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
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
142.240 g/mol
XLogP3
2.400
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
1
Rotatable Bond Count
2
Exact Mass
142.136 Da
Monoisotopic Mass
142.136 Da
Topological Polar Surface Area
20.200 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
92.900
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
Lösungsrechner
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Application Protocols
No assay/antibody protocols apply to this small-molecule reagent.
General handling notes for synthetic use
If moisture-sensitive steps are planned (e.g., acid chloride esterifications), dry the alcohol over molecular sieves (3Å/4Å) or by co-evaporation with dry toluene/benzene under reduced pressure.
For analytical methods, prepare stock solutions in an appropriate organic solvent (e.g., hexane, DCM, acetonitrile) at known concentration; use glassware to avoid adsorption.
For partitioning or membrane studies, prepare solutions using minimal DMSO/EtOH cosolvent, ensuring final cosolvent content is compatible with the system under investigation.
For detailed experimental conditions, see the Reaction Conditions tab and consult primary literature.
Biological Roles
This compound is an aliphatic tertiary alcohol and is intended for research and laboratory use only.
General biochemical context (literature/general)
Small, hydrophobic alcohols can partition into lipid phases and may serve as model compounds to study membrane–solute interactions, solvent effects on enzymes, or protein stability in mixed solvent systems.
Lacking heteroatoms beyond a single hydroxyl and with no obvious biological recognition motifs, 1-propylcyclohexanol is not associated with specific metabolic pathways beyond generic alcohol oxidation/phase I–II metabolism in biological systems (e.g., oxidation by alcohol/aldehyde dehydrogenase is limited for tertiary alcohols; conjugation such as glucuronidation/sulfation can occur on the hydroxyl group in vivo in general models).
Tertiary alcohols typically resist metabolic oxidation to carbonyl compounds; instead, they may undergo conjugation or oxidative fragmentation under specialized conditions.
Laboratory relevance
Potential use as a hydrophobic cosolute in model membranes, micelles, or partitioning experiments.
Could serve as a test molecule in ADME method development (e.g., logP, solubility screens) without implying any therapeutic application.
No medical, diagnostic, or clinical use is implied or recommended. For any work involving biological systems, follow institutional biosafety and chemical safety guidelines.
Buffer Applications
Not typically applicable. 1-Propylcyclohexanol is a non-buffering, hydrophobic alcohol and does not form classical aqueous buffer systems.
Practical notes (if used near biological buffers)
Expect poor water solubility; introduce via cosolvents (e.g., DMSO, ethanol) at low percentages to avoid phase separation, if absolutely required for assays.
Verify that added organic cosolvent does not disrupt buffer capacity, pH, or biomolecule stability.
For aqueous buffer selection and recipes, refer instead to dedicated buffering agents (e.g., phosphate, Tris, HEPES).
Green Alternatives
Context: 1-Propylcyclohexanol is a specialty reagent/building block, not a bulk process solvent. “Green alternatives” therefore focus on reaction media and coupling strategies rather than replacing the reagent itself.
Greener solvent choices (when feasible)
Replace chlorinated solvents (e.g., DCM) with ethyl acetate, 2-MeTHF, CPME, or toluene where solubility and selectivity permit.
Use bio-derived solvents (2-MeTHF, EtOAc) to reduce petrochemical footprint; note differing polarity/boiling points.
Greener activation/coupling strategies
Esterifications: adopt catalytic acid with azeotropic water removal (Dean–Stark in toluene) or solid-acid resins (Amberlyst-15) to reduce waste versus stoichiometric carbodiimides.
Carbonate formation: use dimethyl carbonate or diphenyl carbonate as safer phosgene substitutes; apply catalyst systems (e.g., organobases) under mild conditions.
Avoid halogenating reagents where possible; consider enzymatic esterification in green solvents or solvent-free conditions for select transformations, recognizing steric limits of tertiary alcohols.
Tradeoffs
2-MeTHF/CPME may change reaction rates/selectivity and can form peroxides over time—manage with inhibitor testing and regular peroxide checks.
Solid-acid catalysis simplifies separation but may require higher temperatures.
Waste and energy
Opt for higher-boiling, recyclable solvents when distillation recovery is practical.
Implement in-process controls to minimize over-reaction and byproduct formation (particularly for dehydration and rearrangements).
These strategies are general guidance; optimize per reaction and consult EHS for solvent substitution approval.
Pharmaceutical Uses
No therapeutic or clinical claims. This product is offered for research use only.
