p-Bromophenyltrimethoxysilane - ≥95% , CAS No.17043-05-9

CAS: 17043-05-9 Cat. No.: P1003248 Fórmula: C₉H₁₃BrO₃Si Peso molecular: 277.189 Número CE: 605-580-4 PubChem CID: 14993398

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

• Sorrisos canónicos: CO[Si](C1=CC=C(C=C1)Br)(OC)OC
• IUPAC Name: (4-bromophenyl)-trimethoxysilane
• InChIKey: BRXDAEMGSYZHGK-UHFFFAOYSA-N
• INCHI: 1S/C9H13BrO3Si/c1-11-14(12-2,13-3)9-6-4-8(10)5-7-9/h4-7H,1-3H3
• SMILES isoméricas: CO[Si](C1=CC=C(C=C1)Br)(OC)OC
• PubChem CID: 14993398
• Peso molecular: 277.189

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: Bromobenzenes Aryl bromides Silyl ethers Organoheterosilanes Organic metalloid salts Organooxygen compounds Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Trialkoxysilane - Bromobenzene - Halobenzene - Aryl bromide - Aryl halide - Monocyclic benzene moiety - Benzenoid - Silyl ether - Organoheterosilane - Organic metalloid salt - Organooxygen compound - Organic oxygen compound - Hydrocarbon derivative - Organohalogen compound - Organobromide - Aromatic homomonocyclic 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

• Ponto de ebulição (°C): 136°
• Peso molecular: 277.190 g/mol
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 275.982 Da
• Monoisotopic Mass: 275.982 Da
• Topological Polar Surface Area: 27.700 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 159.000
• 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 provided for this item in the Product Data. The compound is typically used in chemical synthesis and surface modification rather than gel-based or immunoassays.

• General reference protocols (literature-based, to be adapted as needed):
  • Glass silanization (outline):
    1. Clean glass (piranha or oxygen plasma; follow institutional safety SOPs).
    2. Dry substrate (110–150 °C, ≥30 min).
    3. Immerse in 1–2% v/v silane in dry toluene under N2 for 1–2 h.
    4. Rinse with dry solvent sequence (toluene → acetone → isopropanol), then cure at 120 °C for 30–60 min.
  • Suzuki coupling at Ar–Br (outline):
    1. Combine aryl boronic acid, base (K2CO3), Pd catalyst (1–2 mol%), and this reagent in dry dioxane under N2.
    2. Heat 80–90 °C for 6–12 h; monitor by TLC/GC.
    3. Work up and purify; avoid aqueous/protic conditions if the silane must remain intact.

These are literature-style guides only. Optimize per your substrate, scale, and EHS policies. Always consult the SDS and primary literature.

Biological Roles

Not a biomolecule and not intended for biological systems. As an organosilane building block, p-bromophenyltrimethoxysilane has no known physiological role.

• General context (literature):

  • Organosilanes are widely used to functionalize inorganic surfaces in biointerface engineering (e.g., glass slides, silica nanoparticles) to immobilize biomolecules. In such workflows, the silane is a chemical linkage agent; it is not biologically active itself.
  • The para-bromophenyl terminus can serve as a synthetic handle for post-grafting derivatization (e.g., Pd-catalyzed coupling to install linkers), enabling construction of biosensing interfaces. This is a chemical functionalization step rather than a biological function.

• Compliance note:

  • For research use only (per Product Data). Not for use in diagnostic procedures, foods, drugs, or medical devices.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare aqueous buffers. Trialkoxysilanes react with water, releasing methanol and forming silanols/siloxanes, which is incompatible with standard buffer preparation.

• Practical note: If used in biointerface work, aqueous buffers may be employed only after surface silanization and curing steps are complete and the surface is thoroughly rinsed. The silane itself should be handled in anhydrous organic media.

Green Alternatives

Perspective: Organosilanes are often considered greener alternatives to organostannanes for cross-coupling due to lower toxicity and better waste profiles, but they still pose hydrolysis risks and generate methanol.

