1-(2-Bromo-3-fluorophenyl)ethanone - ≥97% , CAS No.161957-58-0

CAS: 161957-58-0 Cat. No.: B191293 Formula: C₈H₆BrFO Peso molecolare: 217.04

GRADE & PURITY ≥97%

Storage

Room temperature

Shipped In

Normal

Specifications

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥97%

Nomi e identificatori

Pubchem Sid

488196903

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/488196903

Sorrisi canonici

CC(=O)C1=C(C(=CC=C1)F)Br

IUPAC Name

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

InChIKey

WBMUEFOEEVGDNQ-UHFFFAOYSA-N

INCHI

1S/C8H6BrFO/c1-5(11)6-3-2-4-7(10)8(6)9/h2-4H,1H3

Isomeri SMILES

CC(=O)C1=C(C(=CC=C1)F)Br

Peso molecolare

217.04

Reaxy-Rn

7127020

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=7127020&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Classe Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Aryl ketones
            • Level7 Phenylketones
              • Level8 Alkyl-phenylketones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Classe: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Aryl ketones - Phenylketones
• Direct Parent: Alkyl-phenylketones
• Alternative Parents: Acetophenones Benzoyl derivatives Aryl alkyl ketones Fluorobenzenes Bromobenzenes Aryl fluorides Aryl bromides Vinylogous halides Organofluorides Organobromides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alkyl-phenylketone - Acetophenone - Benzoyl - Aryl alkyl ketone - Bromobenzene - Fluorobenzene - Halobenzene - Aryl bromide - Aryl fluoride - Aryl halide - Monocyclic benzene moiety - Benzenoid - Vinylogous halide - Hydrocarbon derivative - Organic oxide - Organofluoride - Organohalogen compound - Organobromide - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
• 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: 217.030 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 215.959 Da
• Monoisotopic Mass: 215.959 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 160.000
• 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 tested bioassay or immunoassay application protocols are provided for this small-molecule reagent.

• If employing in screening assays or chemical biology, develop protocol-specific handling:
  • Prepare stock solutions in dry DMSO or acetonitrile; filter if necessary (PTFE syringe filter).
  • Determine solubility limits and vehicle tolerances for your assay system.
  • Incorporate appropriate negative controls (vehicle) and, where relevant, orthogonal analytical confirmation (LC/MS, 19F NMR).

Biological Roles

This product is a small-molecule synthetic building block with no known physiological role. It is not typically used to probe biological pathways directly.

• General notes (informational only)
  • Aromatic ketones can act as hydrophobic scaffolds in medicinal chemistry programs, but this specific compound is primarily a chemical intermediate.
  • The aryl fluoride is often used as an NMR handle (19F) in chemical biology; however, any biological testing would be part of bespoke research. No biological activity is implied by this listing.

For research use only; not intended for human or animal diagnostic or therapeutic applications.

Buffer Applications

Not typically applicable. 1-(2-Bromo-3-fluorophenyl)ethanone is an organic building block rather than a buffering agent.

• Practical note
  • If used in biochemical assays, dissolution typically requires polar aprotic solvents (e.g., DMSO) before dilution into assay media. Confirm solubility and vehicle tolerability for the specific system.

Green Alternatives

While the molecule itself is a fixed structure, greener choices can be made around its use, particularly solvent and reagent selection.

• Greener solvent choices (general guidance)
  • Replace DCM with:
    • 2-Methyltetrahydrofuran (2-MeTHF): bio-based, higher boiling point, good for organometallics and many Pd couplings.
    • Cyclopentyl methyl ether (CPME): low peroxide formation tendency, hydrophobic; suitable for extractions and couplings.
  • Replace DMF/NMP where possible with:
    • Acetonitrile, 2-MeTHF, or propylene carbonate (depending on reaction class and catalyst tolerance).
• Bases and additives
  • In Suzuki couplings, aqueous K2CO3, Na2CO3, or KOAc in ethanol/water or 2-MeTHF/water mixtures can reduce reliance on strong inorganic bases and high-boiling dipolar aprotics.
• Energy and process considerations
  • Microwave-assisted couplings can decrease reaction time/energy usage compared to prolonged reflux.
  • Flow chemistry for halogen–metal exchange and rapid quench can improve safety and reduce solvent inventory.
• Waste minimization
  • Choose boron partners that generate benign byproducts (e.g., boronic acids/esters vs. stannanes). Avoid organotin (Stille) unless necessary due to toxicity/waste concerns.

Comparison snapshot (general)

• Conventional: DCM, DMF, toluene; SnBu3 partners.
• Greener direction: 2-MeTHF/CPME, MeCN/EtOH–water, boronic acids/esters; catalytic loads optimized with modern ligands.

Pharmaceutical Uses

No pharmacopeial or excipient status is specified for this item.

