BOC-NH-PEG2-propene , CAS No.2410236-85-8

CAS: 2410236-85-8 Cat. No.: B1445715 Formule: C₁₂H₂₃NO₄ Poids moléculaire: 245.32

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

BOC-NH-PEG2-propene is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs.

Specifications

Conditions de stockage de stockage

Store at -20°C

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

Poids moléculaire

245.32

Application Protocols

No manufacturer‑validated protocols are provided for this SKU. Below are general, non‑item‑specific outlines for common uses; optimize for your system.

Example: Thiol–ene conjugation to a cysteine‑bearing peptide (general)

• Dissolve the linker and peptide (1.2–1.5 eq thiol) in MeCN/H2O (1:1) with 10–20% EtOH; add 0.5–1 mol% water‑compatible photoinitiator (e.g., LAP).
• Degas by nitrogen sparging, irradiate at 365–405 nm for 10–60 min while stirring.
• Quench light, analyze by LC–MS, purify by RP‑HPLC.

Example: Boc deprotection (general)

• Cool a DCM solution of the linker to 0 °C, add TFA (final 50–100%). Stir 30–90 min at 0–25 °C.
• Evaporate solvents; co‑evaporate with toluene. Neutralize or proceed to coupling as the amine salt.

Example: Amide coupling post‑deprotection

• Dissolve free amine and carboxylic acid (1.0–1.2 eq) in DMF. Add HATU (1.1–1.5 eq) and DIPEA (2–3 eq). Stir at RT for 1–4 h. Work up and purify.

Note: These are illustrative starting points; adjust concentration, equivalents, and conditions to your substrates. Always validate analytically.

Biological Roles

This product is a synthetic linker intended for research use and does not possess an intrinsic biological role. However, its design leverages principles relevant to chemical biology and bioconjugation.

Context and implications (general):

• PEG2 segment: increases aqueous compatibility, reduces nonspecific adsorption, and can diminish hydrophobic interactions in conjugates. Even short PEG chains can help mitigate aggregation and improve handling in biochemical assays.
• Boc‑protected amine: allows strategic timing for unveiling a primary amine to couple to carboxylates (e.g., activated esters) on biomolecules or surfaces.
• Terminal alkene: compatible with bioorthogonal‑leaning reactions such as thiol–ene under mild photochemical conditions. While not strictly bioorthogonal in every setting, thiol–ene can proceed in buffered media with minimal metal catalysts.

Use cases in chemical biology research (non‑clinical):

• Installation of short, flexible spacers between ligands and reporter groups to reduce steric hindrance.
• Surface functionalization on particles or plates to present ligands at a defined distance from the surface.
• Preparation of soluble probe libraries where hydrophilicity tuning via PEG length is desirable.

Note: Any use with biological materials must be validated for compatibility, cytotoxicity, and assay interference in the specific system. This product is for research use only and not for diagnostic or therapeutic applications.

Buffer Applications

This item is not a buffering reagent and does not form a defined acid/base buffer system. It is a synthetic linker used in organic and bioconjugation chemistry.

Practical note:

• If employed in aqueous or mixed aqueous–organic media (e.g., thiol–ene on peptides), select buffers that do not compromise Boc protection or alkene integrity. Avoid strong acids (which remove Boc) and strong oxidants.
• Commonly compatible buffers for conjugation work include phosphate or HEPES at neutral pH, often with co‑solvents (MeCN, EtOH) to aid solubility as needed.

For precise buffer compositions and pH/stability windows, optimize empirically for the specific reaction and substrate.

Green Alternatives

This linker already benefits from a PEG motif (generally considered to have a favorable EHS profile compared with halogenated/hydrocarbon spacers). Greener choices center on solvent selection and reaction modality rather than the core reagent.