• Greener choices by task (literature/general):

  • Cross-coupling nucleophiles: Consider boronic acids/esters (Suzuki) as broadly greener and operationally simple alternatives to arylsilanes where surface anchoring is not required.
  • Solvents for silanization: Replace toluene/DCM with 2-MeTHF, cyclopentyl methyl ether (CPME), or ethyl acetate when compatible with moisture control and reaction kinetics.
  • Fluoride activators: Minimize fluoride load or use Denmark-type base activation (e.g., hydroxide with silanol formation) to reduce fluoride waste.

• Trade-offs:

  • Using boron reagents sacrifices the Si-anchoring functionality intrinsic to this molecule; thus not a drop-in replacement if surface grafting is desired.
  • 2-MeTHF/CPME improve safety and sustainability but may alter silanization film morphology; drying these solvents to low ppm water can be more challenging than toluene/hexanes.

• Comparison snapshot (general):

  • Aryl silane vs aryl stannane: lower toxicity and easier waste handling for silane; stannanes offer high reactivity but poor EHS profile.
  • Toluene vs 2-MeTHF: similar solvency; 2-MeTHF is bio-based and has better safety metrics, but can absorb water faster—critical for silane storage/handling.

Adopt greener options where they do not compromise the core functional role (surface anchoring via Si–OR) or required selectivity.

Pharmaceutical Uses

No direct pharmaceutical or clinical use is claimed. For research and manufacturing contexts only.

• General roles (literature/general):

  • Stationary phase derivatization: Trialkoxysilanes functionalize silica for chromatographic media. A p-bromophenyl surface can be a precursor to tailored stationary phases via post-grafting coupling.
  • Device/surface engineering: Organosilanes are used to modify glass or silica components in analytical devices (e.g., microfluidics) to adjust wettability and enable ligand attachment.

• Regulatory note:

  • Pharmacopeial monograph status is not applicable/unknown for this specific reagent. Users should qualify materials per internal specifications when used in process development or analytical tool preparation.

• Item-specific:

  • Grade/purity and excipient status: Not specified for this item; refer to CoA/Spec Sheet.
  • For research use only (per Product Data).

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.
  • Other specifications (bp, mp, density, refractive index, UV cutoff, water/peroxide/metal content): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general reference values (for context; not item specifications):

  • Physical state: typically a colorless to pale yellow liquid for many aryltrialkoxysilanes.
  • Hydrolytic behavior: trialkoxysilanes hydrolyze in the presence of moisture to form silanols with release of methanol; subsequent condensation yields siloxanes on oxide surfaces.
  • Solubility: generally soluble in common aprotic organics (toluene, hexanes, DCM, THF); reacts with water and alcohol–water mixtures (hydrolysis/condensation rather than true dissolution).
  • Estimated MW (from literature formula C9H13BrO3Si): ~277.18 g/mol.

• Practical notes for users (general chemistry knowledge):

  • Handle under dry conditions; even brief exposure to humid air can change composition via partial hydrolysis/condensation, affecting performance in surface treatments or coupling reactions.
  • Use freshly opened material or store under inert atmosphere when high fidelity monomeric silane behavior is required (e.g., monolayer formation).

Authoritative and lot-specific physical property data should be confirmed from the product’s CoA/Spec Sheet and SDS.

Quality and Grades

• Item-specific (Product Data):

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Stabilizers/assay limits (water, alcohol content, hydrolyzable chloride, metals, UV cutoff): Not specified for this item; refer to CoA/Spec Sheet.

• Context for organosilane quality (general/literature):

  • Purity in silanes: Effective surface functionalization and coupling require low levels of hydrolysis/condensation byproducts (oligosiloxanes). Karl Fischer water, GC purity, and 29Si/1H NMR are typically used to qualify lots.
  • Acid/base content: Trace acid or base catalyzes self-condensation; neutral, low-moisture packaging extends shelf life.
  • Trace metals: For cross-coupling applications (e.g., Pd-catalyzed), low halide/metal contamination minimizes catalyst poisoning and side reactions.

