2,2′-Difluorobiphenyl - ≥98% , CAS No.388-82-9

CAS: 388-82-9 Cat. No.: D472434 Formula: FC₆H₄C₆H₄F Peso molecolare: 190.19 Numero EC: 206-863-1

GRADE & PURITY ≥98%

Synonyms

2,2'-Difluorobiphenyl | BB 0258984 | ZINCPEROXIDE | 2,2'-Difluorobiphenyl, 98% | O,O'-DIFLUOROBIPHENYL | 2,2'-Difluorobiphenyl, analytical standard | AKOS015890250 | DTXSID70192067 | Biphenyl, 2,2'-difluoro | NQ5S46N6ZC | 1,1'-Biphenyl,2,2'-difluoro- | 2,

Storage

Room temperature

Specifications

Sinonimi

2,2'-Difluorobiphenyl | BB 0258984 | ZINCPEROXIDE | 2,2'-Difluorobiphenyl, 98% | O,O'-DIFLUOROBIPHENYL | 2,2'-Difluorobiphenyl, analytical standard | AKOS015890250 | DTXSID70192067 | Biphenyl, 2,2'-difluoro | NQ5S46N6ZC | 1,1'-Biphenyl,2,2'-difluoro- | 2,

Specifiche e purezza

≥98%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥98%

Nomi e identificatori

• Pubchem Sid: 488187703
• Sorrisi canonici: C1=CC=C(C(=C1)C2=CC=CC=C2F)F
• IUPAC Name: 1-fluoro-2-(2-fluorophenyl)benzene
• InChIKey: PXFIPIAXFGAEMJ-UHFFFAOYSA-N
• INCHI: 1S/C12H8F2/c13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14/h1-8H
• Isomeri SMILES: C1=CC=C(C(=C1)C2=CC=CC=C2F)F
• WGK Germania: 3
• Peso molecolare: 190.19
• Reaxy-Rn: 2047231
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2047231&ln=

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: Biphenyls and derivatives
• Alternative Parents: Fluorobenzenes Aryl fluorides Organofluorides Hydrofluorocarbons Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Biphenyl - Halobenzene - Fluorobenzene - Aryl halide - Aryl fluoride - Hydrofluorocarbon - Hydrocarbon derivative - Organofluoride - Organohalogen compound - Aromatic homomonocyclic compound
• Descrizione: 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

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

Proprietà chimiche e fisiche

• Punto di fusione (°C): 117 -121 °C
• Peso molecolare: 190.190 g/mol
• XLogP3: 3.900
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 190.059 Da
• Monoisotopic Mass: 190.059 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 161.000
• 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

Riferimenti

1. Kang Cheng, Weichao Huang, Xinyong Gong, Chaoyong Deng.  (2024)  Dual substitution of host lattice ions to enhance the luminescence properties of Zn2TiO4:Cr3+ phosphor.  LUMINESCENCE,  39  (4): (e4730).  [PMID:38548694] [10.1002/bio.4730]

2. Sun Yongsheng, Wang Yuzhen, Chen Weibin, Jiang Qingquan, Chen Dongdan, Dong Guoping, Xia Zhiguo.  (2024)  Rapid synthesis of phosphor-glass composites in seconds based on particle self-stabilization.  Nature Communications,  15  (1): (1-8).  [PMID:38310125] [10.1038/s41467-024-45293-0]

Application Protocols

Not applicable. No immunoassay or bioassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. Use according to standard synthetic organic chemistry procedures relevant to your chosen transformation.

Biological Roles

This compound is a simple hydrophobic aromatic building block without known intrinsic biological function. It is not typically used to probe biological pathways on its own. Any biological utility would arise only after conversion into bioactive derivatives or as a 19F NMR label within a designed molecule.

Buffer Applications

Not applicable. 2,2′-Difluorobiphenyl is an organic building block, not a buffering agent. It is essentially insoluble in water and has no relevant acid/base pair for aqueous buffer preparation.

Green Alternatives

Because 2,2′-difluorobiphenyl is a solid building block (not a solvent), “green alternatives” focus on greener methodologies to elaborate this scaffold rather than replacing the compound itself.

