mPEG benzaldehyde - MW 5000 Da

Cat. No.: m163984

GRADE & PURITY MW 5000 Da

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

mPEG benzaldehyde is a monofunctional, site specific PEG derivative with amine reactive aldehyde group. Aldeyde PEG is a common N-terminal amine group pegylation reagent. The reaction between aldehyde group with the α-amine at the N-terminus produces an intermediate Schiff base. Further reduction with hydride will form a stable C-N bond. PEG aldehydes react with n-terminus amine groups at a pH of from 5.0 to 9.5. Higher pH will result in multiple Pegylation with both terminal and lysine groups. Aromatic aldehyde PEG shows better stability in aqueous solution.

Specifications

Specifications & Purity

MW 5000 Da

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Chemical and Physical Properties

• Sensitivity: Light sensitive; Moisture sensitive

Application Protocols

No item-specific, validated application protocols are provided for this SKU. The following is general, literature-based guidance for common uses of mPEG-benzaldehyde; adjust to your system.

• Reductive amination to an amine-bearing peptide/protein (research-scale):
  1. Dissolve protein in 50 mM sodium phosphate, pH 6.5 (0.15 M NaCl if needed). Concentration: 0.5–5 mg/mL protein.
  2. Dissolve mPEG-benzaldehyde in minimal DMSO; add to protein to achieve 3–10 molar equiv per accessible amine (optimize empirically). Keep final DMSO ≤10%.
  3. Incubate 2–4 h at RT. Add NaBH3CN to 20–30 mM final and continue 12–16 h at RT.
  4. Quench by buffer exchange (spin column) and purify by SEC or dialysis (MWCO chosen per protein/PEG Mn).
  5. Characterize by SDS-PAGE shift and MS (if feasible).
• Oxime ligation to an aminooxy-functional dye/small molecule:
  1. Prepare 100 mM sodium acetate, pH 5.0, containing 20 mM aniline catalyst.
  2. Mix mPEG-benzaldehyde (1.0 equiv) with aminooxy partner (1.5 equiv). Total concentration: 1–10 mM.
  3. Stir at RT 1–3 h; monitor by 1H NMR or LC (if small-molecule tag) and precipitate/dialyze to purify.
• Surface coupling (amine-functional nanoparticles):
  • Suspend particles in pH 6.0 acetate buffer; add mPEG-benzaldehyde (excess) and picoline borane (25 mM). Tumble 4–16 h, wash by centrifugation/filtration.

Note: These are generic procedures; ensure compatibility with your substrate and consult SDS for all reagents.

Biological Roles

This product is a synthetic polymer reagent designed for laboratory use. It does not possess an intrinsic biological role. The following notes reflect general, literature-based properties of PEG and aryl aldehydes relevant to research workflows (not clinical claims).

• PEG attributes (general):
  • Poly(ethylene glycol) is hydrophilic, biocompatible, and reduces protein adsorption and aggregation in many in vitro settings. When grafted onto surfaces or biomolecules, PEG can impart “stealth-like” behavior, reducing nonspecific interactions during assays and separations.
  • PEG chains increase hydrodynamic size and alter solubility/phase behavior of conjugated species.
• Aldehyde functionality:
  • Reacts selectively with primary amines and aminooxy/hydrazide groups under mild aqueous conditions, enabling targeted covalent modification of biomolecules (e.g., proteins, peptides, oligonucleotides with amine-bearing tags) for research.
  • The imine/hydrazone/oxime linkages formed can be tuned for stability (oximes typically most hydrolytically stable; imines stabilized by reductive amination).
• Applications (research context):
  • Preparation of PEGylated enzymes, antibodies, or nanoparticles for in vitro studies of stability, fouling resistance, and assay performance.
  • Fabrication of PEGylated surfaces, hydrogels, and matrices to modulate cell adhesion in basic research (using amine-reactive aldehyde chemistry as a coupling step).

Note: No pharmacological, therapeutic, or in vivo performance claims are made for this item. Suitability for any biological system should be validated empirically and with appropriate approvals.

