This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
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
No application protocols are specified for this item in the Product Data. As a general small-molecule building block, usage protocols depend on the intended synthetic transformation (see Reaction Conditions and Synthetic Utility tabs). For analytical reference uses, prepare accurately weighed solutions in suitable solvents (e.g., DMSO, MeOH, acetonitrile) and calibrate methods (HPLC/GC-MS) accordingly.
Biological Roles
General literature context (not product-specific; no medical/clinical claims)
Xenobiotic metabolism: 3,4-dihydroxybiphenyl is described in biodegradation pathways of biphenyl/PCBs by dioxygenase-initiated ring hydroxylation followed by ring-cleavage enzymes in bacteria. Such catecholic intermediates are central to ortho/meta cleavage routes in environmental microbiology.
Chemical reactivity in biology: The vicinal diol (catechol-like) motif can chelate metal ions and undergo redox cycling to semiquinone/quinone species under oxidative conditions, impacting oxidative stress chemistry in vitro.
Protein/enzymatic interactions: Phenolic biphenyls can act as substrates or inhibitors for oxidative enzymes (peroxidases, laccases) in model assays, though specificity depends on substitution pattern and conditions.
Assay utility: Used as a reference compound in studies of phenol oxidation, radical coupling, and as a standard for HPLC/GC-MS method development in environmental metabolite profiling.
Note
Any biological roles should be interpreted in the context of controlled laboratory studies. This product is for research use only (as stated in Product Data).
Buffer Applications
Not typically applicable. 3,4-Biphenyldiol is an aromatic diol and does not serve as a conventional buffering agent. It lacks a suitable conjugate acid/base pair in the physiological pH window to provide robust buffering capacity. For experimental work, choose an appropriate buffer (e.g., phosphate, Tris, HEPES) and dissolve 3,4-biphenyldiol separately in a compatible co-solvent (DMSO, ethanol) or in basic aqueous media as the phenolate if required.
Green Alternatives
Context: As a solid aromatic diol/building block, “alternatives” typically concern solvent choice and protecting-group/activation strategies rather than replacing the scaffold itself.
Greener processing choices (literature guidance)
Solvent selection: Prefer biobased/safer solvents when feasible.
2-MeTHF or CPME can replace THF/1,4-dioxane in many O-alkylations and acylations.
Acetonitrile or propylene carbonate may substitute for DMF/DMSO in certain base-promoted etherifications.
Activation reagents: Use CDI for carbonate/ester formation in place of phosgene/diphosgene; avoid chlorinated reagents where possible.
Catalysis: Employ catalytic DMAP or enzymatic acylations (vinyl esters, lipases) to reduce stoichiometric activating agents.
Energy: Conduct reactions under microwave/flow to reduce time/energy consumption; solventless melt transesterifications are sometimes viable for polymer precursors.
Trade-offs
Solubility vs greenness: DMSO/DMF give superior solubility but have burdensome EHS profiles; greener solvents may require higher temperatures or longer times.
Product isolation: Greener high-boilers (e.g., propylene carbonate) complicate workup; ensure downstream removal by extraction or antisolvent precipitation (leveraging phenol acidity).
Quick comparison (general)
DMF/DMSO: high solubility, easy etherification; EHS concerns.
2-MeTHF/CPME: greener, easier workup; may reduce rates/solubility.
Ethyl acetate/MeCN: moderate greenness, good workup; may need stronger base or catalysts.
Pharmaceutical Uses
Formulation/use context (general; no therapeutic claims)
Not commonly employed as a pharmacopeial excipient. Aromatic diols like 3,4-biphenyldiol are more frequently used as synthetic intermediates in the preparation of monomers, ligands, or small-molecule leads rather than as direct components of dosage forms.
Potential roles in process chemistry: May serve as a building block for prodrugs (via carbonate/ester linkages) or polymeric carriers in early-stage research; however, such uses are highly application-specific and require case-by-case evaluation of safety and regulatory status.
