1-(Pentyldisulfanyl)pentane - Reagent grade

Cat. No.: P483949

GRADE & PURITY Reagent Grade

Storage

Room temperature

Specifications

Specifiche e purezza

Reagent grade

Condizioni di conservazione di stoccaggio

Room temperature

Grado

Reagent Grade

Application Protocols

Not applicable. No validated bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic uses, refer to the Reaction Conditions and Synthetic Utility sections for general procedural guidance.

Biological Roles

This compound is a synthetic dialkyl disulfide and is not a native metabolite. However, general principles about disulfides in biology (literature context; not product-specific) are useful for understanding reactivity:

• Disulfide bonds (R–S–S–R):

  • Ubiquitous in proteins where cystine crosslinks stabilize tertiary/quaternary structure (e.g., extracellular proteins, secretory pathways). Formation is typically oxidative (e.g., DsbA/DsbB in bacteria; PDI in eukaryotes), while reduction is mediated by thiol–disulfide oxidoreductases (thioredoxin, glutaredoxin).

• Redox buffering:

  • Small-molecule disulfides such as cystine participate in cellular redox couples (e.g., GSH/GSSG). These equilibria underpin oxidative protein folding and redox signaling.

• Chemical biology relevance:

  • Disulfide exchange is exploited in designing redox-responsive linkers and prodrugs that are cleaved in reductive environments (e.g., intracellular GSH). Although 1-(pentyldisulfanyl)pentane is not itself a biomedical tool, its disulfide linkage models thiol–disulfide exchange kinetics in hydrophobic contexts.

• Membrane interactions:

  • Hydrophobic disulfides partition strongly into lipid phases; this can influence their behavior in biomimetic systems (micelles, liposomes) used for studying redox-triggered release.

No biological activity or function is claimed for this product. It is supplied strictly for research and laboratory use.

Buffer Applications

Not typically applicable. 1-(Pentyldisulfanyl)pentane is a highly hydrophobic organic reagent and is essentially insoluble in aqueous buffers. It is not used to prepare biological buffers or pH standards.

Practical note: If conducting thiol–disulfide exchange studies in aqueous media, employ co-solvents (e.g., MeCN, DMSO) or surfactants/micelles to solubilize the disulfide, or work with water-miscible model disulfides instead.

Green Alternatives

• Greener handling of disulfide chemistry:

  • If the goal is to access 1-pentanethiol, consider generating the disulfide in situ from the thiol using green oxidants (e.g., catalytic TEMPO/bleach in biphasic media, O2 with base) and then directly proceeding to exchange/reduction without isolating the disulfide, minimizing solvent use and transport.
  • Employ solvent selection guides: replace chlorinated solvents with toluene, 2-MeTHF, CPME, or ethyl acetate when compatible.

• Representative comparisons (general guidance; not product specifications):

  Greener option | Use case | Benefits | Trade-offs --- | --- | --- | --- 2-MeTHF or CPME | Exchange/reduction/thiol–ene | Renewable/safer ethers; good solubility of organosulfur | Peroxide management for ethers; ensure inhibitor control Ethyl acetate | Workups/extractions | Low toxicity, biodegradable | Limited solubility for very hydrophobic substrates MeCN (over DMF/DMSO) | Base-promoted exchange | Easier recovery, lower toxicity than DMF/DMSO | Flammable; still requires careful handling Aqueous ethanol (with phase-transfer) | Disulfide exchange | Reduced VOC footprint | May require PTC and careful pH control

• Waste minimization:

  • Capture organosulfur vapors using carbon traps; segregate sulfur-containing waste for appropriate treatment.
  • Favor catalytic over stoichiometric reagents (e.g., catalytic photoredox for thiol–ene vs excess initiators).

Always evaluate solvent/reagent choices using a recognized solvent selection guide and your process safety constraints.

Pharmaceutical Uses

No excipient designation or pharmacopeial monograph is provided for this item. Not specified for this item; refer to CoA/Spec Sheet.

General, non-clinical context:

• Organosulfur compounds and disulfides can be used as intermediates or protecting-group equivalents in process chemistry during the synthesis of drug candidates, particularly where thiol functionality must be masked or transferred.
• Hydrophobic disulfides may serve as model compounds for studying redox-triggered linker cleavage in drug delivery research, but this product is not intended for clinical or therapeutic use.