Buffer Applications

Although mPEG-benzaldehyde is not itself a buffering agent, many of its key bioconjugation reactions occur in specific buffers. The following literature-based guidance can help select and prepare media for aldehyde chemistry.

• Imine (Schiff base) formation and reductive amination:
  • Buffer: sodium phosphate (20–100 mM), pH 6.0–7.0; or sodium acetate (50–200 mM), pH 5.0–6.0 for faster imine formation.
  • Additives: 50–200 mM NaCl can stabilize proteins; 10–50 mM NaBH3CN or picoline borane for in situ reduction (handle with care; toxic cyanoborohydride—follow SDS).
  • Conditions: RT to 37 °C, 1–24 h; use 0–30% DMSO/DMF if solubility requires.
• Oxime/hydrazone ligation:
  • Buffer: acetate or citrate, pH 4.5–6.0; optional 10–50 mM aniline or p-anisidine catalyst to accelerate.
  • Hydroxylamine or aminooxy reagent at 1.2–5.0 equiv relative to aldehyde-bearing PEG (or vice versa if PEG is limiting).
• Practical notes:
  • Avoid Tris and other primary amine-containing buffers—they compete with intended amine targets and quench aldehydes.
  • Maintain moderate ionic strength and avoid high pH (>8), which promotes side reactions (e.g., Cannizzaro for non-enolizable aldehydes) and aldehyde hydration.
  • Degas buffers (argon sparge) and include antioxidants (where compatible) to limit oxidation of the aldehyde to the corresponding acid.
• Post-reaction cleanup:
  • Desalt by spin columns, dialysis (MWCO ~0.5× to 1× below PEG Mn of conjugate), or SEC.
  • Validate conjugation by UV–Vis (label-dependent), SDS-PAGE shift (for proteins), or MALDI/ESI (for small molecules/peptides).

Green Alternatives

While mPEG-benzaldehyde itself is the intended functional reagent, greener choices often relate to solvent and reagent selection for its use.

• Solvent choices (comparison, literature/general):

  Greener option | Conventional | Notes --- | --- | --- Water/acetate or phosphate buffer (pH 5.5–6.5) | DMF/DMSO-rich media | Aqueous media reduce solvent hazards; use aniline catalysts to maintain rates for oxime/hydrazone formation. Ethanol (anhydrous) | Acetonitrile/THF | Ethanol is bio-based and low-tox; works for some condensations; control for acetalization under acid. 2-MeTHF or CPME | THF/Et2O | Improved safety/renewability; verify PEG solubility (often good at lower Mn, variable at higher Mn).

• Reducing agents:

  • Picoline borane (water-compatible, milder toxicity profile) can substitute for NaBH3CN in reductive amination under appropriate conditions.
  • Ascorbate-mediated reductions are generally unsuitable for imine reduction but can support complementary transformations.

• Process considerations:

  • Use catalytic aniline for oxime/hydrazone ligation to enable lower solvent and energy input.
  • Favor precipitation-based or dialysis purification over extensive chromatographic solvent use.

• Tradeoffs:

  • Greener solvents may reduce reaction rates (especially for imine formation). Balance with mild heating (≤37 °C) and catalysts.
  • PEG’s high water affinity simplifies green workups but may demand energy for solvent removal (lyophilization). Choose minimal volumes and concentrate efficiently.

Pharmaceutical Uses

No pharmacopeial status, grade, or clinical application is specified for this item; refer to CoA/Spec Sheet. The following information is general background on PEG-type materials in pharmaceutical development and is provided solely for laboratory/formulation context (not as a claim for this product).

• PEGs as excipients (general/literature):
  • Serve as solubilizers, plasticizers, and stabilizers in solid and liquid dosage prototypes; modulate viscosity and wetting.
  • PEGylation (covalent PEG attachment) is used in research-scale studies to alter biomolecule properties (solubility, stability, circulation in model systems). mPEG-benzaldehyde provides an aldehyde route to such conjugates via reductive amination or oxime formation.
• Considerations for pre-formulation research:
  • End-group functionality (aldehyde) is reactive; ensure it is either consumed (conjugated) or masked in final lab formulations to avoid unintended reactions with amine-bearing actives or excipients.
  • Residual solvents and polydispersity impact viscosity and reproducibility; confirm with CoA.
• Compatibility (general):
  • Typically compatible with many aqueous vehicles and co-solvents (propylene glycol, glycerol, ethanol). Avoid primary amine excipients (e.g., trometamol/Tris) unless they are intended reactants.

