4-Methyltetradecane - ≥95% , CAS No.25117-24-2

CAS: 25117-24-2 Cat. No.: M1026708 Summenformel: C₁₅H₃₂ Molekulargewicht: 212.410

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Reinheit

≥95%

Namen und Kennungen

• Kanonisches Lächeln: CCCCCCCCCCC(C)CCC
• IUPAC Name: 4-methyltetradecane
• InChIKey: ITVMHPMCNRGCIY-UHFFFAOYSA-N
• INCHI: 1S/C15H32/c1-4-6-7-8-9-10-11-12-14-15(3)13-5-2/h15H,4-14H2,1-3H3
• Molekulargewicht: 212.410

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Hydrocarbons
    • Klasse Saturated hydrocarbons
      • Subclass Alkanes

• Kingdom: Organic compounds
• Superclass: Hydrocarbons
• Klasse: Saturated hydrocarbons
• Subclass: Alkanes
• Intermediate Tree Nodes: Not available
• Direct Parent: Branched alkanes
• Alternative Parents: Not available
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Branched alkane - Aliphatic acyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as branched alkanes. These are acyclic branched hydrocarbons having the general formula CnH2n+2.
• 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: 212.410 g/mol
• XLogP3: 8.100
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 11
• Exact Mass: 212.25 Da
• Monoisotopic Mass: 212.25 Da
• Topological Polar Surface Area: 0.000 Ų
• Heavy Atom Count: 15
• Formal Charge: 0
• Complexity: 107.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 1
• 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 assay or immunoapplication protocols apply to this small-molecule hydrocarbon. For practical laboratory use:

• For GC reference: dilute to appropriate concentration in a volatile, compatible solvent (e.g., isooctane or heptane) using hydrocarbon-clean glassware; document lot and purity from the CoA.
• For biphasic studies: pre-equilibrate the hydrocarbon with buffer to remove dissolved gases if needed; maintain constant temperature to control partitioning. Adjust to your specific analytical or process method; consult your method SOP and the product’s CoA for any lot-specific parameters.

Biological Roles

This product is a simple branched alkane and does not possess specific biochemical functionality. The following points provide general context for saturated hydrocarbons (literature/general; not product-specific claims):

• Occurrence
  • Long-chain alkanes are found in epicuticular waxes of plants and in some insect cuticular layers, contributing to water repellency and barrier functions.
  • Certain microbes biosynthesize or degrade alkanes via alkane monooxygenases, integrating them into metabolic pathways under specialized conditions.
• Physicochemical interactions
  • Due to very high hydrophobicity and lack of functional groups, branched alkanes partition strongly into hydrophobic phases (e.g., lipid-like environments) but do not engage in specific binding or enzymatic interactions without prior oxidation.
• Research uses in biochemistry/biophysics
  • Model hydrophobic phase in studies of membrane-mimetic systems, oil–water partitioning, or protein adsorption at hydrocarbon interfaces.

No clinical or therapeutic roles are implied. Any use in biological systems should be limited to laboratory research with appropriate controls and containment.

Buffer Applications

Not typically applicable. 4-Methyltetradecane is a nonpolar hydrocarbon and is immiscible with water; it does not participate in aqueous acid–base equilibria or buffer systems. For relevant uses, see Solvent Selection and Reaction & Applications.

Green Alternatives

Context: 4-Methyltetradecane is a high-boiling, hydrophobic hydrocarbon. While generally of low intrinsic toxicity compared to aromatics, it is a volatile organic compound (VOC) with persistence concerns and limited biodegradability. Consider the following alternatives when functionally appropriate.

Comparison (literature/general)

• Heptane / Cycloheptane
  • Pros: lower boiling points enable energy-efficient removal; widely available in high purity; lower viscosity; good nonpolar solvency.
  • Cons: higher vapor pressure and flammability risk; less thermal headroom than C15.
• Isoparaffinic solvents (narrow-cut, low-aromatic)
  • Pros: often low odor, low aromatics, consistent performance; can be sourced from more controlled cuts; some have better environmental profiles.
  • Cons: proprietary compositions; data sheets needed for exact properties; still VOCs.
• 2-Methyltetrahydrofuran (2-MeTHF) or CPME (if some polarity tolerated)
  • Pros: bio-based origins possible (2-MeTHF); improved solvency for organics; often better process mass intensity versus halogenated solvents.
  • Cons: introduce ether functionality (peroxide risk), higher polarity may affect selectivity; not as inert/nonpolar as alkanes.

