Pentabromo benzene-C , CAS No.P1442155

CAS: P1442155 Cat. No.: P1442155 Formule: ₁₃C₆HBr₅ Poids moléculaire: 478.55

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

Pentabromo benzene- 13 C 6 is 13 C labeled 1,2,3,4,5-Pentabromobenzene.

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: 478.55

Application Protocols

No tested bioassay or immunoassay applications are provided for this item. As a synthetic building block, application protocols are reaction- and project-specific.

General laboratory guidance:

• For solution preparation, warm compatible solvent (e.g., chlorobenzene, toluene, NMP) and add solid incrementally with stirring to ensure complete dissolution.
• For cross-coupling screens, use microplate or parallel reactors to vary ligand/base/solvent systematically; analyze by LC–MS.
• For purification, prefer crystallization or trituration to reduce solvent/silica usage; when chromatography is required, use halogenated-eluent minimization strategies.

Refer to the Reaction Conditions and Synthetic Utility tabs for detailed chemistry-focused guidance.

Biological Roles

This product is intended for research use only and is supplied as a synthetic organic building block. It does not have a defined biological role in cells or organisms.

General literature context (not product-specific, not a claim of use):

• Polybrominated aromatic compounds are widely studied in environmental science due to their persistence and hydrophobicity; however, pentabromobenzene itself is not a natural metabolite and has no established physiological function.
• Any interactions with biomolecules would be nonspecific (hydrophobic/aromatic) rather than target-directed. Such effects are outside the scope of typical laboratory synthesis workflows and should not be inferred as intended uses for this item.

Practical guidance:

• If handling in a bioanalytical setting (e.g., partitioning studies), use appropriate controls and solvent carriers; avoid DMSO concentrations that confound assays.
• Dispose of solutions and residues as halogenated organic waste; prevent environmental release.

For any biological testing, ensure alignment with institutional approvals and recognize that this material is not supplied for clinical or diagnostic use.

Buffer Applications

Not typically applicable. This product is a hydrophobic, nonionic aromatic building block and does not serve as a buffering agent or pH control component.

Practical note: If it must be introduced into aqueous systems for research purposes, use suitable cosolvents (e.g., DMSO, PEG-400) or emulsification strategies; however, such formulations are outside standard practice for this substrate and should be validated for your specific application.

Green Alternatives

For a polybrominated aromatic building block, “greener” strategies focus on how you use it (solvent and catalyst choices, waste minimization) rather than substituting the substrate itself. Consider the following to reduce environmental footprint while maintaining performance.

• Solvent choices (coupling chemistry):

  • Prefer 2-MeTHF, CPME, anisole, or aqueous micellar media over chlorinated solvents when solubility and reactivity allow.
  • Dioxane alternatives: Replace 1,4-dioxane with 2-MeTHF or tert-amyl alcohol/water blends where feasible.

• Catalyst economy and recovery:

  • Use highly active Pd or Ni catalysts at low loadings (≤0.5 mol%) with robust ligands (XPhos/SPhos/ECPhos; SIPr/IPr for NHC routes).
  • Heterogeneous or supported catalysts (Pd/C, SiliaCat Pd) can simplify recovery and reduce dissolved metal in waste.

• Base and workup:

  • Favor inorganic carbonate/bicarbonate bases in water-containing systems to lower E-factors and improve safety.
  • Implement aqueous workups that allow clear phase separation and minimize chlorinated waste; use antisolvent crystallizations to avoid silica-intensive purifications.

• Energy and process intensification:

  • Microwave or flow chemistry can shorten reaction times and reduce energy use.
  • Continuous-flow cross-coupling with inline metal scavenging lowers solvent and catalyst inventory.

• Comparative snapshot (general):

  • Chlorobenzene/DCM: strong solvency but high environmental impact and halogenated waste.
  • 2-MeTHF/anisole: renewable or lower-toxicity options; may require slightly higher temperature or longer time to achieve full conversion.

