This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
282.950 g/mol
XLogP3
3.000
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
280.901 Da
Monoisotopic Mass
280.901 Da
Topological Polar Surface Area
29.100 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
191.000
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
Calcolatori di soluzioni
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Recensioni
Recensioni dei clienti
Application Protocols
No assay- or kit-specific application protocols are provided for this small-molecule reagent in the Product Data. For practical use, refer to the Reaction Conditions, Synthetic Utility, and Solvent Selection sections for guidance on setting up SN2 substitutions or cross-couplings involving this scaffold.
Biological Roles
Item-specific (Product Data)
Research use note: For research use only.
General/biochemistry context (no clinical claims)
This compound is a synthetic small molecule without known endogenous biological role. The α-bromoacetamide functionality is broadly recognized as an electrophile toward nucleophilic thiols and amines. In biochemical method development (outside living systems), such motifs are sometimes employed to derivatize thiol-containing small molecules or to create affinity tags on nucleophile-bearing scaffolds.
The 2,5-dichloroanilide moiety provides hydrophobic character and an H-bond donor/acceptor pattern (amide N–H / C=O) that can influence binding interactions in target discovery campaigns; however, any biological activity would be target- and context-dependent and must be determined empirically.
Caution: Because α-halo carbonyls are alkylating, handle solutions carefully to avoid unintended modification of biomolecules during lab handling. All uses should remain within research and in vitro experimentation boundaries, following institutional safety guidance.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare pH buffer systems. If used in biochemical assays, select a compatible buffer (e.g., phosphate, HEPES, Tris) based on the needs of your nucleophile and reaction pathway, ensuring the buffer components do not react with α-bromoacetamide groups (avoid primary amines and free thiols unless intended). Focus instead on the synthetic and reactivity sections for practical use guidance.
Green Alternatives
Solvent-level improvements (literature/general)
Replace DMF/DMSO where possible with greener polar aprotics such as 2-MeTHF, CPME, propylene carbonate, or dimethyl carbonate, balancing solubility and kinetics.
For cross-coupling on aryl chlorides, aqueous micellar catalysis (TPGS-750-M systems) or bio-derived solvents (2-MeTHF) can reduce environmental footprint.
Reagent/handle considerations
α-Bromoacetamides are efficient but relatively reactive electrophiles. Where feasible, α-chloroacetamides or mesylate/tosylate analogs can offer safer handling with slightly diminished reactivity. Trade-off: longer reaction times or higher temperatures may be required.
Small comparison (general guidance)
| Aspect | This product (α-bromo) | Potential alternative (α-chloro) |
|---|---|---|
| Electrophilicity (SN2) | Higher; faster reactions at RT | Lower; may need heat/catalysis |
| Byproduct concern | Bromide waste (halide load) | Chloride waste (still halide) |
| Safety | More alkylating; handle carefully | Generally less aggressive |
| Selectivity | Good for soft nucleophiles | May require stronger bases (risk of side rxns) |
Process suggestions
Minimize halogenated solvent use (prefer EtOAc, 2-MeTHF, or alcohols where compatible).
Apply catalysis and telescoping to reduce solvent exchanges.
Ensure efficient halide capture in waste treatment to reduce environmental impact.
Pharmaceutical Uses
No excipient role is indicated. Not specified for pharmacopeial grade; refer to CoA/Spec Sheet for any quality certifications.
Contextual (general, non-clinical): The scaffold can serve as a medicinal chemistry building block, enabling installation of a –CH2–CONH–Ar motif and subsequent aryl diversification via cross-coupling of the 2,5-dichloro substituents. Any use in drug substance or product manufacture would require full qualification of impurities, residual solvents, and halide content—parameters Not specified for this item; refer to CoA/Spec Sheet.
Process considerations (general)
Residual bromide and chloride must be controlled; plan for appropriate quench and washes.
For GMP contexts, evaluate potential genotoxic impurities associated with alkylating agents; adopt suitable control strategies per ICH M7. This is general guidance only and not a claim of compliance.
Physical Properties
Item-specific (Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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.
Literature/computed (for general reference; not item specifications)
Expected physical state: crystalline solid (typical for aryl α-bromoacetamides).
