Cyclohexanol, 4-ethoxy- - ≥98% , CAS No.192504-14-6

CAS: 192504-14-6 Cat. No.: C971326 Summenformel: C₈H₁₆O₂ Molekulargewicht: 144.210

GRADE & PURITY ≥98%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥98%

Storage

Room temperature

Reinheit

≥98%

Namen und Kennungen

• Kanonisches Lächeln: CCOC1CCC(CC1)O
• IUPAC Name: 4-ethoxycyclohexan-1-ol
• InChIKey: LXRDCGVUPNWEGX-UHFFFAOYSA-N
• INCHI: 1S/C8H16O2/c1-2-10-8-5-3-7(9)4-6-8/h7-9H,2-6H2,1H3
• Molekulargewicht: 144.210

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Klasse Organooxygen compounds
      • Subclass Alcohols and polyols
        • Ebene5 Secondary alcohols
          • Ebene6 Cyclohexanols

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Klasse: Organooxygen compounds
• Subclass: Alcohols and polyols
• Intermediate Tree Nodes: Secondary alcohols
• Direct Parent: Cyclohexanols
• Alternative Parents: Cyclic alcohols and derivatives Dialkyl ethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclohexanol - Cyclic alcohol - Ether - Dialkyl ether - Hydrocarbon derivative - Aliphatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as cyclohexanols. These are compounds containing an alcohol group attached to a cyclohexane ring.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 144.210 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 144.115 Da
• Monoisotopic Mass: 144.115 Da
• Topological Polar Surface Area: 29.500 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 85.300
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• 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

No assay-specific protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule reagent, and none are provided in the Product Data. For synthetic applications, see the Reaction Conditions and Synthetic Utility tabs for general literature-guided procedures. Always adapt protocols to your laboratory’s safety standards and confirm by small-scale trials.

Biological Roles

This product is intended strictly for research use (per Product Data) and is not supplied for biological administration. No biological role is specified for this item.

General context (literature-based):

• 4-Ethoxycyclohexanol is a small alicyclic organic compound with one hydrogen-bond donor and two acceptor sites. It does not correspond to a known endogenous metabolite in primary metabolic pathways.
• In biochemical assay development, related alicyclic alcohols are sometimes used as hydrophobic probes or as starting points for generating ligands by diversification (e.g., ester/urethane libraries). Any such applications require appropriate toxicology and safety assessment and remain at exploratory, non-clinical stages.
• The mixture of cis/trans diastereomers (if present) can influence physicochemical properties (e.g., lipophilicity, solubility) that in turn modulate nonspecific binding to proteins or membranes in in vitro studies; these effects are empirical and system-specific.

No enzyme targets, transporters, or signaling pathways are specifically associated with 4-ethoxycyclohexanol in the literature. Users pursuing bioassays should treat it as a generic hydrophobic secondary alcohol/ether scaffold and validate assay compatibility (e.g., solvent tolerance, protein binding) experimentally.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare biological or analytical buffers. It lacks acid/base functionality with pKa values in the physiological range that would enable effective buffering in water.

Practical note:

• When used in biochemical experiments, it is commonly dissolved in organic co-solvents (e.g., DMSO, EtOH) and then diluted into buffered aqueous media; ensure final co-solvent content is compatible with the biological system. Perform solvent-only controls.
• For pH control in reactions involving this substrate (e.g., TEMPO/bleach oxidations), select standard buffer systems appropriate to the chemistry (carbonate, phosphate, acetate), rather than relying on the substrate itself for buffering capacity.

Green Alternatives

Because Cyclohexanol, 4-ethoxy- is a building block rather than a process solvent, green considerations center on solvent choice and oxidation/activation chemistry used with this substrate.

• Greener solvent choices (literature-based):

  • Prefer 2-MeTHF or CPME over THF/Et2O for extractions and SN2 chemistry—higher boiling points, reduced peroxide risk, and biorenewable sourcing for 2-MeTHF.
  • Replace DCM with ethyl acetate or toluene where feasible (e.g., esterifications, some oxidations). MeCN can be a lower-toxicity alternative to DMF/DMSO in certain couplings.

