m-PEG5-phosphonic acid - ≥98% , CAS No.1807512-39-5

CAS: 1807512-39-5 Cat. No.: M595723 Fórmula: C₁₁H₂₅O₈P Peso molecular: 316.3

GRADE & PURITY ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Application

227,228,229

Descripción general

m-PEG5-phosphonic acid ethyl ester is a PEG chain derivative. The hydrophilic PEG linkers increase the water solubility of compound in aqueous media. Longer PEG chains have better water solubility properties relative to shorter PEG chains.

Specifications

Especificaciones y pureza

≥98%

Condiciones de almacenamiento de almacenamiento

Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Pureza

≥98%

Nombres e identificadores

Peso molecular

316.3

Application Protocols

No manufacturer-validated protocols are provided for this specific item. Below are general, literature-informed outlines to aid method development.

• Oxide surface coating (planar)

  • Clean substrate (solvent rinse, UV-ozone/plasma).
  • Prepare 0.5–2 mM solution in EtOH/water (pH ≈2–3 with HCl).
  • Immerse 1–12 h at room temperature; rinse thoroughly with solvent, then water.
  • Optional cure at 100 °C for 30–60 min; cool and store desiccated.

• Nanoparticle ligand exchange (oxide NPs)

  • Disperse NPs in EtOH or DMF. Add 10–100× molar excess ligand relative to NP surface sites.
  • Stir 4–16 h at room temperature; separate and wash (centrifugation/redispersion) with fresh solvent.
  • Transfer to water; dialyze to remove free ligand. Verify stability by DLS and zeta potential.

• Patterned/co-functionalized surfaces

  • Co-adsorb m-PEG–phosphonic acid with a small fraction of reactive PEG–phosphonate (e.g., azide) to enable subsequent click attachment of biomolecules while maintaining antifouling background.

• Notes

  • Filter all solutions (0.22 µm). Control humidity during drying to avoid coffee-ring effects. Validate coverage by contact angle and XPS.

• Item-specific conditions and concentrations: Not specified; refer to CoA/Spec Sheet or develop empirically.

Biological Roles

• Item-specific (Product Data)

  • No biological annotations provided. For research use only.

• General/biochemistry perspective

  • PEG surface layers: Methoxy-terminated PEG chains are widely used to reduce nonspecific protein adsorption and cell adhesion by creating a hydrated, sterically repulsive interface. This is beneficial in biosensing, diagnostic surfaces, and antifouling materials.
  • Phosphonic acid anchoring: Phosphonates exhibit strong affinity for metal-oxide surfaces in aqueous environments, enabling stable biomaterial interfaces even under physiological ionic strengths.
  • Colloidal stabilization: On nanoparticles (e.g., iron oxide), PEG–phosphonates provide electrosteric stabilization, mitigating aggregation and opsonization in model biological media. Choice of chain length (n≈5 here) balances compact coatings with accessibility of the nanoparticle surface.
  • Biofunctional patterning: Blends of inert m-PEG–phosphonate with a minority of reactive PEG–phosphonate (bearing azide, alkyne, NHS, or maleimide ends) allow creation of micropatterned or selectively functionalized surfaces for studying protein–surface interactions, enzyme immobilization, or cell adhesion on defined ligands.

• Notes and limitations

  • No intrinsic enzymatic or receptor-specific activity is implied for m-PEG5-phosphonic acid; its function is structural/interfacial.
  • For any biological testing, ensure complete removal of residual solvents and confirm endotoxin levels if surface–bio interactions are critical (not specified for this item; request data if needed).

Buffer Applications

This product is not a buffering reagent per se. Phosphonic acids are diprotic, but m-PEG5-phosphonic acid is primarily intended as a surface-anchoring ligand rather than a defined pH buffer.

