Indate-Hexyl-Bis-Aldehyde , CAS No.1883441-93-7

CAS: 1883441-93-7 Cat. No.: I1503596

Storage

Room temperature

Specifiche

Condizioni di conservazione di stoccaggio

Room temperature

Application Protocols

No item-specific, tested biological application protocols are provided for this product. For chemical synthesis, follow standard procedures for aldehyde condensations, reductions, or protections as outlined under Reaction Conditions. Always validate reaction conditions on small scale and consult the SDS before scaling up.

Biological Roles

This product is intended for materials science and general chemical research and is not a biological molecule. No endogenous biological role is indicated.

General context (literature):

• Dialdehydes can react with biomolecular amines to form Schiff bases; this underlies classical fixation chemistry (e.g., glutaraldehyde), but applicability and toxicity profiles vary widely. The present item is for research use only and not intended for in vivo or clinical use.
• In vitro, aldehyde–amine conjugation can be exploited for temporary linkages in biosensors or immobilization platforms; stability depends on imine reduction (to secondary amines) and environment pH/water activity.

Caution: Avoid extrapolating to biological systems without thorough risk assessment and validation. Always consult your institution’s EHS office before any bio-adjacent experimentation.

Buffer Applications

Not a typical buffering reagent. Aldehydes do not provide defined acid–base buffering capacity.

Practical notes (general):

• If using in aqueous buffers for bioconjugation (imine/oxime/hydrazone formation), choose buffers lacking primary amines (avoid Tris, glycine). Phosphate, acetate, or citrate buffers (pH ~4.5–6 for oxime/hydrazone; pH ~6–7.5 for imine) are commonly used in literature.
• Remove dissolved oxygen and minimize high pH to avoid oxidative degradation and aldol reactions.
• For stable conjugates, follow with reductive amination (e.g., NaBH3CN in buffered alcohol/water, literature guidance) in research settings; confirm compatibility with your system.

Green Alternatives

Greener considerations focus on solvent and process, as the dialdehyde functionality is central to performance.

Strategies (literature, general):

• Switch solvents: Replace dichloromethane/toluene with 2-MeTHF or CPME to enable efficient water removal and lower VOC impact. Acetonitrile can often be replaced by ethanol or isopropanol for oxime/hydrazone formations when compatible.
• Aqueous or biphasic protocols: Oxime/hydrazone formation may proceed in water/ethanol with catalytic acid, minimizing hazardous solvent use. Employ surfactants or phase-transfer catalysts if needed.
• Catalysis: Use catalytic organic acids (e.g., p-toluenesulfonic acid) instead of stoichiometric reagents; solid acids (Amberlyst-15) offer easy recovery.
• Energy efficiency: Conduct condensations at ambient temperature with desiccants (3Å sieves) to avoid reflux; microwave or flow can reduce time and solvent volumes.

Illustrative comparison (general):

• Conventional: DCM or toluene with Dean–Stark; efficient but higher environmental burden.
• Greener: 2-MeTHF/CPME or ethanol/water with sieves; lower toxicity, often comparable yields in imine/oxime chemistry.

Trade-offs:

• Greener ethers may retain peroxides; implement routine peroxide testing and scavenging.
• Ethanol/water systems can slow kinetics and shift equilibria; compensate by removing water or using mild catalysts.

Pharmaceutical Uses

No pharmacopeial status or excipient role is provided and none should be inferred. This product is supplied strictly for research use only.

General context (non-clinical, literature):

• Bifunctional aldehydes can serve as synthetic intermediates in discovery workflows (e.g., for linker installation or pro-materials), but translation to pharmaceutical manufacturing requires extensive safety, impurity, and regulatory evaluation not covered here.
• For any pre-formulation experimentation, ensure trace acid and peroxide levels (if relevant) are controlled and that residual solvents meet ICH Q3C, but such specifications are not provided for this item.

Physical Properties

Item-specific values are not provided in the product data. For authoritative numbers, consult the CoA/Spec Sheet and SDS.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not specified for this item; refer to CoA/Spec Sheet.
• pKa: Aldehydes do not possess an acidic proton suitable for pKa in water; hydration equilibria may occur (literature, general).
• LogP/solubility: Aliphatic dialdehydes with hexyl spacers are typically hydrophobic and soluble in common organic solvents (e.g., dichloromethane, THF, toluene, acetonitrile); water solubility is generally low but hydration/oligomerization can occur (literature, general).

Practical notes (general for dialdehydes):

• Aldehydes can undergo air oxidation to carboxylic acids and self-aldolization under basic conditions; inhibitors or low-basicity conditions help maintain stability.
• Removal of trace moisture (molecular sieves) suppresses hydrate formation and favors imine/oxime coupling reactions.
• Use amber glass to limit light-catalyzed degradation in sensitive systems (general best practice).

