1,6-Hexadecanediol , CAS No.28047-88-3

CAS: 28047-88-3 Cat. No.: H1436580 Summenformel: C₁₆H₃₄O₂ Molekulargewicht: 258.44

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Übersicht

1,6-Hexadecanediol (Hexadecane-1,6-diol) is an ester product.

Specifications

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Namen und Kennungen

Molekulargewicht

258.44

Application Protocols

No kit- or assay-specific protocols are provided for this small-molecule reagent. Typical laboratory use cases include:

• Polymerization trials (polyester/urethane): Define stoichiometry, catalyst, and thermal/vacuum profile; monitor by FTIR, GPC, and titration (acid/OH number).
• Derivatization and activation: Plan selective protection/activation sequences to differentiate the primary vs secondary OH; verify by NMR (1H, 13C) and MS. For detailed, application-specific SOPs, adapt standard organic synthesis or polymer chemistry protocols to this substrate.

Biological Roles

No item-specific biological data are provided. The following are general observations about long-chain aliphatic diols in biochemistry (literature; not product specifications):

• Structural motifs: Long-chain diols and related hydroxyfatty derivatives are found in natural protective barriers (e.g., plant cutin/suberin monomers) and wax esters, contributing to hydrophobicity and flexibility.
• Metabolic handling: Organisms can oxidize primary alcohols to aldehydes/acids and further metabolize through β-oxidation; secondary alcohols may be oxidized to ketones prior to chain-shortening pathways.
• Materials interfaces: Diol-functional long chains can anchor to surfaces (via ester/ether linkages) to modulate wettability in biomaterials research.

Research implications:

• Surface modification: Diol termini allow covalent grafting onto carboxylated or isocyanate-bearing polymers for tuning protein adsorption.
• Probing hydrophobic interactions: As a scaffold, derivatized long-chain diols can model lipid-like segments in synthetic amphiphiles.

Note: This product is for research use only. It is not intended for diagnostic or therapeutic use.

Buffer Applications

Not typically applicable. 1,6-Hexadecanediol is a hydrophobic diol and is not used as an aqueous buffering agent. For laboratory work, consider the sections on Reaction & Applications, Synthetic Utility, and Reaction Conditions for relevant uses.

Green Alternatives

Greener practice considerations revolve around solvent choice, coupling methods, and sourcing.

• Bio-based sourcing (general): Long-chain diols can be derived from hydrogenation of bio-based fatty esters/acids. Where possible, prefer suppliers offering renewable or mass-balance certified feedstocks (not specified for this item; verify via CoA/supplier declarations).
• Solvent selection: Replace chlorinated solvents with greener options where feasible.

Comparison (general, literature-based):

• DCM/CHCl3 vs EtOAc/2-MeTHF
  • Greener option: EtOAc or 2-MeTHF reduce halogenated waste and often provide adequate solvency for diol derivatizations.
  • Trade-offs: Different evaporation rates and polarity; may need temperature or catalyst adjustments.
• DMF/DMSO vs Cyrene/GVL/PC (propylene carbonate)
  • Greener option: Cyrene or GVL can substitute in some coupling/esterification contexts.
  • Trade-offs: Higher viscosity/boiling point; compatibility with reagents must be validated.
• Dean–Stark in toluene/xylene vs azeotropes with bio-based solvents (e.g., CPME, 2-MeTHF)
  • Greener option: CPME/2-MeTHF enable efficient water removal with improved safety profiles.
  • Trade-offs: Different azeotrope behavior; check catalyst solubility.

Process intensification:

• Enzymatic esterifications (lipases) in green solvents or solvent-free melt can reduce energy input and byproducts.
• Solid acid catalysts (e.g., sulfonated resins) enable reusable systems and minimize corrosive mineral acids.

Pharmaceutical Uses

Item-specific pharmacopeial status or excipient role is not provided.

