≥98% per flussi di lavoro cromatografici e analitici sensibili che richiedono un'interferenza minima della linea di base.
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Stoccaggio e spedizione
Room temperature Spedizione . Consultare il COA specifico del lotto per le specifiche esatte.
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Documenti di qualità
SDS, COA, scheda tecnica e scheda delle specifiche disponibili per il download. COA specifico del lotto accessibile tramite ricerca per numero di lotto.
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Prova documentale
Citato in 0 pubblicazioni peer-reviewed su cromatografia, sintesi organica e reazioni di accoppiamento incrociato.
This compound belongs to the class of organic compounds known as n-acylethanolamines. These are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
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
210.070 g/mol
XLogP3
0.200
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Exact Mass
209.005 Da
Monoisotopic Mass
209.005 Da
Topological Polar Surface Area
49.300 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
125.000
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‑type protocols (e.g., WB, IHC, IF, FC) apply to this small‑molecule reagent.
Methodology notes (general):
For ATRP: prepare dry, degassed monomer/solvent; pre‑complex Cu(I) with ligand; add initiator last under inert gas; maintain constant temperature; sample periodically for SEC/NMR.
For surface grafting: derivatize the terminal OH to a reactive carbonate; couple to amines on substrates (pH 8–9 in buffered aqueous/organic biphasic systems), wash extensively, then initiate polymerization from the surface.
Refer to peer‑reviewed protocols for your specific monomer and catalyst system. This guidance is methodological and not product‑validated.
Biological Roles
This compound is a synthetic small molecule reagent and is not known to have endogenous biological roles.
General considerations (literature):
Structural features (amide, alcohol) are common in biomolecules, but the presence of a tertiary α‑bromide imparts significant reactivity uncommon in native metabolites.
In biochemical method development, 2‑bromoisobutyramide derivatives have been employed to introduce polymerizable handles to biomacromolecules (proteins/peptides, polysaccharides) via amide or carbonate linkages prior to controlled radical polymerization. Such uses are methodological and not biological functions.
Biocompatibility context:
Free α‑bromo carbonyls may alkylate nucleophiles (thiols, amines) and are therefore generally incompatible with live‑cell systems. Any contact with biological matrices should be controlled and followed by thorough purification of modified constructs.
No clinical or therapeutic claims are made or implied. For research use only.
Buffer Applications
Not a buffering reagent. It lacks a conjugate acid/base pair with a pKa in a biologically useful range for preparing buffering systems.
Practical note: In workflows where this initiator is coupled to biomolecules or surfaces, common buffers (e.g., phosphate, HEPES) are used for conjugation steps that target the terminal OH (via activated carbonates) or other handles introduced synthetically. Avoid strongly basic buffers during handling to minimize E1/E2 elimination of the α‑bromo center.
For details on solvent and reaction media, see Solvent Selection and Reaction Conditions.
Green Alternatives
Greener processing choices (literature/general):
Solvent selection: Prefer anisole, 2‑MeTHF, propylene carbonate, dimethyl carbonate, or alcohol/water mixtures for ATRP when compatible with monomer and catalyst. These reduce environmental impact versus DMF/DMSO and chlorinated solvents.
Catalysis: Employ ARGET‑ATRP or photo‑ATRP (O‑ATRP) to decrease copper loadings (ppm levels), simplifying workup and lowering metal waste. Organic photocatalysts (e.g., phenoxazines) can enable metal‑free protocols for some monomers.
Energy footprint: Photoinduced or room‑temperature ATRP reduces thermal energy consumption compared with high‑temperature radical methods.
Alternative initiator motifs (trade‑offs):
2‑Chloroisobutyryl analogs: less reactive than bromo, potentially lower acute aquatic toxicity of bromide waste, but often require higher temperatures/longer times.
Alkyl hypohalites or sulfonate esters (e.g., tosylates) as leaving groups: greener halogen footprint but different activation profiles; may not generalize across monomer classes.
Comparison snapshot (general):
Parameter | This product (α‑bromoamide) | Alternative
Reactivity in ATRP | High activation rate | Lower (Cl) / variable (sulfonates)
Hydrolytic stability | Higher than ester initiators | Ester: lower in base
Metal load required | Low to moderate with ARGET/photo | Similar or higher (Cl)
Note: Any substitution of initiator should be validated experimentally for the target monomer and process constraints.
