3-Iododibenzofuran , CAS No.5896-29-7

CAS: 5896-29-7 Cat. No.: I942017 Formula: C₁₂H₇IO Peso molecolare: 294.090

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

C1=CC=C2C(=C1)C3=C(O2)C=C(C=C3)I

IUPAC Name

3-iododibenzofuran

InChIKey

ZMFYMIKRDGURNT-UHFFFAOYSA-N

INCHI

1S/C12H7IO/c13-8-5-6-10-9-3-1-2-4-11(9)14-12(10)7-8/h1-7H

Peso molecolare

294.090

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Benzofurans
      • Subclass Dibenzofurans

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Benzofurans
• Subclass: Dibenzofurans
• Intermediate Tree Nodes: Not available
• Direct Parent: Dibenzofurans
• Alternative Parents: Benzenoids Aryl iodides Heteroaromatic compounds Furans Oxacyclic compounds Organooxygen compounds Organoiodides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Dibenzofuran - Benzenoid - Aryl iodide - Aryl halide - Heteroaromatic compound - Furan - Oxacycle - Organic oxygen compound - Hydrocarbon derivative - Organooxygen compound - Organoiodide - Organohalogen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as dibenzofurans. These are compounds containing a dibenzofuran moiety, which consists of two benzene rings fused to a central furan ring.
• 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

• Peso molecolare: 294.090 g/mol
• XLogP3: 4.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 293.954 Da
• Monoisotopic Mass: 293.954 Da
• Topological Polar Surface Area: 13.100 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 218.000
• 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 application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule building block, and none are provided in the Product Data. For practical use, consult the Reaction Conditions and Application sections for synthetic procedures.

Biological Roles

This product is a synthetic aryl iodide building block and is not intended for biological use. No endogenous biological role is established for 3-iododibenzofuran.

General context (informational):

• Dibenzofuran frameworks are used in research materials chemistry (e.g., OLED/OPV scaffolds, ligands) due to their rigid, electron-rich, planar structures.
• Iodo substituents can serve as radiolabeling handles in tracer synthesis (e.g., radioiodination) in research settings; however, such applications require specialized facilities and are outside the scope of this product listing.

Research Use Note: For research use only. Not for human or animal therapeutic or diagnostic use.

Buffer Applications

Not typically applicable. 3-Iododibenzofuran is a hydrophobic aryl iodide building block and is not used to prepare aqueous buffer systems. For practical guidance, refer instead to the Reaction & Applications, Synthetic Utility, and Reaction Conditions sections for organic synthesis usage.

Green Alternatives

Greener practice centers on solvent/catalyst choices and minimizing halogenated waste while leveraging the high reactivity of the aryl iodide to reduce energy and catalyst loadings.

• Solvent considerations (literature/general):

  • Replace dioxane/DMF where feasible with bio-derived ethers such as 2-MeTHF or cyclopentyl methyl ether (CPME), or with green esters like propylene carbonate, balancing solubility/catalyst compatibility.
  • Perform Suzuki couplings in water-rich media or aqueous micellar systems (e.g., with surfactants like TPGS-750-M) to cut organic solvent usage.

• Catalyst and process:

  • Use highly active Pd precatalysts with bulky biaryl phosphines to lower Pd loading (≤0.1–0.5 mol%) and enable lower temperatures.
  • Explore nickel catalysis for certain couplings to reduce reliance on Pd, noting potential trade-offs in scope and functional-group tolerance.

• Energy efficiency:

  • The iodo leaving group typically allows shorter reaction times and reduced temperatures versus bromo/chloro counterparts—less heating means lower energy demand.

Comparison highlights (general):

• 3-Iododibenzofuran vs 3-bromodibenzofuran:
  • Reactivity: I > Br (allows milder conditions)
  • Cost/waste: I generally higher cost; iodide waste requires halogenated disposal streams
  • Selectivity: iodides may minimize side reactions by enabling faster oxidative addition

Trade-offs should be evaluated case-by-case; process safety and product quality remain primary.

Pharmaceutical Uses

No excipient or pharmacopeial role is specified for this item. It is supplied for research use as a synthetic intermediate.