Regulatory status: No specific USP/Ph.Eur monograph is known for this compound; if pharmaceutical manufacturing use is contemplated, establish full impurity profiles and toxicology.
Item-specific information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Research Use Note: For research use only (from Product Data).
Physical Properties
Item-specific specs
Not specified for this item; refer to CoA/Spec Sheet for definitive values.
Literature/typical values (for reference only; not product specifications)
Appearance: off-white to beige crystalline solid is commonly reported for phenolic biphenyls.
Molecular weight: ~186.21 g/mol (C12H10O2)
Melting point: literature reports are typically in the mid‑160s °C range (e.g., ~164–170 °C); verify on CoA for this lot.
Boiling point: decomposes before distillation under ambient pressure; purification usually by recrystallization. Sublimation possible under high vacuum.
pKa (phenolic OH): typical phenol pKa ~9–10; catechol-like systems can show slightly enhanced acidity due to intraring H‑bonding/electronics.
LogP (octanol/water): expected moderate hydrophobicity for a biphenyl bearing two phenols (literature estimates often ~2–3).
Solubility: sparingly soluble in water; soluble in polar organic solvents (DMSO, DMF, acetone) and moderately in alcohols; increased solubility as phenolate in basic aqueous media.
UV/Vis: aromatic π–π* absorption typical of biphenyl/phenols (e.g., bands in 200–300 nm region; exact cutoffs not specified for this item).
Notes for practitioners
Solubility can be significantly enhanced by forming alkali phenolates in situ (Na/K carbonate or hydroxide) or by warming in polar aprotic solvents.
Hygroscopicity/peroxide formation: not known to form peroxides; phenols can undergo slow oxidation—store under air‑tight conditions.
Quality and Grades
Item-specific grade/purity
Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades for phenolic building blocks (general)
Research grade: Suitable for most synthetic and materials applications. Typical control parameters include identity (NMR/IR/MS), assay, and residual solvents.
High-purity/low-metal grades: Beneficial for catalytic reactions (e.g., C–O coupling, polymerizations) where trace metals/halides impact performance. If required, request CoA with specific impurity/metal limits.
Water/peroxide/UV specs: Not specified for this item; refer to CoA/Spec Sheet. Phenolic solids generally do not have peroxide stabilizers; antioxidants are unnecessary if stored properly.
Practical considerations
For polymer synthesis (e.g., carbonates/ethers), low water content can be critical to drive equilibrium—dry material under vacuum if needed and confirm by KF where your process is moisture‑sensitive.
For analytical uses (e.g., as reference), verify isomeric purity (positional isomers of dihydroxybiphenyl exist) by 1H/13C NMR and HPLC.
Reaction and Applications
Roles in synthesis and materials (general, literature-based)
Aromatic diol building block for synthesis of diaryl ethers, carbonates, esters, and polymers (e.g., poly(arylene ether)s) via O-functionalization.
Ligand/precursor: O-alkylation or phosphorylation affords chelating aryl ether/phosphite ligands; diols can be converted to di-silyl ethers for directed metalation strategies.
Oxidation chemistry: Can be oxidized to o‑quinonoid species under strong oxidants (catechol-like ring), enabling redox-active materials or conjugation.
Cross-coupling platform: While the parent compound is not halogenated, selective halogenation of the unsubstituted ring enables Suzuki–Miyaura, Buchwald–Hartwig (after O‑triflation), or Ullmann-type couplings to elaborate the biphenyl scaffold.
Named/representative transformations
Williamson ether synthesis: R–X (primary) + base (K2CO3/Cs2CO3) in DMF/acetone → di- or mono-aryl ethers.
Mitsunobu O-alkylation: ROH + DEAD/DIAD, PPh3 affords inversion at alcohol partner; useful for sensitive substrates.
Acylation/carbonate formation: Acid chlorides/anhydrides or carbonyl diimidazole (CDI) or triphosgene/diphosgene surrogates to make diesters/dicarbonates.
O‑Triflation: Tf2O/pyridine to form aryl triflates, enabling Pd-catalyzed C–C/C–N couplings on the catechol ring.