• Practical notes (general)

  • Working solutions for coating are often prepared in water, water/ethanol, or alcohols with controlled pH (e.g., pH 2–4 using dilute mineral acid) to promote coordination to metal oxides. Buffer species that chelate metals (e.g., phosphate, citrate) may compete with surface binding—minimize or avoid during the adsorption step.
  • For biological media exposure after coating, thoroughly rinse to remove free ligand, then exchange into the desired buffer (PBS, HEPES, etc.).

• Item-specific buffer recommendations: Not specified for this item; optimize empirically for your substrate and application.

Green Alternatives

• Context: Solvent and process choices dominate the environmental profile when using m-PEG5-phosphonic acid. The molecule itself is a specialty surface modifier; “greener” considerations focus on solvent selection, concentration, and energy inputs.

• Greener options (literature/general)

  • Prefer water or aqueous ethanol/isopropanol over high-boiling polar aprotics (DMF, NMP, DMSO) when compatible with substrate and process.
  • Employ room-temperature self-assembly where possible; if thermal curing is required, use the minimum effective temperature/time.
  • Minimize surfactants and salts; they complicate wastewater treatment.

• Comparison of common solvent systems (general)

  • Water: Highest EHS profile; excellent for oxide binding with pH control. Tradeoff: slower drying, potential for film defects without humidity control.
  • Ethanol/iPrOH: Low toxicity and fast evaporation; flammable. Good for dip- and spin-coating.
  • Acetone/EtOAc: Sometimes dissolve PEG oligomers; greener than chlorinated solvents but may have limited solubility.
  • DMF/DMSO/NMP: Powerful solvation and ligand exchange media; less favorable EHS. Use only if required.

• Process intensification

  • Use concentrated stock solutions to reduce solvent volumes.
  • Recycle alcohol solvents via fractional distillation when appropriate.

• Item-specific environmental attributes: Not specified for this item; consult SDS for disposal guidance.

Pharmaceutical Uses

• Scope: No pharmacopeial grade or compendial listing is provided for this item. It is supplied for research use only and is not intended for human or veterinary use.

• Formulation/context uses (general, non-clinical)

  • Surface modification of oxide-containing devices or particles to impart hydrophilicity and reduce protein adsorption (e.g., model nanoparticle systems for research).
  • Stabilization of colloidal dispersions in development settings (screening studies, process development) where PEG coatings improve dispersion stability in high-ionic-strength media.
  • Adhesion promotion layers between inorganic substrates and hydrophilic polymer coatings in prototype manufacturing.

• Technical considerations

  • Residual solvent and water levels can affect device/process performance; confirm by KF and GC-HS when critical.
  • Endotoxin/bioburden control may be necessary for sensitive biointerface studies (not specified for this item; request data or depyrogenate surfaces post-coating).

• Regulatory note

  • No medical or clinical claims are made. Any translation to cGMP or clinical manufacturing would require separate qualification, supplier audits, and compendial conformance if applicable.

Physical Properties

• Item-specific (Product Data)

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

• Literature/general expectations for m-PEG oligomers bearing phosphonic acid

  • Physical state: Typically a white to off-white solid or waxy semi-solid for low-n PEGs; deliquescent tendencies possible due to hydrophilicity.
  • Solubility: High in water and polar protic solvents (water, methanol, ethanol); generally soluble in polar aprotic media (DMF, DMSO). Solubility in nonpolar solvents is poor to negligible. Actual solubility for this item: Not specified; verify experimentally.
  • Acid–base: Phosphonic acids are diprotic; typical pKa values for simple alkyl phosphonic acids are roughly pKa1 ~1–2 and pKa2 ~6–8 (literature, compound-dependent). PEG substitution and chain length can shift values; use empirical titration if pH control is critical.
  • Hygroscopicity: PEG chains readily hydrogen-bond with water; solid may absorb moisture.
  • Thermal behavior: PEG oligomers generally melt below 100 °C (n- and end group–dependent); phosphonic acid end-groups can promote higher softening points and strong glass transition features. Specific MP/BP for this item: Not specified; refer to CoA/Spec Sheet.
  • Partitioning: Strongly hydrophilic; very low logP expected (literature, qualitative).

