N-(2,5-Dibromophenyl)acetamide - ≥95% , CAS No.25462-66-2

CAS: 25462-66-2 Cat. No.: N735932 Formula: C₈H₇Br₂NO Peso molecolare: 292.95 PubChem CID: 11358316

GRADE & PURITY ≥95%

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Store at 2-8°C,Protected from light,Desiccated

Spedito in

Wet ice

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Purezza

≥95%

Proprietà del prodotto

• ALogP: 2.3

Nomi e identificatori

• Sorrisi canonici: CC(=O)NC1=C(C=CC(=C1)Br)Br
• IUPAC Name: N-(2,5-dibromophenyl)acetamide
• InChIKey: DDGKGRZXBVALJN-UHFFFAOYSA-N
• INCHI: 1S/C8H7Br2NO/c1-5(12)11-8-4-6(9)2-3-7(8)10/h2-4H,1H3,(H,11,12)
• Isomeri SMILES: CC(=O)NC1=C(C=CC(=C1)Br)Br
• PubChem CID: 11358316
• Peso molecolare: 292.95

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Classe Benzene and substituted derivatives
      • Subclass Anilides
        • Level5 Acetanilides
          • Level6 Haloacetanilides
            • Level7 O-haloacetanilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: Benzene and substituted derivatives
• Subclass: Anilides
• Intermediate Tree Nodes: Acetanilides - Haloacetanilides
• Direct Parent: O-haloacetanilides
• Alternative Parents: M-haloacetanilides N-acetylarylamines Bromobenzenes Aryl bromides Acetamides Secondary carboxylic acid amides Organobromides Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: O-haloacetanilide - M-haloacetanilide - N-acetylarylamine - N-arylamide - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Acetamide - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Organic nitrogen compound - Organobromide - Organohalogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Aromatic homomonocyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as o-haloacetanilides. These are organic compounds containing an acetamide group conjugated to a phenyl group, which is in turn ortho-substituted with a halogen atom.
• 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: 292.950 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 292.887 Da
• Monoisotopic Mass: 290.889 Da
• Topological Polar Surface Area: 29.100 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 174.000
• 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

Not applicable. This catalog item is not an antibody, enzyme, or assay kit. No tested biological application protocols (e.g., WB, IHC, IF, FC) are provided for this product. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general literature guidance.

Biological Roles

• Item-specific biological information: Not specified for this item; refer to literature if needed.

• General chemistry/biochemistry context

  • N-(2,5-Dibromophenyl)acetamide is a small-molecule aryl amide bearing two bromine atoms. It is primarily a synthetic intermediate rather than a characterized biological metabolite or cofactor.
  • Aromatic amides can engage in hydrogen bonding and π–π interactions, but the presence of two aryl bromides typically reflects design for further derivatization (e.g., in SAR campaigns) rather than intrinsic biological function.
  • Any bioactivity would be scaffold-dependent and typically emerges after diversification (e.g., via cross-coupling to introduce pharmacophores). As such, this parent compound has no established endogenous role.

• Research use note

  • For research use only (per Product Data). Not for human or veterinary use. If used in biological assays, prepare solutions in DMSO or other compatible vehicles and verify solubility, aggregation, and purity suitable for the intended concentration range.

Buffer Applications

• Applicability

  • This compound is a neutral, poorly water-soluble aryl amide and is not a buffering agent. It does not participate in classical buffer systems.

• Practical note

  • When used in biochemical assays, prepare stock solutions in DMSO or other miscible organic solvents, then dilute into the assay buffer keeping final organic co-solvent typically ≤1–2% v/v to maintain assay integrity. Adjust buffer pH with appropriate buffer systems (e.g., phosphate, HEPES) independent of this compound.

• Item-specific buffer data

  • No buffer-related specifications are provided for this item; refer to CoA/Spec Sheet for any solubility notes if available.

Green Alternatives

• Greener solvent and process choices (general guidance)

  • Replace conventional polar aprotics (DMF, DMAc, NMP) where feasible with greener options such as 2-MeTHF, CPME, propylene carbonate, or water/ethanol with surfactant-enabled micellar catalysis (e.g., TPGS-750-M) for cross-couplings.
  • Use aqueous bases (K2CO3, K3PO4) with water-miscible co-solvents to reduce solvent load; consider solvent recycling.

