≥97%, stabilized with 60-100 ppm BHT for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Storage & shipping
Room temperature Ships FedEx DG Service Check lot-specific COA for exact specifications.
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Quality documents
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
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Literature proof
Cited in 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Panoramica
2,5-Dimethyl-2,4-hexadiene is an electron-rich alkene. It induces photodechlorination of 9,10-dichloroanthracene and its mechanism has been investigated. Asymmetric cyclopropanation of 2,5-dimethyl-2,4-hexadiene with tert-butyl diazoacetate catalyzed by the new copper-bisoxazoline complex has been reported. 2,5-Dimethyl-2,4-hexadiene has been investigated as a singlet oxygen acceptor in various solvents. Mechanism of addition reaction of aromatic and aliphatic thiols with 2,5-dimethyl-2,4-hexadiene has been investigated. 2,5-Dimethyl-2,4-hexadiene may be used in the synthesis of (+)-trans-(1R,3R)-chrysanthemic acid methyl ester.
This compound belongs to the class of organic compounds known as branched unsaturated hydrocarbons. These are hydrocarbons that contains one or more unsaturated carbon atoms, and an aliphatic branch.
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.
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Recensioni
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Application Protocols
Not applicable. No immunoassay, staining, or enzyme application protocols are associated with this small-molecule hydrocarbon. For synthetic use, refer to the Reaction Conditions and Application sections for general guidance and tailor to your specific transformation.
Biological Roles
Applicability: This product is a synthetic hydrocarbon reagent and is not intended for biological use. No item-specific biological function is provided.
General/literature context:
Conjugated dienes, as a class, appear in natural products (e.g., terpenes) and in lipid peroxidation pathways; however, 2,5-dimethyl-2,4-hexadiene itself is not a known endogenous metabolite.
Hydrocarbon dienes can undergo autoxidation to form peroxides and hydroperoxides in biological-like environments; such processes are mainly relevant to stability and handling, not to a physiological role.
Volatile organic compounds with similar structures can be environmental emissions from petroleum processing; any toxicological or environmental fate assessments must be taken from the SDS and primary literature, not inferred from this listing.
Research use only: Per Product Data, this material is for research use only and not for diagnostic, therapeutic, or in vivo applications.
Buffer Applications
Not typically applicable. 2,5-Dimethyl-2,4-hexadiene is a hydrophobic hydrocarbon reagent with negligible water solubility and no acid/base buffering capacity. For aqueous systems, select appropriate buffer salts (e.g., phosphate, HEPES, Tris) described elsewhere. Use this section’s compound in organic-phase synthetic steps rather than as a buffering agent.
Green Alternatives
Context: 2,5-Dimethyl-2,4-hexadiene is a hydrocarbon building block. “Greener alternatives” depend on the transformation rather than the reagent itself. Consider the following strategies (literature/general guidance):
Bio-based feedstocks: If the target structure tolerates, bio-derived dienes (e.g., isoprene from fermentation, myrcene/ocimene from terpenes, or sorbate derivatives) can substitute in cycloadditions to deliver analogous motifs with renewable origins.
Process intensification: Apply solvent minimization, flow chemistry for exothermic additions (e.g., halogenations, epoxidations), or solid-supported reagents to reduce waste.
Greener solvents: Replace chlorinated media with toluene, EtOAc, 2-MeTHF, CPME, or supercritical CO2 when compatible with reagents/catalysts.
Benign oxidants/reductants: Use O2 (with proper catalysts), H2O2, or electrochemical methods in place of stoichiometric halogenating/oxidizing agents where feasible.
Illustrative comparison (general):
Diels–Alder solvent choice
Conventional: CH2Cl2 or toluene.
Greener swap: 2-MeTHF or CPME; often similar rates/selectivity with improved safety and renewability.
Epoxidation
Conventional: mCPBA in CH2Cl2.
Greener swap: Aqueous H2O2 with catalytic tungstate or Ti-silicalite in MeOH/EtOH or Me-THF.