Again, this product is supplied strictly for research use only, not for drug, diagnostic, or clinical applications.

Physical Properties

Item-specific numerical specifications are not provided. The following are general/literature characteristics of mPEG-benzaldehyde materials and should be treated as guidance only, not specifications.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet. (mPEG derivatives can range from viscous liquids to waxy solids depending on Mn.)
• Molecular Weight (Mn): Not specified for this item; refer to CoA/Spec Sheet (common offerings span ~1–20 kDa, each with distinct handling).
• Solubility (literature/general):
  • Highly soluble in polar organic solvents: DMSO, DMF, NMP, acetone, acetonitrile, THF, dioxane, methanol, ethanol, isopropanol.
  • Soluble to miscible in water (solubility increases as Mn decreases and temperature increases; aldehyde end-group does not abolish hydrophilicity).
  • Limited solubility in nonpolar solvents (toluene, hexanes) unless Mn is very low.
• Density, refractive index, logP: Not applicable as single values for polydisperse PEGs; Not specified for this item.
• Melting/softening range (literature/general): low-Mn mPEGs can be liquids near RT; higher-Mn forms often soften/melt between ~40–65 °C depending on chain length and crystallinity.
• pKa: not applicable (neutral polymer with terminal aldehyde).
• Vapor pressure: negligible (nonvolatile polymer).
• UV characteristics (literature/general): aryl aldehyde exhibits absorption in near-UV (approx. 250–290 nm); PEG backbone is UV-transparent above ~210 nm. Exact UV cutoff/ε: Not specified for this item.
• Hygroscopicity: PEGs are mildly hygroscopic; aldehyde end-groups are moisture/air sensitive to oxidation—handle under inert gas as directed.

Quality & Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• PEG polymer quality considerations (general/literature):
  • End-group fidelity: For mPEG-benzaldehyde, the aldehyde end-group content (often reported as functionality, e.g., >95%) is critical for reproducible conjugations. Verification via titration (e.g., hydroxylamine), 1H NMR (formyl integration), or HPLC derivatization is common.
  • Polydispersity (PDI, Đ): Reported by GPC/SEC; lower Đ (e.g., ~1.05–1.20 for narrow-distribution PEG) improves material uniformity. Actual PDI for this item: Not specified; see CoA.
  • Residuals: Trace metals, solvent residues, and unfunctionalized mPEG content can impact sensitive applications. Specific impurity limits for this item: Not specified; refer to CoA/Spec Sheet.
  • Stabilization: Aldehyde end-groups can oxidize to acids or hydrate; inert gas backfilling and light protection (as specified) help preserve functionality. Any added stabilizers for this item: Not specified.
• What grade implies in practice (definitions, general):
  • “Bioconjugation grade” or “functional PEG grade” (when stated) typically indicates tight control of functionality and low residuals; “technical” grades may have broader specs. Since grade is not stated here, confirm suitability with QC data on the CoA.
• Recommended incoming QC (best practice):
  • Check appearance and Mn/PDI by SEC if critical.
  • Confirm aldehyde content by 1H NMR (formyl proton ~9.8–10.1 ppm) or hydroxylamine assay.
  • Run a small-scale model conjugation to verify performance before committing valuable biomaterials.

Reaction & Applications

The benzaldehyde terminus enables classic carbonyl condensation chemistry, making mPEG-benzaldehyde a versatile platform for labeling, surface modification, and polymer–small molecule assembly.

