This compound belongs to the class of organic compounds known as o-fluorophenols. These are fluorophenols carrying a iodine at the C2 position of the benzene ring.
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
316.890 g/mol
XLogP3
3.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
315.84 Da
Monoisotopic Mass
315.84 Da
Topological Polar Surface Area
20.200 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
124.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
No application protocols are specified for this item.
General usage notes (informational):
For cross-coupling screens, prepare 0.1–0.5 M stock solutions in dry DMSO, DMF, or 2-MeTHF under inert atmosphere.
If biological assays are contemplated for downstream products, limit DMSO content to ≤1–2% v/v upon dilution and filter stock solutions (0.2 µm PTFE) to remove particulates.
For any assay- or platform-specific protocols, consult the primary literature and adapt to your instrumentation.
Biological Roles
This material is a synthetic aromatic building block and is not a biological buffer, metabolite, or biopolymer component.
No endogenous biological role is known for 6-bromo-2-fluoro-3-iodophenol (general statement).
Phenolic and halogenated aryl motifs occur in various bioactive research compounds, but any biological activity would be context-dependent on the final molecule rather than this intermediate.
Note: This product is supplied for research use only and is not intended for diagnostic, therapeutic, or clinical applications.
Buffer Applications
Not typically applicable. 6-Bromo-2-fluoro-3-iodophenol is not used as a buffering agent or pH stabilizer.
Practical note: If preparing analytical stocks (e.g., for screening or biotesting), dissolve in suitable organic co-solvents (DMSO, DMF) before dilution into assay media, ensuring final organic content remains compatible with the system.
Green Alternatives
As a substrate/building block, this compound itself has no direct “green” substitute with identical reactivity. However, greener choices can be made in its use and in selecting adjacent chemistry.
Greener considerations (general literature guidance):
Solvent selection: Favor 2-MeTHF, CPME, Me-THF/water, or toluene/water biphasic systems over DMF/DMAc/dioxane when compatible with the desired coupling.
Catalyst economy: Employ low-load Pd or Ni with modern bulky biaryl phosphines or NHCs; consider ligand-free Ni in aqueous micelles (TPGS-750-M) to reduce organic solvent use.
Base choice: K3PO4 or K2CO3 in water/green ethers; avoid strong inorganic bases that generate problematic salt waste unless required.
Protection economy: Minimize protecting-group operations on the phenol; when needed, choose removable groups under mild, waste-minimizing conditions (e.g., carbonate/benzoate cleavable under catalytic transesterification).
Illustrative comparison (general):
DMF (benchmark for solubility) vs 2-MeTHF (greener):
Worker exposure/toxicity: higher for DMF; lower for 2-MeTHF.
Workup/recycling: DMF challenging; 2-MeTHF easier to recover, forms separable aqueous layers.
Reaction rate/selectivity: DMF often faster; 2-MeTHF may need higher temperature or longer time.
Process intensification:
Flow coupling of aryl iodides can reduce catalyst loading and improve heat/mass transfer.
Trade-offs: Greener media may reduce solubility or rate; empirical optimization is recommended.
Pharmaceutical Uses
Not typically applicable as an excipient or formulation aid. This compound is a synthetic intermediate used in research-scale route scouting and library synthesis.
No pharmacopeial monograph or excipient role is known for this specific compound (general statement).
In process chemistry contexts, polyhalogenated phenols may be precursors to drug-like scaffolds; however, such uses are confined to research and development.
This product is for research use only and is not intended for human or veterinary use.
Physical Properties
Item-specific physicochemical specifications (bp, mp, density, solubility, UV cutoff, metal/peroxide/water limits) are not provided in the product data.
Appearance (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed values and general expectations for 6-bromo-2-fluoro-3-iodophenol (informational, not item-specific):
Empirical formula: C6H3BrFIO (derived from substitution pattern).
Formula weight: ~316.9 g/mol (calculated from standard isotopic masses).
