2-(3-Bromophenyl)-3'-iodoacetophenone , CAS No.898783-90-9

CAS: 898783-90-9 Cat. No.: B1253230 분자식: C₁₄H₁₀BrIO 분자량: 401.04

Storage

Room temperature

Shipped In

Normal

Specifications

보관 조건

Room temperature

배송

Normal

이름과 식별자

정식 스마일

C1=CC(=CC(=C1)Br)CC(=O)C2=CC(=CC=C2)I

IUPAC Name

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

InChIKey

PGRQWDQIOQFSOF-UHFFFAOYSA-N

INCHI

1S/C14H10BrIO/c15-12-5-1-3-10(7-12)8-14(17)11-4-2-6-13(16)9-11/h1-7,9H,8H2

분자량

401.04

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• 분류: Stilbenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Stilbenes
• Alternative Parents: Alkyl-phenylketones Benzoyl derivatives Aryl alkyl ketones Iodobenzenes Bromobenzenes Aryl iodides Aryl bromides Organoiodides Organobromides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Stilbene - Alkyl-phenylketone - Phenylketone - Benzoyl - Aryl ketone - Aryl alkyl ketone - Bromobenzene - Halobenzene - Iodobenzene - Aryl halide - Aryl iodide - Monocyclic benzene moiety - Aryl bromide - Benzenoid - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organohalogen compound - Organobromide - Organoiodide - Organooxygen compound - Aromatic homomonocyclic compound
• 설명: 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

화학 및 물리적 특성

• 분자량: 401.040 g/mol
• XLogP3: 4.500
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 399.896 Da
• Monoisotopic Mass: 399.896 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 biological assay protocols (WB, IHC, IF, FC) are applicable to this product. For synthetic use, see Reaction Conditions for general coupling and carbonyl-transformation guidelines. Any laboratory procedure should be adapted and validated for the user’s specific substrates, equipment, and safety requirements.

Biological Roles

This product is a synthetic organic building block without established biological function. It is not intended for use in biological systems except as a research chemical precursor.

• No endogenous role: Halogenated biaryl ketones of this type are not natural metabolites or cofactors.
• Possible research context (general): May serve as an intermediate toward ligands, probes, or materials; any biological activity would derive from downstream molecules synthesized from this building block, not from the building block itself.

Research Use Note: For research use only (per Product Data).

Buffer Applications

Not typically applicable. 2-(3-Bromophenyl)-3'-iodoacetophenone is a hydrophobic organic synthesis intermediate and is not used to prepare aqueous buffer systems. For practical guidance, see Solvent Selection (organic media) and Reaction & Applications for its use in synthetic transformations.

Green Alternatives

While the substrate itself is fixed, greener choices can be made in the transformations it participates in.

• Solvent substitutions (literature/green chemistry guidance):
  • Replace DCM/CHCl3 with ethyl acetate, 2-MeTHF, or CPME for workups and reactions where polarity permits.
  • Favor aqueous ethanol or isopropanol for recrystallizations over acetone/MeOH when solubility behavior allows.
• Cross-coupling media:
  • Employ bio-derived 2-MeTHF or water-lean aqueous micellar systems (e.g., TPGS-750-M) for Suzuki couplings, reducing organic solvent load.
  • Use dioxane alternatives (2-MeTHF, CPME, propylene carbonate) to avoid problematic ethers where feasible.
• Catalysis and bases:
  • Utilize precatalysts enabling low Pd loadings (≤0.1–0.5 mol%) and air-stable ligands; explore nickel catalysis for Ar–Br couplings.
  • Choose inorganic carbonate/phosphate bases over strong alkoxides to limit side reactions and improve safety.
• Energy efficiency:
  • Microwave or flow-assisted couplings can shorten reaction times and lower energy consumption.

Example solvent comparison (general):

• THF vs 2-MeTHF: 2-MeTHF offers similar polarity, is biomass-derived, has higher boiling point and better water immiscibility, simplifying workups.
• DCM vs EtOAc: EtOAc is less toxic and readily biodegradable; often suitable for extractions and chromatography.

Adopt greener alternatives subject to reaction compatibility and desired selectivity (particularly important for I vs Br selectivity).

Pharmaceutical Uses

No excipient or formulation role is expected for this compound. As a halogenated aryl-ketone building block, its relevance to the pharmaceutical sector is as a synthetic intermediate during discovery and process R&D.

• Potential roles (general, non-clinical):
  • Intermediate for constructing biaryl or triaryl pharmacophores via selective Ar–I/Ar–Br couplings.
  • Precursor to substituted diaryl ethanols or diarylmethanes after carbonyl manipulation.
• Regulatory status: No pharmacopeial monograph is anticipated for this specialized intermediate.

