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
295.560 g/mol
XLogP3
4.900
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
293.945 Da
Monoisotopic Mass
293.945 Da
Topological Polar Surface Area
17.100 Ų
Heavy Atom Count
16
Formal Charge
0
Complexity
248.000
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
No antibody- or assay-specific protocols are associated with this small-molecule building block.
Not applicable: WB, IHC, IF, FC, ELISA protocols and dilutions do not apply.
Practical laboratory usage (general):
Weigh solid quickly to minimize ambient moisture/contaminants.
Prepare stock solutions in suitable organic solvents (e.g., DCM, THF, toluene, DMF/DMSO) at known concentration for reproducible dosing into reactions.
For sequential cross-coupling, plan orthogonal conditions (e.g., Ar–Br first at milder conditions; reserve Ar–Cl for stronger ligand/catalyst systems). Record exact conditions per lot.
For any analytical protocols, validate methods (HPLC/GC, NMR) with appropriate reference standards.
Biological Roles
Item-specific biological information: Not specified for this item; refer to literature if designing biochemical experiments.
Literature/general context:
4-Bromo-3′-chlorobenzophenone is a synthetic, halogenated aromatic ketone with no known natural metabolic role. It is not a buffer component, nutrient, or typical cofactor.
Benzophenone chromophores are widely used as photoaffinity labels due to efficient triplet-state formation and C–H insertion under UV irradiation. While this particular derivative is not itself a probe, its benzophenone core can be elaborated into photo-crosslinking tools by appending handles (e.g., amines/azides) via the aryl halide sites.
Physicochemical profile (lipophilic, aromatic): tends to associate with hydrophobic environments (membranes, protein pockets) in model systems; however, binding is nonspecific without additional recognition elements.
Environmental/biological caution (general): Halogenated aromatics can exhibit persistence and bioaccumulation tendencies; handle with care to prevent environmental release. No item-specific ecotoxicology data are provided; consult SDS.
Use in biochemistry workflows:
As a scaffold to construct ligands, photoprobes, or affinity tags where the carbonyl provides spectroscopic handle and the dual aryl halides enable modular diversification.
Any biological testing should include appropriate controls and adhere to the “for research use only” restriction.
Buffer Applications
This compound is a hydrophobic aromatic ketone and is not used as a buffering agent or pH control component.
Applicability: Not typically applicable to buffer preparation, electrophoresis buffers, or cell culture media.
Practical note: If it must be introduced into aqueous biological systems, dissolve first in a compatible co-solvent (e.g., DMSO or ethanol) and then dilute into buffer with attention to final solvent percentage to avoid precipitation; verify compatibility with your bioassay.
Green Alternatives
While the substance itself is a solid building block (not readily replaced by a “green solvent” alternative), greener choices can be made in its use-phase and in route design.
Greener solvents for typical operations (literature/general):
Replace DMF/DMAc/NMP with 2-MeTHF, CPME, propylene carbonate, or toluene/ethanol mixtures when compatible with the catalyst/base.
Use aqueous micellar catalysis (e.g., TPGS-750-M) for Suzuki couplings at room temperature to reduce organic solvent load.
Catalysis choices:
Employ highly active Pd–ligand systems (SPhos/XPhos, PEPPSI-type NHCs) or Ni catalysts to enable lower catalyst loadings, milder temperatures, and improved energy efficiency.
Explore base and boron reagent selection (K3PO4, K2CO3 in water/green co-solvents; MIDA boronates for stability) to minimize waste.
Process intensification:
Continuous flow cross-coupling in safer solvents (e.g., 2-MeTHF or CPME) can enhance heat/mass transfer and reduce solvent volumes.
Comparative note (illustrative):
Traditional: Suzuki in DMF or dioxane, 100–120°C, 2–5 mol% Pd.
Greener option: Suzuki in 2-MeTHF/H2O or micellar water, 40–80°C, 0.1–1 mol% Pd or Ni (literature-reported), similar or improved yields.
Waste considerations:
Capture and recycle Pd/Ni from spent catalyst; select bases that produce benign salts (e.g., K2CO3). Avoid chlorinated solvents for scale where possible; if used for solubility, reclaim via solvent recovery.
Pharmaceutical Uses
Item-specific pharmacopeial status/grade: Not specified for this item; refer to CoA/Spec Sheet.