Greener processing options (literature/practice):

• Solvents:
  • Replace DCM with 2‑MeTHF, CPME, or ethyl acetate for nonpolar to mid‑polarity steps (e.g., extractions, metathesis setup).
  • Use MeCN or EtOAc instead of chlorinated solvents where compatible with reactivity.
  • For photochemical thiol–ene, EtOAc, MeCN, or solvent‑free/dispersion conditions can work and reduce environmental impact.
• Catalysis and initiators:
  • Employ visible‑light photoinitiators and LED sources to lower energy footprint in thiol–ene processes.
  • For metathesis, consider robust 2nd‑generation ruthenium catalysts that operate at lower loadings and ambient temperatures.
• Workup/waste:
  • Minimize excess acid for Boc deprotection; recover solvents via distillation when feasible.
  • Utilize aqueous ethanol or isopropanol for precipitations to avoid chlorinated waste.

Comparison (general considerations):

• Alkene linker (this item): versatile, catalyst‑enabled, with mild photochemical options.
• Azide/alkyne linkers: enable click chemistry in water/ethanol; avoid copper (SPAAC) to reduce metal waste, but azides require additional hazard controls.
• NHS‑ester linkers: fast amidation in aqueous buffer; shorter reaction times but limited selectivity with multiple nucleophiles.

Tradeoffs: Greener solvents can modestly change rates/selectivities (e.g., metathesis in 2‑MeTHF vs DCM). Always verify performance in small‑scale trials.

Pharmaceutical Uses

No pharmacopeial status or excipient designation is provided for this SKU. It is supplied for research use only.

General formulation/manufacturing context (non‑clinical, research):

• Linker design: Short PEG linkers are widely explored in discovery chemistry to tune solubility, permeability, and target engagement of bi‑functional molecules, and to space ligands from surfaces or carriers.
• Process development: The Boc‑protected amine enables late‑stage convergence in library synthesis; the alkene handle supports catalyst‑based diversification (metathesis, thiol–ene), potentially streamlining parallel synthesis.
• Analytical considerations: PEGylated entities can show broadened NMR signals and multiple adducts in MS (Na+, K+); LC method development (HILIC or mixed‑mode) may improve retention and peak shape.

If considering use toward regulated applications, full qualification (identity, purity, residual solvents, elemental impurities, stability) and a defined impurity profile would be required; consult your QA framework. This listing makes no claim for clinical or diagnostic use.

Physical Properties

Item-specific numerical specifications have not been provided for this SKU.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, water/peroxide content, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.

General expectations for PEG2 Boc–amine allyl linkers (literature/general):

• Physical state: often a colorless to pale viscous liquid or low‑melting waxy solid, depending on exact substitution and purity.
• Solubility: good solubility in polar aprotic organics (DMF, DMSO, MeCN), chlorinated solvents, esters, and alcohols; moderate to good solubility in water due to PEG2, though terminal hydrophobic groups can reduce water miscibility.
• Volatility: low; PEG oligomers are nonvolatile under ambient conditions.
• Hygroscopicity: PEG chains can be mildly hygroscopic; drying before moisture‑sensitive reactions is recommended.

Computed/literature guidance (non‑spec, indicative):

• LogP: typically low to moderate (PEG lowers lipophilicity; allyl increases slightly); exact value depends on the full structure.
• pKa: Boc carbamate is nonbasic; free amine after deprotection would exhibit pKa ~9–10 (literature, for primary aliphatic amines). Boc group is acid‑labile.

Important: For process design or QC thresholds (mp/bp, water, metals), use the Certificate of Analysis and product Specification Sheet for this exact SKU.

Quality and Grades

Item-specific grade/purity and stabilizers were not provided for this SKU.

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

General guidance on grades relevant to this class of product:

• Research grade: typical for organic synthesis linkers; suitable for discovery chemistry, library synthesis, and bioconjugation method development. May not include trace-metal or residual solvent certifications unless specified.
• High-purity (>95–98% by HPLC/LC–MS) lots are preferred for bioconjugation to minimize byproducts in end‑products; check chromatographic purity on CoA.
• Water content: PEG motifs can retain water; Karl Fischer values are often included in high-spec listings. If critical, dry under high vacuum (e.g., 40–50 °C) before use.
• Low UV absorbance may be desirable if using in analytical workflows; HPLC-grade solvents and clean glassware minimize baseline artifacts.

