Tris (O-TBDMS)3 - ≥96% , CAS No.102522-47-4

CAS: 102522-47-4 Cat. No.: T595177 Summenformel: C₂₂H₅₃NO₃Si₃ Molekulargewicht: 463.92 PubChem CID: 15299066

GRADE & PURITY ≥96%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

Tris (O-TBDMS)3 is a Tris derivative with 3 TBDMS protecting groups. The TBDMS is an acid labile protecting group.

Specifications

Spezifikationen & Reinheit

≥96%

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥96%

Namen und Kennungen

Kanonisches Lächeln

CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)N

IUPAC Name

1,3-bis[[tert-butyl(dimethyl)silyl]oxy]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]propan-2-amine

InChIKey

VPKYOQBACGWZCO-UHFFFAOYSA-N

INCHI

1S/C22H53NO3Si3/c1-19(2,3)27(10,11)24-16-22(23,17-25-28(12,13)20(4,5)6)18-26-29(14,15)21(7,8)9/h16-18,23H2,1-15H3

Isomere SMILES

CC(C)(C)[Si](C)(C)OCC(CO[Si](C)(C)C(C)(C)C)(CO[Si](C)(C)C(C)(C)C)N

PubChem CID

15299066

Molekulargewicht

463.92

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organometallic compounds
    • Klasse Organometalloid compounds
      • Subclass Organosilicon compounds
        • Ebene5 Organoheterosilanes
          • Ebene6 Trialkylheterosilanes

• Kingdom: Organic compounds
• Superclass: Organometallic compounds
• Klasse: Organometalloid compounds
• Subclass: Organosilicon compounds
• Intermediate Tree Nodes: Organoheterosilanes
• Direct Parent: Trialkylheterosilanes
• Alternative Parents: Silyl ethers Organic metalloid salts Organooxygen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Trialkylheterosilane - Silyl ether - Organic metalloid salt - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Primary aliphatic amine - Amine - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as trialkylheterosilanes. These are organoheterosilanes, bearing a silicon atom linked to three alkyl groups and one heteroatom.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Chemische und physikalische Eigenschaften

• Molekulargewicht: 463.900 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 12
• Exact Mass: 463.333 Da
• Monoisotopic Mass: 463.333 Da
• Topological Polar Surface Area: 53.700 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 453.000
• 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

XLogP3

Application Protocols

No standardized bioassay or immunoassay protocols apply to this small-molecule building block.

Chemistry-focused usage notes (literature-based)

• N‑Acylation protocol (example): Dissolve the compound in dry DCM under N2, cool to 0°C, add Et3N (3 equiv) followed by acyl chloride (1.2 equiv) dropwise. Stir 1 h at 0–5°C then warm to rt and monitor. Quench with sat. NaHCO3, extract, dry, and purify on base‑modified silica.
• Deprotection protocol (example): To a THF solution under N2, add 1.2 equiv TBAF per TBDMS moiety at 0–25°C. Stir 1–3 h, monitoring by TLC. Quench with aqueous NH4Cl, extract with EtOAc, dry, and concentrate. Purify the triol by chromatography or trituration.

For application-specific details, consult relevant synthetic literature and adapt scales/stoichiometries to your system. Always review the SDS before use.

Biological Roles

This compound is a synthetic, hydrophobic, tri‑silyl‑protected derivative of TRIS and is not known to occur in biological systems.

• No endogenous role: The tert‑butyldimethylsilyl ether motif is absent from natural metabolites; biological pathways do not natively process TBDMS groups.
• Biochemical interaction (general): Primary amines can form salts with acids and engage in hydrogen bonding; however, the overall hydrophobicity and steric bulk of three TBDMS groups limit aqueous biointeractions.
• Research context: In chemical biology or materials interfaces, the molecule may be used as a protected precursor to triol-bearing linkers after deprotection, enabling attachment of biomolecules through ester/urethane formation. Any such use remains at the chemistry interface; no biological activity is implied.

Note

• Any assessments of biocompatibility, toxicity, or cellular uptake would be highly application-dependent and are not provided for this item. For research use only, not for diagnostic, therapeutic, or in vivo applications.

Buffer Applications

Not typically applicable to this protected species.