Note: Polybrominated aromatics can be environmentally persistent; design campaigns that maximize atom economy and minimize off-spec material and halogenated waste.

Pharmaceutical Uses

No pharmacopeial or excipient role is provided for this item. It is supplied strictly for research use as an organic synthesis building block.

General formulation context (non-therapeutic):

• Heavily halogenated aromatics are rarely used as excipients due to hydrophobicity and environmental considerations.
• If used in process development studies (e.g., as a coupling substrate for medicinal chemistry SAR), ensure complete removal from final API candidates and compliance with ICH guidelines for residual reagents and elemental impurities.

Research Use Note: For research use only (not for human or veterinary use, not for diagnostic procedures).

Physical Properties

Item-specific physicochemical specifications (melting point, solubility limit, refractive index, metal/peroxide content, etc.) are not provided in the Product Data. Consult the CoA/Spec Sheet for authoritative values for this SKU.

Literature/general properties for pentabromobenzene (for context only; not product specifications):

• Physical state: crystalline solid; high lattice energy due to multiple heavy halogens.
• Color/appearance: typically off-white to light tan crystals (can vary with trace impurities).
• Melting point: reported in the ~300–310 °C range (literature, varies by isomer and purity).
• Boiling/decomposition: aryl polybromides generally show very low volatility and may decompose before boiling at ambient pressure.
• Density: expected substantially greater than 1 g/mL (heavy-atom content); literature values for related polybrominated benzenes are >2 g/cm3 (qualitative context).
• Solubility (qualitative):
  • Water: negligible.
  • Organic solvents: sparingly to moderately soluble in nonpolar and halogenated organics (e.g., toluene, chlorobenzene, dichloromethane) and in some polar aprotics upon heating (DMF, DMSO, NMP). Solubility generally increases with temperature.
• Vapor pressure: very low at room temperature.
• LogP: expected high (hydrophobic), consistent with poor aqueous solubility.

Practical notes (general):

• For solution preparation, gentle heating and use of halogenated or aromatic solvents often aids dissolution.
• Because polybrominated aromatics can be dense and slow-dissolving, allow adequate time and agitation for complete dissolution before making volumetric adjustments.
• If crystallinity or polymorph affects processing, confirm by DSC/XRPD as needed (project-dependent).

Quality and Grades

Item-specific quality attributes are not listed in the Product Data.

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

Guidance on interpreting quality for polyhalogenated building blocks (general):

• Purity reporting: For aryl polybromides, HPLC/GC can under-report inorganic halide residues; NMR (1H, 13C), HRMS, and elemental analysis are often included on the CoA to substantiate material identity and halogen content.
• Residual metals: If the material is produced via bromination using catalytic metal halides, residual metal levels may be relevant for catalysis-sensitive applications. Absence of item-specific limits here means you should consult the CoA for any ICP data. Where no limit is stated: Not specified for this item; refer to CoA/Spec Sheet.
• Stabilizers/inhibitors: None are typically used for neutral, crystalline aryl bromides; if a stabilizer were present it would be disclosed on the CoA. For this item: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoffs/UV-Vis profile: Often not specified for solids used as building blocks; if needed for photochemical work, request spectral data.

Fit-for-purpose recommendations:

• For stepwise cross-coupling campaigns, prioritize lots with well-defined isomer composition (if applicable) and tight impurity profiles (especially lower bromination homologs). Confirm by 1H/13C NMR and, when necessary, 79/81Br isotopic pattern in MS.
• If trace halide or residual acid could affect your catalyst, consider a pre-wash or slurry in dry nonpolar solvent, then dry under vacuum prior to use.

