Dodecyltrimethoxysilane - ≥93%(GC) , CAS No.3069-21-4

CAS: 3069-21-4 Cat. No.: D155296 Fórmula: C₁₅H₃₄O₃Si Peso molecular: 290.52 Número CE: 221-332-4

GRADE & PURITY ≥93%(GC)

Synonyms

AS-15225 | dodecyl(trimethoxy)silane | Silane, dodecyltrimethoxy- | SCHEMBL57462 | AKOS015839853 | D3383 | Dodecyltrimethoxysilane(1-trimethoxysilyldodecane) | FT-0688115 | n-dodecytrimethoxysilane | n-Dodecyltrimethoxysilane | Lauryltrimethoxysilane | EI

Storage

Room temperature,Argon charged

Shipped In

Normal

Specifications

Sinónimos

AS-15225 | dodecyl(trimethoxy)silane | Silane, dodecyltrimethoxy- | SCHEMBL57462 | AKOS015839853 | D3383 | Dodecyltrimethoxysilane(1-trimethoxysilyldodecane) | FT-0688115 | n-dodecytrimethoxysilane | n-Dodecyltrimethoxysilane | Lauryltrimethoxysilane | EI

Especificações e pureza

≥93%(GC)

Condições de armazenamento de armazenamento

Room temperature,Argon charged

Enviado em

Normal

Pureza

≥93%(GC)

Nomes e identificadores

Pubchem Sid

504755068

Pubchem Sid Url

https://pubchem.ncbi.nlm.nih.gov/substance/504755068

Sorrisos canónicos

CCCCCCCCCCCC[Si](OC)(OC)OC

IUPAC Name

dodecyl(trimethoxy)silane

InChIKey

SCPWMSBAGXEGPW-UHFFFAOYSA-N

INCHI

1S/C15H34O3Si/c1-5-6-7-8-9-10-11-12-13-14-15-19(16-2,17-3)18-4/h5-15H2,1-4H3

SMILES isoméricas

CCCCCCCCCCCC[Si](OC)(OC)OC

Peso molecular

290.52

Reaxy-Rn

2356323

Reaxys-RN_link_address

https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2356323&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organometallic compounds
    • Classe Organometalloid compounds
      • Subclass Organosilicon compounds
        • Level5 Alkoxysilanes
          • Level6 Trialkoxysilanes

• Kingdom: Organic compounds
• Superclass: Organometallic compounds
• Classe: Organometalloid compounds
• Subclass: Organosilicon compounds
• Intermediate Tree Nodes: Alkoxysilanes
• Direct Parent: Trialkoxysilanes
• Alternative Parents: Silyl ethers Organoheterosilanes Organic metalloid salts Organooxygen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Trialkoxysilane - Silyl ether - Organoheterosilane - Organic metalloid salt - Organic oxygen compound - Hydrocarbon derivative - Organic salt - Organooxygen compound - Aliphatic acyclic compound
• Descrição: This compound belongs to the class of organic compounds known as trialkoxysilanes. These are organosilicon compounds with the general formula RO[Si](R')(OR'')OR''' (R-R''' = aliphatic organyl group).
• 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

Propriedades químicas e físicas

• Sensibilidade: Moisture sensitive
• Índice de refração: 1.43
• Ponto de inflamação (°F): 226.4℉
• Ponto de inflamação (°C): 108°C(lit.)
• Ponto de ebulição (°C): 118°C/1.3mmHg(lit.)
• Ponto de fusão (°C): -40°C
• Peso molecular: 290.510 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 290.228 Da
• Monoisotopic Mass: 290.228 Da
• Topological Polar Surface Area: 27.700 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 176.000
• 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 vendor-validated biological assay protocols are specified for this item; refer to CoA/Spec Sheet.

General surface silanization workflows (literature guidance):

• Glass/Silica Hydrophobization (dip‑coat)

  1. Clean slides (piranha or O2 plasma). Rinse thoroughly; dry at 120 °C for 15–30 min.
  2. Prepare 1% v/v dodecyltrimethoxysilane in EtOH/H2O (95:5) with 0.5% acetic acid freshly.
  3. Immerse 10–20 min at RT with gentle agitation.
  4. Rinse with ethanol, then isopropanol; dry with N2.
  5. Cure 110 °C, 1 h.
  6. Assess contact angle; repeat brief exposure if necessary.

