Decane-1,9-diol - ≥95% , CAS No.3208-05-7

CAS: 3208-05-7 Cat. No.: D952114 Formula: C₁₀H₂₂O₂ Molecular Weight: 174.280 EC Number: 823-792-7

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifications & Purity

≥95%

Storage

Room temperature

Purity

≥95%

Names and Identifiers

• Canonical Smiles: CC(CCCCCCCCO)O
• IUPAC Name: decane-1,9-diol
• InChIKey: BRBMYNGGGPTKKL-UHFFFAOYSA-N
• INCHI: 1S/C10H22O2/c1-10(12)8-6-4-2-3-5-7-9-11/h10-12H,2-9H2,1H3
• Molecular Weight: 174.280

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Fatty Acyls
      • Subclass Fatty alcohols

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Fatty Acyls
• Subclass: Fatty alcohols
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty alcohols
• Alternative Parents: Secondary alcohols Primary alcohols Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty alcohol - Secondary alcohol - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Alcohol - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms.
• 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

Chemical and Physical Properties

• Molecular Weight: 174.280 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 8
• Exact Mass: 174.162 Da
• Monoisotopic Mass: 174.162 Da
• Topological Polar Surface Area: 40.500 Ų
• Heavy Atom Count: 12
• Formal Charge: 0
• Complexity: 83.900
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

Not applicable in the immunoassay/diagnostic sense.

• No WB/IHC/IF/FC protocols apply to this small‑molecule reagent. For synthetic applications, see the Reaction Conditions and Synthetic Utility sections for practical guidance on typical transformations.

Biological Roles

Applicability

• Decane-1,9-diol is a synthetic aliphatic diol and is not a known primary metabolite. Biological roles are limited and indirect.

General context (literature)

• Long‑chain aliphatic diols and related fatty alcohol derivatives can appear as minor constituents in waxes, coatings, and hydrophobic barriers in biological systems, but specific occurrence of 1,9‑decanediol is not documented as a major natural metabolite.
• Hydroxylated decanes may interact with lipid bilayers due to the hydrophobic C10 chain and hydrophilic headgroups, but defined biochemical signaling roles are not established.

Laboratory use related to biology (non‑clinical)

• As a hydrophobic diol, it can be used to prepare surface coatings, polymer matrices, or amphiphiles for biochemical assays after further derivatization (e.g., forming diesters, carbamates, or attaching linkers). Such uses depend on downstream chemistry rather than inherent biological activity.

Note

• No therapeutic, diagnostic, or in vivo claims are made for this product. It is supplied strictly for research use only.

Buffer Applications

Not typically applicable.

• Decane-1,9-diol is a hydrophobic diol and does not function as an acid–base buffer in aqueous systems. If used in biological workflows, it would be as a component of materials or as a substrate for derivatization, not as a buffering agent.
• For work requiring aqueous handling, use co‑solvents or emulsifiers; select conventional buffer systems (e.g., phosphate, HEPES) appropriate to your pH range.

Green Alternatives

Context

• Decane-1,9-diol is a hydrocarbon‑based diol used as a building block. Green considerations therefore focus on solvent choice, catalysts, and sourcing rather than substituting the diol itself.

Greener processing options (literature/general)

• Bio‑based sourcing: Consider bio‑derived long‑chain alcohols/diols (from fatty acid hydrogenation/bioconversion) to reduce fossil carbon intensity when specifications allow.
• Solvent selection: Favor low‑toxicity, recyclable solvents—e.g., 2‑MeTHF or CPME in place of THF/toluene where compatible; ethyl acetate instead of dichloromethane for extractions.
• Catalysis: Employ organocatalysts (e.g., TBD, DBU) or enzyme catalysis (lipases) for esterifications at lower temperatures and with reduced waste; avoid stoichiometric chlorinating agents by using DMC (dimethyl carbonate) for carbonate/urethane formation.
• Energy: Conduct melt or solvent‑free reactions where feasible (bulk esterification/urethane formation), with vacuum or inert sweep to remove condensates.