Reaction and Applications

While item-specific application notes were not provided, pentabrominated benzenes are versatile electrophilic building blocks in aryl–carbon and aryl–heteroatom bond formation. Representative uses (literature/general):

• Iterative cross-coupling: The five C–Br bonds can undergo Pd- or Ni-catalyzed couplings (Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Stille, Negishi). Strategic ligand/catalyst selection enables stepwise functionalization to access densely substituted (up to penta-substituted) benzenes.
• Reactivity differentiation: Oxidative addition rates to different C–Br positions can vary with sterics and electronics. Bulky monodentate biaryl phosphines (e.g., XPhos/SPhos) or NHCs can promote selective activation patterns; temperature and solvent further tune selectivity.
• Polyarylation platforms: Starting from pentabromobenzene allows rapid generation of libraries where five distinct substituents are introduced, enabling materials discovery (OLEDs, conjugated systems), medicinal chemistry SAR maps, and dendron cores.
• Halogen–metal exchange: With RLi or Mg reagents under cryogenic conditions, selective exchange at the most activated C–Br site can generate arylmetals for subsequent electrophile trapping (formylation, borylation, etc.). Careful control is essential to avoid multiple exchanges.
• Aryl–heteroatom installation: Copper- or palladium-catalyzed C–N, C–O, and C–S couplings can install heteroatoms selectively; orthogonality across five sites requires condition scouting.
• Further halogenation/derivatization: Pentabromobenzene can be a precursor to hexabromobenzene or mixed-halide scaffolds (e.g., I/Br patterns) for reactivity tuning.

Practical tips:

• Conduct small-scale screens varying ligand class, base, and solvent to encode positional selectivity.
• Monitor by LC–MS with bromine isotope patterning for clear speciation. Employ scavenger resins or silica plugs to remove residual Pd/Ni when material purity is critical.

Reaction Conditions

General literature guidance for transforming aryl bromides on a pentabrominated benzene scaffold (values are typical ranges; optimize for your system):

• Suzuki–Miyaura arylation:

  • Catalyst/ligand: Pd2(dba)3 (0.5–1 mol% Pd) with SPhos/XPhos (1–2 mol%); or Pd(PPh3)4 (1–3 mol%).
  • Base: K2CO3, Cs2CO3, or K3PO4 (2–3 equiv).
  • Solvent: 1,4-dioxane/H2O (3:1), 2-MeTHF/H2O, toluene/H2O, or anisole/H2O.
  • Temperature/time: 60–110 °C, 2–16 h.
  • Notes: To achieve site-selectivity, lower temperature and bulkier ligands can favor less hindered positions first.

• Sonogashira coupling (alkynylation):

  • Catalyst: PdCl2(PPh3)2 (1–2 mol%) + CuI (2–5 mol%) or copper-free with strong σ-donor ligands.
  • Base: Et3N, i-Pr2NH, or Cs2CO3.
  • Solvent: THF, 2-MeTHF, DMF, or toluene.
  • Temperature: 40–90 °C.

• Buchwald–Hartwig amination:

  • Catalyst/ligand: Pd2(dba)3 (1 mol% Pd) + BrettPhos/RuPhos; or Pd-PEPPSI (NHC).
  • Base: NaOtBu, KOtBu, or Cs2CO3.
  • Solvent: t-AmOH, toluene, 1,4-dioxane, or CPME.
  • Temperature: 60–110 °C.

• Halogen–metal exchange and electrophile trapping:

  • Reagent: n-BuLi or t-BuLi (1.0–1.2 equiv) at −78 to −40 °C in THF or 2-MeTHF; quench with electrophiles (B(OMe)3, DMF, CO2, etc.).
  • Note: Highly exothermic; quench carefully and manage multiple reactive sites by stoichiometry and temperature control.

• Nickel catalysis (cost-effective):

  • Catalyst: Ni(cod)2 (2–5 mol%) with SIPr/IPr or bathophenanthroline-type ligands.
  • Conditions: Similar temperatures; may require additives (Zn, Mn) for cross-electrophile coupling.

Analytical control: Use LC–MS with bromine isotope patterns and 1H/13C NMR to track degree and position of substitution. Always run small-scale scouting to map selectivity before scale-up.

