This compound belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4.
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
116.160 g/mol
XLogP3
0.600
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
0
Exact Mass
116.084 Da
Monoisotopic Mass
116.084 Da
Topological Polar Surface Area
18.500 Ų
Heavy Atom Count
8
Formal Charge
0
Complexity
64.900
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
2
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 application protocols are provided for this SKU. As a general-purpose laboratory solvent/reagent, procedures are reaction-specific. For synthetic applications, consult peer-reviewed literature or method compendia using dioxane-type solvents and adapt conditions with appropriate controls (drying, inert atmosphere, peroxide testing). For any new use, perform small-scale feasibility trials and document solvent quality from the CoA/SDS.
Biological Roles
This compound is a small, non-ionic cyclic diether intended for laboratory/industrial chemical use. It has no established physiological role.
Endogenous occurrence: None known (literature).
Biochemical interactions: Ethers of this type can act as relatively inert hydrophobic cosolvents in biochemical extractions, but they are typically avoided in cellular systems due to membrane perturbation and solvent toxicity concerns (literature/general).
Metabolism/biodegradation: Data specific to 2,6-dimethyl-1,4-dioxane are limited in the open literature; dialkylated dioxanes are expected to be more hydrophobic than 1,4-dioxane and thus may exhibit different environmental fate and bioaccumulation profiles (literature trend). Item-specific data: Not specified for this item; refer to SDS.
Research note: For research use only. Do not use in diagnostic or therapeutic applications. If employing as a cosolvent in enzyme assays or extraction workflows, confirm compatibility and enzyme stability empirically, and keep solvent percentages as low as practical.
Buffer Applications
Not typically applicable. 2,6-Dimethyl-1,4-dioxane is not a buffering agent and lacks acid/base functionality to establish a defined pH range. It is not commonly used to prepare biological buffers or electrophoresis running solutions. For aqueous systems requiring an organic cosolvent, consider water-miscible options (e.g., acetonitrile, DMSO, or ethanol) as appropriate and verify biocompatibility.
Green Alternatives
Context: While cyclic diethers can be effective solvents, 1,4-dioxane and its analogs face scrutiny for environmental persistence and potential health concerns. For some transformations, greener ethers may provide similar performance with improved safety profiles (literature/general).
Comparison (literature/general; qualitative):
2,6-Dimethyl-1,4-dioxane: Moderately polar aprotic ether; forms peroxides; petroleum-derived; biodegradation may be limited; water miscibility reduced relative to dioxane.
2-Methyltetrahydrofuran (2-MeTHF): Bio-based (from furfural) availability; lower peroxide tendency than diethyl ether but still possible; partial water miscibility; bp ~80 °C; good for Grignard/reductions and many catalytic couplings.
Cyclopentyl methyl ether (CPME): Low peroxide formation tendency, hydrophobic, high boiling (~106 °C), robust azeotrope behavior aiding water removal; good stability under acidic/basic conditions.
Dimethyl carbonate (DMC): Green solvent/reactant; polar aprotic; non-peroxide forming; limited utility for strongly basic organometallics but attractive for substitution/transcarbonylation chemistry.
Trade-offs:
Coordination strength: Dioxane-type diethers can coordinate metals more strongly than some green ethers; this can be beneficial or detrimental depending on the catalyst.
Boiling point and process temperature: If a higher reflux is needed, CPME or toluene may substitute; if lower, 2-MeTHF may be preferable.
Regulatory acceptance: 2-MeTHF and CPME have increasing adoption in pharma process development; review solvent selection guides (e.g., CHEM21/ACS GSK) for ranking.
Recommendation: Screen 2-MeTHF or CPME when starting from methods that historically used dioxane-like solvents, while benchmarking yield, selectivity, and workup simplicity.
Pharmaceutical Uses
No pharmacopeial grade or excipient designation is provided for this SKU, and this product is for research use only.
General context (literature/industry):
Role: Dioxane-type ethers are occasionally encountered as process solvents in route scouting or early-stage synthesis due to their coordinating ability and polarity. They are generally not preferred in final drug product formulations.
Regulatory perspective: 1,4-dioxane is a substance of concern; alkylated analogs may share some liability as ethers and are not common excipients. If process use is contemplated, ensure appropriate control strategies for residual solvents per ICH Q3C, noting that this specific compound does not have an assigned permitted daily exposure and would require case-by-case risk assessment.