Formulation/excipient context (general)
Aliphatic alcohols may sometimes be explored as hydrophobic modifiers, pro-moieties (via ester formation), or permeation study probes in pre-formulation research. 1-Propylcyclohexanol could be investigated as a bulky hydrophobic alcohol component in synthetic ester screening for materials or delivery research.
Limited aqueous solubility and tertiary alcohol character reduce direct excipient utility in conventional aqueous dosage forms.
Standards and compendia
Not listed here with any pharmacopeial monograph. If a compendial grade is required, consult the CoA/Spec Sheet or contact technical support.
All pharmaceutical-related discussion is restricted to non-clinical R&D contexts (e.g., materials screening, in vitro method development).
Physical Properties
Item-specific specifications
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
Water/peroxide/UV cutoff/trace metals: Not specified for this item; refer to CoA/Spec Sheet.
Literature/typical values (reference only; not item specifications)
Physical state: liquid at ambient temperature (typical for C9 aliphatic alcohols).
Odor: faint alcohol/hydrocarbon-like (general for aliphatic tertiary alcohols).
Boiling point: typically in the high 180s–200 °C range for C9 tertiary alcohols; consult primary data sources for this exact isomer.
Melting point: often below 0 °C for comparable structures; specific value should be verified in the literature.
Density (20–25 °C): expected around 0.85–0.90 g/mL for a C9 alicyclic alcohol; check references for precise value.
Refractive index (n20 D): commonly ~1.44–1.46 for related cyclohexyl alcohols; confirm with measured data.
LogP/logD: hydrophobic; calculated logP typically >2 for C9 alcohols.
Solubility: sparingly soluble in water; miscible with common organic solvents (e.g., diethyl ether, hexanes, toluene, THF, dichloromethane, acetone, alcohols).
Vapor pressure: low at room temperature compared to lower alcohols.
Notes
Values above are literature/general expectations for closely related structures and should not be treated as specifications for this catalog item.
For method development (e.g., GC), determine exact constants experimentally or from an authoritative database.
Quality and Grades
Item-specific grade/purity information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on quality considerations for this material class
Alcohols for synthetic use: When grade is unspecified, typical expectations include low water content and low acidic/basic impurities to ensure predictable reactivity in esterification, carbonate formation, or coupling steps. Verify actual limits on the CoA (e.g., GC purity, residual solvents).
Chromatography/analytical use: If employing as a standard or matrix component, ensure a high-purity lot with well-resolved GC profile and documented identity (e.g., NMR, IR, MS). Low UV background is usually not critical for this non-aromatic alcohol, but for HPLC detection below 210 nm, check UV absorbance if relevant.
Stereochemical content: Unless stated as a single stereoisomer, 1-propylcyclohexanol is generally supplied as racemic at C-1. If stereochemical purity matters (e.g., for chiral method development), request a chiral GC/HPLC trace on the CoA.
Water content: Karl Fischer specifications, if provided, impact reactions sensitive to moisture (e.g., acid chloride esterifications). Dry if needed prior to use (e.g., molecular sieves), consistent with CoA guidance.
Metals and other trace contaminants: For catalysis-sensitive steps, review metal limits on the CoA; none are specified here.
Reaction and Applications
Use profile: 1-Propylcyclohexanol functions primarily as a hydrophobic tertiary alcohol building block and as a precursor to more complex derivatives.
Esterification and transesterification: formation of sterically hindered esters (e.g., with acyl chlorides/anhydrides, DCC/EDC coupling). Tertiary alcohols may require stronger catalysts (e.g., acid catalysis) due to lower nucleophilicity.
Carbonate and carbamate synthesis: reaction with phosgene equivalents (triphosgene, CDI) or chloroformates; useful for protecting-group or materials applications.
Ether formation: via activation (e.g., with Tf2O or using Mitsunobu-type variants—though tertiary alcohols typically do not undergo SN2 Mitsunobu; alternative routes involve carbocation pathways leading to rearrangement—use caution).
Dehydration: acid-catalyzed elimination (H2SO4, p-TsOH, Amberlyst-15) to give propylcyclohexenes; regioselectivity can depend on conditions and ring conformation.
Oxidation: tertiary alcohols are generally resistant to classical oxidation to carbonyls; harsh or radical conditions may yield fragmentation rather than simple ketone formation.
Halogenation/activation: conversion to tert-alkyl halides or sulfonates (e.g., with SOCl2, MsCl/TsCl) may proceed via carbocationic pathways; monitor for rearrangements.
Application contexts
Hydrophobic ester formation for materials or surface-modified polymers.
Intermediate in fragrance or specialty chemical synthesis where cyclohexyl-derived tertiary alcohol motifs modulate volatility and odor profile (industrial chemistry; no consumer or clinical claims).