Illustrative comparison (general)

• THF vs 2‑MeTHF: Similar solvency and reactivity support for many transformations; 2‑MeTHF often affords easier phase separations and is produced from bio‑based furfural, though it can have higher peroxide tendency than THF and different azeotropes.
• Dichloromethane vs Ethyl acetate: EA offers lower toxicity and easier biodegradability but may require higher temperatures and offers different solubility windows.

Trade‑offs

• High‑boiling green ethers/esters can complicate solvent recovery. Ensure LCA/energy balances consider distillation loads. Catalyst recyclability and product color are also practical constraints in polymer work.

Pharmaceutical Uses

Formulation/manufacturing context (general; no clinical claims)

• Excipients/building blocks: Long‑chain diols can serve as intermediates to synthesize specialty excipients (e.g., diesters used as hydrophobic plasticizers in coatings or sustained‑release matrices). The asymmetry of 1,9‑decanediol offers opportunities for regioselective derivatization to produce mono‑functionalized materials.
• Surface and device modification: After further functionalization, diol‑derived coatings can modulate hydrophobicity or provide anchor points for PEGylation or ligand attachment on device surfaces.
• Prodrug/linker chemistry: The diol motif can be transformed into carbonate/carbamate linkers; the secondary hydroxyl can offer different stability and enzymatic cleavage profiles relative to primary hydroxyls, enabling fine‑tuning in research settings.

Regulatory/quality note for this item

• Pharmacopeial status (USP/Ph. Eur.) and specific excipient grades are Not specified for this item; refer to CoA/Spec Sheet if a compendial grade is required.
• For GMP or clinical manufacturing, ensure appropriate qualification, impurity control (including residual solvents and aldehydes), and extractables/leachables assessments for the intended use.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff, metal/peroxide/water limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general physical data for 1,9-decanediol (for context only; not item specifications)

• Molecular formula: C10H22O2
• Formula weight: ~174.28 g/mol
• Phase at ambient: Typically a low‑melting waxy solid or high‑boiling viscous liquid among C10 diols; exact mp/bp for the 1,9‑isomer varies by source.
• Polarity: Moderately polar due to two hydroxyls; substantially less polar than short‑chain diols because of the long aliphatic segment.
• Solubility: Sparingly soluble in water; miscible with many organic solvents capable of hydrogen bonding (alcohols, ketones, ethers such as THF) and soluble in chlorinated and aromatic solvents upon warming.
• Partitioning: Expected high logP relative to short‑chain diols owing to the C10 chain (qualitative).

Practical handling notes (general)

• Melting behavior of long‑chain diols can show range/broadness due to crystallinity; gentle warming may be required for dissolution or transfer.
• Drying can be achieved by azeotropic removal of water with toluene or by storing over molecular sieves in suitable solvents.

Always consult the item’s CoA/SDS for authoritative, item-specific physico-chemical data.

Quality & Grades

Item-specific

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

General guidance for this class of material

• Research grade diols are commonly offered with assay by GC/GC–MS or 1H NMR, and controlled limits on related alcohols/alkenes and residual solvents. When used for polymer synthesis (polyesters, polyurethanes), trace water and acidity can affect molecular weights—request Karl Fischer and acid value data if critical.
• Color/appearance: Long‑chain diols may range from white/off‑white solids to colorless viscous liquids. Color numbers (APHA/Hazen) are sometimes reported for polymer‑grade material to control chromophore formation during melt processing.
• Metals/ions: For catalysis‑sensitive processes, low metals may be desired. If your application is catalyst‑mediated (e.g., Ru, Pd), ask for ICP trace metals when needed.
• Low UV/Chromatography suitability: If the diol is to be used as a mobile phase modifier or analyzed by HPLC/UV, low UV‑absorbing impurities are beneficial; “HPLC grade” denotes minimized background but is uncommon for diols.
• Peroxide content: Not generally applicable (diols are not autoxidizable ethers); however, oxidative impurities can form upon prolonged heating/air exposure—specify peroxide or carbonyl limits if photostability is critical.