• Greener strategy options (literature/general)

  • Direct C–H functionalization: Use Pd, Ru, or Ni catalysis to functionalize C–H bonds on biphenyl cores, reducing the need for halogenated starting materials; however, selectivity for the 2,2′-difluoro pattern may be challenging.
  • Base selection: Prefer LiTMP or milder superbases in toluene over high-load n-BuLi/THF when feasible to reduce peroxide-related solvent hazards.
  • Boronate installation: Employ catalytic C–F borylation under nickel catalysis with lower catalyst loadings and greener solvents (e.g., 2-MeTHF) where demonstrated.
  • Solvent replacement: For organolithium steps, 2-MeTHF or CPME can sometimes substitute for THF/Et2O, offering better safety and renewability; validate reactivity.

• Trade-offs

  • While 2-MeTHF/CPME are greener, they can alter DoM kinetics and lithiation site selectivity. Pilot trials are advised.
  • C–H activation routes may reduce steps and waste but often require rare metals and elevated temperatures, impacting energy and PMI.

• Quick comparison (general)

  • THF vs 2-MeTHF: THF offers faster lithiation and broader literature precedent; 2-MeTHF provides lower toxicity and biorenewable sourcing but may demand longer times or higher base loadings.

Pharmaceutical Uses

No pharmacopeial excipient role is typical for 2,2′-difluorobiphenyl. In a research context, it may serve as a synthetic intermediate toward APIs or materials, but it is not formulated directly. No medical or clinical claims are made; for research and process development use only.

Physical Properties

• Item-specific specifications

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Measured BP/MP, density, water content, metals, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general (for context; not item specifications)

  • State at ambient: typically a low-melting solid or high-boiling liquid depending on purity and isomer content; many sources report a crystalline solid for the 2,2′-isomer.
  • Hydrophobicity: strongly hydrophobic, expected negligible solubility in water; readily soluble in common organic solvents (e.g., dichloromethane, THF, toluene, hexanes, ethers, aromatics).
  • Volatility: substantially lower than mono-phenyl fluorides; expect low vapor pressure at room temperature due to the biaryl core.
  • Polarity: non-polar to weakly polar; no H-bond donors/acceptors besides aryl C–F.
  • Optical properties: aromatic UV absorption typical of biphenyls (π–π* in near-UV); exact UV cutoff not specified for this item.

• Practical notes (general)

  • Crystallization/handling: if solid, it commonly crystallizes from alcohols or hydrocarbons; if oily at RT, gentle cooling can assist solidification for weighing.
  • Impurity sensitivity: not moisture sensitive; stable to air and light under normal lab conditions.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grades (general guidance)

  • Research/technical grade: Suitable for most synthetic applications; impurity profile may include trace regioisomers or residual solvents.
  • High-purity or ≥98–99% assay (when specified): Preferred for structure–property studies, materials applications, and reactions sensitive to adventitious aromatics.
  • Chromatography/HPLC purity statements (if provided): Indicate low UV-active impurities; useful when product will be analyzed by UV or used as a calibration standard.

• Stabilizers/additives

  • None are typically required for difluorobiphenyls; if any stabilizer is used, it will be declared on the CoA/Spec Sheet. In absence of such notation, assume neat material.

• What to check on receipt (practical)

  • Verify CAS (388-82-9), isomer assignment (2,2′- substitution), appearance, and assay.
  • For sensitive transformations (e.g., directed ortho-metalation), consider drying the solid under vacuum at ambient–40 °C before use to remove residual solvent.
  • Keep records of lot-specific CoA: assay method, residual solvents, GC/HPLC traces, and any inorganic residues if reported.

Reaction and Applications

• Role in synthesis

  • 2,2′-Difluorobiphenyl serves as a hydrophobic, ortho-fluorinated biaryl scaffold. The aryl–F groups are poor leaving groups in classical cross-couplings, but they are powerful directing groups for metalation. This makes the compound valuable for site-selective functionalization at positions ortho to F via directed ortho-metalation (DoM).

• Representative transformations (literature/general)

  • DoM/ate complexes: n-BuLi (±TMEDA) in THF or toluene at −78 to −40 °C to generate aryllithium(s), followed by quenching with CO2 (→ carboxylic acids), DMF (→ aldehydes), B(OMe)3 or iPrOB(pin) (→ boronates), Me3SiCl (→ arylsilanes), or electrophiles (RX, RCHO, R2CO).
  • Halogenation via lithiation–quench: DoM then treat with I2/Br2 to introduce I/Br, enabling subsequent Pd/Ni cross-couplings.
  • C–F activation (advanced): With specialized catalysts (e.g., Ni, Pd, or bimetallic systems), aryl–F bonds in non-activated rings can undergo borylation, silylation, or cross-coupling at elevated temperatures.
  • Orthogonal functionalization: Stepwise, ring-selective derivatization enables asymmetric substitution patterns on each phenyl ring, facilitating ligand and material precursor synthesis.

