4-(2-Bromophenyl)phenol - ≥98% , CAS No.70066-66-9

CAS: 70066-66-9 Cat. No.: B931178 Formule: C₁₂H₉BrO Poids moléculaire: 249.11 Numéro CE: 809-572-3 PubChem CID: 28911485

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spécifications et pureté

≥98%

Conditions de stockage de stockage

Room temperature

Pureté

≥98%

Noms et identifiants

• Sourires canoniques: C1=CC=C(C(=C1)C2=CC=C(C=C2)O)Br
• IUPAC Name: 4-(2-bromophenyl)phenol
• InChIKey: XESUCEJPGYWGSK-UHFFFAOYSA-N
• INCHI: 1S/C12H9BrO/c13-12-4-2-1-3-11(12)9-5-7-10(14)8-6-9/h1-8,14H
• Isomères SMILES: C1=CC=C(C(=C1)C2=CC=C(C=C2)O)Br
• PubChem CID: 28911485
• Poids moléculaire: 249.11

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Biphenyls and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Biphenyls and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Brominated biphenyls
• Alternative Parents: Bromobenzenes 1-hydroxy-2-unsubstituted benzenoids Aryl bromides Organooxygen compounds Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Brominated biphenyl - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Halobenzene - Bromobenzene - Aryl halide - Aryl bromide - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organobromide - Organohalogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as brominated biphenyls. These are organic compounds containing a biphenyl moiety substituted at one or more positions by a bromine atom.
• 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

Propriétés chimiques et physiques

• Poids moléculaire: 249.100 g/mol
• XLogP3: 4.200
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 247.984 Da
• Monoisotopic Mass: 247.984 Da
• Topological Polar Surface Area: 20.200 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 175.000
• 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 standardized bioassay or immunoapplication protocols are associated with this small-molecule building block.
• General usage examples (non-binding guidance)
  • Prepare a stock solution in dry DMSO or MeCN (e.g., 10–100 mM) for high-throughput synthesis or screening; filter through 0.2 µm PTFE if needed.
  • For cross-coupling, pre-dry the solid, charge with base and catalyst under inert atmosphere, add solvent and coupling partner, heat to target temperature, and monitor conversion by LCMS. Refer to the primary literature and your internal SOPs for detailed, validated procedures.

Biological Roles

• This product is a synthetic halogenated biaryl phenol and does not have an inherent biological role. No biological function is assigned for this catalog item.
• General considerations (biochemistry context; not product-specific claims)
  • Phenolic groups can engage in hydrogen bonding and π–π interactions with protein residues and nucleic acid bases; such motifs frequently appear in screening libraries and SAR studies.
  • Bromine substitution modulates lipophilicity and polarizability, which can influence binding in exploratory medicinal chemistry. However, any activity is highly scaffold- and context‑dependent and must be empirically determined.
• Research use note
  • For research use only. Not intended for human or veterinary use, diagnostics, or as a drug substance.

Buffer Applications

• Not typically applicable. 4-(2-Bromophenyl)phenol is a hydrophobic synthetic building block, not a buffering agent.
• Practical note: In biochemical assays, it may be dissolved in DMSO or MeCN as a stock solution and then diluted into buffered systems; maintain final cosolvent fractions (commonly ≤1–2% v/v) to avoid perturbing assay conditions.

Green Alternatives

• Solvent and process choices (general guidance)
  • Replace chlorinated solvents (DCM) with greener ethers or esters where possible: 2‑MeTHF or CPME for organometallic steps; EtOAc or propylene carbonate for extractions and medium‑polarity reactions.
  • In Pd cross‑couplings, aqueous micellar catalysis (e.g., TPGS‑750‑M surfactant in water) or bio‑derived solvents (2‑MeTHF) can reduce VOC impact while maintaining high conversions.
  • Bases with lower EHS footprint (K3PO4, K2CO3) can substitute for Cs2CO3 where reactivity allows.
• Comparison snapshot (general)
  • THF vs 2‑MeTHF: 2‑MeTHF is bio‑sourced, higher boiling (bp ~80 °C vs 66 °C for THF), less peroxide‑prone, and eases phase separations; THF remains superior for very low‑temperature lithiation.
  • Toluene vs CPME: CPME offers hydrophobicity, broad stability window, and easier workups; toluene widely available but higher VOC concerns.
  • DMF/DMSO vs MeCN/PC: MeCN and propylene carbonate can lower worker exposure and simplify solvent recovery, though polarity/boiling constraints must be considered.
• Waste minimization
  • Use catalytic bases or flow setups for cross‑couplings to reduce stoichiometric waste.
  • Telescoping protection–coupling–deprotection steps can decrease solvent and purification cycles. Note: These are general green chemistry considerations for this scaffold; adapt to your reaction’s specific requirements.

