2-bromo-N-phenethyl-acetamide - Reagent grade

Cat. No.: B483847

QUALITÀ & PUREZZA Reagent Grade

Storage

Room temperature

Specifiche

Specifiche e purezza

Reagent grade

Condizioni di conservazione di stoccaggio

Room temperature

Grado

Reagent Grade

Application Protocols

No assay or immunoapplication protocols are specified for this small-molecule reagent. For synthetic uses, see the Reaction Conditions and Reaction & Applications sections for general, literature-informed procedures that can be adapted to your substrates and scales.

Biological Roles

This product is a small organic electrophile intended for laboratory research and synthesis. No endogenous biological role is attributable to 2-bromo-N-phenethyl-acetamide.

General/literature context (non-clinical, for research use only):

• Electrophile reactivity: α-Bromoacetamides preferentially alkylate soft nucleophiles (notably thiols) under mild conditions. This property is leveraged in chemical biology and materials chemistry to modify thiol-bearing molecules and surfaces. The N-phenethyl substituent increases hydrophobic character, which can influence partitioning into organic phases or hydrophobic microenvironments.
• Stability in biological-like media: In aqueous buffer, hydrolysis or reaction with buffer nucleophiles competes with targeted alkylation; control of pH (typically neutral to slightly basic) and co-solvent is critical to manage selectivity (literature guidance).

No claims are made regarding pharmacology, toxicity in vivo, or therapeutic effects. Any experiments involving biological macromolecules should be designed and assessed using appropriate controls, with safety oversight and institutional approvals as required.

Buffer Applications

This compound is not a buffering reagent and is not used to prepare classical pH buffer systems.

Practical note (general): If conducting nucleophilic substitutions in mixed aqueous media (e.g., thiol alkylation), buffers around pH 7–8 (HEPES, phosphate, bicarbonate; literature) can be used to generate thiolate while limiting amine over-alkylation. Include an organic co-solvent (e.g., MeCN, DMF, DMSO, 5–20%) to aid solubility. These are general guidelines only and not product specifications.

Green Alternatives

Greener choices center on solvent selection and process minimization rather than changing the electrophile itself (the α-bromoacetamide motif is inherently reactive). Consider the following (general/literature guidance):

• Solvent swaps for SN2 substitutions:
  • Replace DCM/CHCl3 with EtOAc, 2-MeTHF, or cyclopentyl methyl ether (CPME) when solubility allows.
  • Substitute DMF/DMSO with Cyrene, propylene carbonate, or N-butylpyrrolidone (NBP) where compatible with nucleophile and base.
  • Favor MeCN over DMF for easier removal, or use green MeTHF for organosulfur alkylations.

• Bases and additives:
  • Use carbonate bases (K2CO3, NaHCO3) instead of strong inorganic bases to reduce hazard and side reactions.
  • Phase-transfer catalysis in benign biphasic systems (e.g., toluene/aqueous carbonate or EtOAc/aqueous) can reduce high-boiling polar aprotic usage.

• Process intensification:
  • Employ flow chemistry for improved heat/mass transfer, minimizing excess reagent and enabling safer handling of alkylating agents.
  • Minimize protecting-group steps by leveraging the selective thiol-reactivity of bromoacetamides.

Small comparison (illustrative):

• DCM vs EtOAc: EtOAc is biodegradable, lower toxicity; DCM has better solvency but higher environmental impact.
• DMF vs Cyrene: Cyrene is bio-based with favorable EHS profile; DMF is widely effective but reproductive toxin-classified in many jurisdictions.

Validate green substitutions with pilot experiments to ensure yield/selectivity are maintained.

Pharmaceutical Uses

No pharmacopeial monograph or excipient designation is provided for this item. It is sold for research use only.

General process chemistry context (literature/general):

• Intermediate in API synthesis: The α-bromoacetamide motif serves as a convenient handle to introduce acetamide-linked substituents via SN2, enabling late-stage diversification of small molecules in medicinal chemistry campaigns.
• Conjugation chemistry: Bromoacetamide groups are commonly employed to install stable thioether linkages to thiol-bearing substrates (e.g., small thiols or polymer supports), which can be useful during conjugate intermediate preparation in process development.
• Solid-phase and resin modification: Installation of bromoacetamide sites on resins allows nucleophile capture under mild conditions, aiding library synthesis.