• Item-specific status
  • Pharmaceutical/Excipient designation: Not specified for this item; refer to CoA/Spec Sheet.
• General context (non-clinical)
  • Halogenated acetophenones like this are commonly used as synthetic intermediates in medicinal chemistry campaigns to assemble aryl ketone or biaryl motifs via cross-coupling, followed by carbonyl modifications.
  • Any use in drug substance or product manufacture would require process-specific qualification and regulatory compliance not covered by this listing.

For research and laboratory 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.
  • Water, peroxide, metal content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed descriptors (for context; not item specifications)
  • Molecular formula: C8H6BrFO (derived from structure)
  • Molecular weight: ~217.03 g/mol (calculated)
  • Structural class: halogenated aryl methyl ketone (aryl bromide + aryl fluoride)
  • Polarity: moderately polar due to conjugated carbonyl; ring halogens increase lipophilicity.
  • Expected solubility profile (literature/general):
    • Good solubility in common organic solvents such as dichloromethane, chloroform, THF, acetonitrile, ethyl acetate, and aromatic hydrocarbons; low solubility in water typical of halogenated acetophenones.
  • Hydrogen-bonding: carbonyl oxygen is an H-bond acceptor (no donors).
• Practical notes (general)
  • The ortho-bromine and meta-fluorine can modestly influence melting/boiling behavior relative to unsubstituted acetophenone; confirm actual values on the CoA for this lot.
  • For analytical work, typical methods include 1H/13C NMR (characteristic methyl singlet near 2.5–2.7 ppm, aromatic region with halogen-induced shifts), 19F NMR (single aryl-F resonance), IR (strong C=O stretch ~1680–1710 cm−1; literature ranges), and MS (M/M+2 from bromine isotopes).

Quality and Grades

• Item-specific quality information
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
• How to interpret common grades (general guidance)
  • Research grade: suitable for general synthesis; impurity levels adequate for routine lab use but not necessarily for trace analysis.
  • Purified/≥98% organic building blocks: typical for reproducible reactions and spectral characterization; check residual solvent and isomer content.
  • HPLC grade (for solvents) or LC/MS grade: refers to volatile impurities/UV absorbance—less relevant for solids like this unless specified.
• Quality control considerations for this class of compound (general)
  • Identity: 1H/13C/19F NMR, IR (C=O), HRMS, and melting point (if solid) or refractive index (if liquid). Bromine isotopic pattern (M/M+2 ~1:1) is diagnostic in MS.
  • Purity: quantitative NMR, GC or HPLC with UV detection near 254 nm (aryl chromophore), and KF for trace moisture if relevant to downstream reactions.
  • Typical impurities: positional isomers (e.g., 2-bromo-4-fluoroacetophenone), unreacted precursors, or debrominated/defluorinated analogs.
• Documentation
  • For lot-specific assay, residual solvents, and analytical traces, consult the Aladdin CoA and Specification Sheet supplied with the product.

Reaction and Applications

• As a bifunctional aryl building block
  • Aryl bromide handle (C–Br) enables cross-couplings: Suzuki–Miyaura (to biaryls), Buchwald–Hartwig amination, Sonogashira, Negishi, and Stille. The meta-fluoro remains intact under many Pd-catalyzed conditions, offering divergent late-stage diversification.
  • Halogen–lithium exchange at C–Br (e.g., with n-BuLi) allows access to ortho-lithiated intermediates; subsequent electrophile trapping yields 2-substituted 3-fluoroacetophenone derivatives. Exercise chemoselectivity to avoid lithium–halogen exchange at C–F (less reactive) and protect the ketone if needed (e.g., as ketal) under strong basic conditions.
• Carbonyl transformations on the acetyl group
  • Oxime/hydrazone formation, Wolff–Kishner or Clemmensen-type reductions to the corresponding ethyl arenes (conditions may affect C–Br; plan accordingly).
  • Nucleophilic additions (e.g., hydride reduction to secondary alcohol), Baeyer–Villiger oxidation to aryl acetates (potential migration influences by ring substituents).
  • Enolization/alpha-functionalization (e.g., halogenation, alkylation) at the methyl group; the aryl bromide allows orthogonal diversification.
• Electrophilic aromatic substitution (EAS)
  • The carbonyl (meta-directing, deactivating) and halogens (deactivating) reduce EAS reactivity; if needed, employ strong Lewis acids and controlled conditions. Direct ring nitration/sulfonation should be approached cautiously to retain C–Br.
• Synthesis utility examples (literature/general)
  • Preparation of 2,3-disubstituted acetophenone libraries by Suzuki coupling at C–Br followed by chemoselective ketone derivatization.
  • Access to heteroaryl ketones via Pd-catalyzed coupling with heteroaryl boronates, maintaining the aryl–F as a diagnostic 19F NMR handle.
• Practical tips
  • For couplings, choose catalysts/ligands suited to aryl bromides (e.g., Pd2(dba)3/XPhos systems). Control base strength to avoid ketone enolate side-reactions.
  • If strong bases are required, consider protecting the ketone (ethylene glycol ketal) and deprotect post-transformation.

