Ethane, 1-methoxy-2-(methylthio)- , CAS No.35332-09-3

CAS: 35332-09-3 Cat. No.: E991366 Fórmula: C₄H₁₀OS Peso molecular: 106.190 Número EC: 103-751-3

Storage

Room temperature

Specifications

Condiciones de almacenamiento de almacenamiento

Room temperature

Nombres e identificadores

• Sonrisas canónicas: COCCSC
• IUPAC Name: 1-methoxy-2-methylsulfanylethane
• InChIKey: FIUYYKGOPZCCRI-UHFFFAOYSA-N
• INCHI: 1S/C4H10OS/c1-5-3-4-6-2/h3-4H2,1-2H3
• Peso molecular: 106.190

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Clase Organooxygen compounds
      • Subclass Ethers

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Clase: Organooxygen compounds
• Subclass: Ethers
• Intermediate Tree Nodes: Not available
• Direct Parent: Dialkyl ethers
• Alternative Parents: Sulfenyl compounds Dialkylthioethers Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Dialkylthioether - Sulfenyl compound - Thioether - Dialkyl ether - Hydrocarbon derivative - Organosulfur compound - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as dialkyl ethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are alkyl groups.
• 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

Propiedades químicas y físicas

• Peso molecular: 106.190 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 106.045 Da
• Monoisotopic Mass: 106.045 Da
• Topological Polar Surface Area: 34.500 Ų
• Heavy Atom Count: 6
• Formal Charge: 0
• Complexity: 23.500
• 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

Not applicable to this product.

• No immunoassay or cell-based application protocols (e.g., WB, IHC, IF, FC) are associated with this chemical.
• For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

Item-specific biological data

• Not specified for this item; refer to CoA/Spec Sheet. Product is for research use only.

General context (biochemistry background; not specific to this compound)

• Low–molecular weight thioethers and ethers are common motifs in biology (e.g., methionine, S‑adenosylmethionine, and ether lipids). Thioethers can act as soft nucleophiles and can undergo metabolic oxidation to sulfoxides/sulfones in vivo.
• Small aliphatic ether–thioethers of this type are typically xenobiotic in biological systems and do not have a known physiological role; they may be handled by generic Phase I (oxidation) and Phase II (conjugation) metabolism if encountered.

Practical note

• This product is intended for laboratory research and chemical synthesis. Do not use in humans or animals for diagnostic or therapeutic purposes.

Buffer Applications

Not typically applicable.

• Ethane, 1-methoxy-2-(methylthio)- is a neutral organic ether–thioether and does not function as a conventional buffering agent.
• For aqueous work, select established buffers (e.g., phosphate, HEPES, Tris) appropriate to your pH range and ionic strength requirements.

Green Alternatives

Context

• Organosulