2-Hydroxy-2',3,5-trichlorobenzophenone - ≥95% , CAS No.99585-49-6

CAS: 99585-49-6 Cat. No.: H996837 Formula: C₁₃H₇Cl₃O₂ Molecular Weight: 301.5 EC Number: 620-729-3 PubChem CID: 2736615

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

Canonical Smiles

C1=CC=C(C(=C1)C(=O)C2=C(C(=CC(=C2)Cl)Cl)O)Cl

IUPAC Name

(2-chlorophenyl)-(3,5-dichloro-2-hydroxyphenyl)methanone

InChIKey

NULXTAYCMKNTDL-UHFFFAOYSA-N

INCHI

1S/C13H7Cl3O2/c14-7-5-9(13(18)11(16)6-7)12(17)8-3-1-2-4-10(8)15/h1-6,18H

Isomeric SMILES

C1=CC=C(C(=C1)C(=O)C2=C(C(=CC(=C2)Cl)Cl)O)Cl

PubChem CID

2736615

Molecular Weight

301.5

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzophenones

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzophenones
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzophenones
• Alternative Parents: Diphenylmethanes Aryl-phenylketones P-chlorophenols O-chlorophenols Dichlorobenzenes Benzoyl derivatives Aryl chlorides Vinylogous halides Vinylogous acids Organochlorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Benzophenone - Diphenylmethane - Aryl-phenylketone - Benzoyl - 1,3-dichlorobenzene - 4-halophenol - 2-halophenol - 2-chlorophenol - 4-chlorophenol - Aryl ketone - Halobenzene - Chlorobenzene - Phenol - Aryl halide - Aryl chloride - Vinylogous halide - Vinylogous acid - Ketone - Organochloride - Organohalogen compound - Organic oxygen compound - Organic oxide - Organooxygen compound - Hydrocarbon derivative - Aromatic homomonocyclic compound
• Description: 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

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 301.500 g/mol
• XLogP3: 5.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 299.951 Da
• Monoisotopic Mass: 299.951 Da
• Topological Polar Surface Area: 37.300 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 311.000
• 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

Application Protocols

No vendor‑validated biological assay protocols are provided for this item. Typical laboratory uses are in organic synthesis and photophysical/materials research.

General use suggestions (literature/general):

• For spectroscopic measurements, prepare stock solutions in dry DMSO, DMF, or CH2Cl2 at known concentrations, protect from light, and dilute as needed immediately before measurement.
• For cross‑coupling, follow standard Pd/Ni protocols for aryl chlorides, including degassing, base selection, and inert atmosphere. Pilot small‑scale reactions to establish solubility and kinetics.

For application‑specific SOPs, refer to current literature methods and adapt to your instrumentation and safety requirements.

Biological Roles

No specific biological role is assigned to this chemical in the product data. The compound is supplied for research use only.

Literature/general context:

• 2‑Hydroxybenzophenones are widely studied as model chromophores exhibiting intramolecular H‑bonding and ESIPT, useful in photophysics and as polymer UV‑stabilizer motifs. Such studies focus on fundamental photochemical behavior rather than biological function.
• Halogen substitution can modulate lipophilicity and electronic properties; any biological interactions reported in the literature are context‑ and assay‑specific and should not be generalized.

Note: Not intended for food, drug, cosmetic, or household use. Avoid extrapolating biophysical properties to biological efficacy without controlled experimentation.

Buffer Applications

Not typically applicable. This is a hydrophobic, halogenated aromatic building block rather than a buffering agent. It lacks acid/base pairs with suitable pKa spacing and solubility for preparing standard laboratory buffers.

For work in aqueous systems (e.g., spectroscopy), dissolve first in a miscible co‑solvent (DMSO, DMF, or small volumes of ethanol) before dilution into buffered media, ensuring final co‑solvent content does not perturb the system under study.

Green Alternatives

While the compound itself is a halogenated aromatic, greener choices can be made in its processing and transformations (literature/general guidance).

Greener solvent/process substitutions:

• Replace DCM/CHCl3 with EtOAc, 2‑MeTHF, or CPME for extractions and medium‑polarity reactions when solubility allows.
• Substitute DMF/NMP with Cyrene, GVL, or propylene carbonate for base‑mediated O‑alkylations; confirm solubility and base compatibility.
• Use aqueous micellar catalysis (e.g., TPGS‑750‑M) for cross‑couplings where feasible to reduce organic solvent usage.

Catalysis and energy:

• Employ ligand‑enabled Pd catalysis for aryl chlorides to lower temperature and shorten reaction times (reducing energy input).
• Consider nickel catalysis for certain couplings to reduce precious metal use (tradeoffs: sensitivity, optimization effort).

