2-(2-Fluorophenyl)-3'-iodoacetophenone - ≥95% , CAS No.898784-75-3

CAS: 898784-75-3 Cat. No.: F1253237 Summenformel: C₁₄H₁₀FIO Molekulargewicht: 340.136 PubChem CID: 24723947

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Verschickt in

Normal

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

C1=CC=C(C(=C1)CC(=O)C2=CC(=CC=C2)I)F

IUPAC Name

2-(2-fluorophenyl)-1-(3-iodophenyl)ethanone

InChIKey

XPUXFIZIEPKFEO-UHFFFAOYSA-N

INCHI

1S/C14H10FIO/c15-13-7-2-1-4-10(13)9-14(17)11-5-3-6-12(16)8-11/h1-8H,9H2

Isomere SMILES

C1=CC=C(C(=C1)CC(=O)C2=CC(=CC=C2)I)F

PubChem CID

24723947

Molekulargewicht

340.136

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Klasse Stilbenes

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Klasse: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Alkyl-phenylketones Benzoyl derivatives Aryl alkyl ketones Iodobenzenes Fluorobenzenes Aryl iodides Aryl fluorides Organoiodides Organofluorides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Stilbene - Alkyl-phenylketone - Phenylketone - Benzoyl - Aryl ketone - Aryl alkyl ketone - Fluorobenzene - Halobenzene - Iodobenzene - Aryl halide - Aryl iodide - Monocyclic benzene moiety - Aryl fluoride - Benzenoid - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organohalogen compound - Organofluoride - Organoiodide - Organooxygen compound - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 340.130 g/mol
• XLogP3: 4.000
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 339.976 Da
• Monoisotopic Mass: 339.976 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 269.000
• 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 bioassay or immunoassay application protocols apply to this small-molecule reagent. For chemical synthesis workflows, consider the following general lab protocols:

• Stock solutions for screening: prepare 10–100 mM solutions in DMSO, DMF, THF, or acetonitrile; store aliquots protected from light. Verify stability by LC–MS prior to use in high-throughput experiments.
• Thin-layer chromatography (TLC): visualize under UV (254 nm); iodine staining may also be effective. Expect higher Rf in nonpolar systems due to aryl iodide.
• Column chromatography: start with hexanes/EtOAc 9:1 to 7:3; adjust based on polarity of derivatives. Use light protection if fractionation is prolonged.

These are general synthetic handling notes. For any biological protocol needs, this product is not intended or validated.

Biological Roles

This product is a synthetic organic building block intended for chemical synthesis. It does not have an established biological role.

• No known natural occurrence or metabolic function has been reported for this specific halogenated acetophenone scaffold (literature generalization).
• Any biological evaluation would pertain to user-synthesized derivatives. This listing is for research and laboratory use only and is not intended for use in humans or animals.

For researchers interested in chemical biology applications

• The aryl fluoride provides a convenient 19F NMR handle for probing binding interactions in vitro once incorporated into target molecules.
• The acetophenone carbonyl can, in principle, be derivatized to photoreactive moieties (e.g., aryl azides after further functionalization) for probe development; such uses are user-directed and not specific to this product.

Buffer Applications

Not typically applicable. 2-(2-Fluorophenyl)-3'-iodoacetophenone is a hydrophobic organic building block rather than a buffering agent.

• It does not form defined acid/base conjugate pairs suitable for aqueous pH control.
• For work in aqueous media (e.g., bioconjugations on derivatives), select an appropriate buffer (e.g., phosphate, HEPES) based on the downstream chemistry, and dissolve this compound first in a miscible co-solvent (DMSO, DMF) if needed.

Green Alternatives

Greener considerations focus on solvent and catalyst selection during transformations involving this aryl iodide acetophenone, as the substrate itself contains halogens (I, F) that are integral to its synthetic utility.