• Catalysis and conditions (literature/general)

  • Employ ligand-optimized Pd or Ni catalysts that operate at lower loadings and temperatures; flow chemistry can further minimize solvent and improve safety.
  • Consider base-metal catalysis (nickel) for some couplings to reduce precious metal usage.

• Comparison snapshot (general)

  • DMF/DMSO: excellent solvation; environmental and regulatory concerns; challenging removal.
  • 2-MeTHF/CPME: biorenewable or improved EHS profiles; good for many cross-couplings; lower polarity may require co-solvent for dissolution at RT.
  • Water-micellar: best E-factor potential; may need surfactant and careful workup; substrate solubility can limit scope.

• Waste and safety

  • Segregate halogenated organic waste. Choose crystallization or antisolvent precipitation over chromatography where possible to cut solvent usage.

Note: No process-specific green metrics are specified for this item; adapt based on your reaction and institutional green chemistry policies.

Pharmaceutical Uses

• Item-specific pharmacopeial status/uses: Not specified for this item; refer to CoA/Spec Sheet.

• General formulation/manufacturing context (no medical claims)

  • As a halogenated aryl amide intermediate, this compound is more commonly employed in discovery chemistry and intermediate steps rather than as an excipient or API component.
  • If incorporated into screening libraries, it may be formulated as DMSO stock solutions for high-throughput screening logistics.
  • Any use in GMP settings would require full qualification (identity, purity, impurity profile, residual solvents, elemental impurities) in accordance with ICH guidelines. No such qualifications are stated in the Product Data for this catalog item.

Physical Properties

• Item-specific specifications

  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed properties (context, not item specs)

  • Approx. molecular formula: C8H7Br2NO (from structure).
  • Approx. molecular weight: ~292.96 g/mol (calculated from atoms).
  • Expected phase at ambient: crystalline solid (typical for dihalogenated acetanilides).
  • Solubility (qualitative, literature/general): sparingly soluble in water; soluble in polar aprotic organic solvents (e.g., DMF, DMSO, NMP) and moderately in chlorinated and ethereal solvents; solubility may improve upon gentle warming or ultrasound.
  • UV characteristics: aromatic amide typically shows π→π* absorption around 200–280 nm (literature/general), but exact UV cutoff for THIS item: Not specified; refer to CoA/Spec Sheet.

• Notes for practitioners (general chemistry knowledge)

  • The amide hydrogen can enable intermolecular hydrogen bonding, often elevating melting point and reducing volatility.
  • Two aryl bromides increase molecular mass and can enhance crystallinity and lipophilicity (higher logP vs non-brominated acetanilide). Exact logP/pKa for THIS item: Not specified; refer to CoA/Spec Sheet.

Quality and Grades

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

• General guidance on grades (context for selection)

  • Research grade indicates suitability for general laboratory synthesis and method development; final assay and impurity profile are defined in the product’s CoA/Spec Sheet.
  • If chromatographic use (e.g., as standard) or sensitive catalysis is intended, verify residual solvents, halogen content balance, and trace metal levels on the CoA.
  • For cross-coupling applications, trace palladium or copper contamination from prior processing is generally not expected but may affect some catalytic screens—pre-screen with a small-scale reaction if catalyst poisoning is suspected.

• Stabilizers/additives

  • No stabilizers are listed in the Product Data. If present in a specific lot, they will appear on the CoA/Spec Sheet. Users conducting trace analysis should confirm absence of stabilizers.

• Batch documentation

  • Request CoA and, where available, Spec Sheet for: purity method (HPLC/GC/qNMR), water content (Karl Fischer), residual solvents, and identity confirmation (NMR/IR/MS). Where a specific value is not provided for this catalog item, treat it as Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

• Role in synthesis (general chemistry knowledge)

  • The aryl bromides at C2 and C5 are versatile handles for Pd- or Ni-catalyzed cross-coupling (Suzuki–Miyaura, Sonogashira, Heck, Kumada, Negishi). Orthogonal or sequential couplings can construct 2,5-disubstituted anilide motifs.
  • The acetanilide moiety can modulate directing effects and electronic properties of the ring, influencing regioselectivity and reactivity.