Recommendation

• For polymerization or precision synthesis, request: assay, water (KF), acid value, residual solvents, and where applicable, color and trace metals. Default to the item’s CoA for acceptance criteria.

Reaction & Applications

Focus and use cases (literature/general; expandable from typical manufacturer applications for aliphatic diols)

• Polymer/intermediate synthesis: Serves as a diol comonomer for polyesters, polycarbonates, and polyurethanes. Its asymmetry (primary vs secondary OH) can impart differential reactivity, enabling gradient or blocklike segment incorporation and influencing Tg/Tm.
• Step‑growth esterification: Reacts with diacids/diacyl chlorides under Fischer or Schotten–Baumann conditions to generate polyesters or diesters. Primary OH typically reacts faster than the secondary OH, allowing kinetic control or selective mono‑acylation.
• Urethane formation: Couples with diisocyanates (e.g., MDI, HDI) to form polyurethanes or telechelic prepolymers; catalyzed by organotin or tertiary amines under anhydrous conditions.
• Functional group interconversions: Sequential, chemoselective activation is possible—e.g., selective tosylation/mesylation of the primary alcohol followed by intramolecular cyclization to form substituted cyclic ethers; or displacement with halides/azides to access ω‑functionalized alcohols.
• Oxidations: TEMPO/bleach or Dess–Martin periodinane can oxidize the primary OH to the corresponding aldehyde/acid while leaving the secondary OH intact (with control), enabling hydroxy‑acid or lactone synthesis.
• Surface modification: Long‑chain diols adsorb on hydrophobic substrates and can be used to prepare SAMs or grafted layers after further derivatization.

Practical tips

• Use stoichiometry and catalysts to exploit differential OH reactivity. Protecting groups (e.g., TBDMS for the secondary OH) can provide orthogonality when precise architectures are required.
• Maintain dryness for isocyanate and acyl chloride chemistry; water competes and lowers degree of polymerization.
• For selective transformations, temperature and base choice (pyridine, triethylamine, DMAP) strongly influence rates and selectivity.

Reaction Conditions

General literature guidance (typical ranges; not item-specific)

• Fischer esterification (diesters/polyesters): Carboxylic acid (1.0–1.2 eq per OH), catalytic p‑TsOH (1–5 mol%), toluene or xylene, Dean–Stark water removal, 110–150 °C, 4–24 h. For higher DP polyesters, reduced pressure or inert gas sweep is employed.
• Steglich esterification (selective mono‑acylation): Carboxylic acid (1.0–1.1 eq), DCC or EDC (1.1–1.2 eq), DMAP (5–10 mol%), CH2Cl2/DMF, 0 °C to rt, 2–16 h; primary OH reacts faster than secondary OH.
• Tosylation/mesylation: TsCl or MsCl (1.1–1.5 eq), pyridine or Et3N (2–3 eq), CH2Cl2, 0 °C to rt, 1–6 h; selective activation of the primary OH is favored at lower temperatures and with steric control.
• Urethane formation: Diisocyanate (≈1.0 eq per OH), tin(II) octoate or tertiary amine catalyst (0.01–0.1 wt%), dry THF/EtOAc/DMF or bulk, 50–90 °C, 2–8 h; strictly anhydrous to avoid CO2 foaming and chain termination.
• Oxidation (primary OH to aldehyde/acid): TEMPO (5–10 mol%), NaOCl (bleach), KBr cocatalyst, pH ~9–10, 0–5 °C to rt, 0.5–4 h for aldehyde; extended time or NaClO2 for acid. Alternatively, DMP (1.5 eq), CH2Cl2, 0 °C to rt, 1–2 h.
• Intramolecular etherification: After tosylation, NaH (1.5–2.0 eq), THF, 0 °C to reflux, 1–6 h for cyclization to medium rings; yields depend on ring size and dilution to minimize intermolecular pathways.

