4-Ethynyl-2,6-dimethyl-4-heptanol - Reagent grade

Cat. No.: E483930

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

Specifiche e purezza

Reagent grade

Condizioni di conservazione di stoccaggio

Room temperature

Grado

Reagent Grade

Application Protocols

Not applicable. This product is not an antibody or assay kit and has no tested applications such as WB/IHC/IF/FC. For practical synthetic usage, refer to the Reaction Conditions and Application notes.

Biological Roles

This product is a synthetic, non-natural, branched propargylic alcohol. It is not a biomolecule, metabolite, or cofactor.

• General notes (literature/general)

  • Terminal alkynes are sometimes used as bioorthogonal handles (e.g., CuAAC “click” chemistry) after derivatization; however, this compound’s tertiary alcohol and hydrophobic skeleton limit direct aqueous/biological compatibility.
  • The tertiary alcohol lacks direct enzymatic roles and is not part of known primary metabolic pathways.

• Research-use note

  • For research use only (per Product Data). Not for human or animal therapeutic or diagnostic use.

If biochemical incorporation or labeling is intended, derivatization to more polar, biocompatible conjugates is typically required.

Buffer Applications

Not typically applicable. 4-Ethynyl-2,6-dimethyl-4-heptanol is a hydrophobic organic building block, not a buffering reagent. It does not provide useful acid/base conjugate pairs in the aqueous physiological pH range. For practical guidance, see the Synthetic Utility and Reaction & Applications sections for relevant uses in organic synthesis.

Green Alternatives

• Solvent and process considerations (literature/general)

  • For reactions involving base/acetylide chemistry, replace THF/Et2O with 2-MeTHF (bio-based, higher boiling, easier recovery) when compatible with reagents.
  • For acylations and protections, ethyl acetate or dimethyl carbonate can substitute for chlorinated solvents in many cases, reducing halogenated waste.
  • Aqueous micellar catalysis (e.g., TPGS-750-M systems) can sometimes enable alkyne hydrofunctionalizations under milder, greener conditions.

• Energy and safety

  • Prefer catalysts and conditions enabling room-temperature transformations (e.g., gold- or silver-catalyzed rearrangements in toluene/EtOAc) to lower energy input.
  • Use solid-supported coupling or flow hydrogenation to minimize solvent volumes and improve safety for hydrogenation steps.

• Comparison snapshot (general)

  • Traditional: DCM or toluene; strong bases (n-BuLi) for acetylide; elevated temperatures.
  • Greener: 2-MeTHF or EtOAc; milder bases (K2CO3, NaOtBu in 2-MeTHF) where feasible; catalytic processes (Au, Cu) and flow techniques.

Note: Verify substrate- and catalyst-compatibility experimentally; not all greener substitutions will preserve selectivity for propargylic tertiary alcohols.

Pharmaceutical Uses

This material is not an approved excipient and has no established pharmacopeial monograph (USP/EP) to our knowledge.

• Formulation context (general)

  • Hydrophobic, low-volatility alcohols of this type may occasionally serve as synthetic intermediates toward APIs or functional materials, but are not typically used directly in dosage forms.
  • Terminal alkyne functionality can be leveraged in late-stage conjugation during discovery chemistry (e.g., click-ready intermediates) rather than as a formulation component.

• Compliance note

  • For research use only (per Product Data). It is not intended for human or veterinary use in drug products. Any use in cGMP manufacturing would require independent qualification and method validation.

Physical Properties

• Item-specific specifications (this product)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet. (Literature/computed value for the named structure is ~168.28 g/mol.)
  • Other certificate-style specs (water, metals, UV cutoff, etc.): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed expectations for this structural class (tertiary propargylic alcohol, C11)

  • Physical state: typically a colorless to pale liquid for C11 tertiary alcohols; low volatility relative to lower alcohols (literature/general)
  • Boiling point: expected in the mid-to-high 200 °C range for C11 tertiary alcohols; alkyne may modestly reduce bp vs saturated analogs (literature/general; not item-specific)
  • Melting point: likely below ambient (literature/general)
  • Density: expected ~0.83–0.88 g/mL at 20–25 °C for branched C11 alcohols (literature/general)
  • Solubility: sparingly soluble in water; miscible with common organic solvents (Et2O, THF, DCM, toluene, MeOH) (literature/general)
  • LogP: estimated >2 due to C11 backbone (literature/general)
  • Refractive index: typically n20 D ~1.43–1.46 for similar alcohols (literature/general)

Notes: The above are general expectations for closely related structures and are provided for planning purposes only; do not treat as specifications. Consult the product CoA/SDS for measured values when available.