Reaction Conditions

General literature guidance for aryl bromides bearing ketones (for planning only; optimize experimentally). Not item-specific specifications.

• Suzuki–Miyaura cross-coupling (Ar–Br → Ar–Ar′)
  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (1 mol%) with XPhos/SPhos (2–5 mol%).
  • Base: K2CO3, Cs2CO3, or K3PO4 (2–3 equiv).
  • Solvent: toluene, dioxane, 2-MeTHF, or MeCN; often with 5–20% water.
  • Temperature/time: 60–100°C, 2–16 h. The aryl–F typically remains intact.
• Buchwald–Hartwig amination (Ar–Br → Ar–NR2)
  • Catalyst/ligand: Pd2(dba)3 (1–2 mol%) with BrettPhos/XPhos (2–5 mol%); or Pd(OAc)2 + t-BuXPhos.
  • Base: NaOtBu, KOtBu, or K3PO4 depending on amine nucleophilicity.
  • Solvent: toluene, dioxane, or 2-MeTHF. 80–110°C, 6–18 h.
• Sonogashira coupling
  • Catalyst: Pd(PPh3)2Cl2 (1–3 mol%) + CuI (2–5 mol%).
  • Base: Et3N, i-Pr2NH, or K2CO3.
  • Solvent: THF, DMF, or 2-MeTHF. 40–80°C.
• Halogen–lithium exchange at C–Br
  • Reagent: n-BuLi or s-BuLi (1.1–1.5 equiv) at −78 to −30°C in dry THF or ether; quench with electrophiles (CO2, aldehydes, B(OMe)3, etc.). Consider ketone protection to avoid addition.
• Carbonyl transformations
  • NaBH4 reduction: MeOH/EtOH, 0–25°C, minutes to hours.
  • Baeyer–Villiger: m-CPBA (1.2–2.0 equiv), DCM, 0–25°C → aryl acetate.
  • Oxime formation: hydroxylamine·HCl, pyridine or EtOH, rt–60°C.

Note: Temperatures, catalyst loadings, and times are typical literature ranges and should be optimized for scale, substrate, and equipment.

Safety and Handling

• Item-specific hazard data
  • Signal word: Not specified for this item; refer to SDS.
  • GHS hazard statements/classification/pictograms: Not specified for this item; refer to SDS.
• General safety guidance for halogenated aryl ketones (informational; not a substitute for SDS)
  • Likely hazards: harmful if swallowed/inhaled, skin/eye irritant; handle as a combustible organic. Avoid dust/vapor formation.
  • PPE: lab coat, safety glasses or face shield, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood.
  • Incompatibilities: strong bases (may promote undesired reactions/enolization), strong oxidizers (combustion risk), strong reducing agents (C–Br cleavage), and reactive metals under forcing conditions.
  • First aid (overview):
    • 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; obtain medical advice.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
  • Fire response: use CO2, dry chemical, or foam. Combustion may release hydrogen halides and carbon oxides—firefighters should wear SCBA.
• Handling/storage practices
  • Keep container tightly closed in a dry, well-ventilated area. Avoid exposure to heat sources and direct sunlight.
  • Use clean, dry tools; minimize exposure to moisture if subsequent reactions are moisture-sensitive.
• Definitive guidance
  • Always consult the current SDS for authoritative hazard, exposure limits, and spill/cleanup procedures.

Solvent Selection

This product is an organic building block, not a solvent. However, solvent choice is critical for its use in synthesis and purification.

• Solubility and polarity considerations (general)
  • Expected to dissolve well in moderately polar aprotic media: dichloromethane (DCM), THF, acetonitrile (MeCN), DMF, DMSO, ethyl acetate, and toluene.
  • Poorly soluble in water—liquid–liquid extraction typically favors organic phases.
• Choosing solvents by transformation
  • Cross-coupling (Suzuki/Buchwald–Hartwig): toluene, dioxane, THF, or MeCN with aqueous base; CPME or 2-MeTHF as greener alternatives.
  • Halogen–metal exchange/metalation: anhydrous THF, MTBE, or toluene at low temperature; strictly exclude protic solvents.
  • Electrophilic/nucleophilic aromatic substitutions (on ring) are disfavored by the deactivating carbonyl; if attempted, polar aprotics (DMF/DMSO) often required.
  • Carbonyl chemistry (oxime/hydrazone formation, reductions): alcohols (MeOH/EtOH) or aprotic media (DCM/THF) depending on reagent.
• Workup and purification
  • Normal-phase silica chromatography with hexanes/EtOAc or hexanes/DCM gradients; monitor at 254 nm.
  • Avoid strong basic eluents if preserving the aryl bromide functionality is critical.
• Small comparison (general)
  • DCM: fast kinetics, easy removal, but chlorinated waste.
  • THF/2-MeTHF: good for organometallics; 2-MeTHF offers greener profile and higher boiling point.
  • MeCN: polar, good for couplings; high miscibility with water aids biphasic systems.

