This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
External Descriptors
Not available
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.
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Application Protocols
Not applicable.
No tested bioassay protocols (WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic applications, see Reaction Conditions and Synthetic Utility for general procedural guidance.
Biological Roles
Item-specific (from Product Data)
No biological/biochemical roles are specified. Research use only.
General context
2-(Dimethylsilyl)pyridine is a synthetic organosilicon heteroaromatic and does not have a known natural biological role. While pyridine as a motif appears in many biomolecules and cofactors (e.g., NAD+/NADH contains a pyridinium core; literature, general), the dimethylsilyl substituent is non-natural and typically used for synthetic chemistry rather than biological function.
In biochemical experiments, arylsilanes can occasionally serve as inert tags or handles for derivatization, but this compound is not a buffer, substrate, or cofactor.
Note
No cell biology or clinical applications should be inferred. Any use in biochemical assays should be preceded by compatibility testing for solvent, stability, and potential interference with metal-containing proteins due to pyridine coordination (general caution).
Buffer Applications
Not typically applicable.
2-(Dimethylsilyl)pyridine is a hydrophobic organosilicon reagent and is not used to prepare aqueous buffer systems. It is poorly compatible with water due to potential Si–H hydrolysis. For relevant information, see the Solvent Selection, Reaction & Applications, and Synthetic Utility sections.
Green Alternatives
Context (general)
Organosilicon cross-coupling typically requires fluoride activation (TBAF, CsF), adding toxicity/waste concerns. Greener alternatives may reduce halide/fluoride use, lower energy input, or use safer solvents.
Comparison (general guidance)
2-(Dimethylsilyl)pyridine (Hiyama)
Pros: Stable, often air/moisture-tolerant relative to organolithiums/Grignards; good functional group compatibility; handles pyridyl transfer efficiently.
Cons: Fluoride activators and polar aprotic solvents (THF/DMF) may be required; fluoride waste stream.
Pyridin-2-yl boron reagents (Suzuki)
Pros: Broadly accepted as greener; aqueous-compatible conditions; less hazardous activators (bases like K3PO4, K2CO3).
Cons: Some 2-pyridyl boronates can be unstable (protodeboronation), though stabilized variants exist.
Pyridin-2-yl zinc reagents (Negishi)
Pros: Often high reactivity at lower temperatures.
Cons: Air/moisture sensitive, generate Zn-containing waste; less green.
Greener practice with arylsilanes
Use silanol/silanolate variants enabling Hiyama–Denmark conditions (fluoride-free, base-activated).
Choose greener solvents (2-MeTHF, CPME, toluene) where compatible.
Implement solvent recycling and fluoride capture/neutralization procedures to minimize environmental impact.
Pharmaceutical Uses
Not typically applicable as a formulated excipient.
This product is intended for research and synthetic chemistry. Organosilanes like 2-(dimethylsilyl)pyridine are not standard pharmaceutical excipients and are generally used as building blocks or coupling partners in discovery chemistry. No pharmacopeia monograph is indicated. For medicinal chemistry workflows, it can serve as a coupling precursor to access 2-pyridyl-containing scaffolds via Hiyama-type reactions (see Reaction & Applications).
Physical Properties
Item-specific (from Product Data)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general expectations for 2-(dimethylsilyl)pyridine and related arylsilanes)
Physical state: Typically a colorless to pale liquid for low-mass arylsilanes; may be moisture/air-sensitive (literature, general).
Boiling point, melting point, density, refractive index: Not specified for this item; consult literature or CoA/SDS for definitive values.
Solubility: Expected to be miscible with common aprotic organic solvents (e.g., hexanes, toluene, THF, dichloromethane) and poorly soluble in water (literature, general for arylsilanes).
LogP: Likely positive (hydrophobic), consistent with arylsilane character (literature, general).
pKa/basicity: The pyridine nitrogen is weakly basic (conjugate acid pKa ~5–6 for pyridines; literature, general). The Si–H is not acidic in water but can be activated by bases/fluoride (literature, general).
Notes for use
Due to the Si–H bond and potential air/moisture sensitivity, measurements like density or refractive index should be taken under inert atmosphere when needed for quantitative work (general best practice).
Quality and Grades
Item-specific (from Product Data)
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.
Guidance for interpreting grades (general)
Research grade organosilanes are typically supplied with specifications for assay, GC purity, and limits on related siloxanes/silanols. Low water content and low peroxides are relevant for air/moisture-sensitive Si–H reagents, but exact limits must come from the CoA.
If designated “anhydrous” or “air sensitive,” expect special packaging (septum-cap, argon backfill) to preserve the Si–H functionality. Your item is described as argon charged and shipped on wet ice, consistent with moisture/light sensitivity.