• Clarification: Although TRIS (tris(hydroxymethyl)aminomethane) is a well-known biological buffer, Tris (O‑TBDMS)3 has all three hydroxyls protected with hydrophobic silyl groups and is essentially insoluble in water. It does not function as an aqueous buffer and is not intended for buffer preparation.
• Recommendation: For buffering applications, use analytical‑grade TRIS or TRIS·HCl with appropriate pH range (pKa ≈ 8.1 at 25°C; literature) rather than this protected derivative.

Green Alternatives

Perspective

• The molecule itself is a protecting‑group reagent/precursor; “greenness” is driven primarily by solvent and reagent choices during use.

Greener handling choices (literature-based)

• Solvents: Prefer 2‑MeTHF or CPME over THF/diethyl ether; ethyl acetate over dichloromethane/chloroform; MeCN over DMF/DMAC where feasible.
• Coupling chemistry: Use aqueous micellar catalysis or carbodiimide chemistry with benign byproducts when possible; minimize acid additives that risk desilylation.
• Deprotection: Optimize TBAF usage (stoichiometric, minimal excess) and consider solid‑supported fluoride or buffered HF alternatives in flow to reduce waste.

Comparison table (general guidance)

• DCM vs EtOAc: EtOAc offers lower toxicity and better biodegradability; DCM provides broader solubility but is a chlorinated solvent with higher environmental impact.
• THF vs 2‑MeTHF: 2‑MeTHF is bio‑derived and has improved safety/energy profile; both support similar reactivity for silyl ether chemistry.
• Workup: Employ solvent recycling and avoid acidic aqueous wastes that contain fluoride/silicon species; neutralize and segregate fluoride-containing streams.

Tradeoffs

• Greener solvents can change solubility and reaction rates; ensure adequate dissolution to avoid localized acidity that could promote silyl cleavage. Validate on small scale, then scale with in‑process controls (IPC).

Pharmaceutical Uses

Formulation/processing relevance (general)

• Role: Not used directly as an excipient. As a protected triol bearing a primary amine, it may serve as a synthetic intermediate in the preparation of polymeric excipients, pro-materials, or linkers where controlled unveiling of triol functionality is needed (e.g., for forming carbonates/urethanes/esters after deprotection). No therapeutic or clinical claims are made or implied.
• Pharmacopeial status: No monograph is known for this protected derivative; it is distinct from TRIS/Tris HCl, which do have compendial entries.

Manufacturing considerations

• Benefits: The TBDMS groups impart organic solubility and processing latitude, enabling nonaqueous transformations and selective N‑derivatization before revealing hydroxyls.
• Constraints: Requires deprotection under fluoride or acidic conditions; any pharmaceutical context must control residual fluoride/silicon-containing byproducts rigorously.

Quality notes

• If targeted to regulated applications, ensure comprehensive characterization (identity by NMR/HRMS, residual solvents by GC, water by KF, impurity profile), and assess extractables/leachables of any silicone byproducts post-deprotection. For this catalog item, quality/purity are Not specified for this item; refer to CoA/Spec Sheet.

Physical Properties

Item-specific (from Product Data)

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Physical constants (mp, bp, density, refractive index, solubility): Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed (general guidance; not item-specific specs)

• Aggregation state: typically a hydrophobic, nonvolatile organic solid or viscous oil, depending on purity and microstructure (literature/experience with TBDMS-protected triols).
• Solubility profile: expected to be soluble in nonpolar and moderately polar aprotic solvents (e.g., hexanes, toluene, CH2Cl2, CHCl3, THF, EtOAc) and essentially insoluble in water and most alcohol–water mixtures (literature for TBDMS ethers).
• Polarity/logP: high hydrophobicity due to three tert‑butyldimethylsilyl groups; calculated cLogP typically >3 for related tri‑TBDMS ethers (literature).
• Stability: silyl ethers are stable to many bases and nucleophiles but are labile to fluoride and strong Brønsted acids; hydrolysis accelerated by moisture and acid catalysis (general silyl ether behavior).