Physical state: Typically a crystalline solid for closely related polyhalophenols (literature trend).
Acidity: Phenolic pKa for halogenated phenols commonly shifts to ~8–10; multiple halogens may further acidify vs phenol (pKa 9.99) due to inductive effects (literature trend; exact pKa not established for this specific substitution).
Solubility (qualitative, literature): Poorly soluble in water; soluble in polar aprotic organic solvents (DMSO, DMF, DMAc) and moderately soluble in chlorinated solvents (DCM, CHCl3) and ethyl acetate. Solubility in nonpolar hydrocarbons is limited but can improve upon heating.
LogP: Halogenation generally increases hydrophobicity (literature trend); exact logP not established.
Melting/boiling points: Not located in authoritative databases for this exact isomer at time of writing; expect a melting point in the typical range for polyhalogenated phenols (literature trend). Specific values: Not specified for this item; refer to CoA/Spec Sheet.
Note: For method development or formulation, determine actual solubility and thermal behavior empirically for your lot.
Quality and Grades
Item-specific grade/purity is not provided in the product data and should be verified on the Certificate of Analysis.
Guidance (general, not item-specific):
Research-grade reagents are typically suitable for synthesis and method development. For sensitive cross-coupling chemistry, impurities such as residual halides, phenolic byproducts, or trace metals can affect catalyst performance.
HPLC or LC-MS suitability: If using for analytical reference, look for specifications on purity, water content, UV absorbance profile, and residual solvents. For trace analysis, a tighter spec on related substances is preferable.
Stabilizers/Inhibitors: None specified for this item; halogenated phenols usually do not require stabilizers. If present (e.g., trace acid scavengers), assess compatibility with your reaction.
Impurity concerns: Potential regioisomers (other bromo/iodo positions), dihalogenated byproducts, and residual starting phenols. Confirm identity via NMR/HRMS.
Lot-specific verification: Check CoA for assay/purity, residual solvents, and any method-specific data (GC/HPLC). If conducting metal-catalyzed couplings, consider pre-washing or recrystallization to remove adventitious inhibitors.
What the grade means:
If labeled "≥98%" or similar (not specified here), that indicates assay by HPLC/GC or NMR area %. Absent a stated grade, treat as general research-grade and perform incoming QC as needed.
Reaction and Applications
As a highly functionalized aryl phenol, 6-bromo-2-fluoro-3-iodophenol serves as a versatile linchpin in medicinal and materials synthesis (research context).
Key applications (general literature guidance):
Orthogonal cross-coupling: The aryl iodide (C–I) typically couples fastest, enabling selective mono-coupling at C-3 under milder Pd conditions (Suzuki–Miyaura, Sonogashira, Heck). The bromide (C–Br) can be addressed in a second step at higher temperature or with more active catalysts/ligands.
Ullmann/Buchwald ether/amine formation: Convert the phenol to aryl ethers/carbonates or to aryl amines via Buchwald–Hartwig coupling after pre-activation (e.g., as aryl triflate from the phenol) to diversify substitution.
Directed metalation and SNAr: The ortho-fluoro relative to OH can assist SNAr on appropriately activated positions, and the OH can be protected (TBS, MOM, benzyl) to modulate reactivity.
Protect–couple–deprotect strategies: Temporary protection of the phenol avoids competing O-arylation or catalyst inhibition during C–X cross-couplings.
Late-stage diversification: Ideal for library synthesis where sequential C–I then C–Br functionalization yields two distinct aryl–C(sp2)–C(sp2/sp) bonds, leaving F as a metabolic/physicochemical modulator.
Practical tips:
Use anhydrous, degassed solvents; trace water and base choice strongly influence Pd-catalyzed couplings.
For selective C–I activation: employ Pd(PPh3)4 or Pd2(dba)3/XPhos at ≤50–80 °C. For C–Br: switch to SPhos/XPhos or Ni-catalysis at higher temperatures.
