2TOO8-CHO-Br , CAS No.2568975-69-7

CAS: 2568975-69-7 Cat. No.: T1503789

Storage

Room temperature

Specifications

Storage

Room temperature

Application Protocols

Not applicable as standardized biological assay protocols.

Notes

• No tested applications (e.g., WB, IHC, IF, FC) are provided or expected for this small-molecule building block.
• For synthetic applications, refer to the Reaction Conditions and Reaction & Applications sections for generalized, literature-based procedures that must be adapted to your substrate, scale, and equipment.
• Always verify item-specific parameters (solubility, purity, inhibitors/stabilizers) on the CoA/Spec Sheet before executing protocols.

Biological Roles

Not typically applicable.

General note (not item-specific)

• Small synthetic building blocks bearing aldehyde and bromide functionalities are generally used for chemical synthesis and materials fabrication rather than for probing endogenous biological pathways. While aldehydes can form reversible imines with amines in biomolecules and bromides can participate in alkylation under forcing conditions, these interactions are non-specific and not typically leveraged as “biological roles.”
• If the compound is intended as a linker or handle in bioconjugation chemistry, users may exploit aldehyde–amine chemistry (e.g., oxime/hydrazone formation following aldehyde introduction) after appropriately installing reactive partners on biomacromolecules. Reaction conditions in such contexts are highly system-dependent and require empirical optimization.

Research Use Note

• Per Product Data: For research use only. No medical or clinical use is implied. Any biological testing should be performed by trained personnel under institutional approvals and with appropriate controls.

Buffer Applications

Not typically applicable.

Explanation

• Aldehyde/bromide small molecules are not used as buffering agents and do not constitute classical buffer systems. If used in bioconjugation workflows, the choice of buffer (e.g., phosphate, acetate, carbonate) depends on the transformation at the aldehyde (oxime/hydrazone formation often at mildly acidic to neutral pH). Such buffer selection is application-driven and not intrinsic to this item.
• For practical guidance in these contexts, focus on the Reaction & Applications and Reaction Conditions sections for general chemistry considerations.

Green Alternatives

Context

• Selection of greener solvents and catalytic methods can reduce environmental footprint when working with aldehyde–bromide building blocks. The guidance below is general/literature-based and not specific to this item.

Greener choices and trade-offs

• Solvents
  • Replace DMF/NMP with safer polar aprotics where possible: propylene carbonate, Cyrene (dihydrolevoglucosenone), GBL, or green ethers (2-MeTHF, CPME). Consider solubility and catalyst compatibility.
  • Use ethanol/i-PrOH or water/ethanol mixtures for reductive amination when feasible. Water-tolerant catalysts enable some cross-couplings in aqueous media.
  • Prefer toluene/EtOAc/MeTHF over chlorinated solvents for workups and chromatography when performance allows.
• Catalysis
  • Favor Pd at ppm levels or Ni-based systems for Suzuki and Negishi couplings; employ ligand platforms enabling low-metal loadings and aqueous or micellar media.
  • Borrowing-hydrogen or transfer-hydrogenation protocols in i-PrOH can replace stoichiometric hydrides for reductive aminations.
• Process intensification
  • Continuous flow for exothermic reductions or metal–halogen exchanges improves safety and reduces solvent usage via better heat/mass transfer.
  • In-line drying and Dean–Stark operations reduce desiccant waste.

Mini-comparison (literature)

• 2-MeTHF vs THF: lower peroxide formation tendency, higher bp (simplifies solvent recovery), bio-based origin; slightly different solubility and sometimes slower rates.
• Micellar catalysis vs organic media: dramatic solvent reduction; requires surfactant systems and careful workup.

Always balance EHS benefits with reaction performance, and validate impurity profiles for scale-up.

Pharmaceutical Uses

Scope

• No therapeutic or clinical claims are made. Per Product Data: For research use only.

General/formulation context (not item-specific)

• Aldehyde–bromide intermediates can appear in medicinal chemistry routes as advanced building blocks, enabling rapid scaffold diversification (cross-coupling at C–Br) and installation of side chains or linkers (via –CHO chemistry). They are typically not used as excipients.
• When used in discovery-scale synthesis:
  • Maintain impurity control compatible with SAR studies (residual metals, over-oxidized acids, debrominated byproducts).
  • Protect the aldehyde if long-term storage or multistep sequences are required.
  • Where pharmacopoeial compliance is necessary for later-stage development, route redesign may replace bromides with alternative leaving groups or late-stage functionalization strategies to minimize halogenated waste.