Tradeoffs:
Substrate control (regio-/stereo-) may differ with alternative dienes or solvents; pilot screening is advised.
Renewable feedstocks can carry odor/color impurities; purification protocols may need adjustment.
Pharmaceutical Uses
Item-specific status: Not specified for pharmacopeial grade or excipient status; refer to CoA/Spec Sheet. For research use only.
General/process chemistry context (no therapeutic claims):
Intermediate building block: Conjugated dienes are used in process development to construct substituted cyclohexane/cyclohexene intermediates via Diels–Alder reactions, which can feed into active pharmaceutical ingredient (API) syntheses after functional-group interconversions.
Derivatization platform: Through selective hydrogenation, epoxidation, or hydroboration, this diene can be converted to alcohols, halides, or carbonyl compounds that are further elaborated into chiral auxiliaries or side chains.
Volatility/handling: Compared with lighter dienes (e.g., isoprene), the higher boiling nature of C8 dienes can reduce evaporative losses in scale-up operations, improving mass balance and safety.
Impurity control: Isomeric composition and peroxide content should be monitored in GMP contexts; process controls often include peroxide testing and inhibitor removal before critical steps.
Note: Any use in cGMP manufacturing requires appropriate qualification, supplier audit, and full specification control. No pharmacopeial monograph is implied by this listing.
Physical Properties
Item-specific specifications:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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/general properties (for reference only; not item-specific):
Physical state: Typically a colorless to pale-yellow liquid at ambient conditions.
Odor: Hydrocarbon-like.
Boiling point: Reported in the literature for C8 conjugated diene isomers is in the approximate range expected of light C8 hydrocarbons; consult primary data sources for exact values.
Melting point: Generally below 0 °C for related dienes.
Density (20–25 °C): Typically slightly lower than water for similar C8 hydrocarbons.
Solubility: Practically insoluble in water; miscible with nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, diethyl ether) (literature).
LogP: Expected positive (hydrophobic), consistent with C8 hydrocarbons (literature).
Refractive index: Characteristic of conjugated C=C systems and often higher than saturated analogs; check CoA for actual value.
Notes:
Exact numeric values can vary with isomeric composition (E/Z ratio) and impurity/stabilizer content.
For precise specifications relevant to this SKU, consult the product’s CoA/Spec Sheet.
Quality and Grades
Item-specific quality information:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/Inhibitors: Not specified for this item; refer to CoA/Spec Sheet.
General guidance on quality considerations for 2,5-dimethyl-2,4-hexadiene:
Purity and isomeric composition: Conjugated dienes can exist as E/Z isomer mixtures. The E/E, E/Z, and Z/Z ratios may influence physical constants and reactivity (e.g., Diels–Alder diastereoselectivity). High-purity material may be accompanied by isomer ratio data on the CoA.
Peroxide content: Unsaturated hydrocarbons can form peroxides upon storage. If peroxide specification is critical (e.g., for polymerization or sensitive catalysis), request recent CoA and consider testing prior to use. If supplied with an inhibitor, note its identity and implications for downstream chemistry.
Water/oxygen sensitivity: While hydrophobic, trace oxygen and peroxides can impact reactions (e.g., radical processes). For air- or moisture-sensitive transformations, pre-treat or distill under inert atmosphere as appropriate.
Application-dependent grades:
Synthetic/intermediate grade: Sufficient for general organic synthesis and cycloadditions.
High-purity/low-UV grade: Preferred for photochemical studies or spectrophotometry; ensures minimal baseline absorption from impurities.
Documentation: Rely on the CoA/Spec Sheet for assay, isomer ratios, GC purity, inhibitors, residual solvents, and any metals analysis, if applicable.
