This compound belongs to the class of organic compounds known as secondary alcohols. These are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R') (R,R'=alkyl, aryl).
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.
Certificats (CoA, COO, BSE/TSE et tableau d'analyse)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Propriétés chimiques et physiques
Poids moléculaire
144.210 g/mol
XLogP3
0.900
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
144.115 Da
Monoisotopic Mass
144.115 Da
Topological Polar Surface Area
40.500 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
73.300
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
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Application Protocols
No manufacturer-tested bioanalytical application protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule building block.
For synthetic use, consider general protocols:
Stock solution prep: Dissolve in dry DCM, MeCN, THF, or DMF to desired molarity under inert atmosphere if subsequent reactions are moisture-sensitive.
Drying: If needed, dry material under high vacuum and use anhydrous solvents; include molecular sieves for in-solution steps.
Workup/purification: Standard aqueous workup followed by silica gel chromatography; diols elute with polar eluents (EtOAc/hexanes or MeOH/CH2Cl2 gradients). Consider boronate complexation for purification if necessary.
Note: These are general laboratory practices; consult reaction-specific literature and the CoA/SDS.
Biological Roles
This product is a synthetic organic building block with no established endogenous biological role.
Item-specific biological data
None provided for this item. Research Use Note: For research use only.
General context (literature/general)
Aliphatic cycloalkanediols are occasionally explored as components in materials or as scaffolds for host–guest systems; they are not recognized metabolites or cofactors in primary metabolism.
Diols can engage in hydrogen bonding with biomacromolecules and may be used in affinity systems via reversible boronate interactions, but cis-1,5-cyclooctanediol itself has no specific, characterized biological function.
Implications for lab work
If used in biochemical assays (e.g., as a small-molecule control, derivatization reagent, or scaffold), verify compound solubility and absence of assay-interfering impurities (e.g., residual acids/bases) and ensure appropriate solvent controls (DMSO or ethanol stocks).
No known specific enzyme substrates, transporters, or receptors are associated with this compound in the literature.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare biochemical buffers.
Guidance
Use conventional buffers (e.g., phosphate, HEPES, Tris) for pH control. cis-1,5-Cyclooctanediol does not provide useful buffering capacity in physiological pH ranges and lacks ionizable groups appropriate for buffer systems.
If incorporated into aqueous systems as a co-solute or additive, adjust pH with a proper buffer and consider its limited water solubility.
Green Alternatives
While cis-1,5-cyclooctanediol is a substrate/reagent rather than a process solvent, greener choices can be made in its use and in selecting alternative feedstocks for similar functions.
Greener process choices (general)
Solvents: prefer bio-based and safer solvents (2-MeTHF, CPME, EtOAc, Me-THF/water biphasic) over chlorinated solvents where feasible. For coupling or carbonate formation, acetonitrile or toluene can sometimes be replaced by EtOAc or CPME.
Coupling/activation: use phosgene-free carbonate formation (e.g., CDI, Boc2O variants) over triphosgene. Employ catalytic dehydrative couplings (e.g., boronic acid catalysis) when applicable.
Oxidations: replace chromium(VI) oxidants with TEMPO/bleach, Dess–Martin (with appropriate quench/recovery), or catalytic O2 systems to reduce hazardous waste.
Alternative substrates (contextual)
If only a diol spacer is needed, consider renewable diols (isosorbide, 1,3-propanediol, glycerol derivatives) which may offer improved sustainability, acknowledging that ring geometry of cis-1,5-cyclooctanediol is unique and often not substitutable.
Trade-offs
Safer solvents may change solubility and rates; optimize temperature and catalyst loading accordingly.
Replacing strong activating agents can reduce waste but may require longer reaction times or different bases.
Small comparison (general)
Chlorinated solvents (DCM) vs EtOAc/CPME: similar polarity window for many diol derivatizations; greener alternatives offer lower toxicity and improved lifecycle metrics, but may alter selectivity in tosylation/carbonate formation.
Pharmaceutical Uses
No pharmacopeial or excipient designation is provided for this item.
Item-specific status
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Regulatory listings (USP/Ph. Eur./JP): Not specified for this item; refer to CoA/Spec Sheet.
General context (non-clinical)
Secondary diols can serve as synthetic intermediates en route to APIs or excipients (e.g., formation of carbonates, ethers, or as chiral ligand precursors), but cis-1,5-cyclooctanediol itself is not commonly used directly in dosage forms.
