Cyclohexane, 1,1,4,4-tetramethoxy- - ≥97% , CAS No.10553-38-5

CAS: 10553-38-5 Cat. No.: C997588 Summenformel: C₁₀H₂₀O₄ Molekulargewicht: 204.260

GRADE & PURITY ≥97%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥97%

Storage

Room temperature

Reinheit

≥97%

Namen und Kennungen

Kanonisches Lächeln

COC1(CCC(CC1)(OC)OC)OC

IUPAC Name

1,1,4,4-tetramethoxycyclohexane

InChIKey

YJEPUTKMMMUZAR-UHFFFAOYSA-N

INCHI

1S/C10H20O4/c1-11-9(12-2)5-7-10(13-3,14-4)8-6-9/h5-8H2,1-4H3

Molekulargewicht

204.260

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Klasse Organooxygen compounds
      • Subclass Ethers
        • Ebene5 Acetals
          • Ebene6 Ketals

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Klasse: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Acetals
• Direct Parent: Ketals
• Alternative Parents: Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Ketal - Hydrocarbon derivative - Aliphatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
• 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: 204.260 g/mol
• XLogP3: 0.800
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 204.136 Da
• Monoisotopic Mass: 204.136 Da
• Topological Polar Surface Area: 36.900 Ų
• Heavy Atom Count: 14
• Formal Charge: 0
• Complexity: 141.000
• 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 manufacturer-validated application protocols are provided for this item; refer to CoA/Spec Sheet.

General laboratory usage examples (illustrative, not item-specific validation):

• Hydrolytic deprotection screen:
  1. Dissolve substrate in THF/H2O (9:1) at 0.05–0.2 M.
  2. Add p-TsOH (5 mol%) at rt; stir and monitor by 1H NMR (disappearance of OMe singlets).
  3. Quench with saturated NaHCO3, extract with EtOAc, dry (Na2SO4), concentrate, and purify.
• Transacetalization:
  1. Combine substrate with ROH (5–20 equiv) and catalytic CSA in toluene.
  2. Heat to reflux with Dean–Stark to remove methanol.
  3. After completion, neutralize with Na2CO3, wash, dry, and purify by silica gel.

These examples are provided as general literature-style guidance; optimize conditions for your specific substrate and scale. Always consult the product SDS and CoA before use.

Biological Roles

This product is a small synthetic organic molecule used as a chemical building block/protecting-group equivalent. It does not have an established endogenous biological role.

General considerations:

• Not known as a metabolite, cofactor, or signaling molecule in primary metabolism.
• The multiple ether functionalities lack ionizable groups at physiological pH; passive membrane permeation and bioaccumulation potential would depend on overall lipophilicity, which for polyalkoxy cyclohexanes is typically moderate. No specific biological targets are described in the literature for this scaffold.

Usage context:

• Employed in organic synthesis and materials/medicinal chemistry campaigns as a masked carbonyl synthon or conformationally defined, polyfunctional fragment. Any bioassay use should be considered exploratory screening only.

Compliance note: For research use only. Not intended for food, drug, cosmetic, household, or diagnostic applications.

Buffer Applications

Not typically applicable. This compound is a neutral, non-ionic organic building block and is not used to prepare aqueous buffer systems or to control pH.

Practical note: If aqueous operations are needed (e.g., hydrolysis), conventional buffers/acids (acetate, citrate, phosphate; or dilute mineral acids) may be used to control pH during workup or transformation, but the compound itself is not a buffering agent.

Green Alternatives

This compound is a specialized reagent/building block rather than a bulk solvent; “green alternatives” pertain to process conditions and solvent choices rather than replacing the reagent itself.

Greener process suggestions (general, literature-based):

• Solvent selection: prefer biorenewable ethers such as 2-methyltetrahydrofuran (2-MeTHF) or cyclopentyl methyl ether (CPME) in place of DCM or toluene, where reaction performance allows.
• Acid catalysis: use solid acids (Amberlyst-15, sulfonated silica) to reduce corrosive mineral acid waste during acetal exchange/hydrolysis; they also simplify separation and enable reuse.
• Energy efficiency: conduct transacetalization under azeotropic water removal (Dean–Stark) with lower reflux temperatures using CPME/2-MeTHF rather than high-boiling aromatics.

Illustrative comparison (general guidance):

• DCM: excellent solvating power for acid-catalyzed transformations; concerns include toxicity and halogenated waste.
• 2-MeTHF: renewable feedstock, good for water removal and phase separation; flammable, but lower toxicity profile; may give comparable rates under acid catalysis.
• CPME: hydrophobic, forms azeotrope with water, stable under acidic conditions; higher bp aids equilibrium shifts but increases energy input.