General, non-clinical context:
Role: Synthetic intermediate/building block. The dual aryl halides allow stepwise diversification to access benzophenone-derived scaffolds relevant to medicinal chemistry exploration (structure–activity relationship studies), without implying therapeutic use.
Excipient status: No pharmacopeial excipient role is known for this specific dihalobenzophenone. It is not used as a stabilizer, preservative, or process aid in approved formulations to our knowledge.
Process chemistry considerations: Useful for convergent assembly of diaryl ketone frameworks that can be subsequently functionalized (e.g., amination, arylation, alkynylation). The benzophenone can be reduced or transformed (e.g., to alcohols or benzhydryl derivatives) for further elaboration of lead compounds.
Analytical control: For GMP-related research flows, ensure identity/purity by orthogonal methods (NMR, HRMS with Br/Cl isotope patterns, HPLC). Control residual catalysts/solvents if used downstream in preclinical material synthesis.
Compliance reminder: For research use only. Not for human or veterinary therapeutic or diagnostic applications.
Physical Properties
Item-specific (from Product Data):
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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.
Literature/computed (general guidance; not item-specific specifications):
Expected physical state: Aromatic benzophenone derivatives of this type are typically crystalline solids at ambient conditions.
Solubility profile: Poorly soluble in water; readily soluble in common organic solvents such as dichloromethane, chloroform, THF, toluene, ethers, ethyl acetate, and polar aprotic solvents (DMF, DMSO). (literature/generic)
Density, melting point, boiling point, refractive index, UV cutoff, water content, residual metals: Not specified for this item; consult CoA/Spec Sheet or literature.
Lipophilicity: Dihalogenated benzophenones are typically lipophilic (high logP) owing to two aryl rings and halogens; exact logP not specified for this item.
Acid–base: Neutral aromatic ketone; no titratable protons in typical aqueous ranges (pKa not applicable). The carbonyl oxygen can engage in H-bond acceptance.
Spectroscopy (general):
1H NMR: Aromatic multiplets; downfield shifts influenced by halogens; absence of aliphatic signals.
13C NMR: Carbonyl around ~195–200 ppm; aryl C–Br/C–Cl appear downfield relative to unsubstituted aryl carbons. (literature)
Thermal behavior: Halogenated benzophenones may sublime or discolor on strong heating; avoid prolonged exposure to high temperatures (general precaution).
Quality and Grades
Item-specific quality data (from 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.
Interpreting typical grades (general guidance):
Research/technical grade: Suitable for most synthetic applications; may contain trace impurities that can affect sensitive catalysis.
High-purity/98–99%+ materials (when specified): Preferred for cross-coupling and lithiation chemistry to minimize catalyst poisons and side reactions.
HPLC grade (solvents) vs reagent grade (solids): For organic building blocks like dihalobenzophenones, low UV-absorbing impurities are desirable if using in photochemical studies or analytical method development.
Practical QC considerations for this class of compounds (general):
Identity confirmation: 1H/13C NMR, HRMS (M+ with characteristic isotope patterns of Br/Cl), and IR (strong C=O ~1650–1680 cm−1). The dual halogens produce distinctive M/M+2/M+4 isotopic envelopes.
Purity assessment: GC or HPLC for residual starting materials and positional isomers; check for dehalogenated benzophenones and oxidative byproducts.
Metals/solvent residues: If the material is to be used in Pd-catalyzed couplings, ensure low residual sulfurized impurities and water; specific metal or solvent limits are not specified for this item.
Documentation: Use the lot-specific CoA for definitive assay, residual solvents, and any stabilizer information.
Reaction and Applications
4-Bromo-3′-chlorobenzophenone is a versatile bifunctional building block combining an electrophilic aryl bromide, a less reactive aryl chloride, and an aromatic ketone.
Cross-coupling platform (literature/general):
Suzuki–Miyaura: Preferential coupling at the aryl–Br using Pd(0) catalysts; allows later activation of the aryl–Cl under more forcing conditions or with specialized ligands (XPhos/SPhos). Enables stepwise installation of two different aryl/alkenyl groups.
Buchwald–Hartwig amination: Amination at Ar–Br under mild conditions; Ar–Cl addressable with biaryl phosphines or NHC ligands at higher temperatures.
Sonogashira/Heck: Alkenyl/alkynyl introduction at Ar–Br; subsequent transformations on Ar–Cl.
Orthogonal reactivity:
The reactivity gradient (Br > Cl) supports sequential functionalization without protective groups on the carbonyl.