Green chemistry notes

• Source and life-cycle: where available, selecting bio-based iso-paraffins can reduce fossil carbon footprint.
• Process intensity: choose the lowest-boiling solvent compatible with chemistry to reduce energy for solvent recovery.
• Emissions control: implement condensers and solvent recovery to minimize VOC release irrespective of solvent choice.

Pharmaceutical Uses

No pharmacopeial or excipient status is specified for this item; refer to CoA/Spec Sheet. General context (non-clinical; literature/general):

• Hydrocarbon phases (e.g., liquid paraffins, isoparaffins) are sometimes used as inert vehicles in topical formulations, ointment bases, or as components in microemulsions for research purposes. 4-Methyltetradecane, as a branched C15 hydrocarbon, is chemically similar but is not a designated excipient in major pharmacopeias to our knowledge.
• Potential formulation research roles include
  • Hydrophobic carrier phase in microemulsion or nanoemulsion model systems (with appropriate surfactants) to probe droplet size, stability, and release kinetics.
  • Solvent/diluent for lipophilic actives in preformulation screening, where regulatory-grade excipients are not required.

Note: For any development work toward human or veterinary use, only compendial-grade, approved excipients should be selected; this product is for research use only.

Physical Properties

Item-specific specifications (exact values): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for C15 branched alkanes (informational, not product specifications):

• Physical state/appearance: typically colorless, hydrophobic liquid at ambient temperature for many C15 branched isomers; viscosity modestly higher than C7–C10 alkanes.
• Boiling point: typically in the range ~255–270 °C for C15 isomeric alkanes (literature, varies with branching).
• Melting point: branching strongly depresses melting relative to n-pentadecane (mp ~10 °C); branched C15 isomers are often below 0 °C (literature, isomer-dependent).
• Density (20–25 °C): commonly ~0.74–0.77 g/mL for mid/long-chain alkanes (literature range).
• Refractive index (n20 D): approximately 1.42–1.43 for similar chain-length alkanes (literature).
• Vapor pressure: low at room temperature; increases with temperature (literature qualitative).
• Solubility: practically insoluble in water; miscible with nonpolar organic solvents (hexanes, heptane, isooctane, toluene) and soluble in most ethers and chlorinated solvents (literature/general).
• LogP: very high (>>5) for C15 alkanes (literature qualitative), reflecting strong hydrophobicity.

Notes

• Values above are typical literature ranges for structurally related alkanes and provided for context only. For lot-specific data (e.g., exact density, GC purity, UV cutoff), consult the CoA/Spec Sheet.

Quality and Grades

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

Interpretation and guidance (general)

• Hydrocarbon standards/solvents may be offered in grades such as analytical reagent (AR), GC grade, or high-purity (99%+). In the absence of a stated grade, verify suitability for your use-case (e.g., GC-MS, preparative work) via the CoA.
• Trace impurity profile considerations for branched alkanes
  • Residual lower/higher alkanes or isomeric content can influence physical constants and GC retention. For analytical applications, request GC-FID or GC-MS purity/isomer distribution.
  • Peroxide content is generally not a concern for alkanes (unlike ethers); however, oxidative stability still benefits from minimal oxygen exposure and storage in tight containers.
• UV/fluorescence background
  • Saturated alkanes typically show very low UV absorbance above ~210 nm; if using for HPLC carrier phases or spectroscopic blanks, confirm UV cutoff and background on the CoA.
• Stabilizers
  • None are typically required for saturated alkanes. If any stabilizer is present, it will be listed on the label/CoA and should be considered if the material is used in trace analysis.

Reaction and Applications

Applications (general; expandability depends on grade/purity specified on CoA)

• Inert hydrocarbon medium
  • Serves as a chemically inert, non-coordinating, non-protic medium for processes sensitive to polar contaminants (e.g., certain radical, thermolysis, or polymerization studies). High boiling permits elevated temperatures without significant solvent loss.
• GC/analytical use
  • Component in hydrocarbon standard sets or for retention index calibration across C15 region (subject to purity/isomeric specificity). Low UV background enables use as a non-absorbing diluent in some optical studies.
• Materials and surface science
  • Hydrophobic phase for interfacial tension, wetting, and emulsion/microemulsion research; model hydrocarbon for partitioning and solubilization studies.