Quality and Grades

• Item-specific grade

  • Grade: Reagent Grade (per Product Data)

• What Reagent Grade implies (general guidance)

  • Suitable for most synthetic and preparative laboratory applications where high, but not ultra-trace, purity is required.
  • Not guaranteed for low UV absorbance baselines, LC-MS background, or trace-metal-critical applications unless otherwise specified.
  • Typical controls may include GC purity, identity by NMR/IR, and water content by Karl Fischer—however, exact acceptance criteria for this item are Not specified for this item; refer to CoA/Spec Sheet.

• Stabilizers/additives

  • No stabilizer information provided for this product. If present, stabilizers or inhibitors would be listed on the CoA. Not specified for this item; refer to CoA/Spec Sheet.

• Choosing this grade

  • Appropriate for building-block use, reagent screening, and method development involving alcohol transformations, protection/deprotection sequences, and alkyne chemistry.
  • For photophysical, biological assay, or trace-analysis contexts, consider requesting an application-specific CoA or higher grade if available.

Reaction and Applications

As a tertiary propargylic alcohol, 4-ethynyl-2,6-dimethyl-4-heptanol is a versatile building block in alkyne and alcohol chemistry.

• Representative transformations (literature/general)

  • Protection/deprotection: formation of TBS/TBDPS silyl ethers or carbonate esters to mask the alcohol during metalation or coupling steps.
  • Esterification/acylation: Steglich (DCC/DMAP) or acid chloride–base methods to access sterically hindered esters; useful for probe or monomer synthesis.
  • Oxidation: although tertiary alcohols resist classical oxidation to carbonyls, propargylic tertiary alcohols can undergo rearrangements (e.g., Meyer–Schuster or Ru/Au-catalyzed to enones) under acidic/metal-catalyzed conditions.
  • Dehydration: acid- or Lewis acid-catalyzed formation of conjugated enynes/allenes from propargylic tertiary alcohols.
  • Hydrofunctionalization at the alkyne: hydroboration/oxidation to carbonyl derivatives (via enol/ketone equivalents), hydrohalogenation, or hydration (often Au- or Hg-catalyzed) to give carbonyl compounds distal or proximal depending on conditions.
  • Metalation/cross-coupling: terminal alkyne enables acetylide formation (e.g., with NaNH2, LDA, n-BuLi) and subsequent additions to electrophiles or coupling (e.g., Cadiot–Chodkiewicz or Glaser-type homocoupling after derivatization).
  • Hydrogenation: selective semi-hydrogenation (Lindlar) to Z-alkenes or full saturation to alkanes while retaining/transforming the tertiary alcohol functionality as desired.

• Practical tips

  • If acetylide formation is intended, protect the alcohol (silyl or carbonate) to prevent proton exchange/side reactions.
  • Tertiary alcohol limits SN2-based functionalization at the carbinol carbon; use activation to tertiary cation equivalents (under carefully controlled conditions) or convert to derivatives (e.g., carbonates) for rearrangements.
  • Strictly exclude moisture and oxygen for organometallic steps; pre-dry solvents and glassware.

Reaction Conditions

General literature guidance for propargylic tertiary alcohols similar to 4-ethynyl-2,6-dimethyl-4-heptanol (not item-specific):

• Acetylide formation and alkylation

  • Base: n-BuLi (1.0–1.2 equiv) or NaNH2 (2–3 equiv) at −78 to 0 °C (THF or Et2O), then add electrophile at low temperature; quench at ≤0 °C. Inert atmosphere, rigorously dry glassware.