Good solubility in polar aprotic organic solvents (DMSO, DMF, NMP, acetone, acetonitrile).
Moderate in chlorinated solvents (DCM, CHCl3) and ethyl acetate.
Limited in nonpolar hydrocarbons (hexanes, heptane).
Very low in water due to aryl dihalide content, despite the amide.
Boiling/melting points, density, refractive index, UV cutoff: Not specified here; consult primary literature or CoA.
Practical notes (general)
The α-bromo carbonyl can undergo slow hydrolysis/substitution in moist environments; handle under dry conditions for precise measurements.
For solution preparations, DMSO or DMF stock solutions are commonly used to achieve higher concentrations.
Quality and Grades
Item-specific (Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for professional users (general)
If a specific quality (e.g., synthetic, analytical, or screening grade) is required for your application, verify via the Certificate of Analysis. Key attributes to review include assay purity (%), chromatographic purity profile (HPLC/GC), and residual solvent levels.
For reaction development or library synthesis, common expectations may include tight control of inorganic content and residual halides; however, exact metal/anion limits are Not specified for this item; refer to CoA/Spec Sheet.
UV-absorptivity and baseline behavior for analytical methods (HPLC/UPLC) are influenced by the dichloroarene; if low-UV grades are necessary, confirm that with your QA team. Specific UV cutoff and absorbance specifications are Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: None indicated in the product data. If stabilizers or inhibitors are critical to your workflow, confirm presence/absence on the CoA.
Batch documentation
Always match the SKU (B1306376) and CAS (349120-85-0) to the CoA lot number to ensure traceability and correct identity confirmation.
Reaction and Applications
Bifunctional electrophile (literature/general)
α-Bromoacetamide handle: efficient primary electrophile for SN2 displacement by soft nucleophiles (R–S−, N-nucleophiles, azide, imidazoles). Typical outcomes include thioethers (R–S–CH2–CONH–Ar), secondary/tertiary amide-alkylated products (R–NH–CH2–CONH–Ar or R2N–CH2–CONH–Ar), and azidoacetamide intermediates suitable for Staudinger or CuAAC diversification.
2,5-Dichloroaryl: aryl–Cl bonds participate in Pd-catalyzed cross-couplings (Suzuki–Miyaura, Buchwald–Hartwig, Negishi, Stille) or, where sufficiently activated, SNAr with strong nucleophiles. This allows late-stage diversification of the aryl ring orthogonally to the α-bromo site.
Typical synthetic uses
Cysteine- and thiol-selective alkylations in small-molecule chemistry (non-biological settings), installing a 2,5-dichloroanilide cap via thioether linkage.
Installation of a spacer: formation of –CH2–CONH–Ar motif onto heterocycles (imidazole, triazole) and amines.
Convergent library synthesis: first perform cross-coupling on the aryl chlorides to set aryl substitution, then engage the α-bromoacetamide in SN2 to append linkers or tags.
Practical guidance
Control moisture; α-bromo carbonyls can hydrolyze to hydroxyacetamides.
For thiol alkylation, a mild base (e.g., K2CO3, DIPEA) in DMF/MeCN at ambient to 40 °C gives high conversion with minimal elimination.
For amine substitution, use hindered bases to suppress over-alkylation; monitor to avoid bis-alkylation when reactive secondary amines are used.
For aryl–Cl couplings, employ bulky/electron-rich ligands (e.g., XPhos, SPhos) to activate aryl chlorides; sequence reactions to avoid exposing the α-bromo moiety to prolonged strong base/heat before it’s consumed.
Reaction Conditions
All conditions below are general literature guidance for α-bromoacetamides and aryl chloride couplings; optimize for your substrate set.
SN2 substitutions at –CH2–Br (general)
Thiols: R–SH (1.1–1.5 eq), base (K2CO3, DIPEA, or NaH for less acidic thiols), solvent DMF/DMSO/MeCN, 20–40 °C, 1–6 h. Monitor by LC–MS. Typically high conversion with minimal elimination.