Reaction and Applications
General synthetic roles for 2,5-dimethyl-2,4-hexadiene (literature; expand/adjust per your project needs):
Diels–Alder diene: The conjugated 1,3-diene serves as an electron-rich partner in cycloadditions with activated or neutral dienophiles (e.g., maleimides, acrylates, fumarates, quinones). Methyl substituents can bias regioselectivity and influence endo/exo outcomes. Useful for constructing 1,2,3,4-tetrasubstituted cyclohexenes after subsequent functional adjustments.
Catalytic hydrogenation: Partial or full hydrogenation affords 2,5-dimethylhexenes/hexane derivatives. Selective semihydrogenation (Pd/C, controlled H2) permits access to defined monoenes for further elaboration.
Hydroboration–oxidation: Reaction with BH3 or sterically demanding boranes produces organoboranes that, upon oxidative workup (H2O2/NaOH), give allylic/terminal alcohols patterned by Markovnikov/anti-Markovnikov preferences depending on substitution; with conjugated systems, 1,2- vs 1,4-addition patterns can be leveraged.
Electrophilic additions and halofunctionalizations: Bromination/chlorination, HBr/HCl (with or without peroxides) yield vic-dihalides or allylic halides; NBS enables allylic bromination (radical) for further cross-couplings.
Oxidations: Epoxidation (mCPBA, peracids), dihydroxylation (OsO4, KMnO4), or ozonolysis to provide fragmented carbonyls (ketones/aldehydes) at controlled positions; cleavage patterns reflect double-bond positions and substitution.
Metal-catalyzed functionalization: Hydroformylation (Rh/Co) of conjugated dienes can deliver aldehydes selectively under tuned ligands; hydrosilylation (Pt, Karstedt) and hydroamination (rare-earth, late-transition catalysts) expand downstream handles.
Ligand/templating roles: As a neutral diene, it can transiently coordinate to low-valent metal centers (e.g., Ni(0), Rh(I)) in situ, influencing selectivity in certain transformations.
Practical tips:
Control isomerism: E/Z content impacts reactivity and adduct stereochemistry; assess by GC/1H NMR prior to critical steps.
Oxygen control: Minimize peroxides (test/clear) before radical or anionic reactions. Gentle distillation under inert gas can refresh material.
Temperature: Higher bp than isoprene simplifies elevated-temperature cycloadditions without pressurization losses.
Reaction Conditions
The following are literature/general conditions for common transformations of conjugated C8 dienes; adapt to your substrate and safety constraints. Always conduct preliminary screening and consult primary references.
Temperature: 25–140 °C depending on dienophile reactivity; sealed-vessel heating or reflux in toluene/xylene for less activated partners.
Catalysis: Lewis acids (BF3·Et2O, AlCl3, TiCl4) for electron-poor dienophiles; 0.1–1.0 equiv typical.
Times/Yields: Hours to days; often 50–90% depending on substitution and conditions (literature ranges).
Hydroboration–oxidation:
Reagents: BH3·THF (1–2 equiv) or 9-BBN for regioselectivity.
Solvent: THF, 2-MeTHF; 0–25 °C for addition, then H2O2/NaOH workup.
Notes: Conjugated systems can give mixtures of 1,2- and 1,4-addition; 9-BBN improves selectivity.
Epoxidation:
Reagent: mCPBA (1.1–2.2 equiv) in CH2Cl2 or EtOAc, 0–25 °C.
Alternatives: Aqueous H2O2 with catalytic tungstate or Ti-silicalite in alcohols/Me-THF.
Hydrogenation:
Catalyst: Pd/C (5–10 wt%), PtO2, or Raney Ni.
Conditions: 1–5 bar H2, 20–50 °C for partial; higher pressure/longer time for full saturation.
Allylic bromination (radical):
Reagents: NBS (1.1 equiv), AIBN or light initiation, CCl4 or greener alternatives (e.g., PhMe/MeCN) with careful control.
Ozonolysis:
Solvent: CH2Cl2/MeOH at −78 to −30 °C; workup via Me2S, PPh3, or reductive quench to control product state.
Cautions:
E/Z isomerism impacts rate/selectivity; analyze starting material and products.