• Anhydrous Toluene Route (monolayer quality focus)

  1. Dry glassware and solvent; maintain inert atmosphere.
  2. 1% v/v silane in dry toluene; immerse at 80 °C for 2 h.
  3. Rinse with toluene and IPA; bake 120 °C, 1 h.
  4. Characterize via water contact angle, FTIR (CH2 stretches), and XPS (Si2p, C1s).

Notes:

• Prepare solutions fresh; alkoxysilanes slowly self‑condense.
• Use PTFE containers/caps; avoid soda‑lime leaching in long baths.
• Dispose of methanol‑containing wastes per institutional procedures.

These are literature-style procedures for research use only.

Biological Roles

This product is a synthetic organosilane coupling agent and does not have an intrinsic biological role or function in metabolism.

Relevant laboratory interfaces (general knowledge):

• Surface bioengineering: DTMS can render oxide and glass surfaces hydrophobic, reducing nonspecific adsorption of biomolecules and enabling controlled patterning when combined with microcontact printing or photolithography.
• Biosensor platforms: Hydrophobized regions can confine lipid bilayers or block aqueous wetting, aiding device fabrication (research contexts).
• Cell-interfacing materials: In R&D, hydrophobic silane layers may serve as contrast backgrounds or release layers; however, DTMS is not a biocompatibility reagent per se and hydrolysis releases methanol.

Caveats:

• No endogenous targets, receptors, or enzymatic roles.
• Hydrolysis/condensation chemistry can be cytotoxic in situ due to methanol formation and pH changes; use only on inert substrates and fully cure before any biological exposure.

Research Use Note: For research use only. Not for human or animal therapeutic or diagnostic applications.

Buffer Applications

Dodecyltrimethoxysilane is not a buffering agent and is not used to prepare pH buffer systems.

• If working in aqueous/alcoholic silanization baths, a mild acid such as acetic acid (pH ~4–5) is commonly employed to catalyze hydrolysis; the acid constitutes the buffering component, not the silane.
• For experimental planning, refer instead to the Reaction & Applications and Reaction Conditions sections for practical silanization bath compositions.

Green Alternatives

Green chemistry considerations for using dodecyltrimethoxysilane (DTMS) focus on solvent choice, catalyst selection, and alcohol byproducts.

Key points:

• Alcohol byproduct: DTMS releases methanol upon hydrolysis, which is more toxic than ethanol. An alternative is the ethoxy analogue (dodecyltriethoxysilane, DTEOS), which releases ethanol (lower toxicity) at the expense of slower hydrolysis.
• Solvents: Replace chlorinated solvents and aromatics with safer options when feasible—e.g., 95:5 ethanol/water systems (acidified) or heptane/2-MeTHF when anhydrous conditions are acceptable.
• Catalysis: Use acetic acid as a mild, less hazardous catalyst instead of strong mineral acids. Buffer to pH ~4.5 to control hydrolysis without excess waste.

Illustrative comparison (literature; not product specs):

• Option: DTMS in toluene (dry) • Pros: Dense, ordered monolayers; excellent wetting on oxides
  • Cons: Aromatic solvent; low biodegradability; requires inert handling

• Option: DTMS in EtOH/H2O (95:5), 0.5% AcOH • Pros: Lower solvent hazard; easy cleanup; scalable dip‑coating
  • Cons: Generates methanol; faster condensation can cause inhomogeneity if not controlled

• Option: DTEOS in EtOH/H2O, 0.5% AcOH • Pros: Ethanol byproduct; similar performance; greener solvent matrix
  • Cons: Slower hydrolysis; may require longer cure

Operational suggestions:

• Minimize excess silane (0.5–2% v/v typical).
• Recycle solvents when possible; maintain low water carryover to reduce waste gel formation.

Pharmaceutical Uses

No pharmacopeial monograph or excipient role is specified for this item; refer to CoA/Spec Sheet.

General R&D context (non-clinical):

• Potential role as a surface‑modifying agent for device components (e.g., glass vials, sensors, microfluidic chips) to manage wettability and adsorption during process development.
• Can be used to functionalize inorganic fillers in polymer matrices for prototype medical device materials during early research stages.

Important: This product is for research use only and is not intended for therapeutic, diagnostic, or clinical applications. Any use in regulated manufacturing or medical devices would require appropriate qualification and regulatory assessment independent of this catalog listing.

Physical Properties

Item-specific physico-chemical specifications (BP, MP, density, refractive index, UV cutoffs, metals, water, peroxide, etc.): Not specified for this item; refer to CoA/Spec Sheet.