What to verify on receipt (best practices):

• Identity: 1H/13C NMR consistent with Boc carbamate and allyl signals; HRMS matching the expected [M+H]+.
• Purity: LC–MS/HPLC chromatogram and area % on CoA.
• Residual solvents and inorganic impurities: review if your process is sensitive (e.g., catalytic couplings, metathesis).

Reaction and Applications

BOC‑NH‑PEG2‑propene is designed for orthogonal chemistry, enabling sequence‑controlled assembly in small‑molecule and bioconjugation workflows.

Key application themes:

• Latent amine unveiling: Boc deprotection (acid‑labile) yields a primary amine for downstream amidation, urea/carbamate formation, or NHS‑ester coupling to biomolecules.
• Terminal alkene transformations:
  • Thiol–ene conjugation: radical/photochemical addition of thiols (peptides with Cys, polymer thiols) to the allyl terminus, forming robust thioether linkages.
  • Olefin metathesis: cross‑metathesis with type I olefins (e.g., allyl esters) under Grubbs‑type catalysts, enabling fragment assembly.
  • Hydroboration–oxidation: converts the alkene to a terminal alcohol, unlocking further derivatizations (carbonates, esters, or activation to leaving groups).
  • Epoxidation/aziridination: creates electrophilic epoxides for subsequent nucleophilic opening.
  • Ozonolysis/oxidative cleavage: optional route to carbonyl functionality if desired.
• Linker role: PEG2 imparts hydrophilicity and flexibility, improving solubility and reducing aggregation in conjugates and screening libraries.

Practical notes:

• Moisture management: dry the material (vacuum, mild heat) for moisture‑sensitive steps (e.g., carbodiimide couplings, metathesis).
• Protecting group strategy: using Boc enables acid‑triggered deprotection late in the sequence; avoid acids during steps that require the protected state.
• Photochemistry: for thiol–ene, remove dissolved oxygen (argon sparge) and use a suitable photoinitiator to improve conversion.

Typical use cases include: spacer installation between pharmacophores, surface modification, affinity tag spacing, and preparing solubility‑enhanced probe molecules.

Reaction Conditions

Conditions below are literature/general guidance for the functional groups present; they are not item‑specific specifications.

• Boc deprotection (amine unveiling):
  • Reagents: TFA/DCM (1:1 to neat TFA) at 0–25 °C, 0.5–2 h; or HCl/dioxane (4 M) at RT, 1–3 h.
  • Notes: PEG improves solubility in polar organics; remove volatiles under reduced pressure, co‑evaporate with toluene to purge TFA. Neutralize or capture the amine as a salt as appropriate.
• Thiol–ene conjugation:
  • Typical: substrate (allyl), thiol (1.0–1.5 eq), photoinitiator (0.1–2 mol%), solvent EtOAc/MeCN/MeOH or aqueous co‑solvent, 365–405 nm LED, N2/Ar sparge, 15–120 min.
  • Thermal option: AIBN (5–10 mol%) at 60–80 °C in toluene/EtOAc.
• Cross‑metathesis (allyl terminus):
  • Catalyst: Grubbs 2nd gen (1–5 mol%). Solvent: DCM, toluene, or 2‑MeTHF. Temp: 20–40 °C. Time: 1–6 h. Drive by slight excess of partner olefin.
• Hydroboration–oxidation:
  • Reagents: 9‑BBN or BH3·THF (1.1–1.5 eq), 0–25 °C; then H2O2/NaOH. Solvent: THF or 2‑MeTHF. Anti‑Markovnikov alcohol expected.
• Epoxidation:
  • mCPBA (1.1 eq) in DCM or EtOAc at 0–25 °C; buffer washing to remove acids. Follow with nucleophilic opening as desired.