Site-selectivity can invert under nickel catalysis or with tailored ligands; screen conditions when selective Ar–Cl activation is desired.
Carbonyl transformations:
Reductions: NaBH4 or hydrosilanes typically reduce the ketone to the corresponding benzhydrol; stronger conditions (LiAlH4) tolerated but may risk halogen side reactions.
Nucleophilic additions: Grignard/organolithium additions form tertiary alcohols; control temperature to avoid halogen–metal exchange if undesired.
Baeyer–Villiger oxidation: Can yield aryl esters; migratory aptitude differences may influence regioselectivity.
Applications:
Divergent syntheses of tri- and tetra-aryl frameworks, ligand precursors, materials (OLED/OPV) scaffolds, and photoaffinity probe backbones leveraging the benzophenone chromophore.
Practical tips:
Dry, oxygen-free conditions enhance cross-coupling efficiency. Monitor for dehalogenation side products; use excess base/boronate and fresh Pd sources.
Reaction Conditions
Literature-typical conditions for dihalogenated benzophenones are provided as general guidance (not item-specific specs). Optimize for your substrate and scale.
Suzuki–Miyaura (selective Ar–Br coupling):
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (1 mol%) + PPh3/XPhos.
Base: K2CO3 or K3PO4 (2–3 equiv).
Solvent: Toluene/H2O, dioxane/H2O, 2-MeTHF/H2O.
Temperature/time: 70–100°C, 2–16 h.
Note: Ar–Cl often remains intact under these conditions for subsequent functionalization.
Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%).
Base: Et3N, i-Pr2NH, or Cs2CO3.
Solvent: THF, 2-MeTHF, or toluene; 25–80°C.
Carbonyl reduction to benzhydrol:
Reagent: NaBH4 (1–2 equiv) in MeOH/THF at 0–25°C; workup with water and extract. Stronger hydrides (LiAlH4) at 0–25°C in Et2O/THF if necessary.
Metal–halogen exchange (for lithiation):
n-BuLi or t-BuLi at −78 to −20°C in dry THF/Et2O; quench with electrophiles. Beware competitive addition to the carbonyl; protective strategies or temperature control may be needed.
Notes:
Use inert atmosphere (N2/Ar). Dry glassware/solvents are critical. Adjust catalyst loading based on substrate purity and scale.
Safety and Handling
Item-specific hazard data (from Product 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 halogenated aromatic ketones (literature/general):
Likely hazards: May cause skin/eye irritation and respiratory tract irritation; harmful if swallowed; combustible solid. Avoid dust generation.
PPE: Wear lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust or vapors from heated material.
Handling: Avoid contact with strong bases and strong nucleophiles that can induce undesired reactions at the carbonyl. Prevent exposure to strong reducing agents without proper controls. Minimize exposure to light; benzophenone chromophores can photosensitize under UV.
Storage incompatibilities: Keep away from strong oxidizers and strong bases. Segregate from reactive metals if performing metalation steps downstream.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for several minutes; remove contaminated clothing; seek medical advice if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Fire response: Use dry chemical, CO2, or foam. Combustion may release HBr/HCl and other toxic fumes; firefighters should wear self-contained breathing apparatus.
Always consult the product-specific SDS for authoritative hazard classifications and response measures.
Solvent Selection
This product is a nonpolar to moderately polar aromatic ketone, typically handled as a solid dissolved in organic media.
Poor solvents: Water and highly protic aqueous buffers.
Polarity/electronics:
The benzophenone carbonyl imparts moderate polarity and H-bond acceptor capability; two aryl rings and halogens confer strong hydrophobicity. Overall, solutions behave as nonpolar to moderately polar depending on solvent.
Choosing a solvent by operation:
Cross-coupling (Suzuki/Buchwald): Toluene, dioxane, CPME, 2-MeTHF, or mixed toluene/H2O systems; polar aprotic (DMF/DMAc) for challenging aryl chloride activation.
Metal–halogen exchange or lithiation: Etheral solvents such as THF, 2-MeTHF, or diethyl ether at low temperature; avoid protic media.
Nucleophilic additions/reductions to the carbonyl: THF, Et2O, or toluene for organometallic additions; i-PrOH/EtOH or MeOH for hydride reductions (workup controlled to prevent halogen displacement).
Crystallization/purification: Frequently crystallizable from hexanes/EtOAc or toluene/hexanes blends; adjust based on trial.