General, non-clinical context:

• Intermediate: Long-chain diols serve as intermediates to synthesize hydrophobic segments in excipient polymers (e.g., polyesters, polyurethanes) and specialty esters (emollients, waxes) used in formulations.
• Prodrug/linker research: The primary/secondary diol pattern can be leveraged to install orthogonal handles (carbonate/carbamate linkages) in medicinal chemistry workflows (research stage).
• Processing notes: When used to build polymer excipients, control of hydroxyl number, residual moisture, and color is important to achieve batch-to-batch consistency.

No claims are made regarding therapeutic activity or clinical use for this product. For regulatory suitability or compendial compliance, consult project-specific quality requirements and request a detailed CoA.

Physical Properties

Item-specific specifications not provided in the Product Data. Where literature values are mentioned, they are for general reference only (not product specifications).

Item-specific (product):

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index (if liquid): Not specified for this item; refer to CoA/Spec Sheet.
• Water/impurity limits (ppm): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties (reference, non-binding):

• Long-chain aliphatic diols (C16) are typically waxy solids at ambient temperature, with melting points well above room temperature.
• Solubility: Generally sparingly soluble in water; soluble in many organic solvents (alcohols, chlorinated solvents, ethers, and hot hydrocarbons). Actual solubility depends on temperature and solvent.
• Partitioning: High hydrophobic character from the long alkyl chain; diols exhibit low logP relative to analogous alkanes but remain lipophilic.

Practical handling notes (general):

• Warm gently (e.g., water bath) to aid dissolution or transfer if solid/waxy at room temperature.
• Drying: For water‑sensitive transformations, dry by azeotrope (toluene) or under high vacuum at mild heat; confirm dryness by Karl Fischer where needed.

Quality and Grades

The Product Data do not specify a grade or purity for this item.

• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• UV cutoff, residual solvents, water, metals: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on grades for this compound class (general, non-binding):

• Research grade: Suitable for most synthetic applications (esterification, urethane formation, protection chemistry). Verify moisture and organic impurity profile when used in sensitive polymerizations or living/controlled processes.
• High-purity/low-acid grade: Beneficial for isocyanate reactions and step-growth polymerizations (reduced side reactions, better molecular weight control). Low water and low acid value are often critical.
• Stabilizers: Aliphatic diols are typically not stabilized. If a stabilizer is present in a specific lot, it will be listed on the CoA/SDS; consider implications for downstream catalysis.

Recommendations:

• Request CoA for exact assay, residual water, and impurity profile (e.g., mono‑ols, oligomers).
• For scale-up polymer work, perform a small titration for hydroxyl number (mg KOH/g) to confirm functionality versus spec.

Reaction and Applications

1,6-Hexadecanediol is a versatile long-chain diol used as a hydrophobic, bifunctional building block.

Representative applications (literature/general):

• Polymer and materials synthesis: Monomer/chain extender in polyesters and polyurethanes; introduces flexible, hydrophobic segments that modulate Tg, crystallinity, and water uptake. Useful for polyurethane soft segments and for tailoring surface energy.
• Surfactants and specialty esters: Diester formation with fatty acids or dicarboxylic acids gives waxes and emulsifiers; can be used to tune melting behavior and lubricity.
• Selective derivatization: Exploit differential reactivity—primary OH (C1) is typically more reactive than the secondary OH (C6). Enables monotosylation/monoprotection strategies to make ω-hydroxy alkyl tosylates for further substitution (e.g., intramolecular cyclizations, Williamson ether synthesis).
• Oxidation chemistry: Primary OH can be oxidized to aldehyde/acid (e.g., Swern, TEMPO/bleach) while leaving the secondary OH intact under controlled conditions; or secondary to ketone (e.g., PCC/DMP) for orthogonal functionality.
• Click/ligation strategies: Convert OH groups to azides/halides for CuAAC or SN2 elaborations on the long chain scaffold.

Practical tips:

• For clean monotosylation, use large excess of base (e.g., pyridine or triethylamine) at 0–5 °C and slow addition of TsCl; monitor by TLC/GC.
• In polyurethane formation, maintain very low water content and use tin/bismuth catalysts as appropriate; track conversion by FTIR (NCO/NH bands).