General tips:

• Drying: Azeotrope with toluene or dry under high vacuum at mild heat to remove bound water in PEG segments.
• Oxygen control: For radical or metathesis steps, degas/blanket to improve rates and selectivity.
• Workup: PEGylated products can partition into aqueous phases; salt out with brine or add organic modifiers to improve recovery.

Safety and Handling

Hazard classification details were not supplied for this item.

• GHS classification, signal word, pictograms, H‑statements: Not specified for this item; refer to SDS.

General safety guidance for Boc‑protected PEGylated alkene linkers (literature/practice):

• Primary hazards: organic liquid/solid that may cause skin/eye irritation. Boc carbamates can release CO2/isobutylene under strong acid; avoid acid contact unless deprotecting.
• Sensitization/allergenicity: PEGs are generally of low acute toxicity, but avoid inhalation of aerosols and prolonged skin contact. Handle as a chemical of unknown toxicity.
• PPE: lab coat, safety glasses, and disposable nitrile gloves. Use chemical‑resistant gloves for extended contact. Avoid open handling if aerosols/mists could form.
• Engineering controls: handle in a fume hood. Keep containers tightly closed to minimize moisture uptake and contamination.
• Incompatibilities: strong acids (Boc cleavage), strong oxidizers (allyl oxidation), radical initiators/UV in presence of thiols (thiol–ene can proceed unintentionally). Avoid prolonged exposure to light/UV if an unreacted alkene is required.
• Spill/first aid (overview): absorb liquid with inert material; wash area with detergent. For skin/eye contact, rinse with water for at least 15 minutes and seek medical attention if irritation persists. If inhaled, move to fresh air; if ingested, rinse mouth and seek medical advice.

Always consult the Safety Data Sheet for authoritative, item‑specific hazard and first‑aid information.

Solvent Selection

As a PEG2‑containing, moderately polar organic linker with a terminal alkene, BOC‑NH‑PEG2‑propene dissolves well in polar aprotic media and many common organic solvents.

General miscibility/solubility tendencies (literature/practice):

• Polar aprotic: DMF, DMSO, NMP, and acetonitrile – typically excellent solubility; good for coupling and photochemical additions.
• Chlorinated: DCM, DCE, chloroform – good solubility; useful for Boc deprotection workups (note: acid presence will deprotect).
• Ethers/esters: THF, 2‑MeTHF, CPME, EtOAc – generally good solubility; useful for hydroboration or epoxidation setups.
• Alcohols: MeOH, EtOH, i‑PrOH – usually soluble; may participate in side reactions under strong acid/base.
• Water: PEG2 often affords partial to full solubility; confirm experimentally for your lot and concentration.

When to choose vs alternatives:

• Choose this linker when orthogonal reactivity is needed: protected amine for later unveiling, and a terminal alkene for modular additions or metathesis.
• For higher aqueous solubility or longer reach, consider higher PEG length analogs (PEG3–PEG6). For lower polarity, consider PEG1 or hydrocarbon spacers.

Small comparison (general):

• BOC‑NH‑PEG2‑propene: balanced polarity; alkene handle; amine masked.
• BOC‑NH‑PEG2‑azide: similar polarity; azide handle for CuAAC/SPAAC instead of alkene chemistry.
• Fmoc‑NH‑PEG2‑propene: base‑labile amine protection; compatible with acid‑sensitive systems.

Storage and Reconstitution

Item-specific storage guidance provided by the supplier:

• Storage conditions: Store at −20 °C.
• Shipping: Shipped in ice chest with ice pads.

Additional best practices (general for PEGylated Boc–alkene linkers):

• Protect from moisture and strong acids to preserve Boc protection and prevent hydrolysis.
• Minimize light/UV exposure if retaining the alkene functionality is critical.
• After opening, purge headspace with dry nitrogen/argon and recap tightly. Consider storing under inert gas in a desiccator or dry box.
• If solidifies on cold storage, allow to warm to room temperature before dispensing to ensure homogeneous sampling.