No medical or clinical claims are made. This product is not intended for human or veterinary use, diagnostic procedures, or as a finished drug substance/excipient. For any GMP or regulatory application, appropriate qualification, impurity profiling, and process validation would be required and are outside the scope of this listing.

Physical Properties

Item-specific physico-chemical specifications (mp, bp, density, refractive index, UV cutoff, water/peroxide/metal content) are not provided for this SKU. For release criteria and test limits, see the item’s CoA/Spec Sheet.

Literature/expected characteristics for α-bromoacetamides bearing N-alkyl/aryl groups (informational, not specifications):

• Phase/appearance: Often low-melting solids or pale oils depending on substitution; actual appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (qualitative):
  • Good in polar aprotic solvents (DMF, DMSO, MeCN), chlorinated solvents (DCM, CHCl3).
  • Moderate in ethereal solvents (THF, 2-MeTHF).
  • Limited in water; aqueous solubility can increase with co-solvents or pH control.
  • Note: These are general trends for haloacetamides; verify experimentally for your medium.
• Volatility/thermal behavior: α-Haloacetamides generally decompose before high-temperature distillation; avoid prolonged heating (literature guidance).
• Acid/base: Amide N–H is weakly acidic (typical amide pKa of conjugate acid ~–0.5; amide N–H pKa ~15–17 in DMSO; literature values, class-level). The methylene α to C=O and Br is highly electrophilic toward SN2 and base-sensitive to elimination/solvolysis.
• Partitioning: LogP for analogous N-phenethyl bromoacetamides is expected to be moderate due to the phenyl ring (literature trend, not a specification).

For precise numeric values applicable to this lot, consult the CoA or request a technical data sheet.

Quality and Grades

• Supplied grade: Reagent Grade (as listed for this SKU).
  • Meaning (general): Suitable for most laboratory synthetic and analytical applications. Reagent Grade typically denotes good chemical purity and low levels of common inorganic/organic contaminants adequate for routine research workflows. It is not necessarily optimized for trace analysis, low-UV chromatography, or GMP manufacturing.

• What Reagent Grade implies in practice:
  • Purity sufficient for preparative reactions, method development, and general synthesis.
  • Does not guarantee HPLC-grade low UV absorbance, sub-ppm metal content, or specialized stabilizers unless stated.
  • If ultra-low impurities (water, peroxides, metals) or tight spectroscopic baselines are critical, request an HPLC/LC–MS grade or provide additional purification in-house.

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

• UV cutoff, water, peroxide, metal limits: Not specified for this item; refer to CoA/Spec Sheet.

• Documentation and lot control: CoA and/or Spec Sheet should be consulted for actual lot specifications, analytical methods (e.g., NMR, GC/HPLC area %), and acceptance criteria. For regulated workflows, consider qualifying the material under your internal QA system (incoming ID, purity verification, functionality testing).

Reaction and Applications

This α-bromoacetamide is a versatile electrophile. The benzylic N-phenethyl group modulates lipophilicity while the α-bromomethyl next to the carbonyl is strongly activated for substitution.

Representative application families (literature/general):

• SN2 alkylation of nucleophiles:
  • Thiols → thioether acetamides (classic cysteine-reactive handle in chemical biology workflows; bench-scale small-molecule thiol alkylations proceed readily in MeCN/DMF with base).
  • Amines → tertiary amide formation at the methylene carbon; useful to append the –CON(PhCH2CH2)–CH2– linkage.
  • Alkoxides/phenoxides → ether-linked acetamides (control competing solvolysis).
  • Azide → azidoacetamide intermediates enabling click diversification after reduction or CuAAC (via conversion through azide; two-step strategies are common).
• Halogen exchange/activation:
  • Bromide can be exchanged to iodide with iodide salts (Finkelstein) to enhance reactivity under mild conditions.
• Polymer/solid support modification:
  • Immobilization of nucleophile-bearing surfaces (thiols, amines) via stable C–S or C–N bonds using the bromoacetamide handle.
• Protecting-group tactics:
  • The bromoacetamide carbon can serve as a temporary alkylating tag removable by hydrolysis or reductive methods (strategy-dependent; literature precedents exist for related haloacetamides).

Practical notes:

• Conduct substitutions in dry polar aprotic solvents; exclude water to minimize hydrolysis.
• Use mild bases (K2CO3, DIPEA, NaHCO3) to generate nucleophiles without promoting elimination.
• Monitor by TLC/HPLC; products often show strong UV at 254 nm from the phenyl group.
• Workup: Quench with non-nucleophilic buffers; remove inorganic salts; purify quickly to avoid secondary reactions.