Quality and Grades

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

Interpretation and implications (general):

• When a specific grade is not stated, review the CoA for assay, GC area %, and impurity profile (e.g., acid content from oxidation, aldolized byproducts). For aldehydes, trace acid can catalyze side reactions; stabilizers or storage under inert gas can mitigate drift.
• If supplied unstabilized, expect gradual increase in carboxylic acid content upon air exposure; titration or GC can monitor this. If a stabilizer is used (not specified here), it may slightly affect reactivity in sensitive condensations—remove by vacuum or pre-wash if needed.
• Chromatographic suitability: For applications such as monomer feed in polymer synthesis or surface functionalization, low UV background and minimal peroxide/acid content are advantageous; consult CoA for absorbance or inhibitor data if relevant.
• Lot-to-lot control: Check water content (Karl Fischer), aldehyde concentration (hydroxylamine titration), and residual solvents as appropriate for your process (general recommendations).

Reaction and Applications

Positioned in materials science, a hexyl-bridged bis-aldehyde serves as a versatile difunctional building block. Without item-specific application notes, the following are literature-general use cases for dialdehydes:

• Network and polymer formation: Crosslinking of polymers or small-molecule gelators via Schiff-base chemistry with diamines; dynamic covalent networks with tunable self-healing through imine exchange.
• Functional materials: Preparation of diimines/Schiff-base ligands that chelate metals for coordination polymers, catalysts, or MOF-like constructs; the hexyl spacer imparts flexibility and hydrophobic microenvironments.
• Surface modification: Grafting to amine-functionalized surfaces (silica, polymers) to introduce terminal aldehydes or imines for further elaboration.
• Small-molecule synthesis: Entry to diacetals (protecting-group chemistry), bis-oximes/hydrazones as isolable intermediates, and subsequent reductions to diamines or diols.
• Conjugated systems: Knoevenagel condensations with active methylene compounds (e.g., malononitrile, cyanoacetates) yield push–pull chromophores; bis-condensation can produce oligomeric conjugated segments.

Practical tips (general):

• Use dry, oxygen-poor conditions to suppress oxidation to diacids; store and react under inert gas when feasible.
• Drive equilibria: Add 3Å molecular sieves for imine formation at RT to 60 C; or use Dean–Stark in toluene/xylene at reflux for high conversions.
• Monitor by IR (C=O ~1720–1740 cm−1; C=N ~1640–1690 cm−1 after condensation) and by 1H NMR (formyl ~9–10 ppm).

Reaction Conditions

General, literature-based conditions for dialdehyde transformations; optimize for your substrate and scale:

• Imine formation: Aldehyde + amine (1.0–1.2 eq per –CHO), 3Å MS, dry MeCN or 2-MeTHF, RT–60 C, 2–16 h. Catalytic AcOH (0.1 eq) may accelerate. Remove water (sieves or Dean–Stark in toluene) to drive conversion. Monitor by IR/NMR.
• Oxime/hydrazone: Hydroxylamine·HCl or hydrazine/arylhydrazine (2.2 eq), EtOH/H2O (4:1), NaOAc buffer pH 4.5–5.5, RT–50 C, 1–6 h. Often near-quantitative for each –CHO with appropriate stoichiometry.
• Reductive amination: Aldehyde + amine, NaBH3CN or NaBH(OAc)3, MeOH/THF, pH-adjusted with AcOH, 0–25 C, 2–18 h. For bis-functionalization, use excess amine or stepwise approach.
• Wittig/HWE: Ylide or phosphonate (2.2–2.5 eq), THF or toluene, 0–25 C to reflux, 2–24 h, yielding dienes/diesters depending on reagent; control E/Z via base/temperature.
• Acetalization: Diol (e.g., ethylene glycol, 3–5 eq), catalytic p-TsOH or Amberlyst-15, toluene or CPME, Dean–Stark, reflux, 3–8 h; reversible under acidic hydrolysis.
• Reduction to diols: NaBH4 (2.5–3 eq) in MeOH or EtOH, 0–25 C, 0.5–2 h; or H2, Pd/C (1–10 wt%) in EtOH, 1–5 bar, RT–40 C.

Notes:

• Suppress self-aldol by avoiding strong base and by maintaining dilute conditions.
• Oxygen exclusion minimizes oxidation to acids; add antioxidants only if compatible.

Safety and Handling

Hazard classification specifics are not provided for this item; defer to the SDS for authoritative guidance.

• Signal word: Not specified for this item; refer to CoA/Spec Sheet.
• GHS classification/pictograms/H-statements: Not specified for this item; refer to CoA/Spec Sheet.

General safety guidance for dialdehydes (literature, general):

• Hazards: Aldehydes are typically irritant/sensitizing to skin, eyes, and respiratory tract; many are flammable. Avoid inhalation and skin contact.
• PPE: Use lab coat, safety goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Employ splash protection for scale-up.
• Engineering controls: Handle in a fume hood; provide local exhaust during weighing and transfers.
• Incompatibilities: Strong bases (promote aldol/self-condensation), strong oxidizers (over-oxidation), strong reducing agents (uncontrolled reduction), and amines (reactive imine formation). Avoid prolonged contact with metals that catalyze oxidation.
• First aid (overview): Eye/skin contact—rinse with water for 15 minutes; remove contaminated clothing. Inhalation—move to fresh air. Ingestion—rinse mouth, do not induce vomiting; seek medical attention. Always follow SDS.
• Waste: Collect aldehyde-containing waste in compatible, closed containers; segregate from bases and oxidizers. Quench small residues by controlled bisulfite adduct formation if permitted by your institution.
• Special risks: Aldehydes can polymerize or oxidize on storage; limit air/moisture exposure. Some aldehydes have strong odors—verify containment.