General formulation/manufacturing context (informational, not a claim):

• Aryl iodides like 3-iododibenzofuran are common handles in medicinal chemistry campaigns to access analogs via Pd-catalyzed C–C and C–N bond construction during SAR exploration.
• If used in route scouting for API intermediates, attention should be given to residual palladium control, halogen balance, and purge of aromatic impurities, following ICH Q3 guidelines.

Research Use Note: For research use only. Not for human or animal therapeutic or diagnostic applications.

Physical Properties

Item-specific specifications (this lot):

• 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, water or peroxide limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for 3-iododibenzofuran (informational, not item specifications):

• Physical state: typically a crystalline aromatic solid (literature).
• Molecular formula: C12H7IO (literature/computed)
• Molecular weight: ~294.08 g/mol (literature/computed)
• Solubility: sparingly soluble in water; soluble in common organic solvents such as toluene, dichloromethane, chloroform, THF, DMF, and dioxane (general solubility behavior of aryl iodides and dibenzofurans).
• Partitioning: expected high hydrophobicity due to the polycyclic aromatic framework and iodine substituent (qualitative, literature trend).

Practical handling notes (general):

• Being an aryl iodide, it dissolves well in moderately nonpolar to polar aprotic media used for cross-coupling (e.g., dioxane, THF, DMAc, DMF, toluene) and can be recrystallized from aromatic/chlorinated solvents when needed.
• Hygroscopicity is not typically a concern; nevertheless, keep dry to maintain assay purity and coupling performance.

Quality and Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades and implications (general):

• Research grade aryl iodides are typically supplied with assay suitable for cross-coupling and metalation chemistry. If HPLC/UV grade is required (e.g., for analytical reference), ensure low UV background and controlled residual metals.
• For catalytic C–C/C–N couplings, trace metal content can impact performance. If your application is catalyst-sensitive or for API intermediate work, request CoA details on assay, GC/HPLC purity, residual metals, and halide content.
• Particle size may affect dissolution and dosing accuracy; gentle grinding under inert atmosphere can improve charging in glovebox operations.
• If your workflow is moisture-sensitive (e.g., lithium–halogen exchange), consider drying the solid under vacuum at ambient temperature prior to use and transferring under inert gas.

Documentation: Aladdin provides a CoA/Spec Sheet for lot-specific assay, impurity profile, and handling notes on request.

Reaction and Applications

3-Iododibenzofuran is a versatile electrophile; the aryl iodide enables high-rate cross-couplings and metalations on a rigid, electron-rich dibenzofuran core.

Key reaction families (literature/general):

• C–C bond formations:
  • Suzuki–Miyaura coupling with aryl/heteroaryl/alkenyl boron reagents to access diverse 3-substituted dibenzofurans. The iodo leaving group affords short cycle times and lower catalyst loadings versus Br/Cl analogs.
  • Sonogashira coupling with terminal alkynes (Pd/Cu co-catalysis or Cu-free protocols) to give 3-alkynyl derivatives; useful in materials and ligand synthesis.
  • Negishi/Kumada coupling via organozinc or Grignard reagents formed in situ or ex situ.
  • Heck arylation onto activated alkenes (e.g., acrylates, styrenes) at elevated temperature.
• C–N, C–O, C–S, C–P couplings:
  • Buchwald–Hartwig amination with (hetero)amines.
  • Ullmann-type couplings (Cu catalysis) for O-, N-, and S-arylations under appropriate ligand/base sets.
• Metalation chemistry:
  • Lithium–halogen exchange (e.g., n-BuLi, t-BuLi, iPrMgCl·LiCl) enabling trapping with electrophiles (formylation, acylation, borylation).
  • Grignard formation (Mg, activator such as a crystal of I2) followed by addition to electrophiles.

Practical notes:

• Maintain anhydrous, oxygen-free conditions for Pd-catalyzed and organometallic steps; dry glassware and degassed solvents are recommended.
• For Suzuki couplings, bases such as K3PO4 or Cs2CO3 in dioxane/water at 60–100 °C often deliver excellent conversions. Catalyst systems like Pd(PPh3)4 or Pd-precatalysts with dialkylbiaryl phosphines (XPhos, SPhos) are effective.
• The dibenzofuran oxygen can influence regioselectivity and electronic properties, often improving cross-coupling rates relative to purely carbocyclic analogs.