Item-specific notes:
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Residual solvent limits, elemental impurities, and bioburden: Not specified for this item; refer to CoA/Spec Sheet.
Conclusion: Treat this material as a research solvent/reagent rather than a formulation excipient. For pharmaceutical manufacturing, consider greener, better-characterized solvents with established regulatory precedence (e.g., ethanol, 2-MeTHF, CPME, acetone) where feasible.
Physical Properties
Item-specific specifications are not provided in the product data. The following are literature/general values for the compound class and this structure; do not treat them as specifications for this SKU.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Expected to exceed that of 1,4-dioxane (bp ~101 °C) due to two methyl substituents; literature reports for 2,6-dimethyl-1,4-dioxane are typically in the 120–140 °C range (literature, range reported across sources). Exact value for this item: Not specified; refer to CoA/Spec Sheet.
Melting point: Typically liquid at ambient temperature (literature); item-specific MP: Not specified for this item; refer to CoA/Spec Sheet.
Density: Generally near or slightly below that of water for dialkyl-substituted dioxanes; item-specific density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index (nD): Not specified for this item; refer to CoA/Spec Sheet.
Solubility: Miscible with many organic solvents (ethers, aromatics, chlorinateds); water miscibility is reduced relative to 1,4-dioxane and may be limited (literature trend for alkylated dioxanes). Item-specific solubility: Not specified for this item; refer to CoA/Spec Sheet.
LogP: Expected to be higher (more hydrophobic) than 1,4-dioxane; item-specific value: Not specified for this item; refer to CoA/Spec Sheet.
Vapor pressure: Not specified for this item; refer to CoA/Spec Sheet.
Important: For method development and safety calculations, rely on the product CoA/SDS for definitive properties of the supplied material.
Quality and Grades
Item-specific grade/purity and stabilizers are not listed in the product data for this SKU.
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizer/inhibitor content: Not specified for this item; refer to CoA/Spec Sheet.
General guidance (literature/industry practice):
Research grade solvents and reagents are suitable for most synthetic and analytical method development. If trace-level impurities (water, peroxides, metals) matter, request the detailed CoA and consider additional purification (molecular sieves, peroxide removal cartridges) before critical work.
HPLC/UV grade (when applicable) emphasizes very low non-volatile residue and low UV absorbance; this can be important if using as a chromatography mobile-phase modifier. Since such grade is not specified here, treat as general laboratory grade pending CoA review.
Water, peroxide, and metal specifications: Not specified for this item; refer to CoA/Spec Sheet.
What to verify on receipt:
Conformity with CAS 10138-17-7 and identity testing (e.g., GC purity profile, NMR consistent with 2,6-dimethyl-1,4-dioxane; note potential cis/trans signals).
Peroxide content prior to distillation or concentration (for ethers this is critical).
If enantiomeric/diastereomeric composition matters, confirm via GC or chiral analysis; item-specific isomer ratio is Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
Applications below are general to alkylated 1,4-dioxanes and this structure; item-specific validated uses are not provided.
As a solvent/medium (literature/general):
Organometallics: Ethers solvate cations and stabilize reactive anions; cyclic diethers can be suitable for Grignard, metal hydride reductions, and select transition-metal catalysis. Verify compatibility because steric hindrance from 2,6-dimethyl groups can slightly alter coordination relative to 1,4-dioxane or THF.
Carbocation chemistry: Ether solvents can stabilize carbocationic intermediates in acid-catalyzed rearrangements and solvolysis; caution with strong acids which can promote ring opening.
Polymerization: Ether solvents often serve in anionic or coordination polymerizations; monitor for chain-transfer or complexation effects.
As a weak bidentate donor (literature/general):
The two ether oxygens can chelate to metals, occasionally tuning catalyst activity/selectivity compared with monoethers (e.g., THF). Such effects are substrate- and catalyst-dependent.
Practical tips:
Drying: Treat with 3 Å or 4 Å molecular sieves or distill from drying agents compatible with ethers; avoid sodium/benzophenone unless validated for safety. Confirm dryness by Karl Fischer where critical.
Peroxide control: Test and remediate peroxides (alumina/peroxide scavengers) prior to concentration or distillation; never distill to dryness.
Degassing: Nitrogen or argon sparging or freeze–pump–thaw for O2-sensitive catalysis.