Amines: R1R2NH (1.1–1.5 eq), base (DIPEA, K2CO3), MeCN/DMF, 0–25 °C initially to control exotherm, then to RT–50 °C, 2–12 h. Suppress over-alkylation by limiting equivalents and time.
Azide: NaN3 (1.2–2.0 eq), DMF, 25–60 °C, 2–8 h; follow with CuAAC if desired.
Heterocycles (imidazole, pyridine): base (K2CO3/NaH), DMF/MeCN, 25–60 °C.
Cross-coupling on aryl–Cl (general)
Suzuki–Miyaura: Pd2(dba)3 (1–2 mol%) with SPhos/XPhos (2–4 mol%), base (K3PO4/K2CO3), solvent dioxane/H2O (or 2-MeTHF/H2O), 80–110 °C, 6–16 h. Consider masking or consuming the α-bromo first to avoid side reactions.
Buchwald–Hartwig amination: Pd(OAc)2 or Pd2(dba)3 (1–3 mol%), ligand (BrettPhos/XPhos), base (NaOtBu/Cs2CO3), toluene/dioxane, 90–120 °C.
Negishi/Stille: standard organozinc or stannane partners with Pd catalysts; milder base load but handle toxicity considerations (Sn).
Workup/purification
Quench residual nucleophiles with aqueous NH4Cl/NaHCO3; extract with EtOAc or DCM. For DMSO/DMF, consider dilution then liquid–liquid extraction after salting out, or load onto silica directly after partial concentration.
Analytical monitoring
UV-active aryl ring facilitates HPLC/UPLC detection (check wavelengths empirically). LC–MS readily tracks halide substitution via −79/81 Da isotopic patterns (for Br loss).
Safety and Handling
Item-specific (Product Data)
Storage conditions: Room temperature
Shipped in: Normal
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
General safety considerations (literature/general guidance; defer to SDS for authoritative details)
Hazard profile: α-Halo carbonyls are electrophilic and may be irritating to skin, eyes, and respiratory tract; they can alkylate nucleophiles. Avoid contact and inhalation.
PPE: laboratory coat, chemical-resistant gloves (e.g., nitrile), safety glasses or goggles; use in a chemical fume hood.
Incompatibilities: strong bases (can promote elimination or undesired reactions), strong nucleophiles in uncontrolled conditions, reducing agents, and prolonged exposure to moisture (hydrolysis to hydroxyacetamide). Avoid contact with strong oxidizers.
Handling: Minimize exposure to ambient humidity. Use dry tools and anhydrous solvents when preparing solutions. Cap containers promptly.
First aid (general):
Skin/eye contact: rinse with plenty of water for ≥15 minutes; remove contaminated clothing; seek medical attention per SDS.
Inhalation: move to fresh air; obtain medical advice if symptoms persist.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Waste: Collect halogenated organic waste according to institutional and regulatory guidelines.
Stability notes (general)
α-Bromoacetamides may slowly decompose via hydrolysis/substitution; store dry and avoid prolonged heating. Always consult the product SDS for definitive safety and stability information.
Solvent Selection
This compound is a moderately lipophilic aryl anilide with an α-bromoacetamide electrophile. Solvent choice should balance solubility, nucleophilicity control, and stability of the α-bromo function.
Poorly soluble: aliphatic hydrocarbons (hexane, heptane). Very low in water.
Polarity class
Polar aprotic solvents generally provide both adequate solubility and efficient SN2 performance at the α-bromomethyl position.
Selection tips by use-case (general)
SN2 alkylations with thiols, amines, azide: DMF, DMSO, or acetonitrile to maximize nucleophile reactivity and minimize side reactions; buffer basicity carefully to suppress elimination.
Cross-coupling on aryl chlorides (Suzuki/Buchwald–Hartwig): dioxane, toluene, or CPME/2-MeTHF blends with base and modern ligands; DMF/DMAc for challenging couplings.
Preparative workup and crystallization: ethyl acetate/hexanes or DCM/hexanes are common pairs; adjust based on observed solubility.
Brief comparison (general)
DMSO vs DMF: DMSO maximizes solubility but can complicate workup; DMF offers similar kinetics with easier evaporation. Acetonitrile gives cleaner workups but may require heating for full dissolution.