• Protection as silyl ether

  • Reagents: TBSCl (1.2–1.5 equiv), imidazole (2 equiv), DMF or DCM, 0–25 °C, 1–4 h. Workup with aqueous NH4Cl and silica gel purification.

• Dehydration to enynes/allenes

  • Conditions: catalytic TsOH or camphorsulfonic acid in toluene or CH2Cl2, 0–80 °C; or POCl3/pyridine (Vilsmeier-type) at 0–25 °C. Monitor to minimize over-rearrangement.

• Meyer–Schuster rearrangement to enones

  • Catalysts: Au(I) (e.g., Ph3PAuNTf2, 2–5 mol%) or Ru catalysts; solvent toluene or DCE; 25–80 °C, 1–12 h. Typical isolated yields 60–85% (substrate-dependent; literature).

• Hydroboration/oxidation of alkyne

  • Reagents: 9-BBN (1.1–1.5 equiv), THF, 0–25 °C; oxidative workup H2O2/NaOH. Outcome depends on substitution; terminal alkynes give aldehyde/ketone after tautomerization (literature).

• Semi-hydrogenation

  • Lindlar catalyst, H2 (1 atm), EtOAc or MeOH, 0–25 °C to convert alkyne to Z-alkene. Monitor to avoid over-reduction.

• Oxidative couplings

  • Glaser: Cu(I) salt with base (e.g., CuCl, TMEDA, O2), toluene/DMF, 20–60 °C to form diynes from terminal alkynes.

Notes: Conditions above are representative for the functional group class; optimization is required for this specific substrate due to tertiary center and branching.

Safety and Handling

• GHS/SDS information (item-specific)

  • Signal Word: Not specified for this item; refer to SDS.
  • Hazard Statements, Pictograms, Classification: Not specified for this item; refer to SDS.

• General hazards and precautions for propargylic/tertiary alcohols (literature/general)

  • Expected hazards: combustible liquid; may cause skin/eye irritation; harmful if swallowed. Terminal alkynes can be irritants. Avoid inhalation of vapors/mists.
  • PPE: wear safety glasses or goggles, lab coat, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood.
  • Incompatibilities: strong oxidizers (risk of exotherm/oxidation), strong acids (may promote dehydration/rearrangement), strong bases (can deprotonate alkyne), and reactive metals/alkali metals (acetylide formation). Separate from ignition sources.
  • 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; continue rinsing.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
  • Fire-fighting: use CO2, dry chemical, or alcohol-resistant foam; cool containers with water spray. Combustion may produce CO/CO2.

• Special risks/handling notes

  • This is not an ether; peroxide formation is not a typical concern, but periodic peroxide testing is prudent only if stored in peroxide-prone solvents.
  • Terminal alkyne proton is acidic (pKa ~25, literature) and can form metal acetylides—avoid contact with strong bases unless intended.
  • For organometallic work, dry and oxygen-free handling improves reproducibility.

Solvent Selection

This compound is a moderately hydrophobic tertiary alcohol with a terminal alkyne, expected to be water-insoluble and broadly soluble in common organic solvents.

• Polarity/miscibility profile (literature/general)

  • Water: low solubility expected for C11 tertiary alcohols
  • Miscible/soluble: ethers (THF, MTBE), chlorinated solvents (DCM, CHCl3), aromatics (toluene), and alcohols (MeOH, i-PrOH)
  • Limited solubility: acetonitrile and acetone are typically acceptable; hexanes/alkanes may dissolve depending on branching and temperature

• Selection tips by task

  • Nucleophilic substitutions/esterifications: use polar aprotic (DCM, THF) or alcohol solvents as needed; include base or coupling reagents (e.g., DCC/DMAP) as appropriate.
  • Protection as silyl ether: anhydrous DMF, DCM, or THF with imidazole or tertiary amine base.
  • Metalation of alkyne: strictly anhydrous ethereal solvents (THF, Et2O) under inert atmosphere.
  • Hydrogenation or hydrofunctionalization: toluene, EtOAc, or alcohol solvents are commonly used depending on catalyst system.