Practical implications

• Use anhydrous solvents and minimize exposure to moisture to suppress slow desilylation.
• Avoid prolonged contact with silica gel containing residual acidity during chromatography; pre-neutralization (e.g., with 1–2% Et3N in eluent) is commonly used to limit cleavage of TBDMS ethers (literature practice).

Note

• For authoritative, lot-specific physical data (mp, water content, residual solvents, assay), consult the CoA/Spec Sheet for SKU T595177.

Quality and Grades

Item-specific quality information

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

Context and guidance

• Typical grades you may encounter for this type of building block include:
  • Research grade: suitable for general synthetic use; assay commonly reported by NMR/LC–MS/GC with limits on common impurities (water, residual solvents)—check CoA.
  • High-purity or “anhydrous” selections: may be dried and packaged under inert gas with Karl Fischer water specification to support moisture-sensitive synthesis; UV specs are usually not relevant for this non-chromophoric compound.
• Stabilizers: TBDMS-protected substrates generally do not require added stabilizers; quality is driven by low moisture and low acid content of packaging. If a stabilizer/drying agent is present, it will be declared on the CoA.
• Documentation: For each lot, consult the CoA for assay method (e.g., 1H/13C NMR integration, qNMR), water content (KF), residual solvents, and chromatographic purity (HPLC/GC). Where applicable, metal content (ICP-MS) is reported if the material targets materials science/electronics uses.

Practical tips

• Upon receipt, verify identity/purity by quick 1H NMR; TBDMS methyl (0.0–0.2 ppm) and tert‑butyl (≈0.9 ppm) resonances provide convenient QC markers. Ensure absence of partial desilylation (appearance of –CH2OH signals).

Reaction and Applications

Scope (materials science and synthesis; literature-based)

• Protected triol scaffold: Tris (O‑TBDMS)3 is a tri‑silylated form of TRIS that masks the three alcohols while leaving the primary amine available. This allows selective N‑functionalization (acylation, sulfonylation, carbamate formation, N‑alkylation) without competing O‑acylation/oligomerization.
• Modular linker/core: Serves as a compact C1‑centered, tri-branched core for dendrimers, star polymers, and crosslinkable materials; the TBDMS groups can be deprotected later to reveal a triol for post‑assembly curing (e.g., urethane, carbonate, or ester network formation).
• Surface chemistry: The hydrophobic, bulky periphery can modulate interfacial properties in coatings; subsequent fluoride-triggered deprotection enables on‑surface activation to a triol.
• Protecting‑group relay: Stable to many bases/nucleophiles, enabling multistep sequences at nitrogen; final global deprotection with fluoride or acid reveals polyol functionality.

Practical tips

• N‑Acylation: Perform in DCM/DMF with base (Et3N, DIPEA) and acyl chloride/anhydride or use coupling reagents (EDC/HATU) with carboxylic acids. Monitor to avoid acidic conditions that cleave TBDMS.
• Carbamate formation: React with chloroformates or DSC under basic conditions to generate activated carbamates for further conjugation.
• Stability hierarchy (literature): TBDMS > TMS to acids; TBDMS < TBDPS to strong acids. Choose cleavage reagent accordingly (TBAF for clean deprotection; HF‑pyridine for tougher matrices).

Manufacturer Applications linkage

• Listed under Materials Science: leverage as a protected multifunctional hub for polymer precursors, crosslinkers, and dendritic architectures where staged deprotection is desired.

Reaction Conditions

General conditions (literature; guidance only, not item-specific)

• N‑Acylation (selective at amine):
  • Solvent: DCM, THF, or MeCN (anhydrous).
  • Base: Et3N or DIPEA (2–3 equiv).
  • Electrophile: acyl chloride/anhydride (1.1–1.5 equiv) or carboxylic acid with HATU/EDC (1.2–1.5 equiv) plus catalytic DMAP as appropriate.
  • Temperature/time: 0–25°C, 0.5–4 h; monitor by TLC/LC–MS. Maintain neutral/basic conditions to preserve TBDMS.
• Carbamate formation:
  • Chloroformate (1.1–1.3 equiv) in DCM with Et3N at 0–25°C; 1–3 h.
• N‑Alkylation (SN2):
  • Solvent: DMF/MeCN.
  • Base: K2CO3/Cs2CO3 or NaH (carefully, 0.9–1.2 equiv).
  • Electrophile: primary alkyl bromides/iodides; 25–60°C, 2–12 h.
• TBDMS deprotection (global):
  • Fluoride: TBAF in THF (1.0–1.5 equiv per silyl group) at 0–25°C, 0.5–4 h; add AcOH buffer if needed to manage basicity.
  • Acidic: HF·pyridine (carefully, specialized PPE) or HCl/MeOH for slower cleavage; 0–25°C, hours.