• Oxidation alternatives:

  • Swap chromium(VI) reagents for catalytic TEMPO/bleach (NaOCl, aqueous, pH-buffered) or oxoammonium salts under mild conditions to obtain the corresponding ketone, reducing hazardous waste.
  • Use DMP (Dess–Martin periodinane) in catalytic/stoichiometric variants with careful waste handling as a compromise when selectivity is paramount.

• Coupling/activation:

  • Favor EDC•HCl/NHS (aqueous-compatible) or CDI-mediated couplings over DCC to minimize dicyclohexylurea waste.
  • Employ catalytic acid with azeotropic water removal instead of large excesses of acid anhydrides for ester formations.

• Process intensification:

  • Where applicable, consider flow chemistry for hazardous steps (e.g., acid-catalyzed dehydrations) to improve heat/mass transfer and reduce inventory of reactive intermediates.

Trade-offs: Greener media may alter rates/selectivities; solvent polarity and hydrogen-bonding strongly affect secondary-alcohol reactions. Always re-optimize conditions when changing to greener alternatives.

Pharmaceutical Uses

No pharmacopeial status, dosage form role, or excipient function is specified for this item; it is provided for research use only.

General R&D context (literature-based):

• 4-Ethoxycyclohexanol may serve as a synthetic intermediate in the discovery-phase preparation of drug-like molecules, agrochemicals, or materials. Its secondary alcohol can be converted to esters/urethanes/carbamates for SAR studies, while the ethoxy substituent modulates lipophilicity and conformational preferences on a cyclohexyl scaffold.
• The oxidized analogue (4-ethoxycyclohexanone) can undergo reductive amination to furnish amines with defined spatial arrangement—useful in lead generation.
• Any mention of therapeutic applications is beyond scope; no clinical or medical claims are made here. Compliance with regulatory guidance is required before any use in manufacturing or clinical settings.

Physical Properties

• Item-specific properties (from Product Data):

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Storage Conditions: Room temperature (per Product Data).
  • Shipped In: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed (general reference for 4-ethoxycyclohexanol; values may vary with isomer ratio and purity):

  • Molecular formula: C8H16O2 (literature)
  • Molecular weight: ~144.21 g/mol (literature)
  • Physical state: typically a low-melting solid or high-boiling liquid depending on cis/trans composition (literature, qualitative).
  • Boiling point: not firmly established in the literature for unspecified isomeric mixtures; expect a higher bp than cyclohexanol (bp 161 °C, literature) due to increased molecular weight and polarity of the ether (qualitative guidance).
  • Melting point: isomer-dependent; often below ambient for mixtures; specific mp not established (literature varies).
  • Density, refractive index, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
  • Solubility (qualitative, literature): sparingly soluble in water; miscible with many organic solvents (alcohols, ethers, ketones, esters, chlorinated solvents). Hydrogen-bond donor (OH) and acceptor (both O atoms).
  • logP/pKa: Specific values not established for this item; typical secondary alcohol pKa ~16–18 in water (literature, qualitative). No relevant aqueous pKa in the physiological range.

For authoritative specifications used for QC/release, consult the product CoA.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• Guidance on interpreting grades (general):

  • Research grade: intended for R&D laboratory use; impurity limits tailored to synthetic or analytical use, not for clinical applications.
  • Analytical/HPLC grade (if applicable): stringently controlled for low UV absorbance/particulates to minimize chromatographic baseline noise and ghost peaks.
  • Reagent/ACS grade (if applicable): conforms to compendial impurity limits for common inorganic/organic contaminants, facilitating reproducibility in synthesis.

• Stabilizers and additives: None are specified for this item. If stabilizers or antioxidants were present, they would be listed on the CoA; these can influence reactivity (e.g., acid-catalyzed transformations, oxidative steps) and may require removal prior to sensitive reactions.