• Quick comparison (literature/general)

  • THF: enhances base solubility for acetylide formation; easy to dry; forms peroxides over time (solvent, not solute)
  • DCM: excellent for acylation/esterification with mild bases; non-coordinating; low boiling point
  • Toluene: good for higher-temperature rearrangements/dehydrations; non-polar environment reduces side reactions from ionic species

Note: Optimize solvent choice in the context of the planned transformation and catalyst/base compatibility.

Storage and Reconstitution

• Item-specific instructions (from Product Data)

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

• General handling recommendations (literature/general)

  • Keep container tightly closed in a dry, well-ventilated area. Minimize exposure to strong acids/bases and oxidizers.
  • If long-term storage is planned, consider storing under inert gas (argon or nitrogen) to limit oxidative processes, especially if container headspace is large.
  • No reconstitution is required; this is supplied neat (appearance not specified). If solidification occurs at low temperature, gently warm to ambient and mix thoroughly before use.
  • For air/moisture-sensitive operations (e.g., acetylide formation), transfer under inert atmosphere using dry syringes or cannula.

• Stability notes

  • Tertiary alcohols are generally stable at room temperature. Terminal alkynes can participate in polymerization or oxidative coupling under harsh conditions; keep away from bases and copper salts unless intended.
  • Always consult the SDS for detailed stability and incompatibility information.

Structure and Identity

Short description: 4-Ethynyl-2,6-dimethyl-4-heptanol is a branched, tertiary propargylic alcohol bearing a terminal alkyne on the carbinol carbon and methyl substituents at C2 and C6 of the heptane backbone.

• Item-specific registry data (from Product Data)

  • SKU: E483930
  • Grade: Reagent Grade
  • 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.

• Computed/literature structural interpretation (from the chemical name)

  • Core scaffold: heptane chain with hydroxyl at C4 (4-heptanol)
  • Substituents: methyl at C2 and C6; terminal ethynyl (–C≡CH) at C4
  • Functional groups: tertiary alcohol (at C4), terminal alkyne (propargylic position)
  • Stereochemistry: none specified (C4 is tertiary, but no chiral center is defined in the name)
  • Molecular formula (deduced from name; literature/computed): C11H20O
  • Molecular weight (literature/computed): ~168.28 g/mol
  • 2D description in words: a seven‑carbon main chain; C2 and C6 each carry a methyl branch; C4 is a quaternized center bonded to –OH, to the left and right chain segments (C3 and C5), and to a terminal ethynyl substituent.

Synthetic Utility

• Functional group leverage

  • Terminal alkyne: platform for C–C bond formation (acetylide additions to carbonyls, Sonogashira-type couplings after halogenation), oxidative couplings (Glaser), and selective hydrogenations.
  • Tertiary propargylic alcohol: predisposed to acid- or metal-catalyzed rearrangements (Meyer–Schuster to enones), dehydrations to enynes/allenes, and formation of stable carbonates/ethers for further transformations.

• Retrosynthetic value

  • Serves as a branch point for diversifying into enynes, enones, and conjugated systems by tuning dehydration/rearrangement conditions.
  • Alcohol protection enables orthogonal manipulation of the alkyne (e.g., halogenation to vinyl halides, hydroboration to organoboron species) without competitive proton transfer at the OH.

• Named/representative strategies (literature/general)

  • Meyer–Schuster rearrangement (acid/Au/Ru catalysis) of propargylic alcohols to α,β‑unsaturated carbonyls.
  • Semireduction with Lindlar catalyst to Z-alkenes or dissolving-metal reductions to E-alkenes, followed by further elaboration.
  • Nucleophilic substitutions at the activated propargylic position using carbonate/ester leaving groups under Pd, Cu, or Lewis acid catalysis to forge C–C or C–X bonds.

• Practical notes

  • For acetylide chemistry, protect OH (e.g., TBS) and work strictly anhydrous/inert. Control temperature to avoid rearrangements.
  • Tertiary centers impede SN2 at the carbinol; plan via elimination/rearrangement or via neighboring-group participation using suitable activators.

Target Specificity

Not applicable. This product is a small-molecule organic reagent, not an affinity reagent or biologic. No antigen/epitope or species reactivity is relevant.