Pharmaceutical Uses

• No pharmacopeial/compendial monograph or excipient designation is indicated for this item.
• Typical role in pharma R&D (general)
  • Serves as a synthetic intermediate/building block for SAR exploration. The aryl bromide facilitates cross‑coupling diversification; the phenol allows rapid generation of O‑alkyl/aryl ethers, carbonates, and prodrug-like motifs for property tuning.
  • Suitable for parallel synthesis and library generation, with attention to residual metal control post‑coupling if material is advanced into later-stage studies.
• Regulatory note
  • For research use only. Not for therapeutic, diagnostic, or GMP manufacturing without appropriate qualification and additional documentation.

Physical Properties

• Item-specific values
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Density, melting point, boiling point, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
• General/literature characteristics (for context; not specifications)
  • Aggregate state: Aromatic phenolic biaryls of this size are typically crystalline solids at ambient temperature.
  • Solubility profile: Sparingly soluble in water; soluble in common organic solvents (EtOAc, acetone, acetonitrile, THF, DCM, toluene). Good solubility in polar aprotic media (DMF, DMSO) is expected due to the phenolic functionality.
  • Acid–base: Phenolic OH is weakly acidic; pKa for para‑substituted phenols commonly ~9.5–10.5 (literature, substituent-dependent). Deprotonation affords phenoxide, increasing solubility in basic aqueous/MeOH mixtures.
  • Partitioning: Aryl bromide/biaryl motif implies moderate-to-high hydrophobicity (logP positive; literature expectation), counterbalanced by hydrogen-bonding OH.
  • Thermal behavior: Aryl bromides are generally thermally robust up to typical cross-coupling temperatures (80–120 °C); phenols can undergo etherification under basic/alkylating conditions. For precise values relevant to your lot (mp, purity, residual solvents), consult the CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• Interpreting common grades (general guidance)
  • Research/technical grade: Suitable for most synthetic applications; impurity limits are fit-for-purpose but not necessarily trace-analytical.
  • ≥98–99% (assay): Typically indicates suitability for most coupling/heterocycle-forming steps without prepurification; check water and halide content for moisture/catalyst-sensitive routes.
  • HPLC grade (for solvents) does not apply here; for solids, “HPLC assay” refers to purity determination method, not solvent UV cutoffs.
• Stabilizers/additives
  • None stated for this item. If present in a specific lot (e.g., trace inhibitors), these would be listed on the CoA; verify before catalysis or polymerization-sensitive chemistry.
• Practical QC tips for this scaffold
  • If using in Pd-catalyzed cross-couplings, residual inorganic halides and moisture can impact catalytic turnover. Consider brief drying under high vacuum at ambient-to-mild temperature if compatible (verify mp on CoA) and assay by NMR for adventitious phenoxide salts.
  • Confirm identity by 1H/13C NMR (diagnostic phenolic OH, biaryl coupling), HRMS, and a single-spot TLC/UPLC prior to scale-up.

Reaction and Applications

• Functional handles and typical transformations (general/literature)
  • Aryl bromide enables cross-couplings: Suzuki–Miyaura (to elaborate biaryl frameworks), Negishi, Kumada, Stille. Ortho‑bromide placement can enable access to ortho‑substituted motifs on the distal ring.
  • Phenol can be derivatized: Williamson O‑alkylation (alkyl halides/sulfonates), carbonate/carbamate formation, Mitsunobu inversion chemistry (with appropriate alcohol partners), or conversion to aryl triflate to create a second cross‑coupling site (sequential or orthogonal couplings).
  • Protection strategies: Silyl ethers (TBS, TBDPS) or benzyl/PMB ethers to mask the OH during metalation/coupling.
• Representative synthetic uses
  • Sequential diversification: (1) Protect OH (TBSCl, imidazole, CH2Cl2), (2) Suzuki coupling on the aryl bromide (Pd(PPh3)4, base, boronic acid), (3) Deprotect to phenol for late‑stage O‑functionalization.
  • Halogen–metal exchange on the bromo ring (n‑BuLi or i‑PrMgCl·LiCl in THF, −78 to 0 °C), followed by electrophile trapping to install formyl, carboxyl, or other ortho substituents; protect OH first to avoid deprotonation.
  • Aryl triflation of the phenol (Tf2O, pyridine, −20 to 0 °C) affords an aryl triflate that participates in Pd-catalyzed couplings, enabling iterative biaryl assembly.
• Practical tips
  • Phenolic OH can poison catalysts via coordination; protect or add base (e.g., K3PO4) to keep as phenoxide during couplings.
  • Avoid strong bases with unprotected OH when attempting metal–halogen exchange—prefer protecting groups or use milder turbo‑Grignard conditions.