Note: No medical or therapeutic claims are made. This product is supplied strictly for research and laboratory synthesis.

Physical Properties

• Appearance (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.
• Melting point, boiling point, density, refractive index (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general/literature expectations for halogenated aryl ketones):
  • Typically soluble in chlorinated solvents (e.g., dichloromethane, chloroform), polar aprotic solvents (THF, acetone, acetonitrile, DMF, DMSO), and moderately in ethyl acetate.
  • Poorly soluble in water and aliphatic hydrocarbons.
• Partitioning/polarity (general): Expected to be nonpolar-to-moderately polar due to the aryl ketone; heavy halogens increase lipophilicity and density versus non-halogenated analogs.
• Acid/base behavior (general): Neutral compound; the α-hydrogens adjacent to the carbonyl are mildly acidic and can be deprotonated by strong bases to form enolates; no ionizable groups under neutral aqueous conditions.
• Spectral characteristics (general guidance):
  • IR: strong C=O stretch near ~1660–1685 cm−1 (conjugated aryl ketone; literature).
  • 1H NMR: aromatic multiplets; singlet or quartet for acetyl methyl depending on coupling via long-range; 13C NMR carbonyl ~190–200 ppm (literature).
  • MS: isotopic patterns characteristic of Br (M/M+2 ~1:1) and I (distinct high-mass isotope; literature).

Note: For exact numerical specifications applicable to this SKU, consult the product CoA/Specification Sheet.

Quality and Grades

• Grade/Purity (item-specific): Not specified for this item; refer to CoA/Spec Sheet.
• Typical quality considerations for halogenated aryl-ketone building blocks:
  • Residual halide impurities, di-/polyhalogenated isomers, and trace metal residues (from cross-coupling syntheses) can affect downstream catalysis. CoA typically reports assay (%) and HPLC/GC purity and may include metals by ICP.
  • Moisture is generally not critical for stability but can affect base-sensitive transformations (enolate chemistry); dryness may be relevant for certain reactions.
• Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet. Such materials are rarely added to aryl ketones; verify if present before use.
• What the listed Storage/Shipping imply for quality:
  • Storage: Room temperature (per Product Data) suggests no special cold-chain or peroxide-control requirements; protect from light to minimize any potential photodehalogenation.
  • Shipped in: Normal — standard ambient shipping conditions suitable for stable organic solids.
• Recommended incoming QC (practical guidance):
  • Verify identity by 1H/13C NMR and MS (look for Br/I isotopic patterns); record IR (C=O band) and HPLC/GC purity.
  • For metal-sensitive work (e.g., cross-coupling), consider a brief silica plug or recrystallization if purity is marginal per your application tolerance.

For definitive assay, residual solvents, water, and metals, rely on the certificate of analysis provided with the lot.

Reaction and Applications

2-(3-Bromophenyl)-3'-iodoacetophenone is a versatile bifunctional aryl building block featuring orthogonal aryl halides (Ar–I and Ar–Br) and an enolizable aryl ketone. These handles enable stepwise diversification to densely substituted biaryls and triaryls.

• Cross-coupling platforms (literature):
  • Suzuki–Miyaura: The aryl iodide typically couples first under milder conditions (Pd(0), base: K2CO3/K3PO4/Cs2CO3; solvents: dioxane/H2O, THF/H2O, toluene/H2O) allowing sequential coupling (I then Br) to install two distinct substituents regiocontrolled.
  • Sonogashira: Selective coupling at C–I with terminal alkynes (Pd/Cu, amine base), followed by C–Br coupling if desired using more forcing conditions or ligands that activate Ar–Br.
  • Buchwald–Hartwig amination: Aryl iodide undergoes amination efficiently with Pd precatalysts and dialkylbiaryl phosphines; subsequent amination at Ar–Br possible with stronger ligands/bases and higher temperature.
  • Negishi/Kumada: Oxidative addition preference I > Br enables rapid assembly of C–C bonds using preformed organozinc/magnesium reagents under Pd or Ni catalysis.
• Carbonyl chemistry (literature):
  • Enolate formation (LDA, NaHMDS) supports aldol condensations, Claisen-type transformations, and α-functionalizations (e.g., halogenation, alkylation) without disturbing aryl halides under controlled conditions.
  • Reductions of the ketone (NaBH4, boranes) furnish secondary alcohols; Wolff–Kishner/Clemmensen-type protocols can remove the carbonyl if needed.
• Electrophilic/nucleophilic aromatic chemistry:
  • The heavy halogens direct metal–halogen exchange (e.g., n-BuLi at −78 C, especially for Ar–I) for further elaboration, though care is needed to avoid lithium–halogen scrambling and carbonyl addition.