Compliance note: This product is supplied for research use only and is not for human or animal therapeutic or diagnostic applications.

Physical Properties

• Item-specific properties from Product Data:

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight (hazard info field): Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general reference values (for context; not product specifications):

  • Physical state: typically a colorless to pale yellow liquid (literature, dialkyl disulfides often have characteristic sulfurous odor).
  • Boiling point: often reported around ~260–275 °C at 1 atm for di-n-pentyl disulfide (literature ranges vary by source).
  • Melting point: expected below 0 °C (literature: generally negative for C5 disulfides).
  • Density: approximately 0.87–0.92 g/mL at 20–25 °C (literature, dialkyl disulfides).
  • Refractive index (n20 D): typically ~1.48–1.50 (literature).
  • Water solubility: very low; essentially insoluble in water (literature). Miscible with nonpolar and moderately polar organic solvents (e.g., hexanes, toluene, ether, DCM).
  • LogP (estimated): high, consistent with hydrophobic C10 disulfide; typically >3 (computed/literature estimates).
  • Vapor pressure: low at ambient temperature (literature, consistent with high boiling point).

• Spectral notes (general):

  • IR: S–S stretch is weak; strong C–H stretches (2850–2960 cm−1).
  • NMR: 1H shows aliphatic multiplets (0.9–1.7 ppm) and methylene alpha-to-sulfur around ~2.6–2.8 ppm (literature). 13C alpha-to-sulfur typically downfield relative to other methylenes.

Always consult the item’s CoA for definitive property values measured for this product.

Quality and Grades

• Item-specific grade from Product Data:

  • Grade/Purity: Reagent Grade

• What Reagent Grade implies (general guidance):

  • Suitable for routine synthetic and preparative laboratory use, where trace-level impurities and UV background are not tightly specified.
  • Not intended as a chromatographic solvent grade (e.g., not HPLC/GC grade) and not guaranteed for trace-metal specifications or ultra-low moisture/UV cutoffs unless expressly stated.

• Purity specifics for this SKU:

  • Exact assay, residual solvent profile, peroxides, metal content, water content, and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

• Practical notes for this compound class:

  • Dialkyl disulfides can contain trace thiols or mixed disulfides; if your application is thiol-exchange sensitive or odor-critical, consider polishing by short-path distillation under reduced pressure or by passing through a small plug of basic alumina to remove acidic/thiolic traces (check recovery and purity by GC).
  • If low UV background is required (e.g., UV detection in HPLC of analytes), verify baseline with a small test injection; reagent grade materials are not optimized for UV transparency.

For regulated or highly sensitive applications, request the lot-specific CoA to confirm assay, GC profile, and applicable impurity limits.

Reaction and Applications

• Redox chemistry:

  • Reduction to thiols: Disulfides are classical precursors to the corresponding thiols. Methods include LiAlH4 (THF/Et2O, 0–25 °C), PPh3/H2O or PBu3/H2O (RT to reflux), borohydride with transition-metal salts (NaBH4/NiCl2), or catalytic hydrogenolysis (e.g., Raney Ni). The product yields two equivalents of 1-pentanethiol.

• Disulfide exchange:

  • In the presence of a thiolate (generated with base), 1-(pentyldisulfanyl)pentane undergoes S–S metathesis to afford mixed disulfides. Useful for protecting/activating thiols and for dynamic covalent chemistry. Typical conditions: base (Et3N, DBU) in MeCN/THF at RT to 50 °C; reaction times from minutes to hours.

• Radical chemistry and thiolation:

  • S–S bonds homolyze thermally or photochemically to form thiyl radicals, which can add to alkenes/alkynes, abstract H atoms, or engage in radical chain processes. Initiation with AIBN or peroxides (60–100 °C) in toluene/xylene; or photolysis (near-UV/visible with photosensitizers) for hydrothiolation and thiol–ene protocols (using disulfide as thiol surrogate via in situ reduction or exchange).

• Sulfur transfer and surface modification:

  • Alkyl disulfides are used as precursors to thiols for self-assembled monolayers on gold after reduction to the thiol, and as sulfur sources in organosulfur synthesis.

• Analytical/standards (general):

  • Long-chain disulfides can serve as odorant surrogates or GC retention markers in method development; the low volatility of the C5/C5 disulfide assists in high-temperature GC applications.

All conditions above are general literature guidance; optimize for your specific substrates and scale.