Manufacturing considerations

• Residual palladium or nickel from couplings should be controlled (common limits in internal specs range from low ppm to sub-ppm; set your own targets). Use scavengers and validated analytical methods (ICP-MS).
• Avoid chlorinated solvent entrapment by adequate drying and vacuum protocols. Validate cleaning procedures if used in GMP pilot plants.

All statements above are general and not specific to this item.

Physical Properties

Item-specific facts (from Product Data)

• Physical constants (bp/mp/density/solubility/logP/pKa/RI): Not specified for this item; refer to CoA/Spec Sheet.

General/literature context (not item-specific)

• Typical behavior of aryl bromo-aldehydes:
  • Melting point: often solid at ambient temperature; mp can span ~50–150 °C depending on substitution (literature).
  • Boiling/decomposition: many decompose before boiling at atmospheric pressure; distillation under reduced pressure is sometimes possible (literature).
  • Density: aromatic bromo derivatives frequently show densities >1.3 g/mL if liquid; solids commonly have moderate crystal densities (literature).
  • Solubility: generally low in water; soluble in polar aprotic organic solvents (DMSO, DMF, NMP, acetonitrile) and moderately to well soluble in chlorinated solvents and aromatics (DCM, chloroform, toluene) (literature).
  • LogP: brominated aromatics typically exhibit elevated lipophilicity; aldehyde increases polarity but not enough to drive water solubility (literature).
  • UV-vis: aromatic CHO groups contribute to π→π* absorption; exact λmax depends on conjugation (literature).

Practical notes

• Recrystallization or chromatographic purification is commonly used; aldehydes can hydrate or oxidize, so minimize prolonged exposure to moisture/air and strong base during workup.
• All quantitative values for this item should be verified from the CoA/Spec Sheet or measured in-house before method development.

Quality & Grades

Item-specific facts (from 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.

General guidance (not item-specific)

• Research-use chemicals are often supplied as “technical,” “research,” or “analytical” grades:
  • Analytical/Reagent grade: tight impurity controls; suitable for quantitative work.
  • Research grade: suitable for most synthetic applications; impurity profile may be broader but consistent.
  • HPLC/UV grade (for solvents): controlled UV cutoffs and low residue; less relevant for solid building blocks.
• For aldehyde/halide building blocks, key quality attributes include:
  • Residual halide/metal impurities (if produced via halogenation or coupling).
  • Aldehyde integrity (monitor for over-oxidation to carboxylic acids and for hydrates/acetals). NMR and GC/LC are recommended for lot release.
  • Water content can impact aldehyde stability and downstream reactions; Karl Fischer is commonly tracked, though not specified for this item.
• Stabilization: Some aldehydes are shipped with trace acid inhibitors or under inert atmosphere; none are specified for this item. If inhibitor/stabilizer is critical to your process, verify on the CoA/Spec Sheet.
• Traceability: request CoA with batch-specific purity, residual solvents, and spectral data (1H/13C NMR, LC/GC chromatograms) for method validation and regulatory filings where applicable.

Reaction & Applications

General/literature applications for aldehyde–bromide building blocks (not item-specific)

• Cross-coupling at C–Br: Suzuki–Miyaura (with boronic acids/esters), Sonogashira (with terminal alkynes), Buchwald–Hartwig (after bromo-to-amino via amination), and Kumada/Negishi/Stille variants enable rapid diversification of the core scaffold.
• Carbonyl transformations at –CHO:
  • Reductive amination to secondary/tertiary amines (NaBH3CN, NaBH(OAc)3, catalytic hydrogenation).
  • Oxidation to carboxylic acids (e.g., Pinnick) or reduction to alcohols (NaBH4, DIBAL, catalytic H2).
  • Condensations: Schiff base formation with amines; aldol/crotonization under base; Wittig/HWE/Julia olefinations to install alkenes.
  • Protection as acetals (ethylene glycol, p-TsOH) to mask –CHO during cross-coupling at C–Br, enabling orthogonal sequences.
• Materials science relevance:
  • Aldehyde-functional monomers allow post-polymer modification via imine formation or acetal chemistry.
  • Bromine substituents facilitate aryl–aryl couplings to construct π-extended systems (OLEDs, OPVs, OFETs) and porous frameworks.

Practical sequencing strategies

• Protect the aldehyde (acetal/oxazolidine) before harsh metalation or high-temperature couplings.
• Perform cross-coupling first when the aldehyde is stable under the chosen catalytic system; then execute chemoselective carbonyl chemistry.
• Monitor for debromination or over-reduction during hydrogenation steps; choose catalysts/conditions that preserve the desired handle.

Note: The above are literature-based strategies; confirm compatibility with this specific item via small-scale trials.