Notes

• Monitor chemoselectivity via 1H NMR (diagnostic primary vs secondary CH–OH signals) or LC–MS.
• Use molecular sieves (3 Å) or azeotropic techniques for water management in condensation steps.
• Reported yields vary widely (50–90% for esterifications; polymer DPs are process‑dependent). Optimize stoichiometry and removal of condensates.

Safety & Handling

Item-specific safety info from Product Data

• GHS signal word, hazard statements, classifications, pictograms: Not specified for this item; refer to SDS.

General safety considerations for long‑chain aliphatic diols (literature/industry practice; not item-specific)

• Expected hazards: Typically low acute toxicity and low volatility; may cause skin/eye irritation. Avoid inhalation of aerosols/mists and prolonged skin contact.
• PPE: Safety glasses with side shields, lab coat, and appropriate chemical‑resistant gloves (e.g., nitrile). Use in a well‑ventilated area or fume hood during reactions or heating.
• First aid overview: Eye—rinse cautiously with water for several minutes; remove contact lenses if present. Skin—wash with soap and water. Ingestion—rinse mouth; seek medical advice. Inhalation—move to fresh air.
• Handling: Minimize moisture ingress during reactions where the hydroxyl functionality or dryness is critical (e.g., isocyanate chemistry, acid chloride esterifications). Prevent contact with strong oxidizers and strong acids/bases that may induce side reactions or degradation.
• Thermal considerations: When heating to melt/dissolve, use controlled temperatures to avoid decomposition; do not heat in sealed vessels without appropriate pressure relief.
• Spill/cleanup: Absorb with inert material (vermiculite, sand), collect for disposal. Residuals can be cleaned with warm alcohols or surfactant solutions.
• Waste: Dispose in compliance with local regulations. Do not release to the environment.

Definitive hazard classification, exposure limits, and transport information must be taken from the product’s SDS.

Solvent Selection

Applicability

• Decane-1,9-diol is a reactive building block rather than a routine laboratory solvent. This section discusses solvent choices for dissolving/processing it in synthesis and purification.

General solubility/miscibility guidance (literature/general)

• Polar protic: Good solubility in methanol, ethanol, isopropanol upon warming; hydrogen bonding aids dissolution.
• Polar aprotic: Soluble in DMF, DMSO, NMP, and THF; these are common media for esterifications, tosylations, and polymerizations.
• Less polar: Solubility increases with temperature in toluene, xylene, chlorobenzene, and dichloromethane; often used for Fischer esterification (with Dean–Stark in toluene) or for melt‑phase reactions.
• Aqueous systems: Sparingly soluble in water; use co‑solvents or emulsification if aqueous processing is needed.

Selection tips by operation

• Esterification/polycondensation: Toluene or xylene (azeotropic water removal) or high‑boiling polar aprotics (NMP, DMF) when catalysts like DMAP/EDC are used at moderate temperatures.
• Urethane formation with diisocyanates: Bulk/melt or in dry ethyl acetate, THF, or DMF; rigorously anhydrous conditions are essential.
• Nucleophilic substitution after activation (tosylates/mesylates): Polar aprotic solvents (DMF/DMSO/MeCN) benefit SN2 steps.
• Purification: Recrystallization (if solid) from alcohols or alcohol/toluene mixtures; otherwise vacuum distillation for low‑volatility fractions may be impractical—use column chromatography with polar eluents as needed.

Comparison note

• Versus symmetric α,ω‑diols (e.g., 1,10‑decanediol), the asymmetric 1,9‑isomer may show slightly different solubility/crystallinity; screen solvents accordingly.