Comparison note:
Versus unsubstituted benzophenone, the dihalogenated derivative is less soluble in very nonpolar alkanes and shows higher affinity for chlorinated/aromatic solvents due to increased polarizability.
Storage and Reconstitution
Item-specific storage/shipping:
Storage Conditions: Room temperature (as provided).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General storage guidance for aromatic ketones:
Keep container tightly closed in a dry, well-ventilated place. Store in original container or amber glass to limit light exposure; benzophenone chromophores can photosensitize under UV.
Avoid prolonged heat; store away from strong bases, strong oxidizers, and reactive metals.
Reconstitution/solution preparation (general):
Dissolve in an appropriate organic solvent (e.g., dichloromethane, THF, toluene, ethyl acetate, DMF, DMSO). Gentle warming and sonication can assist dissolution; avoid excessive heat.
Prepare concentrated stock solutions (e.g., 0.1–1.0 M) according to solubility and intended use; filter if needed to remove particulates.
For aqueous work, use co-solvents and add slowly to aqueous phase with vigorous stirring to prevent precipitation.
Stability notes:
Under normal lab conditions, solid aromatic ketones are stable for extended periods. Monitor for discoloration or unexpected odors (indicative of degradation/contamination). For long-term storage, protect from light and moisture.
Always consult the lot-specific CoA/SDS for definitive handling and stability information.
Structure and Identity
Brief intro: 4-Bromo-3'-chlorobenzophenone is a dihalogenated benzophenone building block featuring both an aryl bromide and an aryl chloride on the two phenyl rings flanking a central ketone.
Item-specific (from Product Data):
SKU: B1064856
Product Name: 4-Bromo-3'-chlorobenzophenone
CAS: 27434-90-8
InChIKey: 315013 (as provided; appears non-standard/truncated—refer to CoA/SDS for definitive identifier)
Storage Conditions: Room temperature
Research Use: For research use only
Literature/computed identity (general reference; not item-specific specs):
2D structure (verbal): A benzophenone core (diphenyl ketone) with a carbonyl (C=O) connecting two phenyl rings; one ring bears a para-bromine (4-position relative to the carbonyl ipso carbon), the other ring bears a meta-chlorine (3′-position).
Functional groups/features: Aromatic ketone (benzophenone), one aryl–Br (more reactive in cross-coupling), one aryl–Cl (less reactive but addressable with modern catalysts), two deactivating halogens influencing ring electronics.
Notes:
The dihalogen pattern enables orthogonal cross-coupling strategies (e.g., selective activation of Ar–Br over Ar–Cl).
Synthetic Utility
This substrate offers orthogonal leaving groups on a benzophenone framework, enabling precise, stepwise diversification.
Functional group leverage:
Aryl bromide: Highly competent partner in Pd/Ni cross-couplings (Suzuki, Sonogashira, Heck, Kumada). Often reacts first under standard conditions.
Aryl chloride: Addressable with more active catalysts/ligands, allowing sequential installation strategies (Br then Cl), or selective activation with tailored systems for the reverse order.
Ketone: Platform for reductions (benzhydrol formation), nucleophilic additions (tertiary alcohols), imine/enamine chemistry after derivatization, and Baeyer–Villiger oxidation to aryl esters.
Retrosynthetic value:
Serves as a versatile branch point for libraries of triaryl and diaryl-alkenyl derivatives. The carbonyl can later be manipulated to diversify oxidation states without disturbing aryl substituents.
Suzuki–Miyaura at Ar–Br with boronic acids/esters; subsequent Buchwald–Hartwig amination at Ar–Cl to install anilines.
Sonogashira coupling at Ar–Br followed by hydrosilylation/hydrogenation to alkylarenes.
Wolff–Kishner or Clemmensen reduction of the ketone to diarylmethane motifs (conditions chosen to preserve aryl halides or applied after coupling).
Practical synthesis tips:
Use dry, oxygen-free conditions; halogenated benzophenones can undergo dehalogenation under harsh conditions—optimize catalyst/ligand to suppress.
Monitor regioselectivity carefully when both aryl halides are reactive (high temperatures/strong ligands). Employ stepwise temperature and ligand control to achieve orthogonality.
Target Specificity
This product is a small-molecule building block, not a biological targeting reagent.
Antigen/epitope, clone, isotype, and species reactivity: Not applicable.
No item-specific data for biological target binding or selectivity are provided. Any binding studies would be exploratory and outside the scope of this catalog entry.
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