• What the grade means (general definitions):

  • “Synthesis grade” or “95–98%” indicates suitability for general organic synthesis; may contain minor siloxane content.
  • “High-purity” or “≥99%” organosilane grade often implies tighter control of hydrolytic species and low water content, favoring monolayer-quality silanization.
  • HPLC grade is typically not relevant for reactive silanes; instead, GC purity and hydrolyzable content are the critical metrics.

For this specific SKU, consult the CoA/Spec Sheet for actual assay, stabilizer (if any), water content, and analytical methods used to certify quality.

Reaction and Applications

This molecule unites two orthogonal handles: a para-bromide (Ar–Br) and an aryltrialkoxysilane [Ar–Si(OMe)3]. This duality enables divergent synthetic and surface-chemistry workflows.

• Surface functionalization (literature/general):

  • The trimethoxysilyl group hydrolyzes/condenses onto hydroxylated surfaces (SiO2, glass, alumina, metal oxides), forming robust Si–O–Si interfacial bonds. Resulting surfaces present a para-bromophenyl terminus for subsequent derivatization (e.g., Pd-catalyzed coupling, nucleophilic aromatic substitution unlikely on bromobenzene without activation, or radical additions).
  • Applications: microcontact printing, sensor interfaces, chromatography stationary-phase modification, adhesion promotion for polymer–inorganic interfaces.

• Cross-coupling chemistry (literature/general):

  • At the Ar–Br site: Subject to Pd-catalyzed Suzuki–Miyaura, Sonogashira, Heck, or Buchwald–Hartwig amination, enabling elaboration while retaining the trialkoxysilane for later surface grafting.
  • At the Ar–Si site: Hiyama–Denmark coupling uses the arylsilane as a nucleophilic partner (activation by F− or base, e.g., TBAF, CsF, or hydroxide with silanol pre-formation) to couple with aryl/vinyl electrophiles.

• Orthogonal strategy:

  • Sequence control: Coupling at Ar–Br under conditions benign to Si–OMe (dry, non-alcoholic solvents, mild base) followed by silanization; or first immobilize on oxide surfaces then derivatize the surface-bound aryl bromide.

• Practical notes:

  • Limit moisture to prevent premature silane polymerization during solution-phase coupling.
  • Monitor by GC/MS or 1H/13C/29Si NMR; surface reactions evaluated by contact angle, XPS, ellipsometry, or AFM.

Manufacturer Applications: Not provided in Product Data; the above expands on common literature uses for aryltrialkoxysilanes bearing para-bromophenyl groups.

Reaction Conditions

General literature guidance; adjust to your substrate/catalyst system and consult primary sources.

• Surface silanization (oxide substrates):

  • Solvent: anhydrous toluene, heptane, or dry acetone.
  • Concentration: 0.5–5% v/v silane in solvent for monolayer formation; higher for thicker films.
  • Water control: rigorously dry for self-assembled monolayers; introduce controlled trace water (10–500 ppm) to initiate hydrolysis if needed.
  • Temperature/time: RT to 110 °C; 0.5–24 h depending on substrate and desired thickness.
  • Post-treatment: rinse with solvent; cure at 110–150 °C for 10–60 min to promote condensation and crosslinking.

• Pd-catalyzed coupling at Ar–Br (solution phase):

  • Suzuki–Miyaura example: Pd(PPh3)4 (1–3 mol%), base (K2CO3, Cs2CO3), solvent (toluene/dioxane/H2O biphasic or anhydrous dioxane); 60–100 °C, 2–16 h. For silane integrity, prefer anhydrous conditions or strictly control water.
  • Sonogashira: Pd/Cu catalysts (e.g., Pd(PPh3)2Cl2, CuI), amine base (iPr2NH/Et3N), solvent (THF, toluene); 40–80 °C.

• Hiyama/Denmark coupling via Ar–Si(OMe)3:

  • Activation: TBAF, CsF, or hydroxide with pre-hydrolysis to silanol (Ar–Si(OH)3/Ar–Si(OH)(OMe)2).
  • Catalysts/solvents: Pd(0/II) with phosphine ligands; THF, DMF, or dioxane; 40–90 °C, 2–24 h.