Reaction Conditions

The following are typical literature conditions for aryl iodides on related scaffolds; optimize for your system. Values are general guidance, not item specifications.

• Suzuki–Miyaura coupling:

  • Catalyst: Pd(PPh3)4 (1–2 mol%) or Pd-precatalyst with XPhos/SPhos (0.2–1 mol%).
  • Base: K3PO4, K2CO3, Cs2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O (3:1), THF/H2O, or toluene/H2O.
  • Temperature/time: 60–100 °C, 1–8 h; iodides often reach completion faster than bromides.

• Sonogashira coupling:

  • Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%) or Cu-free systems with bulky ligands.
  • Base: Et3N, iPr2NH, or K2CO3.
  • Solvent: DMF, DMAc, or THF; 40–80 °C, 2–12 h.

• Buchwald–Hartwig amination:

  • Catalyst: Pd2(dba)3 (1 mol% Pd) with BINAP/BrettPhos/XPhos.
  • Base: NaOtBu, Cs2CO3, or K3PO4.
  • Solvent: toluene, dioxane, or CPME; 80–110 °C, 4–16 h.

• Negishi/Kumada:

  • Pre-form organozinc/Grignard or generate in situ; Pd or Ni catalysts (0.5–2 mol%).
  • Etheric or THF solvents; 0–60 °C, 1–6 h.

• Lithium–halogen exchange/trapping:

  • Reagent: n-BuLi (1.1–1.5 equiv) or iPrMgCl·LiCl (Turbo Grignard).
  • Solvent: anhydrous THF; temperature: −78 to −40 °C; quench with electrophile (e.g., DMF for formylation).

Operational notes:

• Use inert atmosphere, dry glassware, and degassed solvents. Monitor by TLC/GC/HPLC; quench metal residues and follow appropriate workup to remove Pd/Ni/Cu.

Safety and Handling

Item-specific hazard details (from Product Data):

• GHS classification: Not specified; consult the SDS.
• Signal word / H-statements / pictograms: Not specified; consult the SDS.

General safety guidance for aryl iodides and polycyclic aromatics (informational only; defer to the SDS for authoritative data):

• Likely hazards: May cause skin/eye irritation and respiratory irritation as particulate/dust. Aromatic halides can be harmful if swallowed or inhaled; avoid dust formation and inhalation of vapors during heating.
• Environmental considerations: Halogenated aromatics can be harmful to aquatic life; prevent release to the environment and collect waste in halogenated organic waste streams.
• PPE: Use lab coat, safety glasses or chemical splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood during weighing, charging, and heating.
• Handling: Avoid strong bases/nucleophiles if undesired metal–halogen exchange is possible. For cross-couplings, exclude air/moisture as required by catalyst system. Avoid prolonged heating to decomposition.
• Incompatibilities (general): Strong reducing metals in the presence of protic solvents can lead to side reactions; strong oxidants may halogenate/oxidize the aromatic framework.
• First aid (overview): If on skin, wash with soap and water; if in eyes, rinse cautiously with water for several minutes; if inhaled, move to fresh air; if ingested, seek medical advice. Always follow institution SOPs.

Always read the current SDS prior to use and follow institutional risk assessments.

Solvent Selection

This product is a solid aryl iodide building block; solvent selection refers to media for its use in synthesis.

• Polarity and miscibility (general):

  • Sparingly water-soluble; prefers organic media.
  • Good solubility in chlorinated (DCM, chloroform), aromatic (toluene), and polar aprotic solvents (THF, 1,4-dioxane, DMF, DMAc, NMP).

• Typical choices by transformation:

  • Suzuki–Miyaura: 1,4-dioxane/water, toluene/water, or THF/water with base (K2CO3, K3PO4, Na2CO3).
  • Sonogashira: DMF, DMAc, or THF with amine base (Et3N, iPr2NH); toluene for higher-temperature runs.
  • Buchwald–Hartwig: toluene, dioxane, or CPME; DMF/DMAc if higher solubility is needed.
  • Lithium–halogen exchange/Grignard: anhydrous THF, Et2O, or MTBE.