Pharmaceutical Uses
This product is intended for research use only and is not an excipient or API specification.
General formulation context (literature/methodology):
2‑Bromoisobutyryl amide derivatives are sometimes used to prepare polymer–drug conjugates or surface‑grafted polymers via ATRP in preclinical materials research. In such cases, the compound functions solely as a synthetic initiator or linker and is removed or converted within the final material.
No pharmacopeial monograph is known for this specific compound.
No medical, diagnostic, or clinical use is claimed or supported for this SKU.
Physical Properties
Item-specific specifications (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 Weight (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (non-spec) information for context:
Molecular formula: C6H12BrNO2 (computed from structure)
Molecular weight: ~210.07 g/mol (computed)
Physical state: typically a low‑melting solid or viscous liquid for analogous N‑(2‑hydroxyethyl) 2‑bromoisobutyramides; exact MP/BP not established in primary literature for this CAS.
Boiling point / melting point: Not reliably reported; values vary across sources for related derivatives; consult CoA/SDS for this lot.
Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Solubility (qualitative, literature):
High in polar aprotic solvents (DMF, DMSO, NMP, acetonitrile).
Miscible with alcohols; moderate in acetone/ethyl acetate; limited in nonpolar hydrocarbons.
Water: expected moderate due to amide and hydroxyl functionality, but brominated tert‑center reduces overall hydrophilicity (check experimentally).
Partitioning: LogP for closely related 2‑bromoisobutyramide derivatives tends to be near neutral to mildly lipophilic; no consensus value published for this exact structure.
Note: Treat all numerical properties above as contextual literature guidance, not product specifications.
Quality and Grades
Item-specific quality details (Product Data):
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
Interpreting common grades (general guidance):
Research/biochemistry grade materials emphasize low residual metal/halide acids and controlled water content for compatibility with organocatalyzed/metal‑mediated polymerizations (e.g., ATRP, SET‑LRP). HPLC grade (for solvents) focuses on low UV background and low nonvolatile residue; for reagents like this, “high purity” typically indicates tight control of isomeric and hydrolytic impurities (e.g., corresponding methacrylamide from elimination, hydrolysis to acid or alcohols).
Stabilizers: α‑Bromo carbonyl reagents are sometimes shipped without stabilizers. If a stabilizer is used (e.g., trace acid inhibitor), it should be disclosed on the CoA; inhibitors can affect initiation kinetics in radical polymerizations and may require pre‑treatment (e.g., basic alumina).
What to check on receipt (best practice):
Appearance and odor; assay by quantitative NMR or HPLC; check for free acid and methacrylamide by LC/MS; Karl Fischer water (if moisture‑sensitive application); residual copper/iron (if pre‑contacted during synthesis) by ICP.
Documentation: Always rely on the item’s CoA/Spec Sheet for definitive grade, purity, residual solvent, and stabilizer information for this SKU (B943228).
Reaction and Applications
Controlled radical polymerization (literature): The 2‑bromoisobutyryl motif efficiently initiates atom transfer radical polymerization (ATRP/SET‑LRP). N‑(2‑hydroxyethyl) substitution imparts hydrophilicity and a handle for further derivatization or immobilization. Typical monomers: methacrylates, acrylates, styrenics, acrylamides. Copper(I)/ligand complexes (e.g., CuBr/PMDETA, CuBr/bipyridine) mediate activation–deactivation cycles to grow polymers with narrow dispersity.
Surface and biomacromolecule modification: The terminal OH permits covalent attachment to carboxylate or isocyanate‑functional substrates, producing surface‑bound ATRP initiator layers (“grafting‑from”). Amide linkage enhances stability compared to ester initiators in aqueous or basic media.
Modular synthesis utility: The α‑bromo tertiary center can undergo radical substitution; thermal or photochemical activation (with or without copper) enables C–C bond formation or polymer chain initiation. Under basic conditions, elimination can yield N‑(2‑hydroxyethyl) methacrylamide, which can be leveraged synthetically but is typically undesired during initiation.
Conjugation strategies: The secondary alcohol can be transformed (tosylation/mesylation → displacement) to introduce spacers, dyes, or affinity tags while retaining the α‑bromoamide. Alternatively, carbonate or carbamate formation tunes hydrophobicity and degradability of initiator‑bearing linkers.