Note: Selection must be validated experimentally; catalytic activity and acetal stability are substrate- and condition-dependent. The reagent itself has no widely adopted “green substitute” when its specific protecting-group or building-block role is required.

Pharmaceutical Uses

No excipient or compendial status is specified for this item; refer to CoA/Spec Sheet. There are no claims of use as an approved pharmaceutical ingredient.

Contextual information (general):

• In drug discovery and process chemistry, such polyalkoxy cyclohexane derivatives may serve as intermediates or protecting-group strategies en route to active pharmaceutical ingredient (API) scaffolds. Their role is synthetic, not functional in a dosage form.
• If considered for GMP-related work, qualification of identity, purity, residual solvents, and elemental impurities per ICH Q3 guidelines would be required. This listing does not imply such qualification.

Compliance note: For research use only; not for use in humans or clinical applications.

Physical Properties

Item-specific specs: BP/MP, density, refractive index, water/peroxide content, UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet.

Literature/computed expectations (for context only; not specifications):

• Molecular formula / FW: C10H20O4 / ~204.26 g/mol (from name interpretation).
• Polarity profile: neutral, non-ionizable under neutral conditions; four ether oxygens provide hydrogen-bond acceptor capacity (HBA = 4), no donors (HBD = 0).
• Volatility: expected to be low-to-moderate volatility relative to low-MW ethers; boiling point likely in the mid-to-high 200 °C range (literature expectations for tetra-alkoxycyclohexanes), but authoritative values should be sourced from primary data.
• Solubility: anticipated high solubility in common organic solvents (Et2O, THF, DCM, MeCN, toluene, alcohols). Water solubility expected to be limited-to-moderate due to multiple methoxy groups balanced by a hydrophobic ring.
• Partitioning: logP likely in the low-to-moderate range for poly-alkoxycyclohexanes; exact value not widely reported in public databases.

Practical implications:

• The multiple ether oxygens can coordinate Lewis acids and certain metal centers; this may modestly increase solubility in polar aprotic media and influence chromatographic retention (silica interactions). Always verify exact constants on the item’s CoA before using as a critical reference in method development.

Quality and Grades

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

Guidance on interpreting grade (general):

• Research or technical grade material is suitable for synthesis, method development, and screening where trace-level UV background, water, or metals are not critical. High-purity grades (e.g., ≥98–99%) are preferred for precise stoichiometry, kinetic studies, and materials applications.
• If an inhibitor or stabilizer is present, it will be declared on the CoA/label. Absence of such a declaration typically means none is intentionally added; verify on the item’s CoA when peroxide formation or acid sensitivity is a concern.
• For chromatography-sensitive applications (e.g., low-UV mobile phase additives), “HPLC grade” refers to stringent UV absorbance and impurity controls. This designation is not implied here unless explicitly stated on the item page/CoA.

What is specific to this item:

• Storage condition is provided as room temperature (see Storage & Reconstitution). Other quality attributes (assay, residual solvents, metals, water) are Not specified for this item; refer to CoA/Spec Sheet.

Best practices:

• For reproducible synthesis, request the current CoA lot and check assay, GC/HPLC area %, and any specified impurity limits. If your application is moisture- or acid-sensitive, confirm Karl Fischer water and acidity/alkalinity tests as available.

Reaction and Applications

Manufacturer-supplied application notes: Not specified for this item; refer to CoA/Spec Sheet.

Literature and synthetic practice (contextual guidance):

• Masked 1,4-dicarbonyl synthon: 1,1,4,4-tetramethoxy substitution can serve as a protected form of a 1,4-dicarbonyl (conceptually related to acetals/ketals). Acid-catalyzed hydrolysis regenerates the carbonyl functionalities under controlled conditions.
• Transacetalization: in the presence of alcohols and Brønsted/Lewis acids (e.g., p-TsOH, BF3·Et2O), the methoxy groups can exchange with other alkoxy groups to tailor protecting group patterns or to incorporate isotopically labeled alcohols.
• Stabilized substrate for electrophilic substitution: the electron-donating methoxy groups can activate adjacent C–H bonds toward certain electrophilic processes on the ring framework, while also influencing conformation.
• Building block in polyfunctional scaffolds: the tetramethoxy pattern provides orthogonal handles for stepwise deprotection/functionalization, enabling access to 1,4-dicarbonyl derivatives, cyclic acetals, or tethered acetal architectures.