Note: Manufacturer-provided specific applications were not listed for this SKU; see literature precedents for solvent selection in your target transformation.
Reaction Conditions
General guidance based on literature for ether solvents of this class (not item-specific specifications):
Drying: 3 Å or 4 Å molecular sieves overnight; or distill from CaH2 or other compatible drying agents. Verify absence of peroxides prior to any distillation. Item-specific water/peroxide specs: Not specified for this item; refer to CoA/Spec Sheet.
Atmosphere: Inert gas (N2/Ar) recommended for air/moisture-sensitive chemistries; sparge to remove dissolved oxygen when required for radical- or metal-catalyzed processes.
Temperature: Reactions are commonly conducted from 0 °C up to reflux. The expected boiling point is higher than 1,4-dioxane (literature), providing a moderate-temperature reflux window. For elevated temperatures (>120 °C), consider sealed vessels with appropriate pressure ratings and safety controls.
Catalysts/bases: Compatible with many bases (amines, alkoxides) and transition-metal catalysts (Pd, Ni, Cu) used in cross-couplings and substitutions. Strong superacids or AlCl3-type Lewis acids may induce solvent participation; validate first.
Concentrations: Typical 0.1–1.0 M for catalytic couplings; more dilute for highly exothermic organometallic additions.
Workup: Quench sensitive reagents at low temperature; wash organics with water/brine to remove polar residues; dry over MgSO4/Na2SO4; evaporate under reduced pressure while monitoring for peroxides.
Expected outcomes: Yields and rates are system-dependent; when replacing 1,4-dioxane, minor adjustments in catalyst/ligand loading or temperature may be necessary to match performance (literature practice). Always perform small-scale scouting.
Safety and Handling
Hazard classification details were not provided for this SKU. Always consult the SDS for authoritative safety information.
Item-specific hazard details
Signal word: Not specified for this item; refer to SDS.
H-statements: Not specified for this item; refer to SDS.
GHS pictograms/classification: Not specified for this item; refer to SDS.
General safety considerations for alkylated 1,4-dioxanes (literature/general):
Flammability: Expected to be a combustible/flammable liquid; keep away from ignition sources and hot surfaces. Use explosion-proof ventilation where appropriate.
Peroxide formation: Ethers (including cyclic diethers) can form hazardous peroxides upon air/oxygen exposure and light over time. Test periodically (e.g., iodide/starch test strips), store under air-tight conditions, and avoid distilling to dryness. Inhibitors are not specified for this item; refer to CoA/SDS.
Incompatibilities: Strong oxidizers, strong acids (which may catalyze ring-opening), alkali metals, and finely divided reactive metals.
PPE: Safety glasses or chemical goggles, lab coat, and appropriate solvent-resistant gloves (e.g., nitrile). Use in a chemical fume hood to control vapors.
First aid (overview; follow SDS):
Inhalation: Move to fresh air, monitor breathing; seek medical attention if symptoms persist.
Skin/eye contact: Rinse with water for at least 15 minutes; remove contaminated clothing.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Storage and handling tips:
Keep tightly closed at room temperature as indicated; minimize light exposure.
Segregate from oxidizers and sources of peroxide contamination; label with peroxide test/inspection dates.
Solvent Selection
Relevance: 2,6-Dimethyl-1,4-dioxane is a cyclic diether structurally related to 1,4-dioxane and can function as a polar, aprotic solvent with reduced water miscibility relative to the parent dioxane (literature/general).
Polarity and miscibility (literature/general):
Polarity class: moderately polar aprotic ether; donor solvent with two Lewis-basic oxygens.
Miscibility: Readily miscible with many organic solvents (ethers, ketones, aromatics, chlorinateds). Water miscibility is expected to be limited compared to 1,4-dioxane due to methyl substitution.
Boiling range: Typically higher than 1,4-dioxane, affording a somewhat higher reflux temperature for reactions requiring gentle heating.
When to choose it (literature/general):
As an alternative to 1,4-dioxane when reduced water content or lower water miscibility is desired.
Medium-polarity reactions where coordination to metal centers is beneficial but excessively strong solvation (e.g., DMSO) is undesirable.
As a homogeneous medium for organometallic transformations that tolerate ethers (test compatibility first).
Comparison snapshot (qualitative, literature):
1,4-Dioxane: fully miscible with water; bp ~101 °C.