Overall, the compound serves as a modular hub for rapid SAR exploration and assembly of poly(hetero)aryl scaffolds using halogen-selective, sequential couplings.

Reaction Conditions

General literature guidance for transformations of aryl iodides/bromides and aryl ketones (adjust to your substrate and scale):

• Suzuki–Miyaura couplings:
  • Typical: Pd(PPh3)4 (1–3 mol%) or Pd-PEPPSI-type precatalysts (0.1–1 mol%); base K3PO4 or K2CO3 (2–3 equiv); solvent dioxane/H2O (3:1) or THF/H2O; 60–90 C, 1–8 h. Iodide reacts fastest; bromide may require higher temperature or stronger ligands (SPhos/XPhos).
• Buchwald–Hartwig amination:
  • For Ar–I: Pd2(dba)3 (1–2 mol%) + tBuBrettPhos or RuPhos; NaOtBu or Cs2CO3; toluene/dioxane; 60–90 C.
  • For Ar–Br: More forcing conditions (90–110 C) or electron-rich ligands (XPhos, tBuBrettPhos); 4–24 h.
• Sonogashira:
  • Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%); Et3N or iPr2NH; THF or DMF; 25–70 C. Copper-free variants with bulky phosphines reduce Glaser byproducts.
• Negishi/Kumada:
  • Ar–I generally couples at room temp to 50 C; Ar–Br may need 50–80 C with Pd or Ni catalysts; inert atmosphere recommended.
• Enolate/α-functionalization:
  • LDA or NaHMDS (1.1–1.5 equiv) in THF at −78 to −20 C; electrophile addition (alkyl halides, aldehydes). Quench at low temperature to preserve halides.
• Reductions of the ketone:
  • NaBH4 in MeOH/EtOH or THF/H2O at 0–25 C, 0.5–2 h; or DIBAL-H in toluene/THF at −78 to 0 C. Monitor for potential dehalogenation under harsh conditions.

Yields are substrate- and partner-dependent; for poly(hetero)aryl couplings, isolated yields of 60–90% are common when conditions are optimized (literature). Always perform small-scale scouting to confirm selectivity (I vs Br) with your catalyst system.

Safety and Handling

• GHS classification, signal word, pictograms, H-statements (item-specific): Not specified for this item; refer to SDS.
• General hazard profile (literature/analog-based):
  • Halogenated aromatic ketones may cause skin/eye irritation and respiratory irritation if dusts/fines are generated. Avoid inhalation, ingestion, and contact.
  • Combustible organic solid; may emit hydrogen halides (HBr/HI) and irritating fumes upon thermal decomposition.
• PPE recommendations (good laboratory practice):
  • Use lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to control vapors/dust.
• Handling guidance:
  • Minimize dust generation; weigh on clean paper/boats within a ventilated enclosure.
  • Avoid strong bases or strong nucleophiles unless intended (can promote enolate formation or halide displacement under forcing conditions).
  • Keep away from strong oxidizers and reducing agents.
• First-aid overview (summarized; defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire-fighting measures (general):
  • Use CO2, dry chemical, or foam; avoid water jets. Fire may produce CO/CO2 and hydrogen halides. Firefighters should wear self-contained breathing apparatus.

Always consult the product SDS for authoritative and item-specific safety information.

Solvent Selection

This compound is a neutral, halogenated biaryl ketone with low aqueous solubility and good solubility in common organic solvents.

• Polarity/solubility profile (general):
  • Readily soluble: dichloromethane (DCM), chloroform, THF, acetone, acetonitrile, ethyl acetate, DMF, DMSO (literature/general for aryl ketones with heavy halogens).
  • Sparingly soluble to insoluble: alkanes (hexanes, heptane), water.
• Selection guidance by task:
  • Reaction setup (cross-coupling): THF, 1,4-dioxane, toluene, DMF, DMAc, or NMP are typical. Dioxane/water or THF/water mixtures aid base solubilization in Suzuki couplings.
  • Purification: Normal-phase silica with hexanes/ethyl acetate or toluene/EtOAc gradients. Bromine/iodine increase retention; modest EtOAc percentages often required.
  • Analytics: ACN or MeOH with 0.1% formic acid or ammonium formate buffers for LC-MS; DCM/MeOH or hexanes/EtOAc for TLC (visualize with UV, then KMnO4).
• Comparison to alternatives:
  • If solubility is limited in hydrocarbon media, introduce a polar co-solvent (EtOAc, MTBE, THF) to assist dissolution during crystallizations or reactions.
  • For greener operation, consider 2-MeTHF or CPME in place of THF/DCM where compatible (see Green Alternatives).
• Practical tips:
  • Warm gently (30–40 C) to accelerate dissolution in less polar solvents; avoid overheating to prevent any potential decomposition.
  • Ensure water-miscible solvents are dry when enolate generation or moisture-sensitive couplings are intended.