Quality and Grades

• Item-specific (Product Data)

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret quality for m-PEG–phosphonic acids (general guidance)

  • Average chain length (n≈5): PEG materials are typically reported as an average degree of polymerization. A tight distribution (low dispersity, Đ) improves reproducibility in self-assembly and surface coverage.
  • End-group fidelity: Correct methoxy capping and full conversion to phosphonic acid at the opposite terminus are critical for predictable binding and antifouling performance. Verify by NMR (31P, 1H, 13C) and IR (P=O, P–OH bands).
  • Inorganic/metal residues: Low residual metal content is desirable for electronic, catalytic, or biointerface applications. If relevant to your use, request ICP data.
  • Volatile/solvent residues: Residual DMF/DMSO/alcohol should be minimal for surface work; TGA and GC-HS can confirm.
  • Water content: Hygroscopic PEGs can retain water; Karl Fischer may be informative prior to moisture-sensitive processing. Item-specific value: Not specified for this item; refer to CoA/Spec Sheet.
  • UV profile: If using in photoactive systems, low UV-absorbing impurities are preferred; measure baseline if necessary.
  • Recommended documentation: Request CoA plus representative NMR, IR, and GPC/SEC (if available) to assess dispersity and end-group integrity for your quality needs.

Reaction and Applications

• Core use (materials/function): m-PEG5-phosphonic acid is an anchoring ligand for robust modification of metal-oxide and mixed-oxide surfaces, imparting a protein-repellent, hydrophilic PEG corona while leaving no additional reactive handle (methoxy-terminated). Typical substrates include TiO2, ZrO2, HfO2, Al2O3, ITO, Fe3O4, and rare-earth oxides.

• Application modes (literature/general)

  • Self-assembly/chemisorption: Phosphonic acid forms mono-/bidentate or tridentate coordination to surface M–OH groups, yielding dense monolayers or polymer brushes (grafting-to). Optimized by pH 2–4 and thermal curing (80–120 °C) to drive condensation to M–O–P linkages.
  • Nanoparticle ligand exchange: Replaces native carboxylate/amine/phosphine ligands to transfer particles into aqueous media and enhance colloidal stability; useful for oxide and some metal chalcogenide NPs.
  • Anti-fouling and bioconjugation platform: The methoxy-PEG terminus minimizes nonspecific adsorption. For subsequent biofunctionalization, blend with a minor fraction of reactive PEG–phosphonic acids (e.g., NHS-, azide-, or maleimide-terminated) during assembly.
  • Adhesion promotion and corrosion protection: Enhances adhesion of hydrophilic coatings on metals via interfacial oxide binding; contributes to barrier properties.

• Practical tips

  • Pre-clean surfaces (UV-ozone or oxygen plasma) to maximize –OH density.
  • Use degassed, filtered solvents; control ionic strength to manage electrostatics.
  • Rinse thoroughly after adsorption; mild thermal cure to strengthen attachment.
  • Characterize with contact angle, ellipsometry, XPS, ATR-IR, and AFM to confirm coverage and binding.

• Item-specific application notes from manufacturer: Not specified for this item.

Reaction Conditions

• Surface assembly (general guidance; literature)

  • Substrates: Clean, hydroxylated oxides (e.g., TiO2, ZrO2, Al2O3, ITO, Fe3O4).
  • Solvents: Water, EtOH/iPrOH, or mixtures; DMF/DMSO for challenging ligand exchanges.
  • Concentration: Often 0.1–5 mM for monolayer formation; higher for thicker coatings or nanoparticle excess ligand protocols.
  • pH: Acidic conditions (≈2–4) promote protonation state conducive to strong adsorption while limiting competitive deprotonation/repulsion.
  • Temperature/time: 20–25 °C for 1–24 h for physisorption/chemisorption; optional thermal cure 80–120 °C for 10–120 min to drive M–O–P condensation (substrate-dependent).
  • Rinsing: Extensive with solvent and then water to remove unbound species; drying under N2.

