–Crafts acylation (or stepwise acylation) using 3,4‑dichlorobenzene derivatives and phosgene equivalents/acid chlorides under Lewis acids, or via coupling of aryl reagents to a benzoyl chloride intermediate, offering multiple synthetic entry points.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent. No antigen/epitope, isotype, or species reactivity information applies.
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