Reaction Conditions

General literature guidance for transformations involving long-chain diols (non-binding; adjust to your system):

• Esterification (to diesters or polyesters):

  • Solvent: Toluene, xylene, or solvent-free melt; Dean–Stark for water removal.
  • Catalysts: p‑TsOH (0.5–5 mol%), sulfuric acid (trace), Ti(OBu)4 (50–200 ppm Ti) for polycondensation; enzymes (CALB) at 40–70 °C for mild conditions.
  • Temperature: 110–220 °C (polycondensation) depending on vacuum and monomer volatility.
  • Notes: Gradual pressure reduction improves molecular weight; monitor acid value and OH number.

• Urethane formation (with diisocyanates):

  • Solvent: Dry THF, toluene, or DMF; inert atmosphere.
  • Catalyst: DBTDL (10–1000 ppm Sn), bismuth or zinc catalysts as alternatives.
  • Temperature: 25–80 °C; avoid moisture; track NCO consumption by FTIR (≈2270 cm−1).

• Monotosylation/activation:

  • Solvent/base: Pyridine or DCM with Et3N; 0–5 °C addition of TsCl, then warm to RT.
  • Selectivity: Primary OH generally reacts faster; use stoichiometric control (≈1.0–1.1 equiv TsCl per diol) and low temperature to minimize ditosylation.

• Oxidations:

  • Primary-selective: TEMPO/NaOCl in biphasic CH2Cl2/H2O with buffer at 0–5 °C to RT.
  • Secondary-selective: DMP in DCM at 0–25 °C.

These ranges are representative from literature precedent; optimize conditions for scale, purity targets, and EHS constraints.

Safety and Handling

Safety details specific to this catalog item are not provided; consult the SDS for authoritative guidance.

Item-specific hazard info (from Product Data):

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

General safety considerations for long-chain aliphatic diols:

• Expected hazards: Low volatility; may cause skin/eye irritation on contact. Avoid inhalation of dust/particulates if powdered.
• PPE: Wear lab coat, safety glasses/goggles, and suitable gloves (e.g., nitrile). Use in a well-ventilated area or fume hood during weighing, melting, or reaction setup.
• Storage incompatibilities: Strong oxidizers (risk of exothermic reactions), strong acids for prolonged contact (dehydration/esterification), acid chlorides/anhydrides (reactive). Keep away from ignition sources during high-temperature operations.
• Thermal handling: If heating to melt or dissolve, avoid localized overheating. Use oil/water baths with temperature control.
• Spills: Absorb with inert material; wash surfaces with detergent. For molten material, allow to solidify where safe and scrape up.
• First aid (overview; refer to SDS): Eye/skin contact—rinse with water for several minutes; remove contaminated clothing. Ingestion—rinse mouth; seek medical advice. Inhalation—move to fresh air.

Special risks:

• Not an ether—peroxide formation is not a typical concern. Combustible organic solid; observe standard fire safety. Always defer to the item’s SDS.

Solvent Selection

As a substrate/reagent (not used as a solvent), 1,6-hexadecanediol is a lipophilic diol that dissolves better in moderately polar organic solvents.

General miscibility/solubility (literature, qualitative):

• Good: Alcohols (MeOH–iPrOH; improved hot), chlorinated solvents (DCM, CHCl3), ethers (THF, MTBE; often better warm), esters (EtOAc), polar aprotics (DMF, DMSO, NMP).
• Limited: Alkanes (hexanes, heptane) unless hot; aromatics (toluene) often require heat.
• Poor: Water at ambient temperature.

Selection tips by application:

• Esterification/transesterification: Toluene, xylene, toluene–heptane, or aromatic solvents under Dean–Stark to remove water; or use polar aprotics (DMF/DMSO) with coupling agents.
• Urethane formation with diisocyanates: Anhydrous toluene, THF, or DMF under inert gas; control viscosity by co-solvent.
• Etherification/tosylation: DCM, CH2Cl2/DMF mixtures, or pyridine as base/solvent.
• Oxidation of the primary vs secondary OH: Choice of solvent can help selectivity (e.g., DCM for Dess–Martin, DMSO/CH2Cl2 for Swern-like conditions).