2-MeTHF: greener ether with lower peroxide tendency and partial water miscibility; bp ~80 °C.
2,6-Dimethyl-1,4-dioxane: less water miscible than dioxane; higher bp than dioxane; similar ether-coordination behavior.
Note: For chromatography or moisture-sensitive applications, verify UV cutoff, water content, and peroxide level – Not specified for this item; refer to CoA/Spec Sheet.
Storage and Reconstitution
Storage conditions (item-specific): Room temperature (per product data). Store tightly closed in a well-ventilated area away from heat, sparks, and open flames. Protect from light to minimize peroxide formation.
Shipping: Shipped under normal conditions (per product data).
Container considerations: Use airtight glass or compatible metal containers with PTFE-lined caps. Label with the date opened and schedule periodic peroxide testing.
Stabilizers/inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution: Not applicable; supplied as a neat liquid (appearance not specified). If solidification occurs at low temperature, warm gently to ambient and mix thoroughly before use.
Before critical use: If required by your application, dry over activated molecular sieves and test for peroxides. For analytical use, filter through 0.2 µm PTFE to remove particulates.
Shelf life: Follow SDS/CoA guidance. As with other ethers, inspect regularly for cloudiness, discoloration, or positive peroxide tests; dispose of aged, peroxide-positive material per institutional hazardous waste protocols.
Research Use Only: Not for human or animal therapeutic, diagnostic, or clinical use.
Structure and Identity
2,6-Dimethyl-1,4-dioxane is a methylated 1,4-dioxane (cyclic diether) bearing methyl groups at the two carbon atoms alpha to each ring oxygen.
SKU: D1341252
CAS: 10138-17-7
PubChem CID: 24984 (literature)
InChIKey: 174501 (provided in product data)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Structural features (literature/general):
Core scaffold: a six-membered 1,4-dioxane ring (two ether oxygens at positions 1 and 4; four ring carbons).
Substitution pattern: methyl groups at C-2 and C-6 (the two carbons adjacent to the ring oxygens). These positions are stereogenic; cis/trans diastereomers are possible and often present as a mixture unless specified otherwise.
Functional groups: two acyclic ether linkages embedded in a saturated heterocycle (diether), no additional heteroatoms or unsaturation.
2D depiction in words: a chair-like 1,4-dioxane ring with O atoms opposite each other; each alpha carbon (next to an O) bears a methyl substituent.
Molecular formula and mass (literature/computed):
Molecular formula: C6H12O2 (literature)
Molecular weight: ~116.16 g/mol (literature)
Notes:
Stereochemistry: Without specification, assume racemic mixture of possible cis/trans diastereomers; item-specific isomer ratio is Not specified for this item; refer to CoA/Spec Sheet.
Synthetic Utility
Functional profile (literature/general):
Neutral, polar aprotic cyclic diether with two Lewis-basic oxygen atoms capable of acting as a weak bidentate ligand/solvent donor. Methyl groups at C-2 and C-6 increase hydrophobicity and boiling point relative to 1,4-dioxane, and may subtly reduce metal coordination sterics.
Uses in synthesis:
Solvent for organometallic reagents and polar transformations where ether solvation is advantageous (e.g., additions of RMgX or RLi to certain electrophiles that tolerate ether media; reductions with borohydrides or aluminum hydrides; base-promoted condensations).
Medium for catalytic coupling: Some Pd- or Ni-catalyzed couplings historically report 1,4-dioxane as a solvent; the 2,6-dimethyl analog can be explored as a substitute when reduced water miscibility or a higher reflux temperature is desired.
Ligand-like effects: As a chelating ether, it can modulate catalyst speciation, occasionally improving selectivity or suppressing side reactions. Effects are highly system-dependent; benchmark against THF, 2-MeTHF, CPME, or anisole.
Limitations and considerations:
Acid sensitivity: Strong acids can catalyze ring-opening or form oxonium intermediates; avoid prolonged exposure to strong Brønsted or Lewis acids without prior validation.
Peroxide hazards necessitate testing and remediation prior to concentration or distillation.
Workup: Ethers can co-elute with organics; consider aqueous washes, brine, and careful evaporation under reduced pressure with peroxide monitoring.
Target Specificity
Not applicable. This product is a small-molecule solvent/reagent and is not an antibody, protein, or nucleic acid probe. No antigen/epitope, clone, isotype, or species reactivity information applies.
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