• Monitoring and workup:

  • Use inert atmosphere, dry glassware. Track by GC/MS or NMR. Quench fluoride carefully; remove Pd by scavengers or filtration through silica/alumina. For silanization, assess surfaces by contact angle, XPS, or ellipsometry.

Note: Conditions are representative literature norms, not specifications for this item.

Safety and Handling

• Item-specific (Product Data):

  • GHS classification, signal word, hazard statements, pictograms: Not specified for this item; refer to SDS.
  • Storage conditions: Room temperature (per Product Data).

• General safety profile for aryltrialkoxysilanes (literature/general):

  • Hydrolysis hazard: Trialkoxysilanes hydrolyze with moisture to silanols, liberating methanol. Methanol is flammable and toxic; hydrolysis may be exothermic.
  • Irritation: Liquid and vapors may cause eye and skin irritation; inhalation of mist/vapor may irritate respiratory tract.
  • Flammability: Many trialkoxysilanes and the released methanol are flammable. Keep away from ignition sources.

• Handling and PPE (best practice; defer to SDS):

  • Use in a fume hood; avoid inhalation and contact.
  • Wear safety glasses or face shield, lab coat, and suitable chemical-resistant gloves (e.g., nitrile). Consider double-gloving for extended handling.
  • Prevent moisture ingress; handle under dry nitrogen/argon when feasible.

• Incompatibilities and reactivity (general):

  • Avoid water, strong acids/bases in the presence of moisture (accelerated hydrolysis/condensation), and strong oxidizers.
  • Glassware and substrates containing hydroxyl groups will promote condensation; for storage, keep containers tightly sealed, with desiccant/inert headspace.

• First-aid overview (general guidance; consult SDS):

  • Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention.
  • Inhalation: Move to fresh air; monitor breathing; seek medical attention if symptoms persist.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.

Always consult the product SDS for definitive hazard classification and response procedures.

Solvent Selection

p-Bromophenyltrimethoxysilane is an organosilane building block and surface modifier. Solvent choice is driven by the intended operation (silanization vs cross-coupling) and the need to suppress hydrolysis.

• Polarity/miscibility (general behavior):

  • Expected to be miscible with common aprotic organic solvents (toluene, THF, dichloromethane, ethyl acetate) and nonpolar solvents (hexanes). Not water-miscible and reacts with aqueous media (hydrolysis/condensation).
  • Alcoholic solvents accelerate hydrolysis; use intentionally for controlled sol–gel/silanization, or avoid to preserve monomeric silane.

• Solvent selection by task (general guidance):

  • Surface silanization on oxides (e.g., SiO2, Al2O3): anhydrous toluene, heptane, or dry acetone. Trace water (ppm-range) is tuned depending on whether you aim for monolayers (very low water, catalyst-controlled) or thin films (slightly higher water to initiate hydrolysis).
  • Hiyama-type cross-coupling (using the aryl–Si motif): polar aprotic solvents such as THF, DMF, or dioxane with fluoride activation (e.g., TBAF) are common.
  • Cross-coupling at the aryl bromide (Suzuki/Negishi/Buchwald–Hartwig): choose solvent per catalyst system (toluene, dioxane, DMAc, Me-THF) ensuring compatibility with the Si–OR groups (avoid strong base/alcoholic conditions that cause hydrolysis unless intended).

• Practical tips:

  • Degas solvents for Pd-catalyzed couplings; rigorously dry for silanization.
  • For surface work, pre-clean substrates (oxygen plasma or piranha per facility SOP) and use anhydrous solvents to maximize monolayer order.

All solvent choices should be validated against your specific protocol and substrate; refer to primary literature and method SOPs.