• What to check on receipt (practical QC tips):

  • Verify stereochemical composition (cis/trans 1,4 isomers) where relevant—diastereomeric ratio can affect physical properties and reactivity (e.g., conformational preferences in esterification or oxidation rates).
  • Confirm identity by 1H/13C NMR and IR (broad OH stretch ~3200–3600 cm−1; C–O stretches for alcohol and ether), and assess purity by GC/GC–MS or HPLC as appropriate.
  • Water content and residual solvents: Not specified for this item; refer to CoA/Spec Sheet if Karl Fischer or residual solvent data are required.

Reaction and Applications

4-Ethoxycyclohexanol is a versatile intermediate combining a secondary alcohol with an alkyl ether on a cyclohexane scaffold. Typical synthetic uses (literature-based) include:

• Oxidation to ketone: The secondary alcohol can be oxidized to 4-ethoxycyclohexanone using DMP, PCC, Swern, or TEMPO-based systems. The resulting ketone is a useful handle for further transformations (e.g., reductive amination, enolate chemistry, Baeyer–Villiger oxidation).
• Esterification/Carbonate formation: Reaction with acyl chlorides/anhydrides (or via DCC/EDC coupling) affords esters; reaction with chloroformates affords carbonates—valuable for polymer and pro-moiety studies in materials chemistry.
• Activation as leaving group: Conversion to tosylate/mesylate enables subsequent SN2 substitutions (e.g., halide, azide, thiolate), mindful that secondary centers may require optimized conditions or neighboring-group assistance.
• Dehydration/Elimination: Acid-catalyzed dehydration can furnish 4-ethoxycyclohexene (or isomeric alkenes), enabling hydrofunctionalization or epoxidation sequences.
• Ether stability/exchange: The ethoxy substituent is robust under many basic/neutral conditions; under strong Lewis/Brønsted acids (BBr3, HI, conc. HBr), ether cleavage to 4-hydroxycyclohexanol may be achieved, allowing orthogonal deprotection strategies.
• Protecting-group logic: The alcohol can be protected (e.g., TBDMS, TMS, benzyl) when orthogonal manipulation of the ether is needed; conversely, the ether can serve as a “permanent” lipophilicity modulator while the alcohol is diversified.

Applications span medicinal chemistry scaffolding, agrochemical intermediate synthesis, and materials monomer development—strictly for research use (per Product Data).

Reaction Conditions

General literature guidance for common transformations of 4-ethoxycyclohexanol (optimize per your substrate, scale, and isomer ratio):

• Oxidation to 4-ethoxycyclohexanone:

  • DMP (1.3–1.6 equiv) in DCM, 0–25 °C, 1–3 h; workup with aqueous NaHCO3/Na2S2O3. Typical good to excellent conversions reported for analogous secondary alcohols.
  • TEMPO (1–5 mol%), NaOCl (1.5–2.0 equiv active chlorine) in biphasic CH2Cl2/H2O or EtOAc/NaHCO3 buffer, 0–10 °C; quench with Na2S2O3.
  • Swern: oxalyl chloride/DMSO at −78 °C, then Et3N, giving ketone cleanly; stringent low-temperature control required.

• Esterification/Carbamate formation:

  • Acyl chloride (1.1–1.5 equiv), base (pyridine, Et3N) in DCM or toluene, 0–25 °C, 1–12 h.
  • CDI (1.2–1.5 equiv) in THF/MeCN, 25–50 °C for carbamates/urethanes with amines/alcohols.

• Activation/substitution (via sulfonate):

  • TsCl (1.2–1.5 equiv), DMAP (0.1 equiv), Et3N (2–3 equiv) in DCM, 0–25 °C; then SN2 with NaN3, NaI, or thiolates in DMF/MeCN, 50–90 °C as needed. Monitor for competing E1/E2.

• Dehydration to alkene:

  • p-TsOH (5–10 mol%) in toluene, reflux with Dean–Stark, 2–6 h; or POCl3/pyridine at 0–25 °C. Secondary substrates can give Zaitsev products; confirm regioisomer ratios by NMR/GC.