Practical tips:

• Acid sensitivity: plan sequences such that strongly acidic steps occur either before installation of the tetramethoxy pattern or after its removal; neutral/basic steps are generally tolerated.
• Workup: after acid-catalyzed steps, neutralize carefully and minimize aqueous exposure to avoid over-hydrolysis. Monitor by GC/MS or 1H NMR (OCH3 singlets) for rapid assessment.

Reaction Conditions

General literature guidance for typical transformations involving tetramethoxy-substituted cyclohexanes (not item-specific specifications):

• Acid-catalyzed hydrolysis (to unveil carbonyl functionality):

  • Solvent: aqueous acetone, THF/H2O, MeOH/H2O.
  • Catalyst: dilute HCl, H2SO4, or p-TsOH (0.5–10 mol%).
  • Temperature: 20–60 °C; higher temperatures accelerate cleavage but increase side-reaction risk.
  • Workup: neutralize with NaHCO3, extract with DCM/EtOAc, dry, and analyze by NMR/LCMS.

• Transacetalization:

  • Solvent/alcohol: ROH (neat) or ROH with toluene/DCM; remove MeOH by azeotrope or nitrogen sweep.
  • Catalyst: p-TsOH, CSA, BF3·Et2O, Amberlyst-15.
  • Temperature: reflux in chosen solvent or 25–80 °C.

• Electrophile-induced transformations on the ring (where applicable):

  • Lewis acids: BF3·Et2O, TiCl4, AlCl3 may coordinate and promote rearrangements or substitution; conduct small-scale trials to assess stability of the acetal under these conditions.

Yields and kinetics: depend strongly on substrate, solvent, and catalyst loading; consult primary references for your specific transformation. Always pilot on millimole scale and monitor by TLC/NMR.

Compatibility note: Avoid strong protic acids in the presence of excess water if preservation of the tetramethoxy pattern is required.

Safety and Handling

GHS/label information for this specific item:

• Signal word, hazard statements, pictograms, classification: Not specified for this item; refer to the SDS provided with the shipment.

General safety guidance (literature-based, not a substitute for the SDS):

• Likely hazards: many dialkyl ethers and polyalkoxy compounds can be irritants. While gem-dimethoxy cyclohexane derivatives are not typically highly volatile, avoid inhalation of vapors/aerosols.
• Peroxide formation: simple dialkyl ethers can form peroxides on air/UV exposure; acetal-like, polyalkoxy cycloalkanes are less prone but good practice includes periodic peroxide checks when stored long term, especially if repeatedly opened.
• Incompatibilities: strong acids can catalyze acetal/ether cleavage; strong oxidizers may oxidize ether functions; strong bases are generally tolerated but can promote transacetalization in alcohol-rich media.
• Recommended PPE: lab coat, safety glasses/goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Use in a fume hood to control vapors and protect from accidental aerosol generation.
• First aid (overview):
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical attention for persistent irritation.
  • Ingestion: rinse mouth; do not induce vomiting unless directed by medical personnel; seek medical advice.
• Spill/Fire: absorb small spills with inert material. For fires, use CO2, dry chemical, or foam; avoid high-pressure water jets. Always defer to the item-specific SDS for authoritative instructions.

Solvent Selection

This product is a small organic reagent, not a general-purpose solvent. However, appropriate solvent choice is important for its handling and use.

General solvent compatibility (literature-based):

• Polarity class: moderately polar, multi-ether functionality; HBA = 4, HBD = 0.
• Likely miscible/soluble in: ethers (THF, MTBE), chlorinated solvents (DCM, CHCl3), polar aprotics (MeCN, DMF, DMSO), and aromatics (toluene). Moderate solubility in alcohols (MeOH, EtOH). Limited solubility expected in water.
• Dielectric considerations: polar aprotic solvents (THF, MeCN, DMF) can enhance solubility and stabilize transition states in reactions involving cationic or polar intermediates.

When to choose certain solvents:

• Protection/deprotection or acetal exchange: use anhydrous, aprotic media (DCM, toluene) for acid-catalyzed transacetalization; remove alcohol byproduct to drive equilibrium.
• Hydrolysis back to the corresponding carbonyl compound(s): aqueous mixtures (acetone–water or THF–water) with catalytic mineral or sulfonic acids.
• Metal-mediated transformations: coordinating solvents (THF, dioxane) can assist with reagent solubilization; ensure compatibility with any Lewis acids (avoid strongly acidic media that could cleave ethers).