Reaction Conditions

General literature guidance (not item-specific; verify with small-scale trials)

• Suzuki–Miyaura coupling (for aryl–Br):
  • Catalyst: Pd(PPh3)4 (0.5–2 mol%) or Pd-PEPPSI/NHC systems; bases K2CO3, Cs2CO3, K3PO4 (1.5–3 equiv).
  • Solvent: dioxane/water, toluene/water, or DMF. Temperature 60–100 °C; 2–16 h. Degas and use inert atmosphere. Monitor for aldehyde tolerance; protect as acetal if necessary.
• Sonogashira coupling:
  • Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%), base Et3N or i-Pr2NH, solvent THF, DMF, or toluene; 25–80 °C. Copper-free variants reduce side reactions.
• Reductive amination of –CHO:
  • Conditions: RNH2 (1.1–1.5 equiv), NaBH3CN or NaBH(OAc)3 in MeOH/EtOH/DCE with AcOH (0.5–1 equiv) at 0–25 °C, 1–6 h. Alternatively, catalytic hydrogenation (Pd/C) under H2 in alcohol solvent.
• Aldehyde protections (acetals):
  • Reagents: ethylene glycol (2–3 equiv), catalytic p-TsOH, solvent toluene; Dean–Stark reflux 2–6 h. Deprotect with dilute aqueous acid at rt–50 °C.
• Oxidations/reductions:
  • Oxidize to acid via Pinnick (NaClO2 with NaH2PO4 and 2-methyl-2-butene) in aq. tert-butanol. Reduce to alcohol with NaBH4 in MeOH at 0–25 °C or to alkane via Wolff–Kishner/Clemmensen depending on compatibility.

Notes

• Aldehydes can undergo self-aldol in basic media; use mild bases or protect –CHO during strong-base couplings (e.g., KOtBu).
• Always confirm catalyst/ligand compatibility with the specific substitution pattern and functional group tolerance of this item.

Safety & Handling

Item-specific facts (from Product Data)

• GHS Classification: Not specified for this item; refer to SDS.
• Signal word: Not specified for this item; refer to SDS.
• Hazard statements (H-phrases): Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.
• Storage conditions: Room temperature (per Product Data).

General safety guidance (not item-specific; consult the SDS for authoritative instructions)

• Likely hazards for aldehyde/brominated organic compounds include: skin/eye irritation, respiratory irritation, and potential sensitization; harmful if swallowed or inhaled. Some brominated organics may be environmentally hazardous. Aldehydes can be lachrymators and can form peracids upon strong oxidation.
• PPE: lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (nitrile as a default; verify material compatibility). Work in a chemical fume hood to control vapors and dust.
• Handling: minimize exposure to air and moisture to limit aldehyde oxidation to acids and polymerization. Keep containers tightly closed when not in use. Avoid strong bases (which can induce aldol/self-condensation) and strong oxidizers or reducing agents unless intended.
• Incompatibilities (general): strong oxidizers, strong bases, and nucleophiles that may attack the carbonyl. Halogenated aromatics can undergo metal–halogen exchange; avoid uncontrolled contact with reactive metals.
• First aid (summary): move to fresh air if inhaled; rinse eyes with water for ≥15 min; wash skin with soap and water; seek medical advice if symptoms persist. Spill control with inert absorbent; prevent entry into drains. Dispose of according to local regulations.
• Always defer to the product-specific SDS for exact hazard classification and response measures.

Solvent Selection

Applicability

• As a bifunctional organic building block (aldehyde + bromide likely), solvent choice is typically driven by the transformation: cross-coupling at C–Br or condensations/reductions at –CHO.

General/literature guidance (not item-specific)

• Polar aprotic solvents (DMF, NMP, DMSO, acetonitrile) support many Pd-catalyzed cross-couplings and nucleophilic substitutions but consider ease of removal and toxicity.
• Ethers (THF, 2-MeTHF, CPME) are preferred for organometallic additions to aldehydes (e.g., Grignard, organolithium) and for metal–halogen exchange protocols; rigorously dry solvents are recommended.
• Aromatics/chlorinated solvents (toluene, xylene, DCM, chloroform) often dissolve brominated aromatics well and are common in Friedel–Crafts or acetalization reactions.
• Alcohols (MeOH, EtOH, i-PrOH) are useful for acetal formation (with acid catalyst) or for reductive aminations (as co-solvents), but can compete in nucleophilic additions.
• Aqueous biphasic systems: generally poor solubility is expected for aryl bromo-aldehydes; use phase-transfer strategies if needed.