• Prefer greener solvents where feasible

  • Replace chlorinated solvents (DCM, chloroform) with 2-MeTHF, CPME, or ethyl acetate for extractions and as reaction media when compatible.
  • Use alcoholic or water-containing biphasic systems for Suzuki couplings (e.g., ethanol/water or 2-MeTHF/water) to reduce environmental burden.

• Catalyst and base choices

  • Employ ligand-efficient or nanoparticle Pd catalysts at low loadings (≤0.5 mol%) when possible. Consider Ni catalysis for certain couplings to reduce reliance on Pd (trade-off: scope and conditions may be more demanding).
  • Use carbonate or phosphate bases in aqueous media instead of strong amide bases when possible.

• Energy and waste minimization

  • Microwave or flow processing can reduce reaction times and solvent volumes.
  • Design sequences that exploit the innate chemoselectivity (I >> F) to minimize protecting-group steps.

Comparison (general)

• DCM vs 2-MeTHF: 2-MeTHF offers renewability, higher boiling point, and lower toxicity; may change solubility and rate.
• DMF/NMP vs Cyrene or propylene carbonate: greener dipolar aprotics, but catalyst/solubility compatibility must be verified.

Caveats

• Aryl iodides are inherently less “green” due to iodine content; however, their high reactivity can reduce catalyst loadings and reaction temperatures, partially offsetting environmental impact.

Pharmaceutical Uses

This material is offered for research use only.

• Role in pharma R&D (general)

  • Functions as a halogenated aromatic building block for discovery chemistry and SAR exploration. The aryl iodide enables rapid diversification via Pd-catalyzed couplings; the acetophenone can be transformed into alcohols, amines, amides, or heterocycles.
  • The aryl fluoride can modulate lipophilicity and metabolic stability in derived candidates.

• Excipient/formulation status

  • Not an excipient and not a compendial (USP/EP) substance as such.

• Process considerations

  • Halogenated intermediates may require specific waste handling in GMP settings. If scaling, ensure control of residual palladium or nickel in compliance with ICH Q3D after cross-coupling steps generating API intermediates.

No therapeutic claims are made or implied. Any use in pharmaceutical manufacturing would be as a synthetic intermediate subject to appropriate regulatory controls.

Physical Properties

Item-specific specifications (this listing)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet. (See literature note below.)
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (See literature note below.)

Literature/computed values and general expectations (for reference only, not product specifications)

• Empirical formula (derived from structure name): C14H10FIO
• Formula weight (calculated): ~340.14 g/mol
• Physical state: typically a crystalline organic solid for analogous ortho‑biaryl acetophenones.
• Solubility: expected to be soluble in common organic solvents (e.g., DCM, chloroform, THF, ethyl acetate, toluene, DMF, DMSO) and essentially insoluble in water due to nonpolar biaryl core; actual solubility should be confirmed experimentally for this item.
• Polarity: moderately lipophilic aryl ketone; aryl iodide increases polarizability.
• UV-vis: aryl ketone chromophore absorbs in near-UV; specific λmax not established for this item.
• Melting point/boiling point, density, refractive index, logP, pKa: Not specified for this item; refer to CoA/Spec Sheet.

Notes for handling based on physical behavior (general)

• Aryl iodides can exhibit light sensitivity; minimize prolonged UV exposure during storage and handling.
• The ketone carbonyl allows for weak H-bond acceptance; however, the overall molecule is dominated by hydrophobic interactions.

Quality and Grades

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

How to interpret grade (general guidance)

• For specialty aryl halide building blocks, specifications typically cover assay/purity by HPLC or GC, identity (NMR, MS), and limits on related impurities (e.g., dehalogenated biaryl, positional isomers), as well as residual solvents and water (Karl Fischer) when relevant.
• If an inhibitor or stabilizer is used (e.g., to suppress iodide/iodonium byproducts), it will be disclosed on the CoA. No stabilizer information is provided for this listing.