Storage and Reconstitution

• Item-specific (Product Data):

  • Storage Conditions: Room temperature.
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• General best practices for organotrialkoxysilanes (literature/general):

  • Moisture control: Store tightly sealed in the original container with desiccant; if possible, blanket headspace with inert gas (N2/Ar) after opening to reduce hydrolysis.
  • Light/heat: Protect from prolonged heating; ambient lab light is typically acceptable, but minimize unnecessary exposure.
  • Handling after opening: Record open date; for critical applications (monolayer-quality silanization), use fresh material and avoid repeated freeze–thaw/heat cycles. If viscosity increases or a haze appears, partial condensation may have occurred.

• Reconstitution: Not applicable; product is typically supplied neat (no reconstitution required). If dilution is needed for application, prepare working solutions in rigorously dry, compatible organic solvents immediately before use.

• Stability notes:

  • Trialkoxysilanes can slowly self-condense over time, especially with trace moisture. Verify integrity by GC or 1H/29Si NMR if performance is critical.

For shipping conditions and any stabilizers or inhibitors, consult the CoA/Spec Sheet and SDS for the specific lot.

Structure and Identity

Brief: p-Bromophenyltrimethoxysilane is an aryltrialkoxysilane featuring a para-brominated phenyl ring bonded through a Si–C linkage to a trimethoxysilyl group.

• Item-specific (Product Data):
  • CAS: 17043-05-9
  • CID: 14993398
  • InChIKey: 32730 (as provided)
  • Storage: Room temperature
  • Research Use: For research use only
• Literature/computed identifiers and descriptors (not item-specific):
  • Typical molecular formula (literature): C9H13BrO3Si
  • Typical molecular weight (literature): ~277.18 g/mol
  • Representative SMILES (literature): COSi(OC)c1ccc(Br)cc1
  • Core structural features:
    • Aromatic ring: para-bromobenzene (p-bromophenyl)
    • Silicon functionality: trialkoxysilane, specifically trimethoxysilyl [Si(OCH3)3]
    • Bonding: direct aryl–silicon carbon–silicon bond (Ar–Si)
    • Substitution pattern: bromine at the para position relative to the Si–C bond on the phenyl ring
• 2D Structure (verbal): A benzene ring bearing a bromine atom at the para position and, at the opposite para site, a single Si center attached to three methoxy groups (–OCH3) in a tetrahedral environment around silicon, connected to the ring via a carbon–silicon bond.

Note: Exact analytical identifiers (e.g., definitive InChIKey for this lot) are not specified for this item beyond what is listed; refer to CoA/Spec Sheet for confirmation.

Synthetic Utility

Key functional elements and how to leverage them in synthesis and materials chemistry:

• Orthogonal functionality:

  • Aryl bromide (para): versatile electrophile for Pd-catalyzed couplings (Suzuki–Miyaura, Sonogashira, Heck), Ni-catalyzed cross-couplings, and nucleophilic metalation (e.g., lithium–halogen exchange under controlled conditions, mindful of Si–OMe sensitivity).
  • Trialkoxysilane: hydrolyzable anchoring group for covalent attachment to oxide surfaces (Si–O–Si bond formation), enabling subsequent on-surface transformations via the retained aryl bromide.

• Retrosynthetic value:

  • As a branch point, it allows late-stage diversification on solid supports: immobilize first, then diversify via the para-bromide to install linkers, dyes, or catalysts. Alternatively, elaborate the aryl core in solution, then graft the silane to substrates.

• Named reactions and pathways (literature):

  • Hiyama/Denmark coupling using the aryl–Si(OMe)3 moiety as a masked nucleophile after activation (fluoride/base) to couple with aryl/vinyl halides or triflates.
  • Post-grafting Pd-catalyzed couplings on surfaces featuring para-bromophenyl termini to build functional interfaces.

• Practical considerations:

  • Protect the silane functionality from hydrolysis during metal-catalyzed coupling (dry solvents, minimal protic additives).
  • For surface monolayers, control water content (ppm), catalyst/acid traces, and curing temperature to tune film density and order.

Target Specificity

Not applicable. This product is a small-molecule organosilane, not an antibody, enzyme, or targeted biological reagent. No antigen/epitope, clone, or species reactivity information applies.