• Conjugation to primary amines (literature/general):
  • Schiff base (imine) formation with lysine side chains, N-termini, amino-terminated surfaces, or amine-bearing small molecules. Typically followed by in situ reduction (NaBH3CN, picoline borane, or NaBH(OAc)3) to give stable secondary amines (PEG–CH2–Ar–CH2–NR2 linkages when benzyl/aryl position allows).
  • Conditions: pH 5.5–7.0 (to maintain amine nucleophilicity while limiting aldehyde hydration), RT to 37 °C, 1–24 h.
• Oxime/semicarbazone/hydrazone ligations:
  • Reaction with hydroxylamine, hydrazides, or aminooxy reagents forms oximes/hydrazones; often catalyzed by anilines (e.g., p-anisidine) in aqueous media at pH ~4.5–6.5. Oximes are hydrolytically robust.
• Polymer and surface modification:
  • Grafting onto amine-functional nanoparticles, hydrogels, and silica/oxide surfaces via reductive amination or oxime chemistry to impart PEGylation (stealth, reduced nonspecific adsorption) for research materials.
• Assembly/synthesis:
  • Knoevenagel-type condensations (with active methylene partners) or Wittig/HWE on the aldehyde (for small-molecule derivatization of the PEG terminus) are feasible in organic media.
• Analytical tagging:
  • Introduction of fluorescent amines (rhodamine, dansyl cadaverine) or affinity tags (biotin hydrazide) to the aldehyde for probe creation.
• Practical tips:
  • Maintain inert, dark conditions; prepare solutions fresh to avoid oxidation to acids or hydration.
  • Use slight molar excess of mPEG-benzaldehyde relative to limiting amine to drive coupling.
  • For bioconjugation, desalting or buffer exchange post-reaction, then reduction, followed by purification (dialysis/SEC) is typical.

Reaction Conditions

General, literature-based conditions for common transformations of the benzaldehyde terminus on mPEG. These are guidance ranges; optimize empirically for your system.

• Imine formation and reductive amination (amine conjugation):
  • Solvent: 50–100 mM phosphate or acetate buffer (pH 5.5–7.0), optionally 0–30% DMSO/DMF for solubility.
  • Stoichiometry: 1.1–2.0 equiv aldehyde per amine site (or vice versa if aldehyde is limiting on the PEG).
  • Temperature/time: RT to 37 °C, 2–24 h.
  • Reductant: 10–50 mM NaBH3CN or 2–3 equiv sodium triacetoxyborohydride (organic media). Picoline borane (20–50 mM) as aqueous alternative.
• Oxime/hydrazone ligation:
  • Solvent: acetate/citrate buffer, pH 4.5–6.0; 0–20% DMSO as needed.
  • Catalyst: aniline or p-anisidine 10–50 mM to accelerate.
  • Temperature/time: RT, 0.5–6 h (often faster than imine under optimal catalysis).
• Reduction to alcohol (PEG–benzyl alcohol derivative):
  • NaBH4 (1.5–3.0 equiv) in MeOH, EtOH, or MeOH/THF at 0–25 °C, 0.5–2 h; quench carefully; note that this removes aldehyde reactivity.
• Wittig/HWE (to install vinyl group):
  • Base: NaH or KOtBu (caution with PEG), solvent THF/DMF, 0–25 °C, 1–4 h; work under inert atmosphere.
• Purification and analysis:
  • Dialysis (appropriate MWCO) or precipitation into cold Et2O/acetone for polymeric products.
  • Monitor by 1H NMR (loss of ~9.8–10.1 ppm CHO), UV–Vis (aryl changes), and SEC for Mn shift.

Note: Avoid primary amine-containing buffers (e.g., Tris) during aldehyde-stage reactions; they compete with intended substrates.