• Representative transformations (literature/general)

  • Suzuki–Miyaura: installation of aryl/heteroaryl/alkenyl groups using boronic acids/esters; typical bases K2CO3, Cs2CO3; solvents dioxane/H2O, toluene, or 2-MeTHF; Pd(PPh3)4, Pd-PEPPSI, or Pd-Phosphine catalysts.
  • Buchwald–Hartwig aryl amination on the ring bromides (to form diaryl amines) using BINAP/XPhos/BrettPhos ligands; the amide N is acylated and generally not reactive under these conditions.
  • Sonogashira: coupling with terminal alkynes (Pd/Cu co-catalysis or copper-free protocols) to access alkynyl derivatives at C2 and/or C5.
  • Lithium–halogen exchange (careful, low temperature) on an aryl bromide followed by electrophile trapping (e.g., formylation, borylation), though cross-coupling is often preferred for functional group tolerance.

• Application spaces (general)

  • Construction of substituted anilide scaffolds for materials, ligands, and SAR libraries.
  • Late-stage diversification: sequential, selective coupling taking advantage of differential reactivity of the two C–Br sites under tailored ligand/catalyst sets.

Note: Manufacturer Applications field provides no additional specifics for this item; the above are literature/general guidelines.

Reaction Conditions

The following are literature/general guidelines for aryl bromide couplings with substrates like N-(2,5-dibromophenyl)acetamide. They are not item-specific specifications.

• Suzuki–Miyaura cross-coupling (general)

  • Catalyst: 1–3 mol% Pd(PPh3)4 or Pd2(dba)3 (0.5–1 mol% Pd) with XPhos/SPhos; base: K2CO3, K3PO4, or Cs2CO3 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O (3:1), toluene/H2O, or 2-MeTHF; 60–100 °C, 2–16 h.
  • Notes: sequence-selective couplings may be achieved by tuning ligand and temperature to differentiate the two C–Br sites.

• Buchwald–Hartwig aryl amination (on ring, general)

  • Catalyst: Pd2(dba)3 or Pd(OAc)2 with BINAP/XPhos/BrettPhos (1–3 mol% Pd), base: NaOtBu or K3PO4.
  • Solvent: toluene, dioxane, CPME, or DMAc; 80–110 °C, 6–18 h.

• Sonogashira (general)

  • Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) with CuI (1–5 mol%) and amine base (iPr2NH, Et3N) in THF/amine or toluene; 25–80 °C.
  • Copper-free variants: Pd with bulky phosphines in polar aprotics to suppress Glaser coupling.

• Borylation (Miyaaura–Ishiyama, general)

  • Catalyst: Pd(dppf)Cl2 (1–3 mol%), bis(pinacolato)diboron (1.2–1.5 equiv), KOAc (3 equiv), dioxane, 80–90 °C, 4–12 h.

• Workup tips

  • Use hot filtration if necessary; crystallization from EtOAc/hexanes often purifies aryl amides. Confirm full conversion at each site before proceeding to the second coupling.

Safety and Handling

• Item-specific hazard information (Product Data)

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety guidance (professional best practice; defer to SDS)

  • PPE: lab coat, suitable gloves (e.g., nitrile), safety glasses or face shield; handle solids in a fume hood to avoid dust inhalation.
  • Avoid generating dust; minimize skin and eye contact. Wash thoroughly after handling.
  • Incompatibilities (general): strong oxidizers; strong bases can catalyze amidic hydrolysis at elevated temperature; halogenated aromatics can be sensitive to highly reducing metals (e.g., Na) in certain solvents.
  • Thermal stability: aromatic amides are generally thermally stable; avoid excessive heating that may cause decomposition with HBr evolution.
  • First aid overview: if inhaled—move to fresh air; if on skin—wash with soap and water; if in eyes—rinse cautiously with water for several minutes; if ingested—rinse mouth, seek medical advice. Always follow institutional SOPs and consult the product SDS for authoritative instructions.

• Environmental notes (general)

  • Halogenated organics should be prevented from entering drains. Collect waste in appropriate halogenated organic waste streams following local regulations.

Solvent Selection

• Compound class and polarity (general chemistry knowledge)

  • Halogenated aromatic amide; relatively non-volatile, moderately lipophilic, hydrogen-bond donor/acceptor at the amide.

• Practical dissolution choices (general guidance)

  • Good: DMSO, DMF, NMP—high polarity aprotics that solvate both the amide and aryl bromides.
  • Moderate: chloroform, dichloromethane, ethyl acetate, acetone, acetonitrile.
  • Limited: alcohols (MeOH/EtOH) depending on temperature; water is typically poor.

• Use-case-driven selection

  • For cross-coupling screening: toluene, dioxane, CPME, 2-MeTHF, or mixed with polar co-solvent (DMF/DMAc) to ensure dissolution at reaction temperature.
  • For analytics and prep HPLC: DMSO stock solutions can be diluted into acetonitrile/water gradients; confirm UV response empirically.