Practical notes

• For carbonyl condensations (Schiff base, aldol), remove adventitious water (molecular sieves, Dean–Stark) to drive equilibrium.
• For cross-coupling, solvent/base matching is key: e.g., DMF/K2CO3, dioxane/KOtBu, toluene/NaOtBu are common pairings (literature). Degas and maintain inert atmosphere for air-sensitive catalysts.
• Verify solvent compatibility with your downstream processing and environmental constraints; scale-up often favors recyclable solvents with higher boiling points for efficient recovery.

Storage & Reconstitution

Item-specific facts (from Product Data)

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

General handling guidance (not item-specific)

• Keep container tightly closed in a dry, well-ventilated place. For aldehydes, limiting exposure to air/moisture slows oxidation to the corresponding acid and minimizes hydrate/acetal formation. If long-term storage is anticipated, consider storing under inert gas (argon/nitrogen) and using desiccant.
• Avoid prolonged exposure to light and heat sources. If the compound is moisture-sensitive, open only in low-humidity conditions or glovebox and recap promptly.
• If solid: break up agglomerates gently; avoid grinding if aldehyde odor suggests volatility. If liquid: dispense with dry syringes/pipettes; purge headspace with inert gas after use.
• Reconstitution: No specific reconstitution instructions are provided. For solution preparation, select dry, oxygen-free solvents compatible with the intended reaction (e.g., anhydrous THF, toluene, DMF). Filter through PTFE syringe filters when particulate contamination is a concern.
• Stability checks: Periodically assay by NMR/LC to ensure the aldehyde content remains within acceptable limits; look for acid formation or debromination products.

Always refer to the product-specific CoA and SDS for definitive storage, stability, and handling instructions.

Structure & Identity

Item-specific facts (from Product Data)

• SKU: T1503789
• Product name: 2TOO8-CHO-Br
• CAS: 2568975-69-7
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

General/literature context (not item-specific)

• The “CHO” tag typically denotes an aldehyde functional group; “Br” often indicates a bromo substituent. Compounds bearing both an aldehyde and a bromine handle are common bifunctional building blocks in materials chemistry and small-molecule synthesis, enabling orthogonal reactivity.
• Structural features often seen in CHO/Br building blocks:
  • An sp2-hybridized carbonyl carbon of an aldehyde (–CHO) capable of nucleophilic addition/condensation.
  • An aryl–Br or alkyl–Br bond serving as a leaving group in cross-coupling or substitution chemistry.
• 2D description (generic for CHO/Br building blocks): A conjugated core (often aromatic) bearing a formyl group para/ortho/meta to a bromine, enabling site-selective transformations on each functionality.

Notes

• Because no structural string (SMILES/InChI) or formula is provided for this specific item, structural assertions above are provided as general guidance based on the product name format only. Consult the CoA/Spec Sheet for definitive identity data, exact substitution pattern, and stereochemistry (if any).

Synthetic Utility

General synthetic value (not item-specific)

• Orthogonal reactivity: The coexistence of an aldehyde (electrophilic carbonyl) and a bromide (pseudohalide leaving group) enables two-directional synthesis. You can elaborate the carbon framework via cross-coupling at C–Br while independently modifying –CHO through condensations, reductions, or oxidations.
• Protect/deprotect strategy: Mask –CHO as dimethyl/diethyl acetal or cyclic acetals (e.g., ethylene glycol) to withstand basic or high-temperature couplings; deprotect under mild acid after C–Br transformations.
• Late-stage diversification: Conduct Suzuki–Miyaura to modify the aryl core, then apply reductive amination to introduce amine-bearing side chains, facilitating library generation for materials or medicinal SAR.
• Retrosynthetic planning:
  • Disconnections at the C–C bond formed by Wittig/HWE from the –CHO enable olefin installation; the bromide can be used to connect to a second fragment by cross-coupling.
  • Metal–halogen exchange (e.g., i-PrMgCl·LiCl or n-BuLi) can introduce electrophiles adjacent to the aryl bromide, provided the aldehyde is protected or masked.
• Polymer/oligomer building: Aldehyde units allow dynamic covalent chemistry (imine-based COFs); bromine sites serve for Suzuki polymerization to form conjugated backbones. Sequence control can be achieved by selective protection or by differential reactivity of multiple halides.

These strategies are literature-based; tailor to the specific substitution pattern and stability profile of the item supplied.

Target Specificity

Not applicable.

Explanation

• This product is a small-molecule building block for materials/synthetic chemistry and is not a biological macromolecule, inhibitor, or affinity reagent. No antigen/epitope, clone, isotype, or species reactivity applies.

Frequently Asked Questions

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 2568975-69-7.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.