Reaction Conditions

General literature guidance (optimize to your system; not product specifications):

• Disulfide reduction to thiol:

  • LiAlH4 (1–2 equiv S–S−1) in anhydrous THF or Et2O, 0 °C to RT, 1–3 h; typical high yields of 1-pentanethiol. Quench carefully (ice, then aqueous workup).
  • NaBH4 (3–4 equiv) with catalytic NiCl2 in MeOH/THF at RT to 40 °C, 1–4 h, provides efficient cleavage.
  • PPh3/H2O or PBu3/H2O in THF or toluene, RT to reflux, can reduce disulfides; base (imidazole) may accelerate.

• Disulfide exchange (formation of mixed disulfides):

  • Generate thiolate (R′S−) using Et3N, DBU, or NaOMe. Solvent: MeCN, THF, DMF. Temperatures: 20–50 °C. Times: 0.5–6 h. Often near-equilibrium; use excess of the incoming thiol or remove byproduct thiol to drive conversion.

• Radical thiol–ene via disulfide:

  • Thermal: AIBN (5–10 mol%) in toluene or chlorobenzene, 80–100 °C, 2–6 h, under N2; S–S homolysis and chain transfer furnish thioether adducts.
  • Photochemical: UV-A/blue LEDs with suitable photoinitiators (e.g., Ir or organic dyes) at RT, 0.5–3 h; oxygen exclusion recommended to suppress side oxidation.

• Oxidative formation (if preparing the disulfide):

  • Air/O2 with base from 1-pentanethiol in EtOH/H2O or MeOH; catalytic TEMPO or I2 can accelerate; monitor by GC.

• Workup/purification:

  • Due to high bp, isolate by extraction and short-path distillation (1–5 mbar). Remove residual thiol odor by brief passage through basic alumina.

Safety: Conduct all radical/oxidation chemistry in a fume hood; control exotherms and oxygen content as appropriate.

Safety and Handling

• Item-specific hazard information from Product Data:

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety guidance for dialkyl disulfides (literature; not product-specific):

  • Hazards: May cause skin and eye irritation; may cause respiratory irritation if aerosolized. Characteristic strong sulfurous odor—use appropriate odor control (caps tightly, work in fume hood). Low acute toxicity is typical for long-chain disulfides, but avoid ingestion/inhalation/skin exposure.
  • Flammability: Combustible liquid; high boiling point but can burn. Keep away from ignition sources.
  • Incompatibilities: Strong oxidizers (risk of over-oxidation to sulfoxides/sulfones); strong reducing agents can cleave to thiols; reactive with nucleophilic thiolates (disulfide exchange). Avoid contact with metals that catalyze radical reactions under UV/heat.
  • PPE: Lab coat, nitrile gloves, splash goggles. Use in a certified chemical fume hood.
  • First aid (general):
    • Skin: Wash with soap and water; remove contaminated clothing.
    • Eyes: Rinse cautiously with water for several minutes; seek medical attention if irritation persists.
    • Inhalation: Move to fresh air; seek medical attention if symptoms occur.
    • Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.

Defer to the official SDS for authoritative hazard classification, exposure limits, and emergency procedures for this item.

Solvent Selection

This product is a nonpolar organic reagent (not primarily used as a solvent). Solvent selection here refers to choosing appropriate media for handling, reaction, and purification.

• Polarity/miscibility (general):

  • Highly hydrophobic; essentially insoluble in water.
  • Freely soluble in nonpolar and moderately polar organics: hexanes/heptane, toluene, DCM, chloroform, diethyl ether, MTBE, CPME.

• Recommended media by task:

  • Disulfide–thiolate exchange: Use aprotic solvents (THF, MeCN, DMF, DMSO) with a base (e.g., Et3N, DBU) to generate thiolates; nonpolar solvents (toluene, hexane) can be used if reagents are soluble.
  • Radical homolysis/thiolation: Nonpolar solvents (toluene, xylene, chlorinated solvents) often favored at 60–120 °C or under photolysis.
  • Reductions to thiols: Etheral solvents (THF/Et2O) for hydride reagents; polar aprotics (DMF/DMSO) for phosphorus-based or borohydride/nickel systems.

• Workup and purification:

  • Due to hydrophobicity and high boiling point, liquid–liquid extractions with brine/hexane are efficient. Final purification by bulb-to-bulb/short-path distillation under high vacuum helps remove high-boilers and residual thiols.