Small comparison (general):

• THF: Good solvency, enables low‑temperature control; must be anhydrous.
• DMF/DMSO: Excellent solvency for polar reagents; challenging workup; consider odor and EHS.
• Toluene/xylene: High-temp esterifications and water removal; lower polarity may limit rates without catalysis.

Storage and Reconstitution

Item-specific instructions (from Product Data):

• Storage: Store at -20°C.
• Shipping: Ice chest + ice pads.
• Research use: For research use only.

General guidance for this compound class:

• Container: Keep tightly closed in a clean, dry, inert container. Protect from moisture and prolonged exposure to air to limit oxidative discoloration.
• Handling state: If solid/waxy at room temperature, warm gently (≤50 °C) to melt for aliquoting or dissolution. Avoid overheating.
• Inerting: For long-term storage after opening, consider purging headspace with dry nitrogen/argon and adding desiccant in the outer container.
• Solubility for use: Dissolve in suitable organic solvents (e.g., THF, DCM, alcohols, DMF/DMSO) as required by the application. Use anhydrous grades for moisture-sensitive reactions.
• Stability: Aliphatic diols are generally stable; avoid strong oxidants and acids during storage. If discoloration occurs, consider purification (recrystallization) prior to critical applications.
• Thawing after cold storage: Allow container to reach room temperature in a desiccator before opening to prevent moisture condensation.

Structure and Identity

1,6-Hexadecanediol is a long-chain aliphatic diol featuring one terminal hydroxyl group and one internal (secondary) hydroxyl along a 16‑carbon saturated backbone.

• Product name: 1,6-Hexadecanediol (SKU: H1436580)
• CAS: 28047-88-3
• Category: Life Science reagents (research use only)
• Structural class: Long-chain aliphatic diol (fatty diol)
• Functional groups: One primary alcohol (C1) and one secondary alcohol (C6) on a C16 saturated chain; no rings; no unsaturation; no heteroatoms beyond the two oxygens.

Item-specific identifiers from Product Data:

• 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.

Literature/general identity (for reference only; not item specifications):

• Typical molecular formula (literature): C16H34O2 for C16 aliphatic diols
• Typical molecular weight (literature): ~258.44 g/mol for C16H34O2
• 2D description (literature): A linear C16 chain with –CH2OH at C1 and –CHOH– at C6; remaining positions are methylene groups. The C6 center is prochiral and bears a hydroxyl substituent (secondary alcohol).

Synthetic Utility

Functional group profile and reactivity (general):

• Two alcohols with differing environments enable selective chemistry: primary OH (C1) more nucleophilic and easier to activate than the secondary OH (C6).
• Activation: Convert to sulfonates (OTs/OMs), halides (Appel, PPh3/CX4), or carbonates for subsequent substitution or coupling.
• Protection: Use silyl ethers (TBDMS/TBS) or acetal/benzyl strategies to mask one OH and functionalize the other; orthogonal protection is feasible given reactivity differences.

Representative transformations:

• Esterification/transesterification with diacids/anhydrides to make polyesters/diesters; catalyze with acids (p‑TsOH), organocatalysts, or enzymes (CALB).
• Urethane/urethane networks via reaction with diisocyanates (MDI, HDI); tune stoichiometry and catalysts (DBTDL, bismuth) for desired mechanical properties.
• Selective oxidation: Primary → aldehyde/acid (TEMPO/NaOCl, Swern), secondary → ketone (DMP, PCC) enabling bifunctional substrates for further elaboration.
• Intramolecular cyclizations after monoactivation to generate medium/large ether rings or to install leaving groups at defined positions along the chain.

Retrosynthetic value:

• Serves as a linear C16 spacer with two handle points; useful for building amphiphiles, surface modifiers, or as a soft segment precursor in segmented copolymers.

Target Specificity

Not applicable. This product is a small-molecule diol, not a biological targeting reagent, antibody, or probe with defined target specificity.

Häufig gestellte Fragen

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

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

The CAS Number is 28047-88-3, the molecular formula is C16H34O2, and the molecular weight is 258.44 g/mol.

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.