Monitor for O-arylation side products; protection or ligand choice can suppress this.
Reaction Conditions
General literature guidance for typical transformations of 6-bromo-2-fluoro-3-iodophenol (informational, not item-specific):
Solvent: Toluene, CPME, or dioxane; DMF/DMAc for high polarity.
Temperature: 90–120 °C.
Phenol transformations:
Triflation: Tf2O (1.1–1.5 equiv), pyridine or 2,6-lutidine, CH2Cl2, 0 °C → rt; then couple as aryl triflate under standard Pd conditions.
Etherification: NaH or Cs2CO3, alkyl halide in DMF; or Buchwald O-arylation with suitable ligands (BrettPhos, tBuXPhos).
Yields: Dependent on substrate/coupling partner; well-optimized protocols for aryl iodides routinely give high conversions (literature precedent). Always confirm conditions empirically.
Safety and Handling
Item-specific hazard classifications are not provided in the product data. Always consult the SDS for authoritative information.
GHS Signal word (item-specific): Not specified; see SDS.
GHS Hazard statements (item-specific): Not specified; see SDS.
GHS Pictograms (item-specific): Not specified; see SDS.
General safety guidance for halogenated phenols (informational, not item-specific):
Hazards: May cause skin/eye irritation; harmful if swallowed or inhaled; phenols can be corrosive to skin with prolonged contact. Avoid aerosols and dust formation.
PPE: Use lab coat, safety glasses or face shield, and chemical-resistant gloves (e.g., nitrile). Employ a fume hood for weighing and handling powders.
Incompatibilities: Strong bases (can form phenolates; exotherm), strong oxidizers, and strong reducing agents/reactive metals. Avoid contact with acylating/alkylating agents unless intended. Halogenated aromatics may release hydrogen halides when combusted.
First aid (overview):
Skin: Remove contaminated clothing, rinse with water and soap; seek medical attention if irritation persists.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present; obtain medical attention.
Inhalation: Move to fresh air, keep at rest, seek medical advice if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; get medical attention.
Spill response: Avoid dust; contain and collect with inert absorbent. Ventilate area.
Fire-fighting: Use CO2, dry chemical, or foam. Combustion may produce toxic halogenated fumes.
Note: This product is for research use only (as provided).
Solvent Selection
This product is an aryl building block (not used as a solvent). The guidance below concerns choosing solvents to dissolve and react 6-bromo-2-fluoro-3-iodophenol.
General solubility/miscibility trends (literature, not item-specific):
Preferred dissolution solvents: DMSO, DMF, DMAc for stock solutions and for transition-metal couplings; moderate solubility in ethyl acetate, acetone, and chlorinated solvents (DCM, CHCl3).
Limited solubility: Alcohols and nonpolar hydrocarbons (hexanes, toluene) at room temperature; heating or co-solvents may be required.
Water: Practically insoluble; use co-solvents if aqueous conditions are necessary (e.g., micellar catalysis).
When to choose particular media:
Palladium cross-coupling (Suzuki, Buchwald–Hartwig): 1,4-dioxane, toluene, CPME, or mixtures with water; DMF/DMAc for challenging substrates.
Nucleophilic substitutions/etherifications: Polar aprotic solvents (DMF, DMSO) enhance phenoxide reactivity; for phase-transfer conditions, toluene or chlorobenzene with aqueous base.
Protection/deprotection of phenol: Use CH2Cl2 or THF for acylations/silylations with base; MeOH/EtOH for carbonate/alkylations with milder bases.
Small comparison (general):
DMSO/DMF: maximize solubility and rate; harder workup and odor (DMF toxicity concerns).
2-MeTHF/CPME: greener, lower polarity; may require heating but simplify workup and are recyclable.
Toluene/dioxane: good for Pd-catalysis; consider safety (dioxane classification) and waste profile.