Model substrate for studying carbocation stability, rearrangements, and elimination on substituted cyclohexanes.
Practical tips
Control acidity to balance activation with minimization of rearrangements.
Employ anhydrous conditions and stoichiometric scavengers when generating acid-sensitive intermediates.
Characterize products by GC/MS and 2D NMR to confirm regiochemistry after dehydration/solvolysis.
Reaction Conditions
General guidance (literature; adjust per substrate and scale)
Esterification of 1-propylcyclohexanol
Reagents: acyl chloride or anhydride; catalytic DMAP/base-assisted (for anhydrides) or pyridine/Et3N; or DCC/EDC with carboxylic acids.
Solvents: DCM, toluene, EtOAc, or acetonitrile.
Temperature/time: 0–25 °C for acid chlorides (1–4 h); 40–80 °C for anhydrides or DCC couplings (2–16 h).
Notes: Tertiary alcohols are less nucleophilic; employ catalysts (DMAP) or stronger activation. Monitor for elimination under strong acid.
Carbonate formation
Reagents: triphosgene or CDI with alcohol plus base (e.g., Et3N); safer alternatives include dimethyl carbonate with base.
Solvent: DCM, THF, MeCN. 0–25 °C (phosgene equivalents) or 60–90 °C (dimethyl carbonate, catalytic DBU/K2CO3).
Dehydration to alkenes
Catalyst: p-TsOH, H2SO4, POCl3/pyridine, or solid acids (Amberlyst-15).
Solvent: toluene, xylene, or solvent-free.
Temperature: 80–140 °C depending on catalyst; 1–6 h typical.
Notes: Regiochemistry may yield mixtures of propylcyclohexenes; control via temperature/catalyst; remove water to drive equilibrium.
Activation to sulfonates/halides
Reagents: MsCl/TsCl with base (Et3N), SOCl2 or PBr3 under carefully controlled conditions.
Solvent: DCM, THF; 0–25 °C then warm as needed.
Caution: Tertiary centers may undergo SN1 and rearrangement; low temperature and non-nucleophilic bases help suppress side processes.
Yields: Highly substrate- and condition-dependent; for hindered esterifications, isolated yields of 60–90% are common in literature when optimized. Always confirm by small-scale screening.
Safety and Handling
Item-specific safety data
GHS classification: Not specified for this item; refer to SDS.
Signal word / H-statements / pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature (per Product Data). Store in a tightly closed container.
General safety guidance for aliphatic alcohols and tertiary alcohols (informational; consult SDS for authoritative details)
Hazards: May cause skin and eye irritation; ingestion or inhalation of vapors/mists can cause irritation and CNS effects. Combustible liquid; avoid ignition sources. Although tertiary alcohols are less prone to autoxidation than ethers, general good practice includes minimizing prolonged air exposure at elevated temperatures.
Incompatibilities: Strong oxidizers (may cause exothermic reactions), strong acids or acid catalysts (can promote dehydration), acid chlorides/anhydrides (react to form esters), alkali metals or strong bases (can deprotonate under forcing conditions).
PPE: Use chemical-resistant gloves (e.g., nitrile), splash goggles, lab coat; handle in a fume hood if heating or generating vapors/aerosols.
First aid (overview):
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation persists.
Skin contact: Wash with soap and water; remove contaminated clothing.
Inhalation: Move to fresh air; seek medical attention if symptoms occur.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Use CO2, dry chemical, or foam. Cool containers with water spray if exposed to fire.
Always consult the product-specific SDS before use.
Solvent Selection
This product is a hydrophobic, aliphatic, tertiary alcohol and is typically used as a reagent/building block rather than as a bulk solvent.
Polarity and miscibility (general behavior)
Polarity: low to moderate (non-aromatic, saturated ring with one hydroxyl).
Organic solvents: miscible with ethers (THF, MTBE), chlorinated solvents (DCM, CHCl3), hydrocarbons (hexanes, toluene), and alcohols (MeOH, EtOH, i-PrOH).
Choosing solvents for reactions with 1-propylcyclohexanol (guidance)
Esterification/Acylation: use aprotic solvents (DCM, toluene, EtOAc) or solvent-free with catalytic acid or coupling reagents; remove water by azeotrope (toluene) or by molecular sieves.
Carbonate/Carbamate formation: DCM, acetonitrile, or THF are common choices; control base strength to avoid elimination.
Dehydration to alkenes: nonpolar or mildly polar solvents (toluene, xylene) under acid catalysis; collect evolved water if helpful.