Representative literature/typical values for dodecyltrimethoxysilane (for context only; not product specifications):

• Appearance: Colorless to pale yellow liquid (literature)
• Boiling point: ~140–150 °C at ~0.2–1 mmHg; decomposes/hydrolyzes in the presence of moisture (literature)
• Density (25 °C): ~0.88–0.90 g/mL (literature)
• Refractive index nD20: ~1.420–1.430 (literature)
• Solubility: Immiscible with water; miscible with nonpolar/low‑polarity organics (e.g., toluene, heptane, dichloromethane). Slowly reacts with protic solvents in the presence of water/acids (general knowledge)
• Vapor pressure: Low at ambient conditions; increases with temperature (literature)
• Hydrolytic behavior: Hydrolyzes to silanols with release of methanol; subsequent condensation to siloxanes, especially under acidic or basic catalysis (general knowledge)

Practical implications:

• Moisture sensitivity: Physical properties (viscosity, refractive index) may drift on exposure to atmospheric moisture due to partial hydrolysis/condensation.
• Handling: For reproducible performance in surface modification, dispense under dry inert gas and use anhydrous solvents; record lot-specific values from CoA when needed for QC.

All safety-critical and specification-critical data should be taken from the SDS/CoA for the specific lot.

Quality and Grades

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

Context for organosilanes (general guidance):

• Typical grades encountered include “technical” (suitable for coatings/adhesion studies), “≥95–98%” (research grade), and specialized “electronic/surface” grades with tight controls on hydrolyzable chloride, alcohol content, color, and low metals/alkali.
• UV/HPLC grades are rarely assigned to alkoxysilanes; instead, quality is judged by GC assay, water content, hydrolyzable content, and residual alcohols.

What grade implies in practice:

• Higher assay and low water favor reproducible monolayer formation and minimize premature condensation (gelation). Tight control of methanol/volatiles ensures predictable hydrolysis kinetics.
• Stabilizers: Many trialkoxysilanes are shipped without stabilizers; some suppliers include traces of acid to improve shelf stability. For this item, stabilizer content is Not specified for this item; refer to CoA/Spec Sheet.

Verification and QC suggestions:

• Record GC assay, water (Karl Fischer), color (APHA), and refractive index upon opening; compare to CoA.
• Filter through PTFE (0.2–0.45 µm) if any haze/particulates develop from partial condensation.
• For advanced surface work (SAMs), consider pre-treatment of solvents to ≤50 ppm water and perform test contact-angle measurements to benchmark lot performance.

Reaction and Applications

Dodecyltrimethoxysilane (DTMS) is a hydrophobizing silane coupling agent widely used to functionalize inorganic surfaces and tune interfacial properties.

Core reaction chemistry (general/literature):

• Hydrolysis: Si(OMe)3 + 3 H2O → Si(OH)3 + 3 MeOH (acid or base catalyzed). Methanol is released.
• Condensation: Silanols condense with surface –OH (e.g., Si–OH, Al–OH, Ti–OH) to form covalent Si–O–M bonds (M = Si, Al, Ti) and with themselves to form siloxane networks.
• Result: A covalently attached monolayer or thin film bearing a terminal C12 alkyl chain, imparting strong hydrophobicity and low surface energy.

Applications:

• Surface modification of silica, glass, alumina, titania for water repellency, anti-fouling, and controlled wettability (contact angles typically >100° for dense films; literature).
• Primer/adhesion promoter between inorganic fillers and nonpolar polymers (PE, PP, elastomers), improving dispersion and mechanical properties.
• Nanomaterials: Ligand exchange/encapsulation on oxide nanoparticles; stabilization in nonpolar media.
• Microfluidics/analytical: Channel de-wetting, anti-stiction coatings, and capillary action control.
• Sol–gel/coatings: Co-monomer in hybrid organosiloxane networks conferring hydrophobic domains.

Practical tips:

• Clean, hydroxylate substrates (e.g., piranha, O2 plasma) immediately before silanization.
• Control water content: 0.5–5% H2O in alcohol for rapid hydrolysis; or anhydrous aromatic solvent with thermal cure for highly ordered films.
• Post-cure at 100–120 °C (0.5–2 h) to drive condensation and improve film durability (literature practice).