What to expect on request

• CoA typically includes: appearance, purity/assay, identity confirmation (1H NMR; sometimes 13C/19F NMR given the F substituent), HRMS or LC–MS, and possibly melting point. For halogenated aromatics, GC residual solvent profile and halide content may be shown.
• Batch-to-batch reproducibility: Iodinated aromatics can be sensitive to light/heat over long storage; verify purity by HPLC/LC–MS before critical applications.

Fit-for-use considerations (general)

• For cross-coupling applications, trace metal content is usually not limiting; however, ensure that halide integrity is high (minimal hydrodeiodinated impurity) to maintain reactivity.
• Low-UV grade is not applicable here unless using as a reference in analytical UV workflows. If required for photochemical studies, request UV-absorbance background data.

Reaction and Applications

This bifunctional building block combines an aryl iodide (highly reactive toward oxidative addition) with an aryl fluoride (electron-withdrawing/inductively deactivating) and an acetyl group. It is well-suited for stepwise diversification in complex-molecule synthesis.

• Cross-coupling at the aryl iodide (primary handle)

  • Suzuki–Miyaura: couples with boronic acids/esters under Pd(0/II) catalysis; the iodide reacts selectively over the aryl fluoride, enabling chemoselective elaboration of the pendant ring.
  • Sonogashira: terminal alkynes can be installed under Pd/Cu co-catalysis, providing alkynylated biaryls for further cyclizations.
  • Buchwald–Hartwig amination: formation of C–N bonds at the iodo position using appropriate ligands (BrettPhos/XPhos series) and bases.
  • Heck: vinylation at the aryl iodide to append alkenes.

• Transformations of the acetophenone unit

  • Enolate chemistry: alpha-alkylation, aldol condensations, and halogenations; potential to direct ortho metalation on the acetophenone ring.
  • Oxime/hydrazone formation followed by Beckmann/Wolff–Kishner reductions or rearrangements (route to amides or deoxygenated frameworks).
  • Baeyer–Villiger oxidation (ketone to ester) to introduce oxygen functionality on the acetophenone ring.

• Exploiting the aryl fluoride (secondary handle)

  • Generally preserved during Pd-catalyzed couplings at iodine; can serve as a spectroscopic tag (19F NMR) and modulate electronics.
  • Under harsh conditions (e.g., SNAr with strong nucleophiles on activated positions), F may be displaced if additional activating groups are introduced.

• Orthogonal sequence planning

  • Typical sequence: first functionalize I (fast), then modify the ketone, finally consider F retention or substitution depending on target. This orthogonality streamlines SAR libraries and scaffolding.

Reaction Conditions

General literature guidance for transformations on aryl iodide acetophenones (adjust to your substrate and scale). Values below are typical ranges, not product specifications.

• Suzuki–Miyaura coupling (at Ar–I)

  • Catalyst: Pd(PPh3)4 (0.5–2 mol%) or Pd2(dba)3 (1 mol%) with SPhos/XPhos (2–4 mol%).
  • Base: K2CO3, K3PO4, or Cs2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O, toluene/H2O, or 2-MeTHF/H2O.
  • Temperature/time: 50–90 °C, 2–12 h. Typical isolated yields for iodides: 70–95% (literature generality).

• Sonogashira coupling

  • Catalyst: PdCl2(PPh3)2 (1–2 mol%) with CuI (5–10 mol%).
  • Base/solvent: Et3N or i-Pr2NH in THF/DMF or 2-MeTHF.
  • Temperature: rt to 60 °C; 1–8 h. High chemoselectivity for I over F.

• Buchwald–Hartwig amination

  • Catalyst/ligand: Pd2(dba)3 (1 mol%) with BrettPhos/XPhos (2–4 mol%).
  • Base: NaOtBu or K3PO4.
  • Solvent: toluene, dioxane, or tAmOH.
  • Temperature: 80–110 °C, 4–16 h.

• Ketone manipulations

  • NaBH4 reduction to secondary alcohol in MeOH/THF at 0–25 °C (0.5–2 h).
  • Enolate alkylation with LDA (1.1–1.5 equiv) in THF at −78 to −40 °C; electrophile then added; quench at ≤0 °C.
  • Baeyer–Villiger: mCPBA (2–3 equiv) in DCM at 0–25 °C; monitor for over-oxidation.