Reaction Conditions

Typical literature conditions for α-bromoacetamide substitutions (informational guidance; optimize per substrate):

• Thiol alkylation (to thioether acetamides):
  • Solvent: MeCN, acetone, DMF, or mixed aqueous buffer/MeCN (10–20%).
  • Base: DIPEA, triethylamine, K2CO3, or NaHCO3 (1.0–1.5 equiv).
  • Temperature: 0–25 °C (often room temperature is sufficient).
  • Time: 0.5–4 h typical.
  • Notes: Maintain pH 7–8 in aqueous media to favor thiolate; exclude excess nucleophiles to limit bis-alkylation.

• Amine substitution (tertiary amide formation):
  • Solvent: MeCN or DMF.
  • Base: K2CO3 or DIPEA (1–2 equiv).
  • Temperature: 20–60 °C depending on amine nucleophilicity.
  • Notes: Secondary amines react faster than anilines; monitor for over-alkylation or competing elimination/hydrolysis.

• Azide displacement (to azidoacetamide):
  • Solvent: DMF or DMSO.
  • Reagents: NaN3 (1.2–2.0 equiv).
  • Temperature: 25–60 °C.
  • Application: Access to amine or triazole motifs after Staudinger or CuAAC.

• Halogen exchange (Finkelstein):
  • Reagent: NaI in acetone (excess).
  • Outcome: In situ iodide improves SN2 rate with weak nucleophiles.

Workup/purification (general): Quench with aqueous ammonium chloride or bicarbonate; extract with EtOAc or DCM; wash, dry (Na2SO4), and concentrate. Purify by flash chromatography using hexanes/EtOAc or DCM/MeOH gradients. Avoid prolonged exposure to strong bases and moisture.

These conditions are general literature ranges and not product specifications.

Safety and Handling

Authoritative safety information must be taken from the product SDS. The following are general considerations for α-bromoacetamides and haloalkylating agents; they are not a substitute for the SDS.

• GHS classification, signal word, pictograms, H/P statements: Not specified for this item; refer to SDS.
• Hazard tendencies (literature/general):
  • α-Bromoacetamides are strong electrophiles that can alkylate nucleophiles (thiols, amines).
  • May cause skin/eye irritation; avoid contact.
  • Potential lachrymatory properties have been reported for related haloacetamides.
  • Harmful if swallowed or inhaled; avoid aerosols and dusts.
• PPE: Use chemical-resistant gloves (e.g., nitrile), lab coat, and splash goggles. Handle in a fume hood. Consider double-gloving for extended contact tasks.
• Handling: Keep containers tightly closed. Minimize exposure to moisture and strong nucleophiles/bases that can induce decomposition or exothermic substitution. Transfer under dry conditions when possible.
• Incompatibilities (general): Strong bases, strong nucleophiles, reducing agents, and active metals. Avoid prolonged contact with amines/thiols unless intended for reaction. Avoid strong oxidants in presence of organics.
• First aid (overview):
  • Skin/eye contact: Immediate decontamination with copious water for ≥15 minutes; remove contaminated clothing; seek medical advice.
  • Inhalation: Move to fresh air; monitor breathing; seek medical attention.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Waste: Treat as halogenated organic waste; segregate per institutional/municipal regulations.

Always consult the current SDS for this product before use.

Solvent Selection

As an α-bromoacetamide with a benzylic N-substituent, this compound is moderately lipophilic yet polar enough to dissolve in a range of organic media.

• Solvent compatibility (general/literature):
  • Polar aprotic: DMF, DMSO, MeCN — typically excellent solubility; promote SN2 reactivity.
  • Chlorinated: DCM, CHCl3 — good to excellent solubility; convenient for extractions and non-protic environments.
  • Ethers: THF, 2-MeTHF — moderate to good; useful for organometallic-compatible conditions.
  • Esters: EtOAc — often reasonable for workups and chromatography.
  • Alcohols/water: Limited; protic media can induce competing solvolysis; use with caution.

• Selection guidance by use case:
  • Nucleophilic substitutions (thiols, amines, azide): Choose MeCN, DMF, or acetone; add a mild base (e.g., K2CO3, DIPEA) as needed.
  • Bioconjugation-like thiol alkylation in mixed media: Aqueous buffer with 5–20% DMF/MeCN/DMSO co-solvent; control pH 7–8 to favor thiolate (general literature guidance).
  • Purification: Normal-phase silica with hexanes/EtOAc or DCM/MeOH gradients; minimize contact time on basic silica to limit decomposition.