Reaction Conditions

Representative laboratory protocols (literature/general guidance; adjust per substrate and desired film):

1. Anhydrous aromatic route (dense monolayers)

• Substrate: Hydroxylated silica or glass (plasma or piranha treated, rinsed, dried at 120 °C).
• Solution: 0.5–2% v/v dodecyltrimethoxysilane in dry toluene or heptane (≤100 ppm H2O). Optional: 0.1% acetic acid is sometimes used, but many protocols omit catalyst.
• Conditions: 50–110 °C, 1–24 h under N2/Ar. Minimal water present; hydrolysis occurs at the surface.
• Workup: Rinse with solvent, then isopropanol; bake/cure 100–120 °C for 0.5–2 h to drive condensation.
• Outcome: High contact angle, good abrasion resistance.

2. Alcohol/water acid-catalyzed route (dip‑coating/priming)

• Bath: Ethanol/water 95:5 to 90:10 with 0.1–1% v/v acetic acid; 0.5–2% v/v silane.
• Conditions: 10–30 min at RT; avoid gelation by preparing fresh and limiting water.
• Rinse/cure: Rinse with ethanol, then bake 100–120 °C for 0.5–2 h.
• Notes: Generates methanol; ensure adequate ventilation.

3. Co‑condensation (hybrid films)

• Combine DTMS with functional silanes (e.g., APTES) at desired ratios in EtOH/H2O (acidified).
• Monitor gel time; use lower total silane (≤2% v/v) for uniform coatings.

Yields: Surface coverages typically 3–5 molecules/nm² for dense SAMs on silica (literature); verify by contact angle, XPS, or ellipsometry.

Always validate conditions on small test coupons before scaling.

Safety and Handling

Authoritative hazard classification for this item: Not specified for this item; refer to SDS.

General GHS guidance for trialkoxysilanes (literature/general knowledge; verify on SDS for this SKU):

• Likely hazards: Flammable liquid/vapor; causes skin/eye irritation; harmful if inhaled or swallowed; moisture sensitive. Hydrolysis releases methanol, a toxicant with systemic effects.
• Pictograms often applicable: Flame, Exclamation mark (literature)

Key precautions:

• Engineering controls: Use in a dry, well‑ventilated fume hood. Employ inert gas blanketing for transfers.
• PPE: Safety glasses or face shield, lab coat, nitrile gloves (change regularly), and appropriate splash protection.
• Incompatibilities: Water, strong acids/bases (accelerate hydrolysis/condensation), oxidizers, moisture‑bearing substrates prior to controlled hydrolysis. Avoid contact with alkali catalysts unless intended.
• Special risks: Peroxide formation is not typical for alkoxysilanes; the primary risk is moisture‑driven hydrolysis producing methanol and forming crosslinked gels that can foul equipment.

First‑aid overview (general):

• Inhalation: Move to fresh air; seek medical attention if symptoms persist.
• Skin/eyes: Immediate decontamination with water for ≥15 min; remove contaminated clothing; seek medical care for eye exposure.
• Ingestion: Rinse mouth; do not induce vomiting; obtain medical attention.

Firefighting: Use CO2, dry chemical, or alcohol‑resistant foam. Cool containers with water spray from a safe distance.

Always defer to the product’s SDS for definitive classification, response measures, and exposure limits.

Solvent Selection

Dodecyltrimethoxysilane is a low‑polarity, moisture‑sensitive liquid. Selecting compatible solvents is crucial to control hydrolysis and surface grafting kinetics.

• Polarity class: Nonpolar to low‑polarity; largely hydrocarbon‑like tail with a hydrolyzable headgroup.
• Water: Immiscible; reacts slowly in presence of water to generate methanol and silanols (intended during coupling).
• Preferred anhydrous solvents (for non‑aqueous silanization): Toluene, heptane/hexane, cyclohexane, dry dichloromethane. Aromatics often provide better wetting of oxide surfaces.
• Alcohols: Ethanol/isopropanol are common for aqueous‑alcohol silanization when acidified (pH ~4–5) and water is intentionally added (1–5%) to pre‑hydrolyze. Without water/acid, prolonged contact with alcohols can still cause slow exchange.
• Esters/ketones: Anhydrous ethyl acetate or MEK may be used; monitor for transesterification under acidic/basic conditions.

Comparison (general guidance):

• Toluene (dry, 0% H2O): Slows hydrolysis; favors direct adsorption and thermal cure—useful for dense monolayers.
• EtOH/H2O (95:5, pH ~4.5): Rapid, controllable hydrolysis to silanols; good for dip‑coating and rapid surface priming.
• Heptane: Excellent for hydrophobic substrates; slower kinetics; minimal side reactions.