• SNAr on aryl fluoride (only under activating conditions)

  • Strong nucleophile (e.g., amines/thiolates) with additional ring activation and elevated temperatures; otherwise F remains intact.

Always monitor reactions by LC–MS/HPLC. Degas solvents for Pd-catalyzed processes; dry conditions improve reproducibility.

Safety and Handling

Authoritative safety data should be taken from the product SDS. The information below provides general guidance for aryl iodide acetophenones.

• GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.
• Likely hazards (general for aryl halides/aryl ketones)
  • May cause skin/eye irritation and respiratory tract irritation upon dust/aerosol exposure.
  • Combustible organic solid; avoid ignition sources and dust accumulation.
• Personal protective equipment (PPE)
  • Lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust or solvent vapors.
• Handling and storage
  • Store tightly closed at room temperature (per Product Data), in a dry place, away from strong oxidizers and bases. Protect from light to limit any potential aryl iodide photolysis (general precaution).
  • Avoid contact with strong reducing metals/agents that could effect dehalogenation; avoid halogen/metal exchange conditions unless intended.
• First aid (general)
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin: wash with soap and water; remove contaminated clothing.
  • Eyes: rinse cautiously with water for several minutes; remove contact lenses if present and easy to do; seek medical advice if irritation continues.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
• Spill and disposal
  • Contain solids to prevent dusting; collect with inert absorbent for disposal. Dispose of contents/container in accordance with local/regional regulations.
• Fire fighting
  • Use dry chemical, CO2, alcohol-resistant foam. Combustion may release corrosive hydrogen halides; wear SCBA.

Solvent Selection

This compound is a moderately lipophilic biaryl ketone with an aryl iodide. It dissolves best in mid- to low-polarity organic solvents; water solubility is expected to be negligible.

• Recommended solvents (general guidance; verify experimentally for your lot)

  • Chlorinated: dichloromethane, chloroform — excellent solubility; convenient for workup and chromatography.
  • Ethers: THF, 2-MeTHF, MTBE — good for metalations and cross-couplings; THF miscibility aids dosing and catalyst dissolution.
  • Esters/aromatics: ethyl acetate, toluene — useful for crystallization, coupling reactions at elevated T.
  • Polar aprotic: DMF, DMAc, DMSO, NMP — enable high concentrations for cross-coupling or SNAr on the aryl fluoride (if attempted under forcing conditions).

• Selection by application

  • Cross-coupling on the aryl iodide: toluene/THF, dioxane, or DMF are common, often with water as co-solvent for boronic acids (Suzuki).
  • Electrophilic aromatic substitution on the acetophenone ring: acylations/halogenations often use glacial AcOH, DCM, or MeCN.
  • Purification: normal-phase silica gel with hexanes/EtOAc or toluene/EtOAc gradients; the aryl iodide increases retention versus non-halogenated analogs.

• Compatibility notes

  • Avoid strongly basic alcohols as primary solvents for prolonged periods if enolate chemistry is not desired; the acetyl group can undergo base-catalyzed side reactions.
  • For air/moisture-sensitive transformations (e.g., metal–halogen exchange), dry, degassed ethereal or hydrocarbon solvents are preferred.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Ship at ambient temperature (normal).
• Container and environment
  • Keep tightly closed in the original container. Store dry and protect from light to minimize potential photodecomposition of aryl iodide functionalities (general best practice).
• Stability notes (general guidance)
  • Halogenated aromatics are typically stable solids under ambient conditions. Prolonged exposure to strong light/UV, heat, or moisture should be avoided.
  • If long-term storage is anticipated, consider desiccation and secondary containment with a light-opaque bottle.
• Reconstitution/solution preparation
  • Prepare stock solutions in dry organic solvents (e.g., DCM, THF, toluene, DMF, DMSO, acetonitrile). Typical screening concentrations: 10–100 mM.
  • Filter solutions (0.2 µm PTFE) for sensitive reactions to remove particulates.
  • Avoid extended storage of solutions, especially in protic solvents; prepare fresh prior to critical transformations. If solution storage is required, keep under inert gas at 2–8 °C and protect from light (general recommendation).
• Freeze–thaw
  • Not typically applicable for solids. If storing solutions as aliquots, minimize freeze–thaw cycles to reduce precipitation or concentration drift.