Storage and Reconstitution

• Item-specific storage/shipping (from Product Data)
  • Storage conditions: Room temperature.
  • Shipped in: Normal.
• General storage guidance for halogenated aryl ketones
  • Keep tightly closed in original container, in a dry, well-ventilated place. Protect from moisture and prolonged light exposure.
  • For long-term storage, consider an inert atmosphere (argon/nitrogen) and a desiccant to maintain dryness, especially if subsequent use involves moisture-sensitive reactions.
• Reconstitution/solution preparation (general)
  • Solvents: DCM, THF, acetonitrile, ethyl acetate, toluene, or DMSO depending on application.
  • Prepare stock solutions using dry, oxygen-free solvents if the next step is air/moisture-sensitive (e.g., organometallics, metal-catalyzed couplings). Use amber vials if light sensitivity is a concern.
  • Filtering: If needed, pass solutions through a PTFE membrane (0.2–0.45 µm) to remove particulates prior to use.
• Stability notes
  • The aryl bromide and ketone are generally robust under neutral conditions. Avoid strong base or reducing conditions during storage.
• Definitive instruction
  • For lot-specific stability and any special storage notes, consult the product label and CoA/Spec Sheet.

Structure and Identity

A halogenated aryl methyl ketone featuring an ortho-bromine and meta-fluorine on an acetophenone scaffold.

• Item-specific identifiers (from Product Data)
  • SKU: B191293
  • Product name: 1-(2-Bromo-3-fluorophenyl)ethanone (aka 2-bromo-3-fluoroacetophenone)
  • CAS: 161957-58-0
  • PubChem CID: 10900066
  • InChIKey: 394039 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Core structural features (general/structural description)
  • Framework: acetophenone (aryl–CO–CH3) bearing two ring halogens.
  • Substitution pattern: acetyl at C1; bromine at C2 (ortho to carbonyl); fluorine at C3 (meta to carbonyl).
  • Functional groups: aryl ketone (conjugated), aryl bromide (C–Br), aryl fluoride (C–F).
  • Conjugation: carbonyl conjugated to an o-/m-dihalosubstituted phenyl ring.
  • Stereochemistry: none (achiral, no stereocenters or E/Z elements).
• Computed/literature formula data (not item-specific)
  • Molecular formula (by composition): C8H6BrFO (literature/computed from name)
  • Average molecular weight: ~217.03 g/mol (literature/computed)
• 2D structure in words
  • A benzene ring with, clockwise from the carbonyl ipso carbon (C1): C1 bears the acetyl (–CO–CH3); C2 = –Br; C3 = –F; remaining ring positions are hydrogen. The carbonyl is directly attached to the ring, forming an aryl methyl ketone.

Synthetic Utility

• Orthogonal functional handles
  • Aryl bromide (C–Br): versatile for Pd-catalyzed couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Negishi). Generally more reactive than aryl chlorides, allowing milder conditions.
  • Aryl fluoride (C–F): robust; typically survives many transformations, serving as a positional tag or enabling late-stage SNAr only with strongly activating conditions or with superbases/Meisenheimer stabilization.
  • Conjugated ketone: platform for reductions, oxidations (Baeyer–Villiger), condensations (oximes/hydrazones), and enolate chemistry.
• Retrosynthetic value
  • Enables stepwise library synthesis: first diversify the aryl bromide via coupling; then tune physicochemical properties via carbonyl transformations. Alternatively, perform carbonyl protection/enolate chemistry first, then cross-couple.
• Protecting group strategy
  • Ketone can be protected as a ketal (ethylene glycol or 1,3-propanediol) for operations requiring strong base or organolithiums. Deprotect under mild acid without affecting aryl–F.
• Selectivity considerations
  • Oxidative additions: Pd(0) inserts at C–Br preferentially over C–F.
  • Base-sensitive pathways: Strong bases may form enolates; choose milder bases (K3PO4, Cs2CO3) or lower temperatures to suppress side reactions in couplings.
• Analytics in synthesis
  • 19F NMR provides a sensitive handle to track transformations at the ring without derivatization. MS shows characteristic M/M+2 for Br, aiding reaction monitoring.

Target Specificity

Not applicable. This product is a small-molecule reagent and is not an antibody, enzyme, or biologic. No target specificity, clone, isotype, or species reactivity data are associated with this catalog item.