• Quick comparison (general):
  • MeCN vs DMF: MeCN is easier to remove; DMF can boost solubility/reactivity with more polar nucleophiles.
  • DCM vs EtOAc: DCM offers stronger elution and inertness; EtOAc is greener but more protic.

Always verify solubility and stability experimentally under your exact conditions.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (as listed for this SKU).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General handling guidance (not specifications):

• Keep container tightly closed in a dry, well-ventilated place. Limit exposure to moisture and strong nucleophiles/bases to reduce hydrolysis or unintended substitution. Amber glass is recommended to limit light exposure.
• If weighing small quantities, minimize time to air; quickly recap to reduce atmospheric moisture uptake.
• Reconstitution/stock solutions:
  • Prepare solutions in dry MeCN, DMF, DMSO, or DCM.
  • For aqueous work, dissolve first in an anhydrous co-solvent (e.g., DMSO or MeCN), then dilute into buffer immediately before use.
  • Store solutions at low temperature when feasible and use promptly; α-bromoacetamides can degrade in protic media.
• Freeze–thaw: For solution stocks, aliquot to avoid repeated freeze–thaw cycles, which can accelerate decomposition in the presence of moisture.

Always consult the current CoA and SDS for authoritative guidance on storage and handling. Research use only.

Structure and Identity

A haloacetamide bearing an N-phenethyl substituent and an α-bromomethyl group adjacent to the amide carbonyl; a secondary amide with a benzylic side chain.

• SKU: B483847
• Product name: 2-bromo-N-phenethyl-acetamide
• CAS: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Note: A commonly referenced composition for this structure is C10H12BrNO (literature, derived from name parsing).
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Literature/calculated for C10H12BrNO ≈ 242.12 g/mol (informational, not a specification).
• SMILES: BrCH2C(=O)NCCc1ccccc1 (literature/representative)
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (descriptive):
  • Functional groups: secondary amide (–CONH–), benzylic ethylene linker (–CH2–CH2–Ph), α-bromomethyl substituent (–CH2Br) adjacent to the carbonyl (haloacetamide).
  • Ring systems: monocyclic aromatic (phenyl).
  • Stereochemistry: none (achiral as named).
  • 2D description in words: A phenethyl group is bound to the amide nitrogen; the carbonyl’s α-carbon is substituted with bromine (–CH2Br), giving a strongly activated primary electrophile next to the amide.

Synthetic Utility

Key functional elements and reactivity (general/literature):

• Electrophilic center: The –CH2Br α to the amide is strongly activated toward backside SN2. This allows efficient C–S, C–N, and C–O bond formation with thiolates, amines, and alkoxides/phenoxides, respectively. Iodide exchange can further accelerate reactions when needed.
• Amide as an anchor: The secondary amide can engage in hydrogen bonding, imparting polarity and enabling crystallization/control of solid-state behavior in targets. The N-phenethyl group can tune lipophilicity and π-stacking interactions in analog series.
• Convergent assembly: Serves as a bifunctional linker to append the –CON(PhCH2CH2)–CH2– fragment onto nucleophile-bearing partners late in synthesis. Useful in SAR campaigns and for preparing affinity tags or immobilization linkers.
• Chemoselectivity: Thiolates typically outcompete amines and alcohols under neutral to mildly basic conditions, offering a selectivity lever in multifunctional substrates. Using bicarbonate/carbonate and controlled pH helps suppress undesired over-alkylation.
• Downstream manipulation: The installed acetamide can be:
  • Hydrolyzed (acidic or basic conditions) to carboxylic acids/amines (substrate-dependent).
  • Reduced (e.g., borane-based reductions in inert solvents) to amines (amide to amine conversion; exercise caution with the benzyl group).
  • Engaged in cross-coupling-like transformations after further functionalization (e.g., N-acyl activation; substrate and method dependent).

Taken together, this reagent is a practical electrophilic hub for building thioether-linked and tertiary-amide scaffolds under mild conditions.

Target Specificity

Not applicable to this product type. This SKU is a small-molecule reagent, not a biological targeting reagent or antibody. No antigen/epitope, species reactivity, clone, or isotype information applies.