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.
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Application Protocols
Not applicable. No bioassay or immunoassay application data (e.g., WB, IHC, IF, FC) are provided for this small-molecule building block.
General handling protocol (chemistry lab context):
Weigh the solid quickly in a dry environment.
Dissolve in an appropriate organic solvent (e.g., DCM, THF, DMF, DMSO) to prepare stock solutions for reactions or analyses.
Filter if necessary to remove particulates prior to chromatographic injection.
For analytical HPLC, use a compatible organic mobile phase (ACN/MeOH with modifier) and monitor at 254–280 nm, exploiting the benzophenone chromophore.
Biological Roles
This product is a synthetic, halogenated benzophenone building block and is not a biological reagent per se.
General/literature context (not product-specific and not for clinical use):
Ortho-hydroxybenzophenones can act as intramolecularly H-bonded phenols with tautomeric (enol–keto) character; some analogs serve as UV absorbers due to excited-state intramolecular proton transfer (ESIPT). The presence of heavy atoms (Br, Cl) can influence intersystem crossing and fluorescence/ phosphorescence yields.
In biochemical settings, hydrophobic benzophenones have been used as photoaffinity labels; however, specific activity requires diazirine/azido functionalities which this molecule lacks. Any biological usage would require derivatization and thorough validation.
Research use only note (from Product Data): For research use only. No medical, diagnostic, or therapeutic claims are made or implied.
Buffer Applications
Not typically applicable. 5-Bromo-2′-chloro-2-hydroxybenzophenone is a hydrophobic organic building block, not a buffering agent.
Practical note:
If preparing assay solutions or stock solutions, dissolve first in a compatible organic co-solvent (e.g., DMSO, ethanol) and then dilute into the system of interest, ensuring final organic content and solubility are acceptable. No standard biochemical buffer systems are relevant to this compound.
Green Alternatives
Green chemistry considerations (general guidance):
Solvent substitution: Replace chlorinated solvents (e.g., DCM, CHCl3) with greener options where feasible. 2-MeTHF and cyclopentyl methyl ether (CPME) often dissolve halogenated benzophenones adequately and provide wider liquidus ranges for crystallization and flow.
Aqueous coupling: For Suzuki–Miyaura couplings at the aryl bromide site, mixed dioxane/water or ethanol/water systems can reduce organic solvent load. Use micellar catalysis (e.g., TPGS-750-M) to enable room-temperature couplings in water (literature), then confirm compatibility with this substrate.
Safer bases: Replace strong inorganic bases in DMF with milder carbonate/phosphate bases in greener solvents (EtOH, 2-MeTHF) when reaction kinetics allow.
Energy efficiency: The aryl bromide typically couples at lower temperatures than the aryl chloride; plan stepwise diversification to minimize heating time. Consider continuous flow for heat/mass transfer efficiency and improved safety with air/moisture-sensitive catalysts.
Illustrative comparison (general):
DCM vs 2-MeTHF: 2-MeTHF is renewable, higher boiling, and less volatile; extraction efficiency can be similar. Tradeoff: peroxide formation risk with ethers (manage with inhibitors and testing) and possible solubility differences.
DMF vs Cyrene/PC: In some transformations, Cyrene or propylene carbonate can substitute for DMF; assess solubility and base compatibility for O-alkylations or condensations.
Waste minimization:
Plan orthogonal protections to avoid redox/protection–deprotection cycles.
Employ catalytic, rather than stoichiometric, halide–lithium exchange by preferring cross-coupling routes over organolithium methods.
Pharmaceutical Uses
No pharmacopeial/excipient status is provided for this item; it is offered for research use only.
General context (non-clinical):
Halogenated benzophenones may serve as synthetic intermediates in medicinal chemistry programs due to their modular diversification (cross-coupling at Ar–Br/Ar–Cl, phenol derivatization, and carbonyl conversions). Any use in a regulated environment would require qualification to appropriate standards (e.g., GMP), which is not indicated here.
Item-specific:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Regulatory listings (USP/Ph.Eur., etc.): Not specified for this item; refer to CoA/Spec Sheet.
Formulation role:
Not typically used as a formulated excipient; primarily a building block for discovery chemistry.