Practical tips (general): rigorously exclude base and moisture during storage/use to minimize hydrolysis/elimination; for ATRP, degas monomer/solvent (freeze–pump–thaw or inert sparge) and pre‑form the Cu(I)/ligand complex before addition. Monitor initiation by 1H NMR (disappearance of N–H environment perturbations and monomer signals) or SEC of polymer.
Reaction Conditions
The following are literature/general conditions for this class of α‑bromoisobutyramide initiators; they are not product specifications.
ATRP of methyl methacrylate (representative):
Catalyst: CuBr (or CuCl) with PMDETA or bpy (ligand); optional Cu(II) deactivator at 5–10% of Cu(I).
Ratios (example): monomer:initiator:catalyst:ligand ≈ 100:1:1:1 (optimize by monomer).
Solvent: anisole, toluene, or bulk; for polar monomers, MeCN, DMSO, or alcohols.
Temperature: 25–70 °C depending on monomer and halide.
Oxygen control: degas by freeze–pump–thaw (3×) or Ar/N2 sparge 20–30 min; seal.
Time/conversion: 1–24 h to high conversion; monitor by 1H NMR/SEC.
ARGET‑ATRP (low copper):
Catalyst: CuBr2/ligand with a reducing agent (e.g., Sn(II) 2‑ethylhexanoate, ascorbate); ppm‑level copper.
Light or ambient temperature optional depending on system; robust to small O2 leaks.
Functionalization of terminal OH:
Esterification: DCC (1.1–1.5 eq) / DMAP (0.1 eq), carboxylic acid (1.1–1.5 eq), solvent DCM or MeCN, 0–25 °C, 2–16 h.
Carbonate formation: p‑NPG/DSC (1.2 eq) with base (DIPEA), MeCN/DCM, 0–25 °C.
Sulfonylation: MsCl or TsCl (1.1–1.5 eq), base (Et3N/DIPEA), 0–5 °C to RT; then SN2 with nucleophile in DMF at 0–40 °C.
Avoid: strong bases (t‑BuOK, NaH) and high temperatures that promote E1/E2 to methacrylamide or decomposition. Always verify conditions on small scale.
Safety and Handling
Item-specific hazard data (Product Data):
Signal word: Not specified for this item; refer to SDS.
H‑statements / Pictograms / GHS classification: Not specified for this item; refer to SDS.
General safety profile (literature/general):
Chemical class: α‑bromo carbonyl compound (alkyl bromide) and secondary amide with a pendant alcohol.
Hazards typical for α‑bromo carbonyls: may act as an alkylating agent; irritant to skin, eyes, and respiratory tract; harmful if swallowed; potential sensitizer. Avoid inhalation of vapors/aerosols and contact.
Incompatibilities: Strong bases (risk of dehydrohalogenation to methacrylamide derivatives); strong nucleophiles (substitution); strong oxidizers; prolonged contact with aqueous media can lead to hydrolysis.
Stability considerations: Tertiary bromo center can undergo radical homolysis or elimination under heat/UV/base. Protect from strong light and heat. Work under inert atmosphere for radical/polymerization work.
PPE and handling:
Use in a fume hood. Wear nitrile gloves (change frequently), lab coat, splash goggles or face shield.
Avoid metal salts/copper residues contacting skin—ATRP catalysts can facilitate radical processes.
First aid (overview; defer to SDS):
Skin/eye contact: Immediate decontamination with running water for ≥15 min; remove contaminated clothing; seek medical evaluation.
Inhalation: Move to fresh air; monitor breathing; medical attention if symptoms persist.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product SDS for authoritative, current hazard and response information.
Solvent Selection
This reagent is moderately polar, hydrogen‑bonding (amide N–H and terminal OH), and contains a tertiary alkyl bromide. Solvent choice should balance solubility, chemical stability (minimizing elimination/substitution), and downstream use (e.g., ATRP initiation).
ATRP/controlled radical polymerization: Dry anisole, toluene, acetonitrile, dimethyl carbonate, or alcohols (for polar monomers) are common. Minimize protic solvents if base is present to suppress E1/E2 to methacrylamide.