Safety & Handling

• Regulatory/safety designations for this specific item:
  • 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.
• Storage conditions (Product Data):
  • Store at −20 °C, protected from light, under argon (argon charged).
  • Shipments: Ice chest + ice pads (maintain cool chain to limit aldehyde oxidation).
• General hazards and precautions (literature/general for aldehyde-functional PEGs):
  • Aldehydes can be skin/eye irritants and may cause sensitization in susceptible individuals. Avoid inhalation of any dust/aerosol and contact with skin/eyes.
  • PEG backbones are of low acute toxicity, but the benzaldehyde end-group is chemically reactive (forms imines/oximes). Prevent exposure and unintended reactions.
• PPE and handling:
  • Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Work in a fume hood, especially during weighing/dissolution.
  • Use dry, oxygen-free solvents for long-term solutions; degas if necessary to minimize oxidation.
• Incompatibilities (general): strong oxidizers; strong bases/acids that can trigger side reactions (aldol, Cannizzaro in strong base without alpha-H), and primary amines (unless desired) which will form imines.
• First aid (summary; defer to SDS): rinse eyes/skin with water for at least 15 minutes if contacted; remove contaminated clothing; if inhaled, move to fresh air; if ingested, rinse mouth—seek medical attention in all cases of significant exposure.
• Waste: collect aldehyde-containing waste in halogenated/non-halogenated organic waste as appropriate; avoid aqueous amine-rich drains due to potential reaction products.

Solvent Selection

mPEG-benzaldehyde combines PEG’s hydrophilicity with an aryl aldehyde handle, providing broad solvent compatibility. Selection depends on the target substrate and reaction type.

• Polarity/miscibility (literature/general trends):
  • Water: typically soluble to highly soluble; solubility increases with temperature and decreases with Mn. Aldehyde remains reactive in mildly aqueous media; avoid high pH.
  • Polar aprotics: DMSO, DMF, NMP, acetonitrile—excellent solvents for dissolving high-Mn PEG and for reductive amination with biomolecules compatible with organic cosolvent.
  • Alcohols: methanol, ethanol, isopropanol—good solvents; watch for acetal/hemiacetal formation under acidic conditions.
  • Ethers/esters: THF, dioxane, ethyl acetate—good for synthetic transformations and moisture-sensitive operations.
  • Nonpolars: toluene, dichloromethane show limited to moderate solubility depending on Mn and temperature.
• Choosing a medium (guidance):
  • Bioconjugation to amines (proteins/peptides): aqueous phosphate or acetate buffer (pH 5.5–7.0) with 0–30% DMSO/DMF to aid solubility; add NaBH3CN for reductive amination.
  • Small-molecule transformations (e.g., oxime formation): anhydrous MeOH/EtOH, MeCN, or THF with catalytic acid or buffer.
  • Purification: precipitation into cold diethyl ether/acetone or dialysis (MWCO chosen relative to Mn) is common; avoid non-solvents that could trap product.
• Quick comparison (general):
  • Water/buffer: green, biocompatible; may slow reaction and risk aldehyde hydration.
  • DMSO/DMF: maximal solubility and rate; harder to remove, may require dialysis.
  • Alcohols: balanced volatility/green metrics; potential acetal formation under acid—control pH.

Storage & Reconstitution

• Storage (Product Data):
  • Store at −20 °C, protected from light, under argon (argon charged). This minimizes oxidation of the aldehyde to carboxylic acid and limits hydrate formation.
  • Shipped in an ice chest with ice pads to maintain a cool chain.
• Handling tips (general):
  • Allow container to warm to room temperature in a desiccator before opening to prevent moisture condensation.
  • Work swiftly under inert atmosphere (glovebox or argon blanket). Reseal promptly; backfill with dry argon.
• Reconstitution/dissolution (general guidance):
  • Suitable solvents: anhydrous DMSO, DMF, THF, MeCN, methanol, ethanol, or water/buffer (pH 5–7). Start at 5–50 mg/mL depending on Mn and application; adjust as needed.
  • For bioconjugation, prepare fresh solutions immediately before use. Filter (0.22 µm) if particulates are present.
• Aliquoting and stability:
  • Prepare single-use aliquots to avoid repeated freeze–thaw and headspace oxygen exposure.
  • Short-term (days to a few weeks) storage at 2–8 °C under inert gas may be acceptable for solutions in dry organic solvents; confirm stability empirically. Aqueous solutions are less stable—use same day when possible.
• Specifications not provided:
  • Grade/purity, exact Mn, water content, residual solvents, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
• Disposal: Follow institutional procedures for aldehyde-bearing organic polymers; avoid release to drains; use appropriate organic waste streams.