• Ether cleavage (if required):

  • Concentrated HI/HBr (aq) or BBr3 (for aryl/activated ethers; aliphatic ethers require harsher conditions). Control temperature and time carefully to avoid overreaction.

These conditions are representative of standard secondary-alcohol chemistry; adjust equivalents, temperature, and time based on scale and desired selectivity.

Safety and Handling

• Item-specific hazard information (per 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 laboratory safety guidance (literature-based, not a substitute for SDS):

  • Likely hazards: Organic alcohol/ether combinations are commonly combustible and may cause skin/eye irritation. Avoid sources of ignition and aerosol formation. Handle in a well-ventilated fume hood.
  • Personal protective equipment: lab coat, safety glasses or chemical splash goggles, and suitable gloves (e.g., nitrile). For bulk handling or heating, consider face shield and flame-resistant lab coat.
  • Incompatibilities: Strong oxidizers (risk of exothermic reaction), strong acids (can catalyze ether cleavage/dehydration), strong bases (can promote deprotonation and elimination). Avoid reactive acid halides/anhydrides without appropriate controls.
  • Special risks: Although not a low-molecular-weight ether solvent, peroxide formation in alkyl ethers can occur under prolonged air/oxygen exposure; the ethoxy substituent itself is generally stable, but routine good practice is to store tightly closed and away from light/heat. Avoid distilling to dryness.
  • First aid overview: Inhalation—move to fresh air. Skin—wash with soap and water. Eyes—rinse cautiously with water for several minutes; remove contact lenses if present and easy. Ingestion—rinse mouth; do not induce vomiting; seek medical attention. Provide SDS to healthcare personnel.

Always consult the product-specific SDS for definitive hazard classification, exposure limits, spill response, and firefighting measures.

Solvent Selection

This product is a cycloaliphatic alcohol/ether building block rather than a common laboratory solvent. Solvent selection guidance here focuses on dissolving and reacting 4-ethoxycyclohexanol efficiently.

• Polarity and miscibility (qualitative, literature):

  • Amphiphilic: hydrogen-bond donor (OH) and acceptor (two O atoms) with a hydrophobic ring/ethyl chain. Sparingly soluble in water; readily soluble in polar aprotic (AcOEt, MeCN, DMSO, DMF), ethers (THF, MTBE), alcohols (MeOH, EtOH), and chlorinated solvents (DCM, CHCl3).

• Choosing media for common operations:

  • Esterifications/acylations: use aprotic solvents (DCM, toluene, THF) with base (pyridine, DIPEA) or acid catalysts (p-TsOH) and water scavengers. For carbodiimide couplings (DCC/EDC), DCM or DMF are typical.
  • Oxidations to ketone: DCM/AcOEt for Dess–Martin or Swern; acetone/MeCN for TEMPO–bleach systems (biphasic with buffer).
  • Nucleophilic substitutions after leaving-group installation (e.g., tosylate): polar aprotic solvents (DMF, DMSO, MeCN) increase SN2 rates.
  • Dehydrations: toluene or xylene with acid catalysts and Dean–Stark to remove water, or neat under reduced pressure.

• Practical tips:

  • If crystallization is desired, screen alcohol/ether/ester solvent mixtures; cis/trans ratio can strongly influence crystallinity.
  • Avoid strong acids in protic media when preservation of the ethoxy ether is required; acid can catalyze C–O bond cleavage in ethers.

For green chemistry considerations, see the Green Alternatives tab.

Storage and Reconstitution

• Storage (Product Data):

  • Store at room temperature.

• Practical storage guidance (general best practices):

  • Keep container tightly closed in a dry, well-ventilated place. Minimize exposure to air and moisture to prevent slow oxidation or hydrolysis under harsh conditions.
  • Protect from strong light and heat sources. If long-term storage is anticipated, consider storing under inert gas (nitrogen/argon) and using amber glass to limit photodegradation.
  • Avoid contact with strong acids or oxidizers in storage areas to prevent accidental reactions.