Reconstitution and handling:

• Solvents: Dissolve in dry DMF, DMSO, MeCN, DCM, THF, or EtOAc. Filter if particulates are present.
• Concentrated stock solutions can be prepared in dry DMF or DMSO and stored aliquoted at −20 °C; avoid repeated freeze–thaw cycles.
• Water content and residual solvents are not specified for this item; refer to CoA/Spec Sheet if these parameters are critical to your application.

Always refer to the product’s CoA and SDS for lot‑specific stability and handling details.

Structure and Identity

A bifunctional PEG linker featuring a Boc-protected amine and a terminal propene (allyl) group for orthogonal chemistry.

• Product name: BOC-NH-PEG2-propene (also described as Boc-protected amino–PEG2–allyl)
• CAS: 2410236-85-8
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (derived from the name; general description):

• Contains a tert‑butoxycarbonyl (Boc)‑protected primary amine: –NH–CO–O–tBu (carbamate protecting group).
• PEG2 spacer: two ethylene glycol repeats, –CH2–CH2–O–CH2–CH2–O–, providing polarity and flexibility.
• Terminal propene (allyl) moiety: –CH2–CH=CH2, enabling alkene chemistry (thiol–ene, metathesis, hydroboration, epoxidation).
• Overall architecture (verbal 2D): Boc–NH–(PEG)2–O–CH2–CH=CH2, where the Boc protects the amine while the opposite terminus is an alkene.
• Functional group set: protected primary amine (latent NH2), ether linkages (PEG), terminal alkene; no stereocenters are implied by the name.

Notes:

• Exact connectivity (e.g., whether the PEG is linked via additional methylene spacers) and terminal heteroatom attachment may vary by supplier convention; consult the CoA/structural sheet for the definitive structure for this SKU.

Synthetic Utility

BOC‑NH‑PEG2‑propene functions as a modular, orthogonally reactive building block.

Functional group logic:

• Protected amine: stable to base/nucleophiles; unmasked by acids to give a primary amine amenable to amide, urea, carbamate formation, or reductive amination (post‑deprotection).
• PEG2 spacer: imparts solubility and conformational flexibility, separating functional heads to reduce intramolecular quenching.
• Allyl terminus: versatile C=C handle for C–S, C–C, and C–O bond formation.

Representative transformations (literature examples):

• Thiol–ene addition: radical addition of thiols (peptides, polymers, small molecules) across the terminal alkene to yield thioethers. Oxygen exclusion and photoinitiators (e.g., DMPA, LAP) accelerate conversion.
• Cross‑metathesis: Grubbs‑type catalysts couple the allyl end with other olefins, expanding structural diversity with high functional group tolerance.
• Hydroboration–oxidation: converts the alkene to a terminal alcohol, enabling further activation (tosylation/mesylation) or carbonate formation.
• Epoxidation then ring opening: mCPBA epoxidation followed by nucleophile addition installs oxygen or nitrogen side chains.
• Boc deprotection: TFA or HCl in appropriate solvents releases the amine, which can be coupled to acids (e.g., EDCI/HOBt, HATU) or isocyanates.

Retrosynthetic value:

• Treat as a masked amino spacer bearing a terminal diversification node (alkene). It can bridge hydrophilic/hydrophobic domains and facilitates late‑stage diversification without protecting group reshuffling.

Target Specificity

Not applicable. This product is a small‑molecule linker and does not have biological target specificity like an antibody or ligand validated against a defined biomolecular target.

• Antigen/epitope, species reactivity, clone, isotype: Not applicable to this item.

For application‑specific selectivity (e.g., preferential conjugation), control arises from reaction chemoselectivity (thiol–ene vs amine coupling) rather than target binding.

Foire aux questions

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 2410236-85-8, the molecular formula is C12H23NO4, and the molecular weight is 245.32 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.