Physical Properties
Item-specific (from Product Data):
Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Computed/literature (general guidance; not product specifications):
Phase at ambient: expected solid (aromatic benzophenones of similar substitution are crystalline solids).
Solubility profile (qualitative, literature):
Water: very low solubility (hydrophobic, halogenated diaryl ketone).
Organic solvents: typically soluble in chlorinated solvents (CH2Cl2, CHCl3), aromatic solvents (toluene), ethers (THF, diethyl ether) and polar aprotics (DMF, DMSO, NMP, acetone).
UV–Vis (qualitative, literature): benzophenone chromophore absorbs in near-UV; intramolecular H-bonding of o-hydroxy group can red-shift n→π* transitions modestly.
Melting/boiling point, density, refractive index, logP, pKa: Not specified for this item; refer to CoA/Spec Sheet. For planning only, compounds of this class often melt in the 100–200 °C range and exhibit high logP due to di-aryl/halogen substitution; confirm experimentally.
Practical implications:
Poor aqueous solubility favors use of organic solvents for handling and reactions.
The chelated O–H can display a downfield 1H NMR signal (often >11 ppm), useful as a diagnostic.
Quality and Grades
Item-specific (from Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on quality considerations (general):
For cross-coupling or other metal-catalyzed transformations, trace metal content and halide purity can impact reaction rates and yields. If using in Pd-catalyzed couplings, consider verifying halide identity (Br vs Cl positions) by NMR/HRMS and, if necessary, trace metal screening.
Chromatography/analytical use: If UV detection is used, benzophenone chromophores have strong UV absorbance; HPLC-grade solvents and pre-rinsed glassware reduce baseline noise during purity assessment.
Water content: Not specified for this item; refer to CoA/Spec Sheet. For moisture-sensitive transformations (e.g., strong-base O-alkylations), dry the solid under vacuum at ambient or mild temperature prior to use.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Typical benzophenone derivatives do not require stabilizers; check CoA to confirm.
Documentation: Request and review the Certificate of Analysis for batch-specific assay, impurity profile, and residual solvent information when work demands stringent specifications (e.g., medicinal chemistry SAR or materials applications).
Reaction and Applications
General applications in synthesis (literature; expand-as-you-use):
Cross-coupling platform: The molecule presents two aryl halides (Ar–Br and Ar–Cl) enabling stepwise diversification. Typical sequences couple the aryl bromide first (Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig), followed by activation/coupling at the aryl chloride using more active catalysts/ligands (e.g., BrettPhos, XPhos families).
Directed reactivity from o-hydroxy: The ortho-OH engages in intramolecular H-bonding to the carbonyl (salicyl-type), facilitating chelation to metal centers under basic conditions. This can enable selective ortho-metalation on the salicyl ring, or serve as an internal directing group in C–H activation protocols after conversion to salicylate salts or O-acyl/iminates.
Carbonyl chemistry: The benzophenone C=O forms oximes, hydrazones, and imines (after reduction to amine-bearing derivatives). It also undergoes selective reductions (e.g., to secondary alcohols) and acyl transfer reactions under strong nucleophiles.
Phenolic functionalization: The phenol can be O-alkylated/acylated (Williamson ether synthesis) to tune electronics and sterics, or converted to salicylates and salen-type ligands after condensation with diamines.
Materials/photochemistry context: While benzophenone cores are classic triplet sensitizers, the strongly intramolecularly H-bonded o-hydroxy group and heavy-atom substituents alter intersystem crossing and photoreactivity; validate photophysical properties experimentally for any sensitization application.
Practical tips:
Sequence-selectivity: Couple the bromide at milder conditions; reserve the chloride for the second step with higher-activity catalysts.
Base choice matters: Cs2CO3 or K3PO4 often improve coupling rates; maintain anhydrous conditions for base-sensitive O-functionalizations.
Monitor for competitive O- vs C-arylation paths in copper chemistry; ligand choice can direct selectivity.
Reaction Conditions
General literature conditions (examples; adjust to substrate/catalyst and verify experimentally):
Suzuki–Miyaura (Ar–Br position): Pd(PPh3)4 (1–3 mol%), K2CO3 or K3PO4 (2–3 equiv), aryl/alkenyl boronic acid (1.2–1.5 equiv), dioxane/H2O (3:1), 80–95 °C, 2–8 h. The phenolic OH may be tolerated; protection can improve yields in some cases.