In process development, it may be used to construct cyclic carbonates or to introduce spaced di-oxygen functionality in macrocyclic scaffolds.
Formulation considerations (if used in R&D)
Solubility: typically requires co-solvents (EtOH, PEGs, propylene glycol) for concentrated solutions; verify compatibility with other excipients.
Stability: secondary alcohols are generally stable; avoid strong oxidants and dehydrating conditions during handling.
All uses are for research and laboratory synthesis only; no medical or clinical claims are made.
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, metals, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Literature/general properties (for reference only; not item specifications)
Molecular weight: 144.21 g/mol
Molecular formula: C8H16O2
Physical state: typically a crystalline solid for isolated cis-1,5 isomer (literature)
Hydrogen bonding: strong H-bond donor/acceptor; likely to exhibit intramolecular H-bonding in certain conformations (literature, qualitative)
Solubility profile (qualitative, literature):
Water: low-to-moderate (diols generally increase hydrophilicity relative to hydrocarbon; medium ring size reduces full miscibility)
Organic solvents: soluble in polar protic (MeOH, EtOH) and polar aprotic solvents (acetone, acetonitrile, DMSO, DMF); limited solubility in nonpolar hydrocarbons.
Partitioning (qualitative): expected intermediate polarity; lower logP than cyclooctane due to diols (literature, qualitative).
Refractive index, mp, bp: Not reported here; consult primary literature or CoA/SDS for exact values.
Practical notes (general)
Diols may exhibit melting point dependence on isomeric purity and residual solvent/water inclusion.
Hygroscopicity for medium-ring diols is typically low-to-moderate; protect from moisture to preserve accurate assay and melting behavior.
Quality and Grades
Item-specific quality information
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance)
Research grade: typical for synthetic building blocks; sufficient for general organic synthesis and materials R&D.
High-purity or assay-specified material: appropriate for quantitative synthesis, catalysis, or materials where trace impurities (e.g., acids, metals, water) affect outcomes. If an assay or water content is critical (e.g., for stoichiometric lithiation or polymerizations), consult the CoA for this specific lot.
Chromatography/UV-appropriate grades: For HPLC/UV applications, low background absorbance is crucial; a diol of this type is not commonly used as a mobile phase component, so UV cutoff is typically irrelevant. If used as an additive or derivatization agent in analytical workflows, ensure impurity profile is documented.
Practical notes
Diol purity can be compromised by residual solvents and stereoisomeric impurities (trans-1,5 isomer). Review the isomeric purity (if reported) on the CoA when stereodefined outcomes are required (e.g., in cyclic carbonate formation or chiral ligand assembly).
If metal content is relevant (e.g., downstream catalysis), request ICP data; otherwise, metals are generally low for such organic solids.
Reaction and Applications
cis-1,5-Cyclooctanediol is a versatile building block whose medium-ring topology and cis-1,5 relationship of secondary alcohols enable selective difunctionalizations and macrocyclic constructs.
Diol activation and substitution: formation of ditosylates/dimesylates followed by intramolecular nucleophilic substitution or external nucleophile installation (halides, azides) to access 1,5-disubstituted cyclooctanes or bicyclic ethers.
Carbonate and carbamate chemistry: conversion to cyclic or bicyclic carbonates using phosgene surrogates (triphosgene, CDI) for polymer building blocks or as protecting groups.
Selective oxidation: stepwise oxidation to hydroxyketones or diketones (cyclooctane-1,5-dione) using PCC/DMP/Swern or catalytic oxidations (e.g., TEMPO-based for alcohol to carbonyl).
Dehydration and etherification: acid-catalyzed intramolecular dehydration to yield cyclic ethers; intermolecular etherification to install protecting groups (e.g., benzylation) or to generate diethers for ligand frameworks.
Macrocyclizations/host–guest scaffolds: the 1,5 spacing supports macrocycle precursors, including crown-ether-like architectures after O-alkylation.
Boronic/boronate ester formation: reversible diol–boronic acid complexation useful in separations/sensing or as temporary protecting/templating interactions.
Practical tips
Stereochemistry: the cis relationship can influence reaction rates and product distributions (e.g., formation of specific cyclic carbonates favored by geometry).
Drying: remove residual moisture for coupling/activation steps (azeotrope with toluene; dry over molecular sieves) to improve yields.
Protecting-group strategy: differentiate the two secondary alcohols via selective silylation under kinetic vs thermodynamic control where needed.