• Application domains (general)

  • Ligand and material precursors: Building block for sterically congested biaryl ligands, OLED/OPV intermediates, and liquid-crystal-like scaffolds where torsion angle control is beneficial.
  • Probe scaffolds: Fluorine atoms enable 19F NMR tracking of intermediates and products.

• Practical tips

  • Ensure rigorous dryness for organolithium chemistry; pretitrate n-BuLi. Control exotherms during electrophile quench. Workup under CO2 quench may generate lithium carboxylates—acidify carefully to avoid emulsions.

Reaction Conditions

General literature guidance (illustrative; not item-specific specifications):

• Directed ortho-metalation (DoM)

  • Reagents: n-BuLi (1.0–2.2 equiv per lithiation site), optionally TMEDA (1–2 equiv) to enhance basicity/chelation.
  • Solvent: anhydrous THF or diethyl ether; toluene viable with stronger bases (e.g., LiTMP).
  • Temperature: −78 to −40 °C for lithiation; gradual warm to −20–0 °C for electrophile addition as appropriate.
  • Times: 0.5–2 h for lithiation; quench times depend on electrophile (minutes to 1 h).
  • Quenches: CO2 (dry ice) → acids after aqueous workup; DMF → aldehydes; I2/Br2 → aryl iodides/bromides; B(OMe)3 or iPrOB(pin) → boronates.
  • Notes: Pretitrate n-BuLi; maintain inert atmosphere. Use excess electrophile to suppress protonation.

• Advanced C–F activation (for reference)

  • Catalysts: Ni(0/II) or Pd systems with strong donor ligands (e.g., NHCs, bulky phosphines) have been reported for aryl–F activation.
  • Solvents: polar aprotics (DMF/DMAc/NMP) or ethers; temperatures often 100–160 °C.
  • Outcomes: borylation or cross-coupling possible but typically lower reactivity vs Ar–Cl/Br/I.

• Workup and purification

  • Quench carefully at low temperature, then allow controlled warm-up.
  • Partition into organic phase (e.g., Et2O/MTBE/DCM), wash, dry (Na2SO4/MgSO4), concentrate, and purify by column chromatography or crystallization.

All parameters above are literature-style guidance only; optimize per your lab’s protocol and the specific transformation.

Safety and Handling

• Item-specific hazard data

  • GHS Classification, Signal Word, H-statements, Pictograms: Not specified for this item; refer to SDS.

• General safety guidance for aromatic hydrocarbons (not a substitute for SDS)

  • Expected hazards: May cause skin/eye irritation and respiratory irritation; harmful if swallowed. Avoid inhalation of dust/vapors and contact with skin/eyes.
  • PPE: Use lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood to control vapors and any dust.
  • First aid overview: If inhaled—move to fresh air; if on skin—wash with soap and water; if in eyes—rinse cautiously with water for several minutes and remove contact lenses; if ingested—rinse mouth, seek medical advice. Always follow the SDS instructions.
  • Fire safety: Combustible organic solid/liquid. Use CO2, dry chemical, or foam to extinguish. Avoid high-temperature decomposition (may emit irritating fumes).
  • Incompatibilities: Strong oxidizers (risk of exotherm), very strong bases in the presence of reactive electrophiles, and halogenating agents.
  • Stability: Stable at room temperature under ambient atmosphere. No known tendency for peroxide formation.

• Environmental handling (general)

  • Prevent release to the environment. Collect organic waste in halogenated or non-halogenated hydrocarbon waste streams per local regulations.

• Authoritative reference

  • Always consult the product’s SDS for definitive hazard classification and emergency measures.

Solvent Selection

This product is a hydrophobic aryl building block rather than a solvent. Selection here refers to solvents used to dissolve it for reaction or processing.

• Solubility/miscibility (general)

  • Expected to dissolve well in nonpolar and moderately polar organic solvents: toluene, xylene, chlorinated solvents (DCM, chloroform), ethers (THF, diethyl ether, MTBE), and hydrocarbons (hexanes/heptane; solubility may be moderate in aliphatic media).
  • Negligible solubility in water and aqueous buffers.