Always refer to the product CoA/SDS for definitive stability and handling parameters. Research use only.

Structure and Identity

Brief description: 2-(2-Fluorophenyl)-3'-iodoacetophenone is an ortho-biaryl acetophenone bearing a fluorine on the pendant ring (at the 2′-position relative to the biaryl bond) and an iodine at the 3′-position. The acetyl (–COCH3) group is on the base ring adjacent (ortho) to the biaryl linkage.

• Item-specific identifiers (from Product Data)

  • SKU: F1253237
  • Product name: 2-(2-Fluorophenyl)-3'-iodoacetophenone
  • CAS: 898784-75-3
  • CID: 24723947
  • InChIKey: 424165 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general description)

  • Core scaffold: acetophenone (aryl–CO–CH3) with an ortho biaryl linkage to a 2-fluorophenyl ring.
  • Functional groups: aryl ketone (conjugated carbonyl), aryl iodide (C–I, highly reactive in cross-coupling), aryl fluoride (C–F, strong inductive effects, relatively inert to oxidative addition).
  • Ring systems: two benzene rings linked biaryl (non-ortho-fused; rotationally hindered by ortho substitution).
  • Stereochemistry: achiral; no stereogenic centers.

• Composition (literature/computed)

  • Empirical formula (literature, inferred from name): C14H10FIO
  • Formula weight (literature calculation): ~340.14 g/mol

• 2D structure in words

  • Base ring: acetophenone with the carbonyl meta/para ring positions unsubstituted, and an ortho carbon bearing a C–C bond to a second ring.
  • Pendant ring: a phenyl ring bearing F at the ortho (2′) position relative to the biaryl bond and I at the meta (3′) position.

Synthetic Utility

Key reactive elements and their strategic value:

• Aryl iodide (primary coupling handle)

  • Fast oxidative addition enables low-temperature and low-loading Pd catalysis for C–C, C–N, and C–S bond formations. High chemoselectivity over the aryl fluoride allows stepwise diversification.

• Acetophenone carbonyl (polarity handle and transformable synthon)

  • Enolate formation (LDA, NaHMDS, KOtBu) gives access to alpha-functionalization (alkylation, halogenation) and to aldol condensations.
  • Reductive transformations yield secondary alcohols (NaBH4, catalytic hydrogenation) which can then be derivatized (e.g., Mitsunobu, esterification, carbamate formation).
  • Oxime/hydrazone formation enables downstream rearrangements (Beckmann to amides; Wolff–Kishner for deoxygenation).

• Aryl fluoride (spectator/handle)

  • Electron-withdrawing inductive effect can tune reactivity of adjacent positions; generally inert to oxidative addition, allowing it to persist through multiple steps. Under activating conditions, can participate in SNAr.

Retrosynthetic perspectives

• Targeting tri- or tetra-substituted biaryls: leverage iodide for first diversification, then manipulate the ketone to introduce heteroatoms or rings; keep F as a late-stage probe or site for potential SNAr.
• Intramolecular cyclizations: post-Sonogashira alkyne installation can enable annulations to indene/indenone-type frameworks or polycycles after electrophilic activation of the ketone.

Analytical facilitation

• The F atom affords 19F NMR traceability; the iodide provides a strong MS handle (characteristic isotopic pattern). These aid in rapid verification of transformations.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and does not possess biological target specificity, antigen reactivity, or immunological attributes. No clone, isotype, or species reactivity information is relevant.