Tradeoffs to consider:

• Greener solvents may reduce solubility of this hydrophobic substrate, requiring higher temperatures or longer times.
• Aqueous systems can be incompatible with phenolate intermediates unless phase‑transfer conditions are optimized.

Mini comparison (general):

• DCM vs 2‑MeTHF: 2‑MeTHF is bio‑based, higher boiling, and more benign; DCM offers superior solubility/volatility but with higher toxicity and emissions.
• DMF vs Cyrene: Cyrene is less hazardous and biodegradable but more viscous and less established; DMF is broadly effective but reproductive‑toxic and regulated.

Pharmaceutical Uses

No pharmacopeial status, excipient grade, or formulation role is specified in the product data for this item.

Literature/general context (non‑clinical):

• Benzophenone chromophores, especially 2‑hydroxy derivatives, are studied as UV absorbers and photostabilizers in materials science. In formulation research, analogous motifs can be evaluated as light‑stabilizing additives or probes for photodegradation studies of drug substances and packaging. These are investigative, not therapeutic, uses.
• For any use in GMP settings, detailed impurity profiles, residual solvents, and elemental analysis would be required. Such specifications are not provided here; refer to CoA/Spec Sheet.

Research‑only notice: This product is for research use only and is not intended for human or animal therapeutic or diagnostic applications.

Physical Properties

Item‑specific specifications are not provided; consult the CoA/SDS for authoritative values.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula / Weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature/computed for the named structure: C13H7Cl3O2; ~301.55 g/mol.)
• Melting point (mp): Not specified for this item; refer to CoA/Spec Sheet. (Benzophenone derivatives with 2‑OH and multiple Cl often melt as crystalline solids in the ~100–180 °C range, literature; exact mp for this isomer not cited here.)
• Boiling point / decomposition: Not specified for this item; refer to CoA/Spec Sheet. (Polyhalogenated benzophenones typically char/decompose before boiling at 1 atm; literature.)
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (literature/general):
  • Water: expected very low (phenolic, polyaryl, halogenated).
  • Organic: good in chlorinated solvents (CH2Cl2, CHCl3), aromatic solvents (toluene), and polar aprotics (DMF, DMSO, NMP); moderate in EtOAc/acetone; poor in alkanes.
• pKa (phenolic OH, literature/general): typically ~7–9 for salicyl benzophenones; electron‑withdrawing Cl substituents can lower pKa modestly.
• LogP (literature/general): expected high (hydrophobic) due to tri‑chloro and diaryl ketone; precise value not specified.
• UV–Vis (literature/general): Benzophenone chromophore shows strong π→π* bands in near‑UV; 2‑OH enables ESIPT behavior and red‑shifts; exact λmax not specified.

Note: Values labeled literature/general are for contextual guidance only and are not the product specification.

Quality & Grades

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and guidance:

• When available, a stated purity (e.g., ≥98%) for aromatic building blocks typically reflects chromatographic assay (GC/HPLC/1H NMR) and low residual solvents. In absence of a declared grade, consult the CoA for assay method, residual solvent profile, and impurity thresholds.
• Chromatography suitability: For applications in photophysics or trace analysis, users often require low UV background and well‑defined impurity profiles; request UV cut‑off and absorbance data if needed. Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: None indicated in the product data. If stabilizers are of concern for your application, confirm by CoA.
• Trace metals/ions: Not specified for this item; refer to CoA/Spec Sheet. For cross‑coupling, trace metal content is usually non‑limiting, but stringent applications may require metal analysis upon receipt.

Recommendation: Define internal acceptance criteria (purity assay type, water content, residual solvents) aligned to your workflow and verify against the batch‑specific CoA.

Reaction & Applications

As a 2‑hydroxybenzophenone with multiple aryl chlorides, this scaffold serves as both a photochemically interesting motif and a versatile synthetic handle.

• Photochemistry/materials (literature/general): 2‑Hydroxybenzophenones exhibit intramolecular H‑bonding and excited‑state intramolecular proton transfer (ESIPT), making them useful in studies of UV absorption, fluorescence quenching, and as model UV‑stabilizing chromophores for polymers and coatings.
• O‑Functionalization:
  • Form phenolates (K2CO3, Cs2CO3, or NaH) in polar aprotics (DMF/DMSO) to access ethers (Williamson), carbonates, or esters.
  • Silylation (TBSCl/imidazole) for protecting the phenol during cross‑coupling.
• Carbonyl chemistry:
  • Participate in acyl transfer or serve as an acyl donor in activated forms (e.g., via Weinreb amide after appropriate conversion; literature/general).
  • Reduction to benzhydrol analogs (NaBH4 or hydrosilanes with Lewis acids) followed by further diversification.
• Aryl chloride diversification:
  • Cross‑coupling: Suzuki–Miyaura, Buchwald–Hartwig, or Sonogashira using Pd catalysts/ligands optimized for aryl chlorides (e.g., Pd2(dba)3/XPhos or BrettPhos; base K3PO4; toluene/1,4‑dioxane) to introduce aryl, amine, or alkyne groups.
  • SNAr (literature/general) is possible at positions activated by the carbonyl-bearing ring; reaction rates are substrate/position dependent.
• Orthogonal tactics: Sequential protection of the phenol, single‑site activation (e.g., via directed metalation on the non‑phenolic ring), and stepwise coupling to construct densely functionalized architectures.