Storage and Reconstitution
Item-specific storage information:
Storage Conditions: Room temperature (as provided).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
General handling and solution preparation (informational, not item-specific):
Container: Store tightly sealed, protected from moisture and light. A desiccator or dry cabinet is recommended to preserve quality of phenolic solids.
Atmosphere: Inert gas blanketing (N2/Ar) is advisable after opening for long-term stability, especially if repeatedly heating/recooling for reactions.
Reconstitution/Solution prep: Dissolve in dry organic solvents (DMSO, DMF, 2-MeTHF, THF, CH2Cl2) to desired concentration. For analytical or screening stocks, typical ranges are 10–100 mM (DMSO) or 10–50 mg/mL (DMF/CH2Cl2), depending on solubility.
Freeze–thaw: For stock solutions, aliquot to minimize freeze–thaw cycles; store at 2–8 °C or −20 °C depending on solvent stability (check solvent freezing points and container compatibility).
Stability: Phenolic compounds can slowly oxidize/discolor on prolonged air/light exposure; if discoloration occurs, re-purify before critical applications.
Note: This product is for research use only.
Structure and Identity
A densely halogenated phenolic building block useful for cross-coupling and diversification of aromatics.
Product Name (item-specific): 6-Bromo-2-fluoro-3-iodophenol
SKU (item-specific): B1018129
CAS (item-specific): 1449008-11-0
PubChem CID (item-specific): 74892766
InChIKey (item-specific): 19484 (as provided)
SMILES (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular Formula (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Molecular Weight (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
Structural description (general, derived from the name):
Core scaffold: Phenol (hydroxybenzene) ring.
Functional groups: One phenolic –OH and three aryl halogens (Br, F, I).
Substitution pattern: Fluorine at C-2 (ortho to OH), iodine at C-3, bromine at C-6 (para to C-3 and meta to OH). The ring retains two unsubstituted aromatic positions.
Stereochemistry: None (achiral, planar aromatic).
Computed/literature identifiers and composition (informational, not item-specific):
Empirical formula (from name, literature): C6H3BrFIO
Formula weight (calculated, literature): ~316.9 g/mol
2D structure in words: a benzene ring bearing an OH at position 1; proceeding clockwise, F at position 2, I at position 3, positions 4–5 are unsubstituted, and Br at position 6.
Synthetic Utility
The combination of phenol (O–H) and differentiated aryl halides (I and Br) provides orthogonal handles for selective bond construction.
Functional group leverage (general literature guidance):
Aryl iodide (C–I): Highest reactivity in oxidative addition; prioritize for first-stage Pd/Ni coupling (Suzuki–Miyaura, Sonogashira, Heck), delivering rapid diversification at C-3.
Aryl bromide (C–Br): Reserved for a second-stage coupling under more forcing conditions or with more active ligands/catalysts, enabling sequential difunctionalization.
Phenol (O–H):
Protect (TBS, TIPS, MOM, benzyl) to avoid O-arylation and H-bonding effects.
Convert to aryl triflate/mesylate to unlock an additional cross-coupling site if needed (triflation with Tf2O/pyridine).
Form aryl ethers/esters to tune electronics and solubility.
Fluorine at C-2: Modulates electronics and can facilitate intramolecular H-bonding or influence SNAr on suitably activated partners; remains intact through many couplings.
Retrosynthetic value:
Acts as a bifunctional hub, enabling rapid entry to tri- or tetra-substituted phenyl motifs with controlled regiochemistry. The unreacted F can serve as a bioisosteric handle or for later C–F activation under specialized conditions.
Analytical tips:
Distinguish I vs Br substitution via HRMS isotopic pattern and 13C NMR (downfield shifts adjacent to I). Verify phenolic proton by D2O exchange.
Target Specificity
Not applicable. This product is a small-molecule synthetic intermediate and is not an antibody, probe, or biologic. No item-specific target, epitope, or isotype information is available.
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