Storage and Reconstitution

• Storage (item-specific): Room temperature (per Product Data). Store tightly closed in a dry place. Protect from prolonged light exposure to minimize any risk of photodehalogenation.
• Shipping (item-specific): Shipped under normal ambient conditions.
• Stability considerations (general): Halogenated aryl ketones are typically stable solids. Avoid strong bases/acids and prolonged heating. Desiccation is recommended to prevent moisture uptake if repeated enolate chemistry is planned.
• Reconstitution/dissolution (general guidance):
  • Readily dissolves in DCM, THF, acetone, acetonitrile, DMF, or DMSO. For stock solutions, use dry, oxygen-free solvent when the material will be used in air/moisture-sensitive transformations (e.g., metal-catalyzed couplings, enolate chemistry).
  • Typical stock concentrations: 10–100 mM for LC-MS or high-throughput screening of reactions; filter through 0.2 µm PTFE prior to use to remove particulates.
• Freeze–thaw guidance: Not applicable to solids; for prepared solutions, store in sealed amber vials at 2–8 C or −20 C as appropriate for the solvent and intended lifetime; limit freeze–thaw cycles to preserve concentration accuracy.

Always refer to the lot-specific CoA and SDS for authoritative handling, stability, and storage details.

Structure and Identity

Brief description: 2-(3-Bromophenyl)-3'-iodoacetophenone is a halogenated biaryl aryl-ketone building block bearing both bromo and iodo substituents orthogonally positioned on a diaryl framework, featuring a reactive acetyl (aryl–CO–CH3) motif.

• Item-specific identifiers (Product Data):

  • CAS: 898783-90-9
  • InChIKey: 276935 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Category: Chemical and Biochemical Reagents (lab/research use only)

• Structural features (general, derived from name):

  • Core: acetophenone (aryl–CO–CH3) embedded in a biaryl system.
  • Substituents: one ring carries an iodine at the 3' position; the adjacent ring is attached at the 2-position and bears a meta-bromine (3-bromophenyl) substituent.
  • Functional groups: aryl ketone (conjugated carbonyl), aryl bromide, aryl iodide.
  • Conjugation/aromaticity: two benzene rings (biaryl) conjugated to the carbonyl; no heteroaromatic atoms.
  • Stereochemistry: none (no stereocenters, planar/aromatic framework with restricted rotation about the biaryl axis but no defined axial chirality in the absence of bulky ortho groups).
  • Reactivity handles: C–I (highly reactive in oxidative addition), C–Br (moderately reactive), and the aryl ketone (enolizable α-position; participates in condensations and reductions).

Synthetic Utility

Key enabling features and how to exploit them in synthesis:

• Orthogonal halides:
  • Iodide site: Highest oxidative addition propensity; prioritize for initial Pd-catalyzed couplings under mild conditions to introduce sensitive fragments (e.g., heteroaryl boronates, alkynes, amines).
  • Bromide site: Engaged in a second coupling using either stronger ligands (e.g., tBuBrettPhos, XPhos) or elevated temperature; enables sequential, regioselective diversification.
• Carbonyl handle (acetophenone):
  • Enolate chemistry allows α-alkylation/arylation, aldolizations, or installation of tracers (e.g., 13C/2H labels) at the α-position.
  • Chemoselective reductions (NaBH4, DIBAL-H) afford secondary alcohols that can be further functionalized (esterification, carbonate formation, Mitsunobu inversion where relevant).
• Retrosynthetic leverage:
  • Disconnection across C–I enables rapid assembly from readily available 3-iodoacetophenone derivatives and 3-bromophenyl boronates (or vice versa), facilitating modular route design.
  • Metal–halogen exchange (especially at I) followed by electrophile trapping offers access to formylated, carboxylated, or direct lithiation–borylation products while retaining the C–Br handle for subsequent steps (with careful temperature control to avoid carbonyl addition).
• Late-stage diversification:
  • Compatible with many heteroaryl partners; judicious ligand/base choice can maintain functional group tolerance (esters, nitriles, sulfonamides).

This combination of orthogonal halides plus an enolizable ketone makes the compound a compact platform for iterative coupling and α-functionalization sequences in medicinal and materials chemistry.

Target Specificity

Not applicable. This product is a small-molecule chemical building block, not a biological macromolecule or affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.

자주 묻는 질문

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.