Solvent Selection

General guidance for dialdehyde handling and reactions (literature, general):

• Polarity class: Moderately polar, aprotic environments often balance solubility and reaction control for condensations (e.g., acetonitrile, dichloromethane, toluene, THF, 2-MeTHF).
• Miscibility profile: Dialdehydes with hexyl spacers are typically soluble in common organic solvents and poorly miscible with water; biphasic setups may be used for oxime/hydrazone formation with aqueous reagents.
• Water activity: For imine formation, lower water activity (molecular sieves, Dean–Stark in toluene/xylene) drives equilibrium toward products; for oxime/hydrazone formation, mildly aqueous alcohols can be effective.
• Acid/base sensitivity: Avoid strong bases that trigger self-aldol; use catalytic Brønsted acids (p-toluenesulfonic acid) or Lewis acids (TiCl4, BF3·OEt2) judiciously for acetalizations/Knoevenagel couplings.

Small comparison (general):

• Acetonitrile: High dielectric, good for imine/oxime; low nucleophilicity.
• Toluene/xylene: Allows azeotropic water removal (Dean–Stark), useful for imine/acetal formation at reflux.
• 2-MeTHF/CPME: Greener ethers with water removal capability; good for moisture-sensitive steps.
• Alcohols (EtOH/i-PrOH): Promote acetal/hemiacetal equilibria; can compete in some condensations.

Storage and Reconstitution

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

Best practices (general for dialdehydes):

• Keep container tightly closed under inert gas (nitrogen/argon) to limit oxidation to acids and polymerization. Use dry, amber glass where possible.
• Minimize moisture: Store with desiccant; dispense using dry syringes or pipettes. If hydrate formation is suspected, dry over 3Å molecular sieves prior to use.
• Avoid repeated freeze–thaw; if a low-melting solid or viscous liquid, aliquot upon receipt.
• Headspace control: Backfill with inert gas after each use. Limit exposure to strong light and heat.

Reconstitution: If supplied as a solid or viscous material, dissolve in a dry, compatible solvent (e.g., anhydrous MeCN, 2-MeTHF, THF, toluene) immediately before use. Filter through a PTFE syringe filter (0.2–0.45 µm) to remove particulates if required for precision applications. Always verify concentration by NMR or titration when stoichiometry is critical.

Structure and Identity

Brief overview: Indate-Hexyl-Bis-Aldehyde is presented as a bifunctional aldehyde (dialdehyde) intended for materials science research, likely featuring two terminal –CHO groups separated by a hydrophobic hexyl spacer for flexible linkage and network formation.

• CAS: 1883441-93-7
• SKU: I1503596
• Synonyms: 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.
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• InChIKey: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (general, literature-based for dialdehydes):

• Functional groups: two aldehydes (–CHO) enabling imine/oxime/hydrazone formation and numerous C–C bond-forming reactions.
• Spacer: a hexyl (–(CH2)6–) segment typically imparts flexibility, hydrophobicity, and lower glass-transition characteristics to crosslinked networks (literature, general).
• 2D description (general): terminal formyl groups at both ends of an aliphatic chain, allowing difunctional reactivity toward nucleophiles (amines, hydroxylamine, hydrazines) and carbon nucleophiles (enolates, ylides).

Synthetic Utility

As a bis-aldehyde, this reagent provides two orthogonal carbonyl handles enabling stepwise or simultaneous transformations (literature, general):

• Condensations: Formation of diimines with diamines; bis-oximes (hydroxylamine) and bis-hydrazones (hydrazine/arylhydrazines). Useful as isolable intermediates and ligands.
• Redox: Chemoselective reduction to primary diols (NaBH4, catalytic hydrogenation). Oxidation to diacids (e.g., via nitric acid or TEMPO/bleach variants) or to dicarboxylates; careful control prevents over-oxidation.
• C–C bond formation: Wittig/Horner–Wadsworth–Emmons to access α,β-unsaturated esters/alkenes; Knoevenagel with active methylenes to create donor–acceptor systems. Aldolization under mild base to build higher frameworks (control required to avoid polymerization).
• Protection: Diacetalization with diols under acid catalysis to stabilize against oxidation during multistep sequences; deprotection regenerates aldehydes.
• Materials synthesis: Construction of dynamic covalent polymers/networks via imine exchange; metal–ligand frameworks from bis-imines.

Strategic value:

• Orthogonality allows iterative functionalization (e.g., mono-protection then diversification, followed by second-site transformation), enabling asymmetric or unsymmetrical architectures in advanced materials.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting agent or antibody. No antigen, epitope, isotype, or species reactivity information applies.

Domande frequenti

How should this product be stored?

Store at room temperature.

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

The CAS Number is 1883441-93-7.

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.