Practical tips: Dry solvents, exclude moisture during base‑mediated O‑alkylations; for couplings, degas and employ ligand sets tailored to aryl chlorides to improve turnover.

Reaction Conditions

General literature guidance for common transformations of 2‑hydroxy, poly‑chloro benzophenones (illustrative, not product specifications):

• O‑Alkylation (Williamson):
  • Base: K2CO3 (2–3 equiv) or Cs2CO3; solvent: DMF, acetone, or acetonitrile; electrophile: primary alkyl halide or sulfate.
  • Typical: 50–80 °C, 2–16 h; monitor by TLC/HPLC. Phenolate formation is key; exclude water.
• Buchwald–Hartwig amination (aryl chloride):
  • Catalyst: Pd2(dba)3 (1–2 mol%) with BrettPhos or XPhos (2–4 mol% ligand); base: NaOtBu or K3PO4; solvent: toluene, 1,4‑dioxane, or CPME.
  • 80–110 °C, 4–24 h; aryl chlorides require stronger ligands and careful degassing.
• Suzuki–Miyaura coupling:
  • Catalyst: Pd(PtBu3)2 or Pd2(dba)3 + SPhos; base: K3PO4 or Cs2CO3; solvent: toluene/H2O or 1,4‑dioxane/H2O (micellar systems possible).
  • 70–100 °C, 2–12 h; aryl boronic acid/ester coupling partners.
• Sonogashira coupling (if terminal alkyne introduction desired):
  • Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%); base: Et3N or DIPEA; solvent: THF, Et3N, or 2‑MeTHF.
  • 25–80 °C, 2–16 h; copper‑free variants reduce Glaser byproducts.
• Carbonyl reduction to benzhydrol:
  • NaBH4 in MeOH/DCM mixtures or hydrosilane/TiCl4 systems; 0–25 °C to reflux depending on method; quench carefully.

Yields and exact conditions are substrate‑ and position‑dependent; optimize ligand/base/temperature for each chloro site to control selectivity. Always employ anhydrous, oxygen‑free techniques for cross‑couplings.

Safety & Handling

GHS and hazard statements are not provided for this specific item; consult the SDS for authoritative safety information.

• GHS classification / pictograms / H‑statements: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• General hazards (literature/general for halogenated benzophenones): May cause irritation to skin, eyes, and respiratory tract. Dust may be harmful if inhaled. Combustible solid.
• Handling recommendations:
  • Use in a chemical fume hood; avoid dust generation.
  • Wear appropriate PPE: lab coat, safety glasses/goggles, and nitrile gloves; consider double‑gloving for extended contact.
  • Avoid contact with strong bases (can form phenolates) and strong oxidizers/reducing agents.
• Storage incompatibilities (general): Separate from strong oxidizing agents; avoid prolonged exposure to strong bases or reactive metals.
• Light sensitivity: Benzophenone chromophores can act as photosensitizers; minimize unnecessary light exposure (general recommendation).
• First aid (general):
  • Skin: Wash with soap and water.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; seek medical advice.

Always defer to the SDS and institutional protocols for risk assessment and emergency procedures.

Solvent Selection

This halogenated, phenolic benzophenone is hydrophobic with limited aqueous solubility. Selection should balance solubilization of the aromatic core and control of phenol ionization.

• Polarity/miscibility (literature/general):
  • Highly soluble: DMSO, DMF, NMP, dichloromethane, chloroform, chlorobenzene.
  • Good: acetone, ethyl acetate, toluene; moderate in MeCN.
  • Poor: alkanes, alcohols (unless warmed or with base for phenolate formation), water.
• Ionization leverage: Deprotonation of the phenolic OH with base (e.g., K2CO3, t‑BuOK) increases solubility in polar aprotics and enables O‑functionalization.
• When to choose chlorinated vs non‑chlorinated:
  • Use DCM/CHCl3 for rapid dissolution and spectroscopic work (strong UV absorption; account for solvent background).
  • Prefer EtOAc, 2‑MeTHF, or toluene for greener processing and extractions when feasible.
• Solid handling: For weighing and transfers, avoid static and dust; pre‑wetting with a small volume of solvent can reduce losses.