• Practical tips:

  • Start with a 0.05–0.25 M substrate concentration to balance solubility and mass transfer.
  • For biphasic Suzuki conditions, add a phase-transfer agent if needed (e.g., TBAB) and ensure adequate agitation.
  • Degas coupling solvents (sparge with N2/Ar or vacuum–backfill cycles) when using O2-sensitive catalysts.

• Comparison notes:

  • Versus bromo/chloro analogs, the iodo derivative dissolves comparably but reacts faster, enabling lower temperature or milder bases in many cases.

Storage and Reconstitution

Item-specific storage/shipping:

• Storage conditions: Room temperature (from Product Data).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance:

• Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged light and heat. For moisture- or air-sensitive operations (e.g., metalation), consider storing under inert gas after opening.
• Reconstitution/solution preparation: Dissolve in dry organic solvents suitable for the intended reaction (e.g., THF, toluene, DCM, DMF, DMAc). Filter if necessary to remove particulates. Prepare fresh solutions for air/moisture-sensitive chemistry.
• Stability: Aryl iodides are generally stable at ambient conditions; avoid strong light/heat that can promote homolysis or decomposition. If long-term storage is anticipated, aliquot and keep sealed.

Always refer to the product’s CoA/Spec Sheet and SDS for lot-specific stability and handling information.

Structure and Identity

3-Iododibenzofuran is an aryl iodide on a rigid dibenzofuran scaffold, useful as a high-reactivity cross-coupling handle.

• Item-specific identifiers (from Product Data):

  • CAS: 5896-29-7
  • PubChem CID: 14290983
  • InChIKey: 460761
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identifiers and descriptors (for reference; not item specifications):

  • Common structural class: polycyclic heteroaromatic (dibenzofuran core) bearing an aryl iodide substituent at the 3-position.
  • Molecular formula (literature/computed): C12H7IO
  • Molecular weight (literature/computed): ~294.08 g/mol

• Structural features (general chemistry description):

  • Ring system: a tricyclic system composed of two benzene rings fused through a central furan (oxygen-bridged) ring (dibenzofuran).
  • Functional groups: aryl iodide (C–I), aryl ether (aryl–O–aryl within the fused framework).
  • Substitution pattern: iodine at the 3-position (on an outer benzene ring adjacent to the oxygen-bridged junction), providing a highly reactive aryl halide site while preserving the electron-rich dibenzofuran core.
  • 2D description: two fused benzene rings flanking a five-membered furan; an iodine atom attached to the perimeter carbon of one benzene ring ortho to the oxygen bridge.

Synthetic Utility

Functional group leverage:

• Aryl iodide: fastest oxidative addition among aryl halides, enabling low-temperature Pd/Ni catalysis and broad coupling scope (C–C, C–N, C–O, C–S, C–P).
• Dibenzofuran core: rigid, π-rich framework that imparts planarity and conjugation; the embedded oxygen can modulate electronics and direct metalation.

Transformations (literature/general):

• Cross-couplings: Suzuki (to install aryl/alkenyl), Sonogashira (alkynyl), Heck (alkenylation), Negishi/Kumada (alkyl/aryl), and Buchwald–Hartwig (amination).
• Borylation: Pd-catalyzed borylation (e.g., with B2pin2) to 3-boryldibenzofuran, enabling subsequent Suzuki diversifications.
• Metal–halogen exchange: n-BuLi or iPrMgCl·LiCl to form arylmetalloid species for electrophile trapping (formylation, acylation, halogenation, silylation, phosphination).
• Reductive transformations: Pd-catalyzed dehalogenation to access the parent dibenzofuran or to tune substitution patterns.

Retrosynthetic value:

• 3-Iododibenzofuran serves as a convergent branching point: install the dibenzofuran scaffold early, then diversify at C3 under catalyst control to explore electronic/steric space without re-engineering the core.

Selectivity and compatibility:

• The iodo handle provides orthogonality vs positions activated for electrophilic substitution on the ring system; many protecting-group strategies are unnecessary due to the stability of the aryl ether within the fused core.

Target Specificity

Not applicable. This product is a small-molecule synthetic building block and is not an antibody, enzyme, or affinity reagent. No target specificity, antigen, epitope, or isotype information is provided in the Product Data.