Application domains
Advanced intermediates for functional materials (optical, resin modifiers), small-molecule probes, and as standards in environmental biotransformation studies (biphenyl metabolism).
Reaction Conditions
General, literature-based guidance (not product specifications)
O‑Alkylation (Williamson): 3,4-biphenyldiol (1.0 eq), alkyl bromide/iodide (2.2–2.5 eq), K2CO3 or Cs2CO3 (2.5–3.0 eq) in DMF, DMSO, MeCN, or acetone; 50–90 °C, 2–18 h. Often affords high conversions; mono‑ vs di‑alkylation controlled by stoichiometry and base.
Mitsunobu O‑Alkylation: Diol (1.0 eq), ROH (2.5–3.0 eq), DIAD/DEAD (1.2–1.5 eq), PPh3 (1.2–1.5 eq) in THF or toluene; 0 °C to rt to 60 °C; inert atmosphere.
O‑Acylation/Carbonate formation: Use acyl chlorides/anhydrides (2.2–2.5 eq) with pyridine/Et3N and catalytic DMAP in CH2Cl2 or toluene at 0–25 °C. For carbonates, CDI or triphosgene in MeCN/CH2Cl2; 0–25 °C.
O‑Triflation: Tf2O (2.2 eq) with pyridine or 2,6‑lutidine in CH2Cl2 at −78 to 0 °C; proceed to Pd-catalyzed coupling (e.g., Pd2(dba)3/XPhos, K3PO4, toluene/MeCN, 80–110 °C).
Oxidation to quinone-like species: Periodate or silver oxide in MeOH/MeCN/H2O mix; 0–25 °C; monitor closely to avoid overoxidation.
Workup/purification tips
Exploit acid/base switching: dissolve phenolates in basic aqueous phase, then acidify to precipitate product/crystals.
Protecting groups: TBS protection (TBSCl, imidazole, DMF, rt) improves solubility in nonpolar media and controls regioselectivity.
Typical yields
Etherifications and acylations commonly provide 70–95% yields under optimized conditions (literature). Actual outcomes depend on substrate and conditions.
Safety and Handling
Item-specific hazard/GHS (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 information for phenolic biphenyls (literature/precautionary guidance)
Hazards: Phenolic compounds are typically irritants to skin/eyes and may cause respiratory irritation as dust. Avoid inhalation and contact.
PPE: Use lab coat, safety glasses or goggles, and suitable chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust exposure.
First aid overview: Eye/skin contact—rinse with water for ≥15 min; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical attention. Always follow site SOPs and the SDS.
Handling: Avoid prolonged exposure to air/oxidants; phenols can slowly oxidize (browning). Use clean, dry tools. If preparing phenolate salts, beware of exotherms on neutralization.
Incompatibilities: Strong oxidizers (risk of exothermic reactions), strong bases/acids (can cause corrosion; forms salts/esters), acyl/alkylating agents (reactivity of phenolic OH), and reactive acid chlorides/anhydrides.
Fire: Organic solid; combustible. Use CO2, dry chemical, or foam. Thermal decomposition may produce CO/CO2 and phenolic vapors.
Waste: Collect organic phenolic waste separately; neutralize bases/acids before disposal per local regulations.
Solvent Selection
Applicability note: 3,4-Biphenyldiol is a solid aromatic diol (not a solvent). This section addresses solvents suitable for dissolving/processing it.
General solubility guidance (literature)
Highly soluble: DMSO, DMF, NMP—use when maximum concentration is required or for SNAr/O-alkylation chemistry.
Low solubility: Water at neutral pH; solubility increases in basic aqueous media as phenolate salts.
Selection by application
O-alkylation/ether formation: Polar aprotics (DMF, DMSO, acetonitrile) with K2CO3/Cs2CO3. Acetone suitable for phase-transfer or with reflux.
Esterification/acylation: Dichloromethane/CH2Cl2 or toluene with base (pyridine, Et3N) or catalytic DMAP.