Nucleophilic substitution/derivatization at the OH: Use polar aprotics (DMF, DMSO, MeCN) with mild bases; avoid strong base that can cause dehydrohalogenation at the α‑bromo center.
Esterification of the terminal OH: Dichloromethane, MeCN, or THF under DCC/EDC and DMAP conditions.
Small comparison (general):
DMSO/DMF: maximal solubility; may complicate workup and promote side reactions at elevated T.
MeCN: good balance of polarity/volatility; compatible with Cu‑ATRP catalysis.
2‑MeTHF/anisole: greener alternatives with adequate solubility; useful for polymerizations.
Dry, oxygen‑free solvents are recommended for radical/polymerization workflows to limit inhibitor formation and side reactions.
Storage and Reconstitution
Item-specific storage/shipping (Product Data):
Storage conditions: Room temperature.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance (literature/practice):
Keep container tightly closed in a cool, dry, well‑ventilated place. Protect from light to minimize radical/photolytic degradation of the C–Br bond.
For moisture‑sensitive applications (e.g., ATRP), consider storing under inert gas with a desiccant. Minimize headspace oxygen.
If solidifies or becomes viscous, gently warm (≤30–35 °C) to facilitate dispensing; avoid prolonged heating.
Solution preparation:
Prepare stock solutions in dry MeCN, DMSO, DMF, or alcohols immediately before use. Filter if particulates are present. For long‑term solution storage, prefer amber vials at 2–8 °C under inert gas; verify stability empirically, as α‑bromo carbonyls can slowly degrade in solution.
Freeze–thaw:
Not typically applicable unless stored as a solution. If freezing solutions, aliquot to avoid repeated freeze–thaw cycles.
Always consult the item’s CoA and SDS for definitive guidance for SKU B943228.
Structure and Identity
A tertiary α‑bromoamide bearing a hydrophilic 2‑hydroxyethyl substituent on nitrogen. The acyl fragment is 2‑bromo‑2‑methylpropionyl ("bromoisobutyryl"), a well‑known ATRP/radical‑initiation motif.
Molecular formula (computed from structure): C6H12BrNO2
Molecular weight (computed): ~210.07 g/mol
Key structural features (general description):
Functional groups: tertiary α‑bromide adjacent to an amide carbonyl; secondary alcohol on a 2‑hydroxyethyl N‑substituent; secondary amide N–H donor;
Substitution pattern: quaternary (tertiary) center at C(α) bearing Br and two methyl groups; amide carbonyl conjugated to the α‑center.
2D structure in words: A brominated tert‑butyl equivalent (bromoisobutyryl) linked through a planar amide to a two‑carbon chain terminating in a hydroxyl group; no rings; no stereocenters (achiral).
Synthetic Utility
Functional group set and reactivity:
α‑Bromo tertiary center: excellent radical leaving group; enables initiation of radical chains (ATRP/SET‑LRP) and radical substitutions. Under basic or thermal conditions, can eliminate HBr to give the corresponding methacrylamide derivative.
Secondary alcohol: platform for downstream functionalization—esterification (DCC/EDC), carbonate/carbamate formation, sulfonylation (Ms/Ts) followed by substitution to install dyes, biotin, azides/alkynes, or spacers.
Secondary amide: robust linkage offering H‑bond donor ability; can be N‑acylated or protected if required, though further acylation reduces ATRP initiation selectivity.
Retrosynthetic value:
Serves as a bench‑stable surrogate for 2‑bromoisobutyryl chloride when an embedded alcohol handle is desired. Can be coupled onto carboxylate or isocyanate‑bearing substrates to create initiator‑functional materials (grafting‑from approaches).
ATRP initiation of methacrylates/acrylates/styrenes under Cu(I)/ligand catalysis.
ARGET‑ATRP and photo‑ATRP enabling low copper loadings and mild conditions.
Tosylation/mesylation of the OH followed by SN2 displacement to append functional groups while retaining the α‑bromoamide center.
Practical cautions:
Avoid strong base or elevated temperatures during derivatization of the OH to prevent dehydrohalogenation. Conduct reactions under inert atmosphere and exclude moisture to minimize hydrolysis to the corresponding acid/alcohols.
Target Specificity
Not applicable. This product is a small‑molecule chemical reagent, not a biological targeting agent or antibody. No antigen/epitope specificity, clone, isotype, or species reactivity applies.
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