Workup and purification

• Avoid acidic silica; pre-treat silica with 1–2% Et3N or use neutral/alumina when purifying silyl ethers. For deprotected triol, switch to polar eluents.
• Typical isolated yields: 70–95% for N‑acylations/carbamates under water-free conditions; deprotection yields depend on substrate and sterics (literature ranges 75–95%).

Controls

• Verify integrity of TBDMS groups by 1H NMR (t‑Bu ~0.9 ppm, SiMe2 ~0.0–0.2 ppm). Loss or broadening indicates partial cleavage.

Safety and Handling

Item-specific hazard data

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.

General safety considerations (literature/chemical class guidance)

• Likely hazards: Organic compounds bearing silyl ethers are generally of low volatility; primary concerns are eye/skin irritation and potential respiratory irritation from dust or aerosols. TBDMS ethers hydrolyze to release alcohols and silanols under acidic/aqueous conditions.
• Incompatibilities: Avoid strong acids, Lewis acids, and fluoride sources (TBAF, HF·pyridine), which can rapidly cleave TBDMS groups. Moisture promotes slow hydrolysis.
• PPE: Wear lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to avoid inhalation of particulates.
• Handling: Work under dry, inert atmosphere when feasible. Use anhydrous solvents and oven-dried glassware. Cap containers promptly; purge headspace with inert gas for long-term storage.
• First aid (summary; defer to SDS): If on skin/eyes, rinse with water for several minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Provide SDS to medical personnel.
• Fire safety: Treat as a combustible organic solid; use CO2, dry chemical, or foam. Thermal decomposition may produce irritating fumes.

Always consult the Aladdin Scientific SDS for SKU T595177 for authoritative hazard classification and response measures.

Solvent Selection

Chemical class perspective

• Polarity/solubility: Highly hydrophobic due to three TBDMS groups; favors nonpolar to moderately polar aprotic media.

Literature-based miscibility guidance (not item-specific specs)

• Preferred solvents for dissolution and reactions: dichloromethane, chloroform, toluene, THF, diethyl ether, CPME, 2‑MeTHF, ethyl acetate, acetonitrile (moderate).
• Poor/limited solubility: water; lower alcohols and buffered aqueous systems.

When to choose what

• DCM/CHCl3: excellent solubility and gentle conditions for amine acylation or carbamate formation; monitor for acid-mediated desilylation on acidic supports.
• THF/2‑MeTHF: good for base-mediated transformations at the amine or for fluoride-mediated deprotection control (if desired) with TBAF.
• Toluene/hexanes: useful for nonpolar workups and crystallizations; maximizes stability of silyl ethers under neutral conditions.
• EtOAc: greener alternative to chlorinated solvents for extractions and chromatographic elution; may require base-modified silica to prevent silyl cleavage.

Comparison snapshot (literature)

• DCM vs EtOAc: DCM offers broader solubility and neutral behavior on silica; EtOAc is greener but can hydrogen-bond to the amine, modestly altering reactivity.
• THF vs 2‑MeTHF: 2‑MeTHF provides similar solvation with improved sustainability and easier separations due to lower miscibility with water.

Practical notes

• Dry your solvent (molecular sieves, solvent system) to suppress hydrolysis. For chromatography, add 0.5–2% Et3N to mobile phase to protect TBDMS groups.

Storage and Reconstitution

Item-specific (from Product Data)

• Storage conditions: Store at −20°C.
• Shipping: Ice chest + ice pads.