Safety and Handling

Authoritative hazard classification for this specific SKU is not provided in the Product Data. Always review the product’s SDS for definitive GHS classification, pictograms, H/P statements, and response measures.

Item-specific safety fields:

• GHS Classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• H-statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General safety considerations for polybrominated aromatic solids (literature/experience-based):

• Likely hazards: May cause irritation to skin/eyes/respiratory tract; harmful if swallowed or inhaled; environmentally hazardous to aquatic life. Low volatility does not preclude dust exposure—avoid generating dust.
• PPE: Laboratory coat, nitrile gloves (double-gloving if extended contact), splash goggles. Use a chemical fume hood for weighing/handling, especially during transfers and heating.
• Handling: Avoid inhalation of dust and contact with skin or clothing. Prevent release to the environment; collect spills promptly using inert absorbent while minimizing dust.
• Incompatibilities: Strong nucleophiles and organolithium reagents (which may perform halogen–metal exchange); finely divided metals; strong bases at elevated temperature; strong oxidizers for waste streams.
• Thermal behavior: High-melting solids can char or decompose on overheating; avoid open flames and uncontrolled heating.
• First aid (overview—defer to SDS):
  • Inhalation: Move to fresh air; seek medical attention if symptoms persist.
  • Skin: Wash with soap and water; remove contaminated clothing.
  • Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

Waste: Treat as halogenated organic waste; follow institutional and local regulations.

Solvent Selection

This product is a nonpolar, highly halogenated aromatic solid. It is not used as a solvent; instead, consider appropriate solvents for dissolution, processing, and reactions.

• Polarity/miscibility profile (general):

  • Water: effectively insoluble.
  • Good solvents: halogenated organics (e.g., dichloromethane, chloroform, chlorobenzene), aromatics (toluene, xylene), high-boiling polar aprotics (DMF, NMP, DMSO) when warmed.
  • Green(er) alternatives: 2-MeTHF, CPME, anisole, and propylene carbonate can sometimes replace chlorinated solvents for coupling chemistry; solubility must be confirmed empirically.

• Selection by use-case (general guidance):

  • Analytical sample prep: DMSO-d6 or CDCl3 for NMR (depending on solubility); HPLC sample prep often uses acetonitrile/THF with a small fraction of DMSO if needed.
  • Cross-couplings (Suzuki/Negishi/Stille/Sonogashira): 1,4-dioxane/water, toluene, anisole, CPME, or 2-MeTHF; for low-solubility regimes, chlorobenzene or NMP can be effective at elevated temperature.
  • Lithiation/halogen–metal exchange: Ethereal solvents (THF, 2-MeTHF) at low temperature.

• Practical tips:

  • Start with small-scale solubility screens at room temperature and 60–120 °C to map workable domains.
  • For viscous/high-boiling options (NMP, DMSO), ensure compatibility with downstream workup and catalyst system. Use antisolvent crystallization or silica plug to remove residues.
  • If selectivity between different C–Br sites is required, solvent polarity and coordinating ability can modulate oxidative addition rates—benchmark ligand/solvent sets for your substrate.

Storage and Reconstitution

Item-specific conditions (from Product Data):

• Storage: Store at −20 °C.
• Shipped in: Ice chest + ice pads.
• Research Use Note: For research use only.

General handling guidance for polybrominated aromatic solids:

• Container: Keep tightly closed in the original container to minimize moisture ingress and contamination. While neutral and non-hygroscopic, fine powders can adsorb contaminants over time.
• Light/temperature: Ambient light is acceptable; avoid prolonged heating. For long-term stability, retain at −20 °C as specified. Allow to equilibrate to room temperature before opening to prevent condensation.
• Drying: If needed, dry under high vacuum at ambient temperature. Avoid aggressive heating that could induce decomposition or discoloration.
• Inerting: Not strictly required, but storage under inert gas headspace (N2/Ar) is prudent for sensitive applications.
• Reconstitution/solution prep: There is no aqueous reconstitution. Prepare solutions in compatible organic solvents (e.g., toluene, chlorobenzene, DMF, DMSO) using mild heating and stirring. Filter warm solutions if particulates persist.
• Freeze–thaw: Not applicable to solids; for prepared stock solutions, store in sealed, inerted vials at low temperature (e.g., 4 °C or −20 °C depending on solvent) and avoid repeated thermal cycling.