Suzuki–Miyaura (Ar–Cl position): Pd2(dba)3 (1–2 mol% Pd) with XPhos/BrettPhos (2–6 mol%), Cs2CO3 (2–3 equiv), toluene or dioxane (with 5–10% H2O), 100–120 °C, 6–16 h. Alternative: Buchwald precatalysts (e.g., XPhos Pd G3).
Buchwald–Hartwig amination (Ar–Br): Pd(OAc)2 (1–2 mol%), BINAP or XPhos (2–4 mol%), NaOtBu (2–3 equiv), toluene or dioxane, 90–110 °C, 4–12 h. For Ar–Cl, use more active ligands (BrettPhos, RuPhos) and higher T.
Sonogashira (Ar–Br): PdCl2(PPh3)2 (1–2 mol%), CuI (5–10 mol%), Et3N or i-Pr2NH base, THF or DMF, rt–60 °C, 2–8 h. Copper-free variants with bulky phosphines can minimize Glaser coupling.
O-Alkylation: Substrate (1.0 equiv), alkyl halide (1.1–1.5 equiv), K2CO3 or Cs2CO3 (2–3 equiv), acetone or acetonitrile, reflux, 2–6 h; or DMF at 50–80 °C. Monitor for C- vs O-alkylation; choose conditions to favor O-alkylation.
Oxime formation: Hydroxylamine·HCl (1.2–2.0 equiv), NaOAc (2–3 equiv), EtOH or EtOH/H2O, 60–80 °C, 2–6 h.
Notes:
Degas solvents and employ inert atmosphere for Pd-catalyzed couplings.
The intramolecularly H-bonded phenol can influence coordination; in sensitive couplings, protect OH or add catalytic fluoride/base to modulate binding.
Reported yield ranges for such substrates commonly fall in 60–90% under optimized conditions; substrate electronics and sterics will govern outcomes.
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 (literature/analog-based; not a substitute for SDS):
Likely hazards: Aromatic halogenated ketones may cause irritation to skin, eyes, and respiratory tract. Avoid dust formation and inhalation. Environmental persistence is possible; prevent release to the environment.
Personal protective equipment: Use lab coat, appropriate chemical-resistant gloves (e.g., nitrile), and splash goggles. Handle in a fume hood to avoid inhalation exposure.
Storage incompatibilities: Keep away from strong bases (may induce O-alkylation/condensation), strong oxidizers, and strong reducing agents. Although benzophenones can undergo photoreactions, this substituted derivative is less photoreactive; nonetheless, store in a light-protected container when feasible.
First-aid overview: In case of skin contact, wash with soap and water. For eye contact, rinse cautiously with water for several minutes and seek medical attention. If inhaled, move to fresh air; if swallowed, rinse mouth and seek medical advice. Always consult the SDS for authoritative guidance.
Fire safety: Combustible organic solid. Use CO2, dry chemical, or foam. Combustion may produce corrosive/toxic fumes (HBr, HCl, CO/CO2). Firefighters should wear self-contained breathing apparatus.
Always defer to the product-specific SDS for definitive hazard classification, exposure limits, and emergency procedures.
Solvent Selection
Compound type and polarity (general):
Halogenated, di-aryl ketone with an ortho-hydroxyl group. Overall nonpolar–moderately polar aromatic with poor water solubility. Exhibits hydrogen bonding (as donor) yet remains dominated by hydrophobic surface area.
Poorly soluble: aliphatic hydrocarbons (hexanes, heptane) and water.
When to choose specific solvents:
Cross-coupling (Suzuki/Negishi/Stille): dioxane/water, toluene, or DMF are typical; aryl bromide site is generally more reactive, while the aryl chloride may require higher-activity ligands.
Nucleophilic substitutions or O-alkylation: polar aprotics (DMF, DMSO, acetone, acetonitrile) with inorganic bases (K2CO3, Cs2CO3) aid solubility and rates.
Carbonyl derivatization (oxime/hydrazone): ethanol, isopropanol, or mixed aqueous alcohols under acid catalysis.