Best practices (general guidance for silyl ethers)

• Atmosphere: Keep tightly sealed under inert gas (N2/Ar) to minimize moisture/CO2 ingress that can promote slow desilylation or salt formation at the amine.
• Container: Use amber glass with PTFE-lined cap; avoid acidic cardboard dust or acidic desiccants. Include a desiccant pouch when possible.
• Handling: Allow container to equilibrate to room temperature before opening to avoid condensation. Reseal promptly after use and return to cold storage.
• Stability: TBDMS ethers are reasonably stable at −20°C when dry and protected from acids/fluoride. Monitor periodically by 1H NMR if stored long term.

Reconstitution/solution preparation

• Solvents: Prepare stock solutions in dry DCM, THF, toluene, CPME, 2‑MeTHF, or EtOAc. Water and aqueous buffers are not recommended.
• Concentrations: Choose based on solubility and application (commonly 0.05–0.5 M for synthesis). Filter through PTFE syringe filters if particulates are present.

Note

• For definitive shelf-life, allowable excursions, and any lot-specific precautions, refer to the Aladdin Scientific CoA/Spec Sheet and SDS for SKU T595177.

Structure and Identity

Item-specific (from Product Data)

• SKU: T595177
• Product name: Tris (O-TBDMS)3
• CAS: 102522-47-4
• PubChem CID: 15299066
• InChIKey: 384990 (as provided; appears truncated)
• 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: Not specified for this item; refer to CoA/Spec Sheet.

Literature/structural description (for reference only)

• Common chemical name: Tris(hydroxymethyl)aminomethane tri-O-tert‑butyldimethylsilyl ether (i.e., TRIS with all three hydroxyls protected as TBDMS ethers; the amine remains free).
• Functional groups/features: one primary amine (–NH2) attached to a neopentyl-like carbon; three tert‑butyldimethylsilyl (TBDMS, tBu–SiMe2–) ether substituents on the formerly hydroxymethyl groups; three Si atoms; no stereocenters.
• 2D description: a central carbon bound to –CH2–O–Si(Me)2–tBu at three positions and to –NH2 at the fourth; each silyl ether presents significant steric bulk and hydrophobic character.
• Typical empirical formula (literature): C22H53NO3Si3; typical formula weight ≈463.9 g/mol (literature, not item-specific).

Notes

• The item’s exact identifiers (fully formatted InChIKey/SMILES, confirmed formula/MW) should be taken from the product’s CoA or specification sheet. The above structural description reflects common usage of the name “Tris (O‑TBDMS)3” in the synthetic/Materials Science literature.

Synthetic Utility

Functional group strategy (literature-based)

• Orthogonal protection: Triply protects the polyol portion of TRIS as TBDMS ethers, leaving the primary amine available for selective transformations (acylation, sulfonylation, carbamate formation, reductive amination, N‑alkylation, N‑protection such as Boc/Alloc).
• Masked triol unveiling: Global deprotection with TBAF or acid (HF·pyridine, HCl/MeOH for slower cleavage) regenerates the triol for downstream coupling (esters, carbonates, urethanes) or polymer network formation.
• Dendritic/polymeric core: Serves as a compact tetrafunctional hub (one N + three latent O) for assembling star polymers and hyperbranched architectures; robust during base-catalyzed growth phases.

Select transformations

• N‑Acylation: Acyl chlorides/anhydrides with Et3N/DIPEA in DCM/THF; coupling reagents (EDC/HATU) with carboxylic acids in DMF/MeCN.
• N‑Alkylation: Alkyl halides under SN2 conditions (NaH/K2CO3) in polar aprotics; avoid prolonged heating with iodides in the presence of adventitious acid.
• Carbamate/urea formation: Chloroformates or isocyanates produce carbamates/ureas on nitrogen without disturbing TBDMS under neutral/basic conditions.
• Post‑deprotection elaboration: Triol enables orthogonal activation (e.g., tosylates/mesylates, CDI carbonates) for further substitution/crosslinking.

Stability window

• TBDMS protects through many bases/nucleophiles and mild oxidants; avoid strong acids, fluoride, and prolonged contact with acidic silica to prevent partial deprotection.

Target Specificity

Not applicable. This product is a small-molecule synthetic building block, not a biological targeting reagent (e.g., antibody, enzyme inhibitor, or ligand with defined biomolecular specificity). No antigen/epitope or species reactivity information applies.