Reaction Conditions
General literature guidance for typical transformations of secondary diols; adjust to your system and consult primary references. Values below are indicative, not specifications for this item.
TOSYLATION/MESYLATION (activation)
Solvent: DCM or THF; Base: pyridine, triethylamine; Temp: 0–25 °C; Time: 1–12 h. Use 2.0–2.2 equiv sulfonyl chloride per diol for di-substitution. Maintain anhydrous conditions to suppress hydrolysis.
CARBONATE FORMATION
Reagents: CDI or triphosgene; Base: DMAP/Et3N; Solvent: DCM/MeCN/toluene; Temp: 0–25 °C; Time: 2–18 h. For cyclic/bicyclic carbonates, slow addition and dilution can favor intramolecular closure.
OXIDATION TO KETONES
Dess–Martin periodinane (DMP) in DCM, 0–25 °C, 1–4 h per hydroxyl; or TEMPO/BAIB systems in MeCN/H2O, 0–25 °C for selective oxidation to carbonyls. Work up with aqueous bicarbonate and sodium thiosulfate as appropriate.
ETHERIFICATION/ALKYLATION
Williamson ether: NaH or K2CO3 in DMF/MeCN, 0–60 °C, 2–16 h. For intramolecular closures, dilute conditions and leaving group differentiation improve selectivity.
PROTECTION WITH SILYL CHLORIDES
TBSCl/imidazole in DMF, 0–25 °C, 2–6 h. Sequential protection can differentiate the two OH groups.
DRYING AND HANDLING
Dry solid at reduced pressure (ambient–40 °C) prior to moisture-sensitive steps. Employ molecular sieves (3Å/4Å) in solution operations.
Note: Reaction times/yields depend on isomeric purity (cis vs trans), steric environment, and conformational dynamics of the 8-membered ring. Optimize on small scale before scale-up.
Safety and Handling
Item-specific hazard information
GHS classification: Not specified for this item; refer to SDS.
Signal word: Not specified for this item; refer to SDS.
H-statements/Pictograms: Not specified for this item; refer to SDS.
General safety considerations for aliphatic diols (literature/general)
Expected hazards: low acute toxicity relative to lower molecular weight glycols; may cause mild skin/eye irritation. Avoid inhalation of dust and prolonged contact.
Recommended PPE: lab coat, safety glasses or face shield, and chemical-resistant gloves (e.g., nitrile). Use local exhaust ventilation when handling powders or during heating.
First aid (overview; defer to SDS):
Inhalation: move to fresh air; seek medical advice if symptoms persist.
Skin contact: wash with soap and water; remove contaminated clothing.
Eye contact: rinse cautiously with water for several minutes; remove contact lenses if present and easy; seek medical attention if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Fire safety: Organic solid; combustible. Use water spray, CO2, dry chemical, or foam. Combustion may produce CO/CO2.
Reactivity/incompatibilities: Strong oxidizers may react exothermically with diols; acid/base-catalyzed dehydration possible at elevated temperature leading to ethers/olefins.
Special risks: Unlike ethers, diols are not prone to autoxidative peroxide formation under normal storage.
Handling/storage best practices (general)
Keep container tightly closed in a cool, dry, well-ventilated area. Minimize dust generation. Defer to SDS for authoritative safety and exposure controls.
Solvent Selection
This product is a neutral, medium-polar secondary diol. Solvent selection depends on the transformation or processing step.
Expected solubility: good in polar protic (MeOH, EtOH, i-PrOH) and polar aprotic solvents (acetone, acetonitrile, DMSO, DMF); limited in alkanes and other nonpolar media. Water solubility is limited to moderate for medium-ring diols.
Selection by use case
Esterification/carbonate formation: use aprotic solvents (DCM, toluene, acetonitrile) with base and coupling agent or phosgene equivalents; azeotropic removal of water (toluene) can drive equilibrium.
Tosylation/mesylation: DCM, THF, or pyridine as solvent/base depending on protocol; low temperature control improves selectivity.
Oxidation to diketone: use acetone, MeCN, DCM, or acetic acid depending on oxidant (e.g., PCC, Swern, Dess–Martin, or catalytic Ru/periodate systems).
Polymer or materials incorporation: use high-boiling polar aprotics (NMP, DMF, DMSO) for solution processing.
Comparison (general)
Versus linear diols (e.g., 1,4-butanediol): ring diol has lower water miscibility and distinct conformational effects on reactivity.