Always consult the CoA/SDS for any lot-specific storage or stability advisories (e.g., limits on residual solvents or recommendations for maximum storage duration).

Structure and Identity

This product name indicates a heavily brominated benzene derivative, most plausibly pentabromobenzene (an aromatic ring bearing five bromine substituents and one remaining hydrogen). Absent a fully specified identifier set, the structural description below is provided as general/literature context for “pentabromobenzene.” Always verify the supplied CoA for the definitive identity of this specific item.

• Item-specific identifiers (from Product Data):

  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature identity (for pentabromobenzene, general reference):

  • Common name: Pentabromobenzene
  • Molecular formula (literature): C6HBr5
  • Molecular weight (literature): ~472.6 g/mol
  • Core scaffold: planar benzene ring
  • Functional groups: five aryl–bromide (C–Br) bonds; one aryl C–H
  • Stereochemistry: none (achiral, symmetric substitution patterns possible)

• 2D structural description (literature, generic): A six-membered aromatic ring with bromine substituents occupying five of the six ring carbons; the remaining ring carbon carries hydrogen. Several constitutional isomers are possible, though commercial pentabromobenzene products are typically highly symmetric (e.g., 1,2,3,4,5-pentabromobenzene). Exact isomer distribution, if relevant, should be confirmed on the CoA.

Notes

• Because item-specific structural fields are not provided, treat all numeric and descriptive identity details above as literature context only, not product specifications.
• For definitive structural assignment (isomer, labeling, isotopic content, if any), consult the product’s CoA and spectral data.

Synthetic Utility

Pentabromobenzene-type substrates provide five aryl bromides on a single ring, enabling dense functionalization. Their value lies in both modular diversification and reactivity control across multiple C–Br bonds.

Key features (general/literature):

• Electrophilic manifold: Five C–Br bonds amenable to Pd/Ni-catalyzed cross-couplings to install aryl, alkenyl, alkynyl, alkyl, amino, alkoxy, and thio substituents.
• Orthogonal reactivity: Site-selectivity can be engineered via sterics/electronics, ligand control (bulky biaryl phosphines or NHCs), temperature, and solvent. Iterative couplings can produce penta-substituted benzenes with programmed substitution patterns.
• Arylmetal generation: Selective halogen–metal exchange (RLi, RMgX) at low temperature provides arylmetals for electrophile trapping (e.g., formylation, borylation to access polyboronates for subsequent Suzuki sequences).
• Building block for materials: Access to highly substituted benzene cores used in OLED emitters, hole/electron-transport materials, and rigid dendritic scaffolds.

Retrosynthetic leverage:

• Start from pentabromobenzene as a convergent hub; each C–Br is a potential disconnection. In SAR campaigns, introduce diversity late-stage by sequential couplings.
• Mixed-halide strategies: Exchange one or more bromides for iodides (for higher reactivity) or chlorides (for cost/scalability) to encode reactivity gradients.

Practical considerations:

• Solubility can be limiting; use higher-boiling or halogenated solvents or increase temperature to maintain homogeneous conditions.
• Catalyst deactivation by adventitious halide or trace acid can occur; pre-wash substrate or add halide scavengers as needed.
• Characterization: MS isotope patterns (79/81Br) aid unambiguous confirmation of substitution level; monitor stepwise transformations by LC–MS and 1H/13C NMR.

Target Specificity

Not applicable. This product is not a biological macromolecule or affinity reagent, and no antigen/epitope specificity applies. No clone, isotype, or species reactivity information is relevant.