• Nanoparticle ligand exchange

  • Use excess ligand in EtOH or DMF; stir from 2–24 h at room temperature or mildly elevated (≤60 °C). Separate by centrifugation or dialysis; repeat to ensure complete exchange.

• Characterization endpoints

  • Contact angle decrease (hydrophilicity increase), XPS phosphorus signal appearance, IR shifts (P=O to lower wavenumber), TGA mass gain consistent with monolayer coverage, DLS/hydrodynamic size increase for nanoparticles.

• Item-specific, validated conditions: Not specified for this item; optimize per substrate and process scale.

Safety and Handling

• Item-specific (Product Data)

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

• General safety guidance (literature/practice)

  • Expected hazards: Phosphonic acids are acidic and can be irritating to skin, eyes, and mucous membranes. PEG backbones are generally of low inherent toxicity but can enhance dermal/ocular absorption of aqueous solutions.
  • PPE: Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood when handling powders/solutions or during drying steps.
  • Handling notes: Avoid generating dust/aerosols. Prevent contact with bases and strong oxidizers. For coating operations, control pH to minimize corrosivity and volatilization of buffers.
  • First aid (overview, not a substitute for SDS):
    • Skin/eye contact: Rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
    • Inhalation: Move to fresh air; seek medical attention if respiratory symptoms occur.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
  • Storage incompatibilities: Avoid strong bases (will form phosphonates/salts), strong dehydrating agents (may promote condensation), and strong oxidizers.
  • Spill response: Absorb with inert material, collect for disposal. Neutralize acidic residues if permitted by local procedures.
  • Always consult the product SDS for authoritative safety and regulatory information.

Solvent Selection

• Polarity and miscibility (general for PEG–phosphonic acids)

  • Highly polar, hydrophilic; typically fully miscible with water.
  • Good solubility in polar protic (water, methanol, ethanol) and many polar aprotic solvents (DMSO, DMF, NMP). Limited solubility in nonpolar hydrocarbons and chlorinated solvents.

• Practical choices by application

  • Aqueous surface modification (metal oxides, ceramics): Water or water/alcohol mixtures. Adjust pH (≈2–4) to favor surface binding while limiting bulk precipitation.
  • Nanoparticle ligand exchange: Dry, anhydrous alcohols (EtOH, iPrOH) or DMF/DMSO to displace native ligands; add small water fractions to assist ionization if needed.
  • Thin-film deposition/dip-coating: Ethanol or isopropanol enable fast evaporation and uniform films; humidity control helps reproducibility.

• Comparison (general)

  • Phosphonic acid vs carboxylic acid anchors: Phosphonates bind more strongly to many oxides (TiO2, ZrO2, ITO, Al2O3, Fe3O4), especially under hydrothermal conditions.
  • PEG5 vs longer PEG: PEG5 offers compact hydrophilic layers; longer PEGs provide thicker steric barriers but can reduce grafting density.

• Item-specific solvent specifications: Not specified for this item; verify empirically. Always filter working solutions (0.22 µm) before coating to remove particulates.

Storage and Reconstitution

• Item-specific (Product Data)

  • Storage Conditions: Store at -20°C.
  • Shipped In: Ice chest + Ice pads.

• General storage guidance for PEG–phosphonic acids

  • Keep tightly sealed in original container under dry, inert atmosphere if possible (desiccant recommended). Minimize headspace moisture to prevent clumping and hydrolytic changes.
  • Allow container to warm to room temperature in a desiccator before opening to avoid condensation.
  • Avoid repeated freeze–thaw of solutions; prepare single-use aliquots.