Reaction Conditions

• General literature conditions (guidance; optimize per substrate)
  • Suzuki–Miyaura coupling at Ar–Br: 0.5–5 mol% Pd(PPh3)4 or Pd2(dba)3/XPhos; base K3PO4, K2CO3, or Cs2CO3 (2–3 equiv); solvent toluene/1,4‑dioxane/2‑MeTHF with 5–20% water or DMA/DMF; 60–100 °C; 2–16 h. Boronic acid/ester 1.2–1.5 equiv. Yields commonly high for aryl bromides.
  • Halogen–metal exchange: n‑BuLi (1.05–1.2 equiv) in anhydrous THF at −78 to −20 °C followed by electrophile quench (e.g., DMF → aldehyde). Protect phenol beforehand (TBS, Bn) to avoid competitive deprotonation.
  • Williamson ether synthesis: K2CO3 or Cs2CO3 (2–3 equiv) in DMF/MeCN/acetone; alkyl halide/mesylate (1.2–1.5 equiv); 25–80 °C; 2–18 h. Phase-transfer variants: K2CO3, TBAB, toluene/H2O.
  • Aryl triflation of phenol: Tf2O (1.1–1.5 equiv), pyridine or 2,6‑lutidine, CH2Cl2, −20 to 0 °C then to rt; 0.5–2 h; follow with Pd-catalyzed coupling under standard conditions.
  • Protection/deprotection: TBSCl (1.2–1.5 equiv), imidazole, DMF/CH2Cl2, 0–25 °C; deprotect with TBAF (1.0–1.5 equiv), THF, 0–25 °C. Notes: Monitor by TLC/UPLC; exclude air/moisture for organometallic steps; scale-up requires calorimetry and gas‑evolution assessment.

Safety and Handling

• Item-specific hazard information
  • Signal word: Not specified for this item; refer to SDS.
  • GHS classification/pictograms/H-statements: Not specified for this item; refer to SDS.
• General safety considerations for halogenated phenolic aromatics (informational; defer to SDS)
  • May cause skin and eye irritation; avoid inhalation of dust and contact with skin/eyes. Handle in a chemical fume hood.
  • PPE: Laboratory coat, nitrile gloves, and splash-resistant safety goggles as a minimum. Change gloves regularly when working in strong organic solvents.
  • First aid (overview): Inhalation—move to fresh air; Skin—wash with soap/water; Eyes—rinse cautiously with water for several minutes; Ingestion—rinse mouth. Seek medical attention as needed. Refer to SDS for detailed instructions.
  • Incompatibilities: Strong oxidizers; strong bases/alkylating agents can deprotonate/etherify the phenol; avoid reactive alkali metals and strong reducing agents when not intended.
  • Environmental note: Halogenated aromatics should be prevented from release to the environment; collect waste in halogenated-organics containers per your institution’s procedures.
  • Fire safety: Combustible organic solid; use CO2, dry chemical, or foam. Thermal decomposition may release HBr/Br2 and irritating fumes—use self-contained breathing apparatus in fires. Always consult the official SDS supplied with the product for authoritative hazard, exposure, and disposal guidance.