Storage & Reconstitution

Item-specific (from Product Data)

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

General guidance for this class of material

• Container: Store in a tightly closed container to limit moisture ingress and contamination. Amber glass is preferred if long storage or elevated temperatures are expected, although aliphatic diols have low photosensitivity.
• Atmosphere: Inert gas blanket (nitrogen/argon) is optional but beneficial for long‑term storage to minimize slow oxidative discoloration.
• Desiccation: Recommended if precise water content is important for your process (e.g., isocyanate reactions). Dry over molecular sieves prior to critical steps if needed.
• Handling: If solid at room temperature, gentle warming (30–60 °C) may be used to liquefy for dispensing. Avoid overheating and prolonged exposure to air when warm.
• Reconstitution: If supplied as a solid/waxy material, dissolve in a compatible dry solvent (e.g., anhydrous THF, DMF, or alcohols) with mild heating and stirring. Filter if needed to remove particulates.
• Freeze–thaw: Not typically applicable; avoid repeated heating/cooling cycles that can introduce moisture and impurities.

Always consult the product’s CoA and SDS for item-specific storage stability, packaging, and handling information.

Structure & Identity

Item-specific (from Product Data)

• SKU: D952114
• Product name: Decane-1,9-diol
• CAS: 3208-05-7
• InChIKey: 32147 (as provided)
• Storage: Room temperature

Literature/computed identifiers and structural description (general reference; not item-specific specifications)

• Synonyms: 1,9-decanediol; decane-1,9-diol; 9-hydroxydecan-1-ol
• Molecular formula (literature): C10H22O2
• Molecular weight (literature): ~174.28 g/mol
• SMILES (literature): OCC(CCCCCCC)CCO or HOCH2-(CH2)7-CH(OH)-CH3 (one of several equivalent linear representations)
• Structural features: A linear C10 aliphatic chain bearing two hydroxyl groups: one primary alcohol at C-1 (–CH2OH) and one secondary alcohol at C-9 (–CHOH–), rendering the molecule an unsymmetrical, near-α,ω-diol.
• Stereochemistry: The carbon at C-9 is a secondary alcohol and can, in principle, be a stereocenter when substituted; for the free diol it is typically supplied as racemic unless otherwise specified.
• 2D description in words: A straight ten‑carbon backbone. At one terminus (C-1) is a primary hydroxymethyl group; near the other terminus (C-9) the methylene is replaced by a methine bearing a hydroxyl, with a terminal methyl at C-10. No rings, no heteroatoms other than oxygen, and no additional functional groups.

Note: Exact identifiers (SMILES/InChIKey) for this catalog item are not specified beyond what is listed above; refer to the CoA/Spec Sheet for definitive item-specific identifiers.

Synthetic Utility

Functional group profile

• Two alcohols of differing substitution—one primary (C‑1) and one secondary (C‑9)—enable chemoselective strategies.

Key transformations (literature/general)

• Selective protection: Preferentially protect the secondary OH (e.g., TBDMS, TBS) leaving the primary OH for further elaboration, or vice versa using bulky chloroformates or cyclic acetals/carbonates.
• Differential acylation/alkylation: Kinetic control often favors acylation of the primary alcohol (DMAP/EDC or acid chloride/pyridine); subsequent steps can target the secondary OH.
• Leaving‑group installation: Convert one OH to tosylate/mesylate; perform SN2 displacement to introduce halide, azide, or other nucleophiles to afford ω‑functionalized alcohols useful as amphiphiles or monomers.
• Oxidation/reduction: TEMPO or Swern oxidation of the primary OH to aldehyde/acid affords hydroxyaldehydes or hydroxyacids; reduction (e.g., with BH3·THF) can differentiate reactivity toward the secondary OH in certain contexts.
• Ring closures: Intramolecular Williamson ether synthesis after selective activation can produce medium‑sized cyclic ethers; alternatively, carbonate formation (triphosgene, CDI, DMC) yields cyclic carbonates.
• Polymer chemistry: Reacts with diacids/diisocyanates to form step‑growth polymers; asymmetry can disrupt crystallinity and tailor mechanical properties.

Retrosynthetic value

• Serves as a handle to introduce a single hydroxyl at either terminus of a C10 chain selectively, enabling access to 1‑hydroxy‑9‑substituted decanes and related amphiphiles.

Target Specificity

Not applicable.

• This product is a small‑molecule aliphatic diol, not a biomolecular reagent or antibody. There are no targets, epitopes, isotypes, or species reactivities associated with this item.