Remove peroxides/inhibitors prior to radical or anionic sequences.
Safety and Handling
Item-specific safety data:
GHS Classification: Not specified for this item; refer to SDS.
Signal Word: Not specified for this item; refer to SDS.
H-Statements: Not specified for this item; refer to SDS.
Pictograms: Not specified for this item; refer to SDS.
General safety considerations for conjugated dienes (literature/general guidance; always defer to the SDS):
Flammability: Likely a flammable liquid/vapor. Keep away from heat/sparks/open flames. Use intrinsically safe equipment and proper grounding/bonding during transfer.
Inhalation: Use in a fume hood to avoid inhalation of hydrocarbon vapors. Provide adequate ventilation.
Skin/eye contact: Wear appropriate PPE (chemical-resistant gloves, safety goggles, lab coat). Avoid prolonged or repeated exposure.
Reactivity/incompatibilities: Conjugated dienes may undergo autoxidation and, over time, can form peroxides in the presence of air and light. Keep away from strong oxidizers, halogens, and radical initiators. Avoid uncontrolled polymerization (heat, peroxides, UV) by minimizing exposure to air and light.
First aid (overview): If inhaled, move to fresh air; seek medical attention if symptoms persist. In case of skin contact, wash with soap and water. If in eyes, rinse cautiously with water for several minutes and seek medical advice if irritation persists. If ingested, do not induce vomiting; seek medical attention.
Spill/Fire response: For small spills, absorb with inert material and ventilate area. For fire, use dry chemical, CO2, or foam. Water spray may be used to cool containers.
Storage note for this SKU: Store at room temperature (per Product Data). For best preservation per literature, consider storing under inert gas in tightly sealed containers and limit air/light exposure. Always consult the SDS for authoritative hazards and controls.
Solvent Selection
Applicability: 2,5-Dimethyl-2,4-hexadiene is a hydrocarbon reagent rather than a laboratory solvent and is not typically used as a bulk solvent.
Solubility and compatibility (literature/general):
Miscibility: Expected to be miscible with nonpolar and moderately polar organic solvents (e.g., n-hexane, heptane, cyclohexane, toluene, diethyl ether, MTBE, CPME). Poorly soluble in water.
Polarity: Nonpolar; behaves similarly to other C8 hydrocarbons but with slightly enhanced polarizability due to conjugated C=C bonds.
Choosing reaction media when using this reagent:
Diels–Alder and electrophilic additions: Toluene, chlorinated solvents (where permitted), or ethers (e.g., diethyl ether, THF) often provide good solubility while moderating reactivity; nonpolar media can favor endo selectivity in some cases.
Hydroboration/hydrosilylation/hydrogenation: Ethers (THF, CPME), alkanes (hexanes), or aromatic solvents (toluene) are commonly used with homogeneous or heterogeneous catalysts.
Oxidations (e.g., epoxidation, dihydroxylation): Dichloromethane or acetonitrile/water biphasic systems are often reported; greener swaps include EtOAc or Me-THF when compatible with reagents.
Comparison notes (general):
Versus more polar dienes (e.g., acrylates): This substrate is less polar and more hydrophobic, necessitating low-polarity media to maintain solubility.
Versus isoprene: Higher boiling and less volatile, which can simplify handling and temperature control during reactions.
Always verify solvent compatibility with catalysts/reagents and any stabilizers present in the lot (refer to CoA).
Storage and Reconstitution
Item-specific storage/shipping:
Storage Conditions: Room temperature (per Product Data).
Shipped In: FedEx DG Service (per Product Data).
General handling and stability (literature/general):
Container: Store in tightly sealed amber glass under air exclusion where feasible (inert gas blanket) to minimize autoxidation/peroxide formation.
Light/air: Limit exposure to light and air; consider adding an appropriate inhibitor if long-term storage is anticipated (if compatible with intended use). Any inhibitor presence should be stated on the CoA.