Carbonate/polymer formation: High-boiling, aprotic media (NMP, sulfolane) or melt processes; remove generated alcohol/CO2 as needed.
Aqueous workup: Briefly basify to dissolve phenolate, then re-acidify to precipitate product—aids purification.
Comparative notes
DMSO vs DMF: DMSO often offers higher solubility; DMF easier to remove. For greener profiles, consider MeCN/2-MeTHF when compatible.
Alcoholic solvents: Facilitate H-bonding but can participate in transesterification—use cautiously in acylations.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (from Product Data).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (phenolic solids)
Storage: Keep tightly closed in a dry, inert atmosphere if possible. Protect from prolonged air/light exposure to minimize slow oxidative discoloration. Store away from strong oxidizers and bases.
Shelf life: Stable under recommended conditions; reassess by NMR/HPLC if stored long-term.
Reconstitution/solution preparation:
Solvents: DMSO, DMF, acetone, MeCN, ethanol/methanol. For aqueous systems, dissolve in minimal organic co‑solvent or convert to phenolate with dilute base (then neutralize after use).
Concentrations: Prepare stock solutions (e.g., 10–100 mM) depending on solubility and intended use. Filter (0.2 µm) if particulates are present.
Avoid repetitive freeze–thaw of solutions; aliquot and store at 2–8 °C (short term) or −20 °C (longer term) in amber vials to limit oxidation.
Research Use Note
For research use only (from Product Data).
Structure and Identity
Item-specific (from Product Data)
SKU: B1072980
Product name: 3,4-Biphenyldiol
CAS: 92-05-7
PubChem CID: 7075
InChIKey (as provided): 294132
Storage conditions: Room temperature
Literature/computed identity (for reference; not item-specific specifications)
InChIKey (literature): commonly reported for 3,4-dihydroxybiphenyl differs from numeric placeholder above; consult databases/CoA
Structural features (general description)
Biphenyl scaffold: two phenyl rings connected by a single C–C bond (restricted but rotatable biaryl axis).
Phenolic diol: two –OH groups positioned at the 3- and 4-positions on one ring (vicinal/meta-adjacent on the same ring), giving a catechol-like subunit fused to a biphenyl.
Functional groups: two phenols (acidic hydrogen donors, weakly coordinating oxygen donors), two aromatic rings (π-rich). No stereocenters; axial chirality not resolved in the free biphenyl.
2D description: One phenyl ring bears two adjacent hydroxyls (–OH) and is bonded at the ipso carbon to the second unsubstituted phenyl ring.
Synthetic Utility
Functional handles and strategies (literature-based)
Dual phenolic OH groups enable:
O‑alkylation (Williamson/Mitsunobu) to access diaryl ethers and spacers.
O‑acylation/carbonation (acyl chlorides, anhydrides, CDI, triphosgene) to form diesters/dicarbonates—useful in polymer precursor synthesis.
O‑silylation (TBS/TBDPS) to protect phenols; enables orthogonal deprotection and regiocontrol in subsequent steps.
Activation to aryl electrophiles:
O‑triflation or O‑mesylation generates aryl electrophiles for Pd-catalyzed cross-couplings (C–C, C–N) on the catechol ring.
Ring functionalization:
Electrophilic substitution is directed by the phenolic groups (strong ortho/para directors) permitting selective halogenation/nitration on the hydroxylated ring if protected.
The unsubstituted second ring offers additional diversification via directed ortho‑metalation or standard EAS after suitable protecting groups.
Redox chemistry:
Oxidation to o‑quinone intermediates (e.g., with periodate, Ag2O, or electrochemistry) enables conjugate additions or Diels–Alder-like reactivity in certain systems.
Retrosynthetic value
Serves as a convergent node for accessing asymmetric biphenyl derivatives where orthogonal protection on the two phenols differentiates downstream elaborations.
Target Specificity
Not applicable. This product is a small-molecule chemical (aromatic diol), not a biological affinity reagent. No antigen/epitope, clone, isotype, or species reactivity applies. Item-specific targeting data are not provided in the Product Data.
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