• Comparison tips:

  • Versus shorter disulfides (e.g., diethyl disulfide), this C10 disulfide is less volatile and less odorous, easing handling but complicating removal. Choose lower-boiling analogs if easy removal is a priority; choose this item when low volatility during heating is beneficial.

Storage and Reconstitution

• Item-specific storage from Product Data:

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

• General storage guidance for dialkyl disulfides (literature; not product-specific):

  • Store tightly sealed in amber glass at ambient temperature, in a well-ventilated area. Although disulfides are relatively stable to air, minimizing headspace oxygen and light exposure helps suppress side oxidation and odor dispersion.
  • Inert gas blanket (N2/Ar) is optional but beneficial for long-term storage. Keep away from strong oxidizers and bases.
  • Use PTFE-lined caps to mitigate odor permeation. Wipe threads and cap after dispensing to prevent persistent sulfur odors.

• Reconstitution/handling:

  • Delivered neat (no reconstitution typically required). If preparing stock solutions, use dry, oxygen-free solvents (e.g., toluene, hexanes, THF) and store aliquots in sealed vials at RT. Clearly label sulfur-containing solutions due to odor.
  • To remove trace thiols before use, consider a brief pass through basic alumina or a micro-distillation step under high vacuum.

• Stability:

  • Under recommended storage, dialkyl disulfides are stable for extended periods. Inspect periodically by GC for the presence of thiol or higher oxidation products if your application is sensitive.

Research Use Note: For research use only.

Structure and Identity

Brief description: 1-(Pentyldisulfanyl)pentane is a linear dialkyl disulfide corresponding to di-n-pentyl disulfide, featuring a central disulfide linkage flanked by two n-pentyl chains.

• Item-specific identifiers from Product Data:

  • CAS: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: 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/computed identity (for reference only; not product specifications):

  • Common synonym: di-n-pentyl disulfide
  • Expected molecular formula (literature): C10H22S2
  • Expected molecular weight (literature): ~206.41 g/mol
  • Typical SMILES (literature): CCCCCSSCCCCC
  • Core structural features: one S–S bond (disulfide), two saturated n-pentyl chains (no rings, no stereocenters). The 2D structure can be viewed as pentyl–S–S–pentyl with all-carbon linear alkyl segments attached to each sulfur.

• Functional group analysis (general):

  • Disulfide linkage (–S–S–) capable of redox transformations (reduction to thiols; homolysis to thiyl radicals) and exchange with thiolates to form mixed disulfides.
  • Nonpolar hydrocarbon domains confer hydrophobicity and low water solubility.

Note: Use the product’s CoA/Spec Sheet for definitive identifiers for this specific lot/item.

Synthetic Utility

• Functional group behavior:

  • Central disulfide (–S–S–) is a versatile handle for redox and exchange chemistry. It can be cleaved to two thiols (useful for generating 1-pentanethiol) or converted to mixed disulfides via reaction with thiolates.

• Protecting/activating strategies:

  • Disulfide formation is a reversible way to mask thiols. 1-(Pentyldisulfanyl)pentane can donate a pentylthio fragment under nucleophilic attack by a thiolate, enabling thiol transfer without handling free, more volatile thiols.

• Radical transformations:

  • Under thermal/photochemical initiation, S–S homolysis yields pentylthiyl radicals that can add to alkenes (thiol–ene), effect hydrogen abstraction, or participate in chain-transfer, enabling C–S bond constructions under mild conditions.

• Cross-coupling analogues:

  • While classical metal-catalyzed cross-couplings target C–X or C–S bonds, disulfides can undergo metal-catalyzed activation (e.g., Ni, Cu) for C–S bond formation or exchange in some modern protocols, offering routes to thioethers from organoboron or organozinc nucleophiles via in situ thiol generation.

• Retrosynthetic value:

  • View as a synthon for HS–(CH2)5– and for hydrophobic disulfide linkers. In dynamic covalent networks, it provides a hydrophobic, redox-responsive crosslink susceptible to exchange under basic or reducing conditions.

These utilities make dialkyl disulfides practical, low-volatility reservoirs of thiol reactivity in synthesis.

Target Specificity

Not applicable. This product is a small-molecule organosulfur reagent and is not an antibody, enzyme, or affinity reagent. No target, epitope, clone, or species reactivity information applies.