Structure & Identity

mPEG benzaldehyde is a monofunctional poly(ethylene glycol) (PEG) bearing a terminal benzaldehyde group for aldehyde-selective conjugation chemistry.

• Item-specific identifiers:
  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight (Mn): Not specified for this item; refer to CoA/Spec Sheet (mPEG materials are typically specified by number-average molecular weight and PDI).
• Structural features (general for mPEG-benzaldehyde, literature/typical):
  • Backbone: a flexible, hydrophilic poly(ethylene oxide) chain –[CH2–CH2–O]n– capped on one end with a methyl ether (mPEG) and on the other with a benzaldehyde-bearing aromatic moiety.
  • Functional group: a terminal aryl aldehyde (–CHO) capable of forming imines (Schiff bases) and oximes; typically presented as a para- or benzyl-linked benzaldehyde unit tethered to PEG via an ether or carbamate linkage depending on synthesis route (exact linkage for this item: Not specified).
  • Stereochemistry: none (PEG is achiral, aldehyde is planar). No defined regiospecificity is implied for the aryl substitution beyond the aldehyde.
• 2D structural description (general): a long repeating –CH2–CH2–O– chain (PEG) terminated on one end with –O–CH3 (methoxy cap), and on the reactive end a phenyl ring bearing a formyl (–CHO) substituent connected to PEG by a short linker.
• Identity confirmation (recommendations): verify by 1H NMR (formyl proton ~9.8–10.1 ppm; aromatic signals ~7–8 ppm; PEG methylenes ~3.4–3.8 ppm), FTIR (C=O ~1690–1710 cm−1), and GPC for Mn/PDI (general guidance; consult CoA for this item).

Synthetic Utility

mPEG-benzaldehyde is a modular, aldehyde-terminated polymer that enables rapid installation of PEG onto diverse nucleophiles and serves as a springboard for further derivatization.

• Functional group leverage (literature/general):
  • Aldehyde → imine/hydrazone/oxime ligations for attaching amines, hydrazides, aminooxy groups; subsequent reduction affords stable C–N bonds.
  • Aldehyde → alcohol (NaBH4) or carboxylic acid (mild oxidation) to access alternate termini (PEG–benzyl alcohol/acid analogs; confirm compatibility with the PEG–aryl linkage of the specific product).
  • Carbon–carbon formation: Wittig/Horner–Wadsworth–Emmons enables vinyl linkers; Knoevenagel with active methylenes yields styryl-type adducts.
• Retrosynthetic value:
  • View the PEG chain as a solubilizing, stealth-conferring handle that can be appended late-stage to amine-bearing scaffolds to rapidly access PEGylated analogs or materials without re-optimizing backbone synthesis.
• Materials chemistry:
  • End-grafting to amine-functional polymers, particles, and surfaces via reductive amination/oxime chemistry yields PEG brushes and antifouling layers.
• Practical synthetic notes:
  • Use anhydrous conditions in organic media to prevent hydrate formation; for aqueous couplings, maintain pH 5–7 and include anilinium catalysts for oxime/hydrazone.
  • Monitor by 1H NMR (disappearance of aldehyde proton; appearance of imine/oxime signals) and by SEC to assess Mn shifts after conjugation.
  • Purify by precipitation into cold ether/acetone or dialysis; avoid silica chromatography for high-Mn PEGs due to streaking and poor recovery.

Target Specificity

Not applicable. This product is a small-molecule/polymer reagent, not an antibody, enzyme, or affinity ligand with defined biological targets. No clone, isotype, antigen, or species reactivity data are relevant. For selective conjugation in biochemical workflows, specificity derives from the aldehyde’s chemoselective reactivity toward primary amines, hydrazides, and aminooxy groups under controlled conditions (general literature guidance).

Frequently Asked Questions

How should this product be stored?

Store at ?20 °C, protected from light, under argon. It is supplied under an argon blanket; reseal under inert gas after each use.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.