Reactivity of 4-methyltetradecane (literature/general)

• C–H functionalization
  • Under strong conditions (photoredox/metal-catalyzed borylation, oxidation, or halogenation), unactivated sp3 C–H bonds can be transformed. Ir-catalyzed borylation of alkanes and decatungstate photocatalysis are representative methodologies.
• Radical halogenation
  • Thermal/photochemical halogenation (Cl2/Br2 with radical initiators) affords mixtures of secondary/primary haloalkanes; branching biases substitution toward secondary C–H sites.
• Oxidation
  • Harsh oxidants (e.g., high-temperature combustion, autoxidation with O2/ROOR) yield alcohols/ketones/acids, generally with poor selectivity without catalysis.

Practical considerations

• Drying typically unnecessary (no heteroatoms), but exclude oxygen for oxidation-sensitive studies; degassing and inert gas blankets improve reproducibility at high temperature.
• Removal post-reaction may require high-vacuum or short-path distillation due to high bp.

Reaction Conditions

Guidance below reflects literature/general conditions for unactivated alkane transformations; they are not product specifications. Optimize for your system and scale.

• Radical halogenation (representative)

  • Reagents: Br2 or NBS with radical initiator (AIBN, peroxides) or photochemical initiation.
  • Solvent: neat or in inert hydrocarbon/halogenated solvent.
  • Temperature: 60–120 °C (thermal) or ambient with photoinitiation.
  • Notes: expect isomeric mixtures; control equivalents, light intensity, and temperature to manage over-halogenation.

• Photocatalytic HAT functionalization (e.g., decatungstate)

  • Catalyst: TBADT (tetrabutylammonium decatungstate) 0.5–2 mol%.
  • Light: UV-A/near-UV LEDs (e.g., 365–390 nm) or mercury lamps.
  • Traps: electron-deficient olefins, nitrones, or O2 depending on target.
  • Solvent: acetonitrile or mixed solvents; hydrocarbon can serve as substrate and co-solvent; ensure efficient irradiation and oxygen control.

• C–H borylation (Ir-catalyzed)

  • Catalyst: [Ir(COD)(OMe)]2 with bipyridine or phenanthroline ligands; B2pin2 as boron source.
  • Conditions: 80–150 °C, closed vessel; some protocols use photochemical assistance at lower temperatures.
  • Outcome: preference for secondary C–H; subsequent oxidation to alcohols or cross-coupling from the C–B pinacol ester.

Safety/process

• Employ inert atmosphere (N2/Ar) for radical/photocatalytic protocols to limit autoxidation.
• Heat and mass transfer are critical with viscous, high-boiling hydrocarbons; use efficient stirring and temperature control.

Safety and Handling

Item-specific hazard data (from Product Data)

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.

General safety information for long-chain alkanes (literature/general; defer to SDS for authoritative guidance)

• Hazards
  • Combustible/flammable hydrocarbon liquid; may form flammable vapors at elevated temperature. Avoid heat, sparks, and open flame.
  • May cause drowsiness or dizziness upon inhalation of concentrated vapors; aspiration into lungs during ingestion/vomiting can be harmful (class effect for hydrocarbons).
  • Environmental persistence and potential aquatic toxicity for hydrocarbons; prevent release to the environment.
• Handling/PPE
  • Use in a fume hood to minimize inhalation; avoid aerosol formation.
  • Wear appropriate PPE: safety glasses, lab coat, and compatible chemical-resistant gloves (e.g., nitrile). Consider hydrocarbon-resistant apron for large volumes.
  • Ground/bond containers during transfer to mitigate static discharge.
• Incompatibilities
  • Strong oxidizers (e.g., nitric acid, chromic acid); halogenation reagents under uncontrolled conditions; powerful electrophiles.
• First-aid (summary; see SDS)
  • Inhalation: move to fresh air; monitor breathing; seek medical advice if symptoms persist.
  • Skin/eyes: wash with soap/water; rinse eyes thoroughly; remove contaminated clothing.
  • Ingestion: do NOT induce vomiting; seek medical attention immediately due to aspiration risk.
• Fire-fighting
  • Use foam, dry chemical, or CO2; water spray to cool containers. Vapors may travel and flash back.

Always consult the product SDS for definitive hazard classification and response measures.

Solvent Selection

Relevance: 4-Methyltetradecane functions as a highly nonpolar, hydrophobic medium/diluent rather than a general-purpose polar solvent. Select it when extreme nonpolarity, chemical inertness, and high boiling temperature are beneficial.