For use in cross-couplings (e.g., Hiyama), trace metal content and UV background are generally less critical than for HPLC solvents but residual halides/peroxides can influence catalyst longevity; verify impurity profiles on the CoA when reaction performance is critical.
Recommendations
Request the CoA lot-specific purity (GC), residual solvents, and water. Confirm absence of inhibitors if you intend to perform hydrosilylation or dehydrocoupling, where inhibitors can suppress reactivity.
Reaction and Applications
Item-specific (from Product Data)
Manufacturer applications: Not provided for this item.
Literature/general applications for 2-(dimethylsilyl)pyridine
Hiyama cross-coupling partner: Pyridin-2-yl-dimethylsilane can serve as a nucleophilic coupling equivalent of 2-pyridyl anion under Pd catalysis with fluoride activation, transferring the 2-pyridyl group to aryl/vinyl halides or triflates.
Silicon–hydrogen reactivity: The Si–H bond can participate in catalytic dehydrogenative silylation or be transformed into more activated derivatives (e.g., silanol, silanolate) that engage in cross-coupling or further functionalization.
Directed transformations on silicon: Oxidation to the corresponding silanol or conversion to siloxanes provides handles for subsequent coupling (e.g., Hiyama–Denmark variants using silanols/silanolates without TBAF).
Orthogonal reactivity: The pyridine nitrogen can coordinate to metals, sometimes influencing regioselectivity or serving as a directing element in C–H functionalization chemistry.
Practical tips
Use rigorously anhydrous conditions for fluoride-activated couplings; water quenches the activated silicate.
Fluoride sources: TBAF (in THF), CsF (in polar aprotic solvents), or KF with phase-transfer agents. Choice affects rate and selectivity.
Monitor reactions by GC or HPLC; arylsilanes often have distinct retention and MS fragments (Si-containing ions).
Reaction Conditions
General literature guidance for related transformations (not item-specific specifications)
Hiyama cross-coupling (2-pyridyl transfer):
Catalyst: Pd(PPh3)4 (1–5 mol%) or Pd2(dba)3 with phosphine ligand.
Activator: TBAF (1.0–2.0 equiv, 1 M in THF) or CsF (2–4 equiv) ± H2O as rate modulator depending on protocol.
Solvent: Dry THF, dioxane, or toluene.
Temperature/time: 40–90 °C for 2–16 h.
Electrophiles: Aryl/vinyl iodides/bromides; aryl triflates; chlorides with more active catalysts.
Hiyama–Denmark variant (fluoride-free):
Pre-oxidize to silanol or generate silanolate in situ; use strong base (e.g., KOSiMe3 or t-BuOK) and a Pd catalyst; polar aprotic solvents; 60–100 °C.
Dehydrogenative silylation (if exploiting Si–H):
Catalyst: Ir, Rh, or late-metal complexes; solvent: toluene; 80–130 °C; H2 evolution observed (literature, general).
Operational tips
Use inert atmosphere (argon) and oven-dried glassware. Add fluoride last to minimize premature activation.
Monitor by GC–MS/LC–MS; Si-containing starting material often gives characteristic m/z with Si isotope patterns.
Quench fluoride carefully and consider downstream fluoride remediation for EHS compliance.
Safety and Handling
Item-specific (from Product Data)
Storage: Store at 2–8 °C, protected from light, argon charged. Shipped on wet ice.
GHS classification, signal word, pictograms, H-statements: Not specified for this item; refer to SDS.
General safety information (literature/good laboratory practice for organosilicon hydrides and pyridines)
Likely hazards: Many hydrosilanes are flammable liquids and may be harmful if inhaled or in contact with skin. They can react with strong oxidizers. Specific classification must be verified in the SDS for this CAS.
Sensitivities: Si–H-containing arylsilanes can be sensitive to moisture/air and light; slow hydrolysis may generate silanols and hydrogen gas. Maintain inert atmosphere (argon) when opening, dispensing, and storing.
PPE: Wear lab coat, safety glasses, and suitable chemical-resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of vapors.
Incompatibilities: Avoid strong oxidizers, strong acids/bases (which can catalyze Si–H reactions/hydrolysis), and protic media if Si–H integrity must be preserved.
First-aid overview: In case of skin contact, wash with soap and water; for eye exposure, rinse cautiously with water for several minutes; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention as per SDS guidance.
Fire-fighting: Use CO2, dry chemical, or alcohol-resistant foam. Fire may produce irritating/noxious fumes (e.g., NOx, SiOx). Defer to SDS for authoritative instructions.
Solvent Selection
Item-specific (from Product Data)
No solvent recommendations specified for this item.