Versus small-ring diols (e.g., cyclohexane-1,2-diol): medium ring enables different chelation geometry and macrocyclization behavior.
Note: No solvent-related specifications are provided for this item; consult the CoA/SDS and optimize empirically for your transformation.
Storage and Reconstitution
Item-specific storage
Storage conditions: Room temperature (per Product Data). Keep container tightly closed in a dry, well-ventilated place.
Shipping: Normal.
General best practices for this compound class
Protection: Store in original, airtight container. Consider desiccation to limit moisture uptake and ensure consistent assay/melting behavior.
Light/heat: Protect from excessive heat; ambient light is generally acceptable. Avoid prolonged exposure to >40 °C to prevent dehydration/side reactions during long-term storage.
Inert atmosphere: Not strictly required for diols, but purging with inert gas can be beneficial before long storage if highly moisture-sensitive derivatizations are planned later.
Reconstitution/solution preparation (general)
Solvents: Prepare stock solutions in dry polar solvents (e.g., DMSO, DMF, MeCN, EtOH, or THF) according to downstream use.
Concentrations: Choose based on solubility and application; filter solutions (0.2 µm PTFE) if needed.
Stability of solutions: In anhydrous aprotic solvents at room temperature, solutions are typically stable for days; refrigerate if storing longer, and bring to ambient before use to avoid precipitation.
Specified item parameters (if required for your QA)
Appearance, assay, water content, and residual solvents: Not specified for this item; refer to CoA/Spec Sheet.
Always consult the product’s SDS for authoritative safety and handling guidance. For research use only.
Structure and Identity
Brief overview: cis-1,5-Cyclooctanediol is a conformationally flexible medium-ring diol in which the two hydroxyl groups are in a cis-1,5 relationship on a cyclooctane framework.
Item-specific (from Product Data)
CAS: 23418-82-8
SKU: C348027
Storage: Room temperature (as supplied)
Shipped: Normal
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data field shows "22070", which is not a standard InChIKey.)
Structural features: medium-sized cycloalkane ring (8-membered) bearing two secondary alcohols at C1 and C5; the substituents are cis (same face of the ring). No additional heteroatoms beyond the two hydroxyl oxygens; no aromaticity.
2D structure description (general)
An eight-membered carbocycle with –OH groups at two carbons separated by three methylenes (1,5-relationship). In the cis isomer, both hydroxyl-bearing stereocenters present substituents oriented to the same side of the mean ring plane, enabling intramolecular H-bonding in certain conformers and facilitating formation of 5- or 8-membered chelates upon diesterification or ditosylation.
Synthetic Utility
Key functional elements: two secondary alcohols in a cis-1,5 relationship on a conformationally flexible 8-membered ring.
Transformations (literature/general)
Protection/deprotection: silylation (TBS/TIPS) or benzylation for orthogonal manipulation; cyclic carbonates or acetonide-type protections are accessible where geometry permits.
Activation: ditosylation/dimesylation enabling SN2 displacements (halogenation, azidation) to build 1,5-disubstituted cyclooctanes or to forge bicyclic ethers via intramolecular substitution.
Oxidation: selective oxidation to hydroxyketones or diketone (cyclooctane-1,5-dione) guides further elaboration (e.g., intramolecular aldolization, Paal–Knorr-type derivatizations are less applicable but diketone opens to heterocycles).
Carbonate/carbamate synthesis: CDI, triphosgene, or organic carbonates to generate di-carbonates useful as monomers or protecting motifs.
Ester synthesis: diacylation to diesters, including polymerizable acrylates/methacrylates for materials.
Boronate formation: reversible complexes for purification, sensing, or as temporary protecting groups.
Retrosynthetic value
Serves as a preorganized diol spacer for macrocycle construction where 1,5 separation is required.
The cis geometry can bias conformations, supporting selective intramolecular reactions compared with the trans isomer.
Practical considerations
Choose bases and temperatures to control competing elimination during sulfonylation/alkylation.
Use anhydrous conditions for high-yield activation and carbonate formation; remove water azeotropically prior to coupling.
Target Specificity
Not applicable to this product type.
This is a small-molecule diol, not an antibody, enzyme, or biological probe with defined biomolecular targets. No antigen/epitope, clone, isotype, or species reactivity data are relevant.
Any interactions (e.g., boronate complexation) are general chemical affinities rather than biological target specificity.
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