• Reconstitution (general)

  • Solvents: Water, ethanol/isopropanol, or polar aprotics (DMF/DMSO) depending on application. Begin with small volumes and sonicate gently if needed.
  • pH control: For oxide surface binding, mildly acidic solutions (pH ~2–4) often improve adsorption; avoid strong chelating buffers that compete with phosphonate binding.
  • Filtration: Pass through 0.22 µm PTFE or PES filter prior to coating/deposition.
  • Working solution stability: Aqueous/alcoholic solutions are typically stable for days at 2–8 °C; for longer storage, freeze aliquots at −20 °C. Actual stability for this item is not specified; verify by analytical methods (NMR/IR) and performance tests.

• Disposal: Follow institutional and local regulations. Consult SDS for detailed guidance.

Structure and Identity

Brief overview: m-PEG5-phosphonic acid is a short methoxy-terminated poly(ethylene glycol) (PEG) chain with approximately five ethylene oxide repeat units (n≈5) bearing a terminal phosphonic acid (–PO3H2) anchoring group. It is commonly used to functionalize metal-oxide and inorganic surfaces, imparting hydrophilicity and protein-repellent PEG character.

• Item-specific (Product Data)

  • Product Name: m-PEG5-phosphonic acid (SKU: M595723)
  • CAS: 1807512-39-5
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: 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.

• Structural features (general description)

  • Backbone: Poly(ethylene glycol) chain with about five –CH2–CH2–O– units.
  • End-groups: One terminus capped with methoxy (–OCH3), the other terminus bearing a phosphonic acid (–PO(OH)2) functionality.
  • Functional group chemistry: The phosphonic acid can bind strongly to metal-oxide surfaces (bidentate/chelating/bridging modes). The methoxy end-group is chemically inert, conferring non-fouling PEG character.
  • 2D description in words: A linear ether chain (–CH2CH2O–)×5 starting from a methyl ether (–OCH3) and terminating in a two-oxygen phosphoryl group (P=O) bearing two hydroxyls (–OH), suitable for surface coordination.

• Stereochemistry: None (achiral, flexible aliphatic polymer-like oligomer).

Synthetic Utility

• Role in synthesis (general)

  • As a small PEGylated phosphonic acid, this compound is primarily a surface modifier rather than a building block for solution-phase organic synthesis. The methoxy terminus is inert; the reactive site is the phosphonic acid, which functions mainly in coordination/condensation to oxide surfaces.

• Transformations of the phosphonic acid (literature/general)

  • Esterification: Conversion to dialkyl or mixed phosphonate esters under dehydrating conditions (e.g., alcohol + acid catalysts) or via activation (POCl3/oxalyl chloride to phosphonodichloridate, then alcoholysis). These are advanced manipulations typically outside routine surface functionalization workflows.
  • Salt formation: Neutralization with bases (Na+, K+, NH4+, amines) to form phosphonates; salts can tune solubility and assembly behavior.
  • Coupling to metals/oxides: Formation of M–O–P linkages by condensation with surface hydroxyls (primary intended use).

• Retrosynthetic value

  • Limited as a fragment donor/acceptor due to PEG and terminal methoxy capping; for functional handles at the distal end, select alternative PEG–phosphonates (e.g., –NHS, –NH2, –COOH, –N3) and co-assemble with m-PEG5–phosphonic acid to modulate surface density and presentation.

• Characterization guidance for synthetic workflows

  • 31P NMR to confirm acid vs ester state and monitor metal binding (line broadening upon coordination).
  • IR (P=O ~1240–1150 cm−1; P–OH 980–900 cm−1 region, broad; shifts upon binding).

Target Specificity

Not applicable. This product is a small-molecule surface modifier (materials science category), not a biological targeting reagent or antibody. No antigen/epitope specificity, clone, isotype, or species reactivity data are relevant to this item.

Preguntas frecuentes

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

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 are the CAS number, molecular formula and molecular weight?

The CAS Number is 1807512-39-5, the molecular formula is C11H25O8P, and the molecular weight is 316.3 g/mol.

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.