Storage and Reconstitution
Item-specific (Product Data)
Storage conditions: Room temperature
Shipped in: Normal
General handling and storage (literature/general)
Keep container tightly closed in a dry environment. Limit exposure to ambient humidity to reduce hydrolysis of the α-bromoacetamide.
Protect from prolonged heat. Store away from strong bases, nucleophiles, and reducing agents.
Reconstitution/preparation of solutions (general guidance)
Recommended solvents for stock solutions: DMSO, DMF, acetonitrile, dichloromethane, or ethyl acetate, selected based on downstream application. Begin with 10–50 mg/mL trial concentrations to assess solubility.
Prepare solutions immediately before use when possible. For short-term storage of solutions, keep tightly capped at 2–8 °C and use within a few days; for DMSO stocks, consider aliquoting and storing at ≤−20 °C to minimize freeze–thaw cycles.
Filtration through PTFE syringe filters can aid in particulate removal prior to reactions or analytics.
Stability notes
The α-bromo functionality can slowly hydrolyze or react with adventitious nucleophiles; monitor stock integrity by LC–MS/1H NMR if stored for extended periods.
Dispose of expired solutions according to halogenated organic waste protocols.
Structure and Identity
Brief overview: 2-bromo-N-(2,5-dichlorophenyl)acetamide is a bifunctional aryl anilide bearing an α-bromoacetamide handle and a 2,5-dichloro-substituted phenyl ring, providing orthogonal reactivity for substitution and cross-coupling chemistry.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Catalog entry lists "417930", which does not match the standard 27-character InChIKey format.)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity (for reference; not item specifications)
Proposed molecular formula (by structure reasoning): C8H6BrCl2NO
InChIKey (not provided in product data): Not specified here; consult literature databases for the exact key.
Structural features (literature/general description)
Functional groups: secondary amide (–CONH–) attached to a 2,5-dichlorophenyl ring; α-bromoacetamide (–CH2–Br adjacent to carbonyl) as a benzylic-like primary electrophile.
Ring system: monosubstituted benzene (anilide) with chlorine atoms at the 2- and 5-positions relative to the anilide nitrogen.
2D description: a benzene ring bearing Cl at ortho (2) and meta (5) to the anilide nitrogen; the anilide carbonyl is bound to a –CH2Br substituent (α-bromide). No stereocenters; achiral.
Reactivity handles: (i) α-bromo for SN2 with soft nucleophiles; (ii) aryl chlorides for Pd-catalyzed cross-coupling or, where activated, SNAr.
Synthetic Utility
Orthogonal electrophilicity (literature/general)
Side chain: α-bromoacetamide enables clean SN2 at a primary carbon adjacent to carbonyl, favoring substitutions with soft nucleophiles (thiolate, azide, pyridine, imidazole, secondary amines) under polar aprotic conditions.
Aryl ring: Two aryl chlorides allow sequential or selective Pd-catalyzed couplings (e.g., install aryl/alkenyl/amine substituents) to modulate electronics and sterics independently of the side-chain.
Named/typical transformations
Thiol alkylation to thioethers (useful for linker installation).
Azidation (NaN3) to azidoacetamide followed by CuAAC (“click”) to triazoles.
Buchwald–Hartwig amination on aryl–Cl to introduce anilines/carbazoles/heteroarylamines.
Suzuki–Miyaura coupling to replace aryl–Cl with (hetero)aryl boron partners.
Intramolecular cyclizations (e.g., to oxazolines or imidazolinones) are conceptually possible from α-haloamides under specific conditions, though substrate control is required.
Retrosynthetic value
Serves as a convergence point: couple the aryl fragment first, then append linkers via the α-bromoacetamide, or reverse the order depending on tolerance of conditions. Protective group strategies can be minimized due to inherent chemoselectivity between sp2–Cl and sp3–Br centers.
Practical notes
Sequence planning is key: consume the α-bromo handle before high-temperature/basic cross-couplings, or protect it via temporary substitution/reversion strategies if needed.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent and is not an antibody, enzyme, or biologic. No target, epitope, or species reactivity information is provided in the Product Data.
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