Literature/general considerations for 2-(dimethylsilyl)pyridine
Polarity class: Moderately nonpolar organosilicon; compatible with many aprotic organic solvents.
Preferred solvents for handling: Dry hydrocarbons (hexanes, heptane, toluene) and ethers (dry THF, MTBE) under inert atmosphere. Chlorinated solvents (DCM) can be used for workup/analytics; ensure dryness to minimize hydrolysis.
Avoid: Protic solvents (water, alcohols) and wet solvents if preservation of the Si–H bond is required; they can induce hydrolysis to silanols with possible H2 evolution.
Miscibility profile (general):
Hydrocarbons: high solubility
Ethers (THF, CPME): high solubility
Polar aprotics (DMF, DMSO): soluble but may not be ideal for moisture-sensitive operations and some Pd-catalyzed couplings.
Choosing among common media (general)
Hiyama cross-coupling: THF, dioxane, or toluene with fluoride activator (e.g., TBAF, CsF) are frequently reported.
Hydrosilylation or dehydrogenative silylation (if applicable): Toluene or xylene at elevated temperature often used.
Tip: Dry and degas solvents (molecular sieves, sparging) and maintain inert atmosphere to protect the Si–H functionality.
Storage and Reconstitution
Item-specific (from Product Data)
Storage conditions: Store at 2–8 °C, protected from light, argon charged.
Shipping: Shipped on wet ice.
General handling/reconstitution guidance (literature/good practice for air/moisture-sensitive organosilanes)
Atmosphere: Maintain under inert gas (argon). Minimize headspace oxygen/moisture; consider glovebox or Schlenk techniques for transfers.
Opening/dispensing: Use a dry syringe/needle through the septum under argon, or perform transfers in a glovebox. Reseal and re-establish inert headspace after use.
Dilution: If stock solutions are needed, prepare under inert atmosphere in dry, oxygen-free solvents (e.g., anhydrous toluene or THF). Store solutions cold and protected from light; verify stability before long-term storage.
Freeze–thaw: Avoid repeated freeze–thaw cycling. If precipitation/crystallization occurs on cold storage, gently warm to room temperature under inert gas and swirl to redissolve.
Disposal: Quench residues cautiously (e.g., with alcohol then water under controlled conditions) to avoid rapid H2 evolution; follow institutional hazardous waste procedures.
Always consult the product’s SDS and lot-specific CoA for authoritative storage and handling instructions.
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/computed (general identity information for 2-(dimethylsilyl)pyridine)
Common structural description: A pyridine ring substituted at the 2-position with a dimethylsilyl group, i.e., a Si(H)(CH3)2 fragment bonded directly to the C2 of pyridine.
Functional groups and features: Heteroaromatic pyridine (sp2 N, basic), organosilicon Si–H bond, two Si–C(sp3) bonds, one Si–C(sp2) bond.
Stereochemistry: None (achiral molecule).
Approximate molecular formula and mass (literature/computed): C7H12NSi; MW ≈ 138.26 g/mol.
2D structure in words: Six-membered aromatic ring containing one ring nitrogen (pyridine); at the carbon ortho to nitrogen (C2), a silicon bearing one hydride and two methyl groups is attached.
Synthetic Utility
Key functional elements (general)
Aryl–Si(H)Me2 motif: Acts as a latent 2-pyridyl nucleophile in Pd-catalyzed Hiyama couplings after fluoride/base activation; Si–H can be oxidized or converted to silanol/silanolate to enhance reactivity in Hiyama–Denmark variants.
Pyridine nitrogen: Can coordinate to transition metals, occasionally affecting catalyst speciation or directing reactivity in C–H functionalization sequences.
Use cases
Cross-coupling: Formation of biaryl and heteroaryl–aryl bonds by transferring the 2-pyridyl unit to aryl/vinyl halides or pseudohalides. Useful when boronates are unstable (2-pyridyl boron species may protodeboronate).
Sequential diversification: Post-coupling functionalization at the pyridine ring (N-oxidation, N-alkylation, lithiation at remote positions) enables scaffold elaboration.
Protective/anchoring role: Conversion to siloxanes or silyl ethers can provide temporary handles for separation or immobilization (general organosilicon strategy).
Practical notes
Fluoride choice and counterion matter: TBAF promotes rapid transmetalation in THF; CsF/KF with crown ethers or PTCs can be effective in less polar media.
Water exclusion is important during activation to avoid premature hydrolysis to silanol (which changes kinetics).
Target Specificity
Not applicable.
This product is a small-molecule synthetic reagent, not a biologic/antibody. No target, epitope, or species specificity applies.
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