Moisture: Not especially moisture-sensitive, but keep dry to maintain material quality and to avoid issues in moisture-sensitive reactions.
Temperature excursions: Stable at ambient laboratory temperatures; avoid heating near the flash/boiling point.
Testing before use: For radical or anionic chemistry, test for peroxides and remove if detected (e.g., pass through basic alumina or carefully distill under inert atmosphere).
Reconstitution: Not applicable; supplied as a neat liquid (appearance for this item not specified). If received with stabilizer or in solution, consult the CoA for composition and recommended pre-use treatment.
Always consult the SDS and lot-specific CoA/Spec Sheet for authoritative storage, inhibitor content, and stability information.
Structure and Identity
Brief description: 2,5-Dimethyl-2,4-hexadiene is a C8 conjugated diene bearing methyl substituents at C-2 and C-5 on a 2,4-hexadiene backbone; multiple E/Z geometrical isomers are possible across the C2=C3 and C4=C5 double bonds (item not specified for isomeric composition).
Item-specific identifiers (from Product Data):
CAS: 764-13-6
CID: 12992
InChIKey: 76979 (as provided; verify against CoA/SDS)
Storage: Room temperature
Shipping: FedEx DG Service
Computed/literature identity (general, not item-specific):
Molecular formula: C8H14 (literature)
Molecular weight: 110.20 g/mol (literature)
Common SMILES (one possible stereochemistry-agnostic form): CC(=C)C=CC(C)=C (literature; reflects a 2,4-hexadiene core with 2,5-dimethyl substitution)
Structural features (general):
Functional groups: two conjugated C=C double bonds (1,3-diene system); two allylic methyl groups.
Conjugation: C2=C3–C4=C5 provides an electron-rich diene suitable for cycloaddition and electrophilic addition chemistry.
Stereochemistry: Potential E/Z isomerism about each double bond; commercial materials may be isomeric mixtures unless otherwise specified (not specified for this item; refer to CoA/Spec Sheet).
2D description: A six-carbon chain bearing double bonds between C2–C3 and C4–C5, with methyl substituents at C2 and C5, yielding a linear, non-cyclic, conjugated hydrocarbon.
Synthetic Utility
Key reactivity features (literature/general):
1,3-Diene functionality: Enables [4+2] cycloadditions with a wide range of dienophiles. Substitution at C2 and C5 can direct regioselectivity and provide steric bias to endo/exo outcomes. Lewis-acid catalysis (e.g., AlCl3, BF3·Et2O) can enhance rates/selectivity when compatible.
Allylic positions: The methyl substituents create activated allylic C–H bonds suitable for selective radical halogenation (NBS/NCS under light) or oxidation to allylic alcohols/ketones via SeO2 or Mn-catalyzed methods.
Electrophilic addition: Halogenation, hydrohalogenation, and oxymercuration-type sequences are viable; conjugation offers 1,2 vs 1,4 control depending on conditions and substituent effects.
Redox versatility: Ozonolysis and Lemieux–Johnson cleavage translate double bonds into carbonyl fragments, enabling convergent routes to diketones, aldehydes, or acids.
Organometallic transformations: Hydroboration followed by Suzuki-type cross-coupling of derived vinyl boronates provides stereodefined C–C bond construction. Hydrosilylation produces vinylsilanes for Hiyama couplings.
Retrosynthetic value:
Serves as a masked synthon for 1,4-dimethyl-substituted cyclohexane rings after DA/hydrogenation sequences.
Fragmentation pathways (ozone/oxidants) allow access to branched C5–C3 or C4–C4 carbonyl partners.
Practical notes:
Isomer ratio control may be necessary before stereosensitive steps—consider photoisomerization or selective derivatization.
Remove peroxides/inhibitors before radical polymerizations or anionic processes; pass through basic alumina or distill under inert gas.
Target Specificity
Not applicable. This product is a small-molecule hydrocarbon reagent with no antigen/epitope or biological target specificity. No clone, isotype, or species reactivity data apply.
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