Comparative notes:
DCM provides rapid dissolution and convenient workup but has environmental/health concerns; ethyl acetate or 2-MeTHF can be greener alternatives for extractions and medium-polarity reactions.
For crystallizations, toluene/EtOAc or EtOH/water mixtures often allow tuning of solubility, exploiting the sharp solubility contrast between hot and cold conditions typical of benzophenone derivatives.
Storage and Reconstitution
Item-specific (from Product Data):
Storage Conditions: Room temperature.
Shipped In: Normal.
General handling/storage guidance (supplemental; not to override Product Data):
Store tightly closed in a dry container, away from moisture and strong oxidizers/bases. While not highly photosensitive, benzophenone chromophores can undergo photochemical processes; store protected from prolonged light exposure if possible.
For long-term storage, consider desiccation and ambient temperature as specified. Avoid repeated heating cycles; dry under vacuum at room temperature if moisture uptake is suspected.
Reconstitution: Not applicable. If preparing stock solutions, dissolve in a compatible, dry organic solvent (e.g., DMSO, DMF, THF, acetone, DCM). Prepare fresh solutions for moisture- or base-sensitive reactions; otherwise, solutions in aprotic solvents can be stored at 2–8 °C short-term under inert gas.
Always consult the product’s CoA/SDS for any batch-specific storage precautions or solution stability information.
Not specified for this item; refer to CoA/Spec Sheet:
SMILES
Grade/Purity
Appearance
Computed/literature (for identity context; not item specifications):
Likely molecular formula for 5-bromo-2′-chloro-2-hydroxybenzophenone: C13H8BrClO2 (derived by substitution on 2-hydroxybenzophenone)
Approximate molecular weight: ~311.56 g/mol (calculated from formula)
Core structural features: benzophenone scaffold (diphenyl ketone) bearing an ortho-hydroxyl group on one ring (salicyl-type), a bromo substituent at the 5-position of the hydroxy-bearing ring, and a chloro substituent at the 2′-position of the opposite ring.
2D description: two phenyl rings connected by a carbonyl (C=O). On ring A (salicyl ring): an OH ortho to the carbonyl enabling intramolecular O–H···O=C hydrogen bonding; a Br meta to the carbonyl (5-position). On ring B: a Cl ortho (2′) to the carbonyl.
General notes:
The ortho-hydroxybenzophenone motif often exists in a chelated, intramolecularly H-bonded conformation, influencing spectroscopy (strongly chelated O–H) and reactivity around the carbonyl.
Synthetic Utility
Functional handles and reactivity (literature/general):
Dual aryl halides: The para/meta-bromide (on the salicyl ring, 5-position) is generally more reactive in Pd-catalyzed cross-coupling than the ortho-chloride (2′) on the other ring. This enables sequential diversification strategies.
Phenolic OH: Under basic conditions, deprotonation yields a phenoxide that can undergo O-alkylation/acylation (Williamson ether synthesis), carbonate/carbamate formation, or serve as a directing/chelating group for metalation or C–H functionalization.
Benzophenone carbonyl: Amenable to formation of oximes/hydrazones, reductive transformations to secondary alcohols (NaBH4, catalytic hydrogenation), or conversion to imines/enamines after amination steps.
Retrosynthetic leverage:
The scaffold can be traced back to substituted salicylaldehydes or salicylic acid derivatives via acylation routes (e.g., Friedel–Crafts acylation followed by halogenation) or cross-couplings from halo-salicylates with aroyl equivalents.
Orthogonal selectivity: Choose catalysts/ligands to differentiate C–Br vs C–Cl bonds, preserving one site while transforming the other.
Practical tips:
Protecting groups: If O-alkylation must be avoided during C–C coupling, transient protection of the phenol (e.g., silyl ethers or carbonate) can suppress side reactions and modify electronic effects.
Purification: Strong UV chromophore aids TLC/HPLC detection; crystallization from EtOH/EtOAc/toluene mixtures often affords high purity.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological targeting reagent (no antigen/epitope/isotype attributes). No item-specific targeting data are provided in the Product Data.
Perguntas frequentes
What is the purity of this product?
This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 332104-54-8, the molecular formula is C13H8BrClO2, and the molecular weight is 311.56 g/mol. InChIKey JTYCQJZUXZTAEK-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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