Tips:

• Degas and dry solvents (molecular sieves 3 Å or 4 Å). Target ≤50–200 ppm H2O for anhydrous routes.
• Avoid amine-containing solvents (can catalyze condensation) unless intended.
• Include acetic acid (0.1–1 vol%) as a mild catalyst in alcohol/water systems to improve film uniformity (literature practice).

Storage and Reconstitution

• Storage Conditions (item-specific): Room temperature, Argon charged. Keep container tightly closed. Protect from moisture and air.
• Shipped In: Normal.

General storage guidance for trialkoxysilanes:

• Store under dry inert gas (Ar/N2), in amber glass or compatible metal containers with PTFE-lined seals. Minimize headspace and moisture ingress.
• Do not refrigerate to the point of condensation upon warm-up; transient moisture can accelerate hydrolysis.
• After opening: Consider aliquoting into small, dry, inert‑gas–flushed vials. Record opening date; monitor for viscosity increase, haze, or precipitate (signs of condensation).

Reconstitution: Not applicable; supplied neat as a liquid. If a working solution is needed, prepare fresh in an appropriate dry solvent (see Solvent Selection) immediately prior to use.

Stability notes (general):

• Sensitive to moisture; gradual hydrolysis releases methanol and can lead to formation of gels/oligomers.
• For consistent surface chemistry results, use within weeks to a few months of opening, depending on storage rigor, and always verify performance on a test substrate.

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

Structure and Identity

Dodecyltrimethoxysilane is a long-chain alkyltrialkoxysilane featuring a hydrophobic dodecyl tail and a hydrolyzable trimethoxysilyl headgroup.

• SKU: D155296
• CAS: 3069-21-4
• CID: 76479
• InChIKey (as provided): 332457
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Representative (literature) SMILES: CCCCCCCCCCCCSi(OC)OC
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Representative (literature) formula: C15H34O3Si
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Representative (literature) MW: ~290.52 g/mol

Structural features (general description):

• Functional groups: trialkoxysilane [Si(OMe)3] capable of hydrolysis/condensation to form Si–O–Si bonds; Si–C(sp3) bond to a linear C12 alkyl chain.
• Topology: Polar head (silane) and nonpolar tail (C12), amphiphilic at interfaces; no rings, unsaturations, or stereocenters.
• 2D structure in words: A linear twelve‑carbon chain terminates at silicon; silicon bears three methoxy substituents arranged tetrahedrally around Si, enabling surface attachment after hydrolysis.

Notes:

• Identity elements marked “literature” are for general reference and should not be interpreted as item-specific specifications. Consult the product’s CoA/SDS for definitive identifiers.

Synthetic Utility

From a synthetic standpoint, dodecyltrimethoxysilane is a versatile surface and network precursor rather than a discrete stoichiometric reagent.

Key reactive elements (general/literature):

• Trialkoxysilyl group: Undergoes hydrolysis to silanols and subsequent condensation to siloxanes. Amenable to acid or base catalysis; kinetics tunable by solvent, water content, pH, and temperature.
• Si–C(alkyl) bond: Robust and not cleaved under standard silanization conditions, preserving the C12 hydrophobe at the interface.

Synthetic transformations/use cases:

• Covalent grafting onto hydroxylated inorganic surfaces to construct self‑assembled monolayers (SAMs) or thin siloxane films with controlled thickness and density.
• Co‑condensation with other trialkoxysilanes (e.g., aminopropyl-, epoxy-, or fluorinated silanes) to create mixed‑functionality films and gradient surfaces.
• Formation of hydrophobic caps on porous oxides, tuning pore accessibility and chromatographic selectivity in stationary phase development.
• Sol–gel hybrid materials: Serves as a hydrophobe‑containing co‑monomer to reduce water uptake and adjust Tg/flexibility of siloxane networks.

Practical notes:

• Strict substrate cleaning and immediate use post‑activation are critical to maximize silane grafting and minimize polymeric byproducts.
• Control silane concentration (0.5–2% v/v typical) and cure conditions to balance monolayer order vs. crosslink density.

Target Specificity

Not applicable. This product is a small-molecule organosilane and does not have antigen/epitope specificity, clone, isotype, or species reactivity. For usage guidance, see Reaction & Applications and Application Protocols (general) sections.