Comparison (literature/general):

• DCM vs EtOAc: DCM dissolves faster but poses higher environmental/health concerns; EtOAc is safer but may require warming/sonication.
• DMF/DMSO vs MeCN: DMF/DMSO offer higher solubility; MeCN is easier to remove but may require larger volumes.

Storage & Reconstitution

• Storage Conditions (as provided): Room temperature.
• Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• Form: Not specified for this item; refer to CoA/Spec Sheet. (Typically supplied as a solid for analogous benzophenones.)

General handling (literature/general):

• Store tightly closed in a dry place, preferably in an amber container or secondary light‑protective packaging to minimize photochemical changes of the benzophenone chromophore.
• If long‑term storage is anticipated, a desiccator or low‑humidity cabinet is recommended to prevent moisture uptake and caking.
• Avoid prolonged exposure to strong light sources and heat.

Reconstitution guidelines (research use):

• Prepare concentrated stocks in dry DMSO, DMF, CH2Cl2, or EtOAc depending on downstream use. Filter if necessary to remove particulates.
• For aqueous work, dissolve first in a miscible organic co‑solvent, then dilute into buffer with vigorous mixing; confirm that final organic content is compatible with the assay.

Always refer to the batch‑specific CoA for any additional storage or handling notes. Product is for research use only.

Structure & Identity

A halogenated benzophenone bearing an intramolecularly chelating 2‑hydroxy group, useful as a photoactive/aromatic building block.

• Product Name: 2‑Hydroxy‑2',3,5‑trichlorobenzophenone (salicyl benzophenone core with three chloro substituents on the second ring)
• SKU: H996837
• CAS: 99585‑49‑6
• CID (PubChem): 2736615
• InChIKey (as provided): 248273 (note: non‑standard length; refer to CoA/SDS for canonical identifier)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet. (Literature/computed for this substitution pattern: C13H7Cl3O2)
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature/computed for C13H7Cl3O2: ~301.55 g/mol)

Structural features (general description):

• Core motif: Benzophenone (diphenyl ketone) scaffold.
• Functional groups: One ketone (–C(=O)–) conjugated to two aryl rings; one ortho‑phenolic hydroxyl (–OH) on one ring enabling intramolecular H‑bonding to the carbonyl (salicyl benzophenone motif).
• Ring substitution: Three chloro substituents on the opposite ring at the 2', 3, and 5 positions (literature description based on the name).
• 2D structure in words: Two benzene rings linked by a carbonyl carbon; on ring A, the 2‑position bears –OH; on ring B, the 2', 3, and 5 positions bear –Cl. The o‑OH and C=O can form a six‑membered intramolecular H‑bond, influencing conformation and spectroscopy.
• Stereochemistry: None (achiral, planar aromatic system with conformational preference from intramolecular H‑bonding).

Synthetic Utility

This substrate integrates three orthogonal handles: a phenolic OH, a benzophenone carbonyl, and multiple aryl chlorides—enabling step‑economical diversification.

• Phenol (–OH):
  • Protection: TBS/TIPS ethers (imidazole) or benzyl carbonates to mask during metal‑catalyzed steps.
  • Transformations: Williamson ether synthesis, carbonate/urethane formation, Mitsunobu etherification (with alcohol partners), and Ullmann‑type O‑arylation.
• Carbonyl (ketone):
  • Reductive routes: NaBH4 or transfer hydrogenation to benzhydrols; subsequent functionalization (e.g., halogenation, esterification via activation).
  • α‑Functionalization: Limited enolization due to diaryl stabilization; however, formation of O‑acyl or O‑silyl enolates (under strong base) can enable electrophilic trapping (literature/general).
• Aryl chlorides:
  • Cross‑coupling platform: Pd‑catalyzed Suzuki, Buchwald–Hartwig, and Sonogashira couplings; Ni catalysts for cost‑effective arylations. Ligand choice (BrettPhos/SPhos/XPhos) is critical for aryl chlorides.
  • SNAr potential where ring activation by the carbonyl is operative; nucleophile choice and temperature control regioselectivity.
• Chelation control: The o‑OH···O=C H‑bond can direct metalation or transiently chelate to metals, sometimes impacting regioselectivity and rates in metal‑mediated transformations (literature/general).

Taken together, the molecule is a compact hub for assembling polyaryl architectures, tuning photophysical properties, and accessing phenoxy‑ and amino‑substituted benzophenone libraries.

Target Specificity

Not applicable. This product is a small‑molecule chemical, not a biological targeting reagent (e.g., antibody, inhibitor panel with defined targets). No antigen/epitope or species reactivity applies.