Comparisons (general)
Versus smaller alcohols (i-PrOH, t-BuOH): 1-propylcyclohexanol is less polar and more hydrophobic, often giving better phase separation from aqueous workups and different reactivity/selectivity in esterification.
Versus benzylic alcohols: lacks aromatic UV absorbance; more resistant to oxidation.
Note: Select solvents based on reaction class, solubility of coupling partners, and heat removal needs. Verify solvent compatibility with downstream purification and EHS constraints.
Storage and Reconstitution
Item-specific information
Storage conditions: Room temperature (per Product Data). Store tightly closed in a dry, well-ventilated area away from incompatible materials (strong oxidizers, strong acids).
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General guidance
Container: Use amber glass if prolonged light exposure is expected; although tertiary alcohols are relatively stable, standard protection minimizes potential discoloration or peroxide formation in mixed systems.
Moisture: While alcohols are not highly hygroscopic, minimize water uptake if the material will be used in moisture-sensitive reactions; recap promptly and consider storing over inert desiccant in a desiccator.
Inert atmosphere: Not typically required; for long-term storage of opened containers, purging headspace with nitrogen can help maintain quality.
Reconstitution: Not applicable—product is typically supplied neat. If a solution is desired, prepare in a dry organic solvent compatible with the intended application (e.g., hexane, toluene, DCM, THF) and label concentration and preparation date.
Freeze–thaw: Not relevant for neat liquids; avoid repeated heating/cooling cycles that can introduce moisture.
Always consult the product’s CoA/Spec Sheet and SDS for lot-specific guidance and any stability data.
Structure and Identity
Brief overview: 1-Propylcyclohexanol is a cyclohexanol derivative bearing a propyl substituent on the ring. It is typically encountered as a mixture of stereoisomers (at the ring carbon bearing the hydroxyl group) unless otherwise specified.
Item-specific identifiers (from Product Data)
CAS: 5445-24-9
SKU: P1067120
Product name: 1-Propylcyclohexanol
InChIKey: 290287 (as provided)
SMILES: 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.
Literature/typical identity information (for reference; not item specification)
Common structural description: cyclohexane ring bearing a hydroxyl (–OH) at C-1 and an n-propyl substituent at C-1 (i.e., 1-propylcyclohexan-1-ol), giving a tertiary alcohol center; racemic unless stated otherwise.
Typical molecular formula (literature): C9H18O.
Typical formula weight (literature): ~142.24 g/mol.
Functional groups: tertiary alcohol; saturated carbocyclic ring; linear propyl side chain.
Stereochemistry: one stereogenic center at C-1; potential for cis/trans ring relationships with adjacent substituents.
2D structure (described): a six-membered cyclohexane chair; at carbon 1, an –OH group and an n-propyl chain extend (axial or equatorial conformers possible), other ring positions are unsubstituted.
Synthetic Utility
Key functional attributes
Tertiary alcohol center at C-1 (on a cyclohexyl carbon) with an n-propyl substituent confers significant steric hindrance and potential carbocation stability under acidic conditions.
Applications in synthesis (literature/general)
Sterically hindered esters: Formation using acyl chlorides/anhydrides or coupling reagents; products often exhibit distinct hydrolytic stability compared with primary/secondary analogs.
Elimination chemistry: Acid-catalyzed dehydration affords substituted cyclohexenes; useful to access defined alkene substitution patterns on the ring for further functionalization (e.g., epoxidation, hydroboration–oxidation).
Protection strategies: While tertiary alcohols are less common as protecting groups, conversion to carbonates/carbamates can mask the hydroxyl and tune lipophilicity.
Leaving-group installation: Conversion to sulfonates (mesylate/tosylate) is feasible but may proceed through SN1-like pathways; rearrangements or eliminations should be monitored.
Cross-coupling adjacency: The alcohol itself is not a direct coupling handle, but dehydration then hydrofunctionalization can introduce halides or boron reagents at defined positions on the ring.
Retrosynthetic value
As a target motif: 1-propylcyclohexyl fragments appear in fragrance/specialty chemicals; the tertiary alcohol node can be retraced to ketone precursors via Grignard/organolithium addition to cyclohexanone-derived substrates (general strategy), though note that 1-propylcyclohexan-1-ol specifically would arise from addition of propyl nucleophiles to cyclohexanone followed by appropriate substitution, or by tertiary center construction via alkylation of cyclohexanone-derived carbocation equivalents under controlled conditions.
Target Specificity
Not applicable. This product is a small-molecule reagent (aliphatic alcohol), not a biological targeting agent. No antigen/epitope, species reactivity, clone, or isotype information applies.
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