• Reconstitution/handling:

  • The product is a neat organic liquid/solid; no aqueous reconstitution is required. For solution preparation, use dry, oxygen-free solvents when conducting moisture-sensitive reactions. Prepare stock solutions in compatible solvents (e.g., DCM, THF, EtOAc, MeCN, or alcohols) and store at 2–8 °C if stability studies indicate benefit; otherwise use fresh.
  • If crystallization or precipitation occurs upon cooling, gently warm to ambient and swirl to redissolve, or sonicate briefly. Record any observed changes as part of material control.

• Shelf-life/specifications:

  • Specific shelf-life, water content, and impurity limits are not specified for this item; refer to the CoA/Spec Sheet and SDS for item-specific guidance.

Structure and Identity

Cyclohexanol, 4-ethoxy- is a bifunctional alicyclic compound bearing both an alcohol and an alkyl ether on a cyclohexane ring.

• Item-specific identifiers (Product Data):

  • SKU: C971326
  • CAS: 192504-14-6
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (general reference information):

  • Common name: 4-ethoxycyclohexanol (para-substituted relative to the ring carbon bearing OH)
  • Molecular formula (literature): C8H16O2
  • Molecular weight (literature): ~144.21 g/mol

• Structural features (general description):

  • Core: saturated six-membered cyclohexane ring.
  • Functional groups: secondary alcohol (–OH) at C1; ethoxy substituent (–O–CH2–CH3) at C4 (1,4-disubstitution pattern).
  • Stereochemistry/conformation: exists as cis/trans 1,4-disubstituted diastereomers; in chair conformations, the lowest-energy forms place both substituents equatorial (trans-1,4-di-eq favored). No defined absolute stereochemistry unless a single diastereomer is specified.
  • 2D depiction in words: a cyclohexane ring with an OH group on one carbon and, four atoms away around the ring, an ethoxy group attached via an oxygen to the ring carbon; remaining positions are unsubstituted hydrogens.

Notes: Exact stereochemical composition, SMILES, and registry-specific identifiers for this catalog item are not specified; consult the CoA/SDS for definitive item-specific identity.

Synthetic Utility

Key functional elements and reactivity (literature-based):

• Secondary alcohol (chemoselective handle):

  • Oxidation to ketone (DMP, Swern, TEMPO/NaOCl) enables enolate chemistry, aldol reactions, and reductive amination from the ketone stage.
  • Esterification/urethane formation with acyl chlorides/anhydrides or chloroformates; CDI or EDC/NHS methods provide milder alternatives.
  • Conversion to sulfonates (Ts, Ms) for substitution chemistry; careful optimization needed due to secondary center and potential elimination.

• Alkyl ether (ethoxy) substituent:

  • Generally inert under many basic conditions, offering orthogonality to alcohol manipulations.
  • Acid-promoted cleavage (HI, HBr, BBr3, strong Lewis/Brønsted acids) returns the corresponding 4-hydroxycyclohexanol, enabling late-stage deprotection should removal be desired.
  • Can direct conformational preferences (favoring equatorial placement) that subtly impact stereochemical outcomes in neighboring transformations.

• Ring-based transformations:

  • Dehydration to alkenes, followed by epoxidation, hydroboration–oxidation, or halofunctionalization to diversify substitution patterns.
  • Oxidative functionalization at benzylic-like positions is not applicable (alicyclic), but radical-based C–H functionalization (e.g., via HAT chemistry) on the ring may be explored with care.

• Retrosynthetic value:

  • Readily accessible from 4-hydroxycyclohexanone/4-hydroxycyclohexanol via Williamson ether synthesis on a pre-installed phenolic-like oxygen equivalent is not possible; instead, install the ethoxy substituent through nucleophilic substitution of a 4-halo/4-sulfonate cyclohexanol derivative with sodium ethoxide, or via hydroxy-directed substitution sequences.

Overall, this substrate offers orthogonal reactivity useful for stepwise elaboration of cyclohexyl frameworks.

Target Specificity

Not applicable. This product is a small-molecule chemical and not a biological affinity reagent or antibody. No target specificity, clone, or isotype information is relevant or provided for this item.