Solvent Selection

• Polarity and interactions (general)
  • The molecule is moderately hydrophobic (biaryl core) with a single hydrogen-bond donor/acceptor (phenol). It dissolves well in polar aprotic organics (DMF, DMSO, NMP, MeCN) and moderately in less polar solvents (EtOAc, THF, toluene, chlorinated solvents). Water solubility is low unless deprotonated to the phenoxide.
• Choosing solvents by application
  • Pd cross-coupling (Suzuki/Miyaura, Buchwald–Hartwig after appropriate electrophile): Toluene, 1,4-dioxane, CPME, 2-MeTHF, or mixed aqueous dioxane/THF are common; DMF/MeCN for more polar systems.
  • O‑alkylation (Williamson ether synthesis): DMF, DMSO, or MeCN with K2CO3/Cs2CO3; acetone for phase-transfer setups.
  • Directed metalation/halogen–metal exchange at the bromo ring: Etheric solvents (THF, MTBE, CPME) at low temperature; ensure rigorous dryness.
  • Protection as silyl carbonate/benzyl ether: CH2Cl2 or THF with imidazole/DMAP.
• Quick comparison (general)
  • THF/2‑MeTHF: good for low‑temperature bases and organometallics; miscible with water for aqueous workups.
  • Toluene/CPME: higher boiling, less polar—useful for high‑temp couplings; easier separations, greener profile for CPME.
  • DMF/DMSO: maximize solubility/reactivity with inorganic bases; harder to remove; consider MeCN as a more volatile alternative when feasible.

Storage and Reconstitution

• Item-specific storage/shipping
  • Storage Conditions: Room temperature (as provided in Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
• General handling and storage advice
  • Keep tightly closed in a dry, well-ventilated place. Minimize exposure to light and moisture to preserve assay and avoid adventitious phenoxide formation.
  • If long-term storage is anticipated, consider desiccation and an inert headspace (e.g., nitrogen/argon), especially after first opening.
  • Allow container to equilibrate to room temperature before opening to avoid condensation.
• Reconstitution/solution preparation
  • Prepare solutions in dry organic solvents (e.g., DMSO, DMF, MeCN, THF, toluene) appropriate to the intended application. For biological assays, DMSO stocks (10–100 mM) are typical; dilute into working media keeping final DMSO ≤1–2% v/v unless your protocol specifies otherwise.
  • Solutions in reactive solvents/bases should be prepared fresh. Label and date all solutions; store at low temperature as appropriate to the solvent (e.g., 2–8 °C for DMSO stocks) and protect from light. Always consult the CoA/SDS for lot-specific guidance.

Structure and Identity

• Item-specific identifiers (from Product Data)
  • CAS: 70066-66-9
  • CID: 28911485
  • InChIKey: 416032 (as provided)
  • 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.
• Structural description (general/literature)
  • 4-(2-Bromophenyl)phenol is a biphenyl derivative bearing a phenolic –OH on one ring (para to the biaryl bond) and a bromine on the second ring (ortho to the biaryl bond). It is thus a bifunctional aryl building block combining a phenol (acidic, H‑bond donor/acceptor) and an aryl bromide (cross-coupling handle).
  • 2D features: two fused-by-bond benzene rings (biaryl), one para‑hydroxy substituent on ring A, one ortho‑bromo substituent on ring B; no stereogenic centers.
• Computed/literature identity values (for reference; not item-specific specifications)
  • Empirical formula (literature, based on name): C12H9BrO
  • Formula weight (literature): ~249.10 g/mol
  • Representative SMILES (literature example): Oc1ccc(cc1)c2ccccc2Br (positional isomerism encoded as given; verify before use) Note: Always verify structure and identifiers on the product CoA/SDS for the supplied lot.

Synthetic Utility

• Orthogonal reactivity
  • C–Br bond: Pd‑catalyzed couplings (Suzuki, Buchwald–Hartwig after amination electrophile generation elsewhere, Negishi, Stille); halogen–metal exchange to access directed ortho metalation chemistry on the brominated ring.
  • O–H group: Protection (TBS, TBDPS, Bn, MOM), O‑alkylation (Williamson), carbonate/carbamate/triflate formation; Mitsunobu chemistry to unite with chiral alcohols for diastereocontrol.
• Retrosynthetic value
  • Functions as a convergent node: assemble complex biaryls via coupling at bromide, then unlock the phenol for late‑stage polarity tuning or as a handle for further activation (e.g., PhOTf → second cross‑coupling). This enables rapid entry into triaryl/heteroaryl arrays and diaryl ether scaffolds.
• Selectivity and protection strategy
  • Unprotected phenol can chelate Pd or be deprotonated by strong bases, impacting couplings and metalations. Protect when using strong bases/n‑BuLi. For couplings under basic conditions, maintaining the phenoxide can sometimes enhance rates but may require ligand/base optimization.
• Downstream functional space
  • Access to: diaryl ethers, aryl carbonates/urethanes, ortho‑functionalized biphenyls, and diversified polyaromatics common in materials (OLEDs, OPVs) and probe molecules.

Target Specificity

• Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or targeted biological reagent. No antigen/epitope or isotype information applies.

Foire aux questions

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.