• Polarity/miscibility (literature/general)
  • Polarity index: effectively ~0 for saturated alkanes; dielectric constant ~2 (cf. n-pentadecane ~2.03 at 20 °C).
  • Miscibility: insoluble in water; miscible with nonpolar media (alkanes, cycloalkanes, aromatics). Limited miscibility with polar solvents; immiscible with highly polar solvents (water, short alcohols) except as minor component.
• When to choose 4-methyltetradecane
  • As a high-boiling, inert diluent for thermal or radical processes where protic/polar solvents are detrimental.
  • As a matrix or carrier in hydrocarbon property studies (viscosity, lubrication, interfacial phenomena) or as a hydrophobic phase in biphasic systems.
  • As a retention time marker or calibration component in GC for hydrocarbon patterns (depending on purity/isomer control).
• Alternatives and contrasts
  • Heptane/Isooctane: lower boiling, less viscous; preferred for easier removal and lower flash point operations.
  • Decalin or squalane: higher boiling and/or viscosity; useful for high-temperature stability but with different cycloalkane properties.
  • Aromatics (toluene, xylene): higher solvency for aromatics/polymers; greater toxicity/UV background than alkanes.

Practical note: For analytical work, match solvent background to detection method; alkanes offer minimal UV absorption but are not suitable for polar solutes.

Storage and Reconstitution

Item-specific storage conditions (from Product Data)

• Storage: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

General guidance for hydrocarbons (literature/general)

• Store tightly closed in a clean, hydrocarbon-compatible container to minimize evaporation and oxidation; keep away from heat, sparks, open flames, and strong oxidizers.
• For highest stability, limit headspace oxygen and moisture; consider inert gas blanket (N2/Ar) for long-term storage, especially if performing oxidation-sensitive work.
• If the material becomes highly viscous at cooler temperatures, warm gently to ambient and mix before use.
• Reconstitution: Not applicable; product is supplied neat. If preparing stock solutions or mixtures, use dry, nonpolar solvents and document solvent grade.
• Shelf-life: Verify by GC (purity/impurities) as needed for critical applications; consult CoA for recommended retest date.

Research use only: not for human or animal use.

Structure and Identity

Short description: 4-Methyltetradecane is a branched, saturated C15 hydrocarbon (an isomer of pentadecane) featuring a single methyl substituent on the tetradecane backbone.

• Item-specific identifiers (from Product Data)
  • CAS: 25117-24-2
  • CID (PubChem): 520179
  • InChIKey: 150379 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed identity details (informational)
  • Molecular formula (literature): C15H32
  • Molecular weight (literature): 212.41 g/mol
  • Example canonical SMILES (literature): CCCC(C)CCCCCCCCCC (one valid representation for 4-methyltetradecane)
• Structural features (general description)
  • Hydrocarbon class: branched alkane (saturated; no unsaturation or heteroatoms)
  • Functional groups: none beyond C–C and C–H bonds; single methyl branch at the 4-position on a C14 chain (total carbon count = 15)
  • Stereochemistry: none (no stereocenters in this isomer as drawn)
  • 2D depiction in words: a long linear C chain with a single CH3 side group on the fourth carbon from one end; entirely sp3-hybridized carbon skeleton.

Synthetic Utility

From a retrosynthetic standpoint, 4-methyltetradecane is an unfunctionalized, branched hydrocarbon. Its primary synthetic value lies in serving as:

• An inert medium for transformations requiring nonpolar environments and high temperatures.
• A probe or substrate in studies of C–H activation/selective functionalization on unactivated alkanes.

Representative transformations on unactivated alkanes (literature/general)

• Photocatalytic C–H functionalization
  • Decatungstate-mediated hydrogen atom transfer (HAT) under UV/near-UV irradiation enabling subsequent trapping (e.g., with electron-deficient olefins) to form C–C bonds.
• Metal-catalyzed borylation of alkanes
  • Iridium-catalyzed borylation using bis(pinacolato)diboron under photochemical or thermal conditions to install B–C bonds at secondary C–H sites preferentially.
• Radical halogenation/oxidation
  • Controlled bromination/chlorination via radical initiators; autoxidation in the presence of O2/ROOR affords hydroperoxides/alcohols/ketones with limited selectivity without catalysts.

Selectivity considerations

• The methyl branch (at C4) increases the population of secondary C–H bonds near the branching point, which generally display lower bond dissociation energies than primary C–H, biasing functionalization patterns under HAT conditions.

Workup/handling

• Due to high bp and hydrophobicity, expect persistence in organic layers; remove by high-vacuum, Kugelrohr/short-path, or chromatographic methods if needed.

Target Specificity

Not applicable. This product is a small-molecule hydrocarbon, not a biological targeting reagent (e.g., antibody, ligand, or inhibitor). No antigen/epitope or species reactivity information applies.