• Brief comparison (general)

  • DMF vs DMSO: DMF often provides better solubility at lower viscosity; DMSO is less volatile and easier for weighing-by-volume stocks.
  • Ethyl acetate: greener workup solvent; may not fully dissolve at RT but useful for crystallization and trituration.

Note: No solvent-specific specifications are provided for this item; optimize based on your application and consult the CoA as needed.

Storage and Reconstitution

• Item-specific storage and shipping (Product Data)

  • Storage Conditions: Store at 2–8 °C, protected from light, desiccated.
  • Shipped In: Wet ice.

• Practical handling (general chemistry knowledge)

  • Store tightly closed in an amber container within a desiccator or with desiccant to limit moisture uptake and photodegradation.
  • Allow the container to equilibrate to room temperature before opening to minimize condensation.
  • If preparing stock solutions for screening, use dry, oxygen-free solvents when relevant to downstream reactions. DMSO or DMF stocks can be aliquoted and stored at 2–8 °C or frozen; avoid repeated freeze–thaw cycles by preparing single-use aliquots.

• Reconstitution guidance

  • Solubility will depend on solvent; start with DMSO or DMF to prepare concentrated stocks (e.g., 10–100 mM), then dilute as needed into reaction media or assay buffers while monitoring for precipitation.
  • No item-specific reconstitution protocol is provided; where a specific value or instruction is required: Not specified for this item; refer to CoA/Spec Sheet.

• Stability notes

  • Aromatic amides are generally stable under recommended storage. Inspect periodically for discoloration or obvious degradation before use.

Structure and Identity

Brief overview: N-(2,5-Dibromophenyl)acetamide is a di-brominated acetanilide derivative and a versatile halogenated aryl amide building block.

• Item-specific facts (Product Data)

  • SKU: N735932
  • Product Name: N-(2,5-Dibromophenyl)acetamide
  • CAS: 25462-66-2
  • CID: 11358316
  • InChIKey: 60441 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Computed/literature identity details (non-spec; for context)

  • Typical molecular formula (by composition from the name): C8H7Br2NO
  • Approx. molecular weight (calculated): ~292.96 g/mol (literature/computed)
  • Core structural features: an acetanilide scaffold (–NH–CO–CH3) attached to a phenyl ring bearing bromine substituents at the 2- and 5-positions (ortho and meta relative to the anilide nitrogen).
  • Functional groups: aromatic ring, primary amide (acetanilide), two aryl bromides.

• 2D structure described in words (general chemistry knowledge)

  • An anilide nitrogen (–NH–) is acylated by an acetyl group, forming an amide linkage to a monosubstituted benzene ring. The benzene ring bears bromine atoms at positions ortho (2) and meta (5) to the amide nitrogen. The amide is planar and conjugated with the aromatic ring; the two C–Br bonds are typical cross-coupling handles.

Synthetic Utility

• Strategic features (general chemistry knowledge)

  • Dual aryl bromides at 2,5 positions enable orthogonal or sequential introduction of diverse substituents, allowing rapid access to 1,4-disubstituted anilide architectures.
  • The acetanilide acts as a protecting/deactivating group on the aniline nitrogen, modulating ring electronics and suppressing undesired N-arylation during cross-couplings. It can be removed (hydrolyzed) post-coupling to regenerate the aniline if desired.

• Transformational repertoire (literature/general)

  • Pd/Ni cross-couplings: Suzuki–Miyaura (aryl/alkenyl/heteroaryl), Sonogashira (alkynyl), Heck (vinyl), Kumada/Negishi (alkyl/aryl/alkenyl), and borylation to install B(pin) groups for subsequent diversification.
  • Electrophilic aromatic substitution is attenuated by the amide’s meta-directing, deactivating nature; C–H activation strategies can leverage amide coordination primarily at ortho sites, though here those positions include a bromide.
  • Post-functionalization: acyl cleavage (acidic or basic hydrolysis) to unveil the aniline; subsequent diazotization or further coupling as needed.

• Retrosynthetic value

  • Serves as a convergent node: diverse coupling partners (boronates, stannanes, halides, alkynes) can be appended in two discrete steps to rapidly build libraries with controlled substitution patterns.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and does not have biological target specificity attributes such as antigen, epitope, clone, or isotype. No item-specific targeting data are provided.