• Choosing a solvent by application

  • Metalation (DoM): anhydrous THF, diethyl ether, or toluene are common. THF often gives faster kinetics and better temperature control at −78 to −40 °C; TMEDA is sometimes added.
  • Electrophilic quench (e.g., carboxylation, formylation): THF or ether; ensure efficient CO2 or DMF introduction at low temperature.
  • Cross-coupling via C–F activation (advanced): polar aprotic solvents (DMF, DMAc, NMP) or ethers depending on the catalyst system; rigorously dry, degassed.
  • Purification/crystallization: hexanes or heptane mixtures with DCM/EtOAc can aid crystallization; adjust polarity to remove minor regioisomers or oligomers.

• Small comparison (general)

  • THF: strong solvating power for organolithiums; low temperature capable; peroxide-former—manage accordingly.
  • Toluene: inert, higher boiling for elevated-temperature steps; organolithium reactions slower but often cleaner.
  • DCM: good for workup/extraction and chromatography; avoid with strong bases/n-BuLi.

Storage and Reconstitution

• Item-specific storage

  • Storage Conditions: Room temperature (per Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General handling

  • Keep container tightly closed in a dry, well-ventilated place. Protect from strong oxidizers.
  • Not moisture sensitive; no special inert-atmosphere storage required, though storing under nitrogen/argon is good practice for long-term quality.

• Reconstitution/solution preparation

  • Not applicable to solids in the bioreagent sense. To prepare solutions, dissolve the weighed solid in a suitable dry organic solvent (e.g., THF, toluene, DCM) at the desired concentration under inert atmosphere if the downstream chemistry is air/moisture sensitive.

• Stability notes (general)

  • Stable under ambient light and air. For highly sensitive reactions (e.g., organolithium chemistry), consider drying under vacuum and using freshly opened material.

Always consult the lot-specific CoA/Spec Sheet for any additional storage or handling instructions.

Structure and Identity

Brief description: 2,2′-Difluorobiphenyl is an ortho,ortho′-difluorinated biphenyl, a twisted, nonplanar biaryl hydrocarbon useful as an aryl building block.

• Item-specific (Product Data)

  • Product Name: 2,2′-Difluorobiphenyl
  • SKU: D472434
  • CAS: 388-82-9
  • PubChem CID: 123055
  • InChIKey: 289310 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Storage Conditions: Room temperature
  • Research Use: For research use only

• Literature/Computed (not item-specific specifications)

  • Typical molecular formula (literature): C12H8F2
  • Typical molecular weight (literature): ~190.19 g/mol
  • Core structural features: two phenyl rings connected at C1–C1′ with fluorine substituents at the 2- and 2′-positions (ortho to the biaryl bond on each ring).
  • 2D structure in words: A biphenyl scaffold; on each ring, the carbon adjacent to the biaryl bond (o-position) bears an F atom. Steric repulsion (F⋯H) enforces a significant dihedral twist between rings, reducing conjugation relative to unsubstituted biphenyl.

• Notes on identity & isomerism (general)

  • Positional isomerism exists (e.g., 3,3′- or 4,4′-difluorobiphenyl); ensure CAS 388-82-9 corresponds to the 2,2′-isomer used here.
  • No stereocenters; atropisomerism is possible in heavily substituted biphenyls, but 2,2′-difluoro alone is typically not configurationally stable at ambient temperature.

Synthetic Utility

• Functional groups and reactivity

  • Two aryl–F bonds on a biphenyl core. The C–F bonds are among the least reactive aryl halides in conventional cross-coupling, but the strong −I effect of F powerfully directs ortho-metalation, enabling highly regioselective functionalizations.

• Strategic value in retrosynthesis (general)

  • Use as a masked di-ortho director: Install substituents adjacent to each F via DoM, then, if desired, replace F by halogenation (lithiation → I2/Br2) to open conventional cross-coupling manifolds.
  • Access to heteroatom-arylated products: Lithiation followed by quench with B, Si, P, or Sn electrophiles creates versatile handles (boronates/silanes/iodides) for Suzuki–Miyaura, Hiyama, or Stille couplings.
  • Differential ring functionalization: Because each ring bears F, sequential DoM with protecting/coordination strategies allows desymmetrization and complex substitution patterns.

• Named/related reactions (literature)

  • Directed ortho-metalation (DoM) with n-BuLi/TMEDA.
  • Halogen–metal exchange is generally not applicable to aryl fluorides; reactivity instead relies on direct metalation.
  • Nickel-catalyzed C–F borylation/silylation (specialized) to convert Ar–F into Ar–B/Ar–Si under forcing conditions.

• Practical insights

  • Temperature control is critical to prevent dilithiation or overmetalation.
  • F serves as a 19F NMR handle to monitor reaction progress and regiochemistry.

Target Specificity

Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or biological probe with defined target specificity.