Tip: Confirm solvent impurities (water, acidity) to avoid unintended acetal cleavage. Where quantitative mass balance is required, pre-dry solvents (molecular sieves) and conduct operations under inert atmosphere.

Storage and Reconstitution

Item-specific storage: Room temperature (per product data).

General handling recommendations:

• Keep container tightly closed and store in a dry, well-ventilated place away from strong acids and oxidizing agents. Minimize exposure to moisture if long-term integrity of acetal/ether functions is critical.
• If frequent opening/closing is expected, consider using a desiccator or adding a dry inert headspace (argon/nitrogen) to limit moisture ingress.
• Do not refrigerate solely to extend shelf life unless specified on the CoA; some ethers can absorb moisture/acidic contaminants from cold storage environments.

Reconstitution/Preparation:

• Supplied neat; no reconstitution required. For solution preparation, use anhydrous solvents as needed (e.g., dry THF, DCM, toluene). Filter through a PTFE syringe filter if particulate contamination is observed.

Stability notes (general):

• Stable under neutral/basic conditions; susceptible to acid-catalyzed cleavage/transacetalization, particularly in the presence of water or alcohols. Avoid prolonged exposure to strong acids unless deprotection is intended.

Always refer to the lot-specific CoA and SDS for definitive storage, stability, and handling information.

Structure and Identity

Item-specific registry fields provided: CAS 10553-38-5; SKU C997588; InChIKey: Not specified for this item; refer to CoA/Spec Sheet. SMILES: Not specified for this item; refer to CoA/Spec Sheet.

Literature/structural description:

• Compound name: Cyclohexane, 1,1,4,4-tetramethoxy- (often described as cyclohexane bearing two geminal dimethoxy substituents at C-1 and C-4).
• Functional groups: four methoxy substituents (–OCH3) attached to the cyclohexane ring as two geminal dimethoxy units; no heteroatoms incorporated into the ring. No stereocenters are inherent to the idealized structure, but conformational isomers (chair/boat) are possible.
• 2D structure in words: a six-membered saturated carbocycle. At carbon 1, two –OCH3 groups (gem-dimethoxy) replace two hydrogens; at carbon 4 (para across the ring), two –OCH3 groups replace two hydrogens. The remaining ring carbons (C-2,3,5,6) are unsubstituted methylene units.
• Empirical formula and formula weight (literature/computed from the name): C10H20O4; FW ≈ 204.26 g/mol. Labelled as literature/computed; not an item-specific specification.
• PubChem CID: 11769610 (literature reference for structure lookup).

Notes:

• If you require definitive identifiers for regulatory or analytical dossiers (e.g., canonical SMILES, full InChI, exact InChIKey), please refer to the product CoA/Spec Sheet or contact Technical Support for the exact item-specific entries.

Synthetic Utility

Key reactivity features (literature-based):

• Protected carbonyl equivalent: gem-dimethoxy substitution behaves as an acetal/ketal motif, enabling installation and later unveiling of carbonyl groups under acid-catalyzed hydrolysis.
• Transacetalization platform: in ROH/acid, –OCH3 groups can exchange to –OR, allowing modulation of sterics/electronics and incorporation of labeled alcohols (e.g., 18O, 13C-labeled methanol/ethanol).
• Lewis acid compatibility: ether oxygens can coordinate to Lewis acids (BF3·Et2O, TiCl4), enabling activation for rearrangements or facilitating subsequent functionalizations adjacent to substituted carbons.

Retrosynthetic value:

• Enables “masking” of 1,4-dicarbonyl frameworks during multi-step sequences to avoid side reactions (e.g., aldol condensations, enolizations) until deprotection.
• Provides conformational control through sterically demanding geminal substituents at 1,4-positions, which can influence diastereoselectivity in ring-functionalization steps.

Practical notes:

• Stability: generally stable to bases and many nucleophiles; sensitive to strong acids and certain Lewis acids in protic media.
• Monitoring: 1H NMR typically shows distinct methoxy singlets (~3.2–3.6 ppm range; literature ranges), facilitating rapid reaction tracking. IR can monitor acetal vs. carbonyl interconversion.
• Purification: silica gel chromatography is normally straightforward; avoid acid-activated silica if acetal cleavage is a concern.

Target Specificity

Not applicable. This product is a small-molecule reagent and does not possess biological target specificity (no antigen/epitope, clone, isotype, or species reactivity). No assay-validated targets are provided for this item.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥97% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 10553-38-5, the molecular formula is C10H20O4, and the molecular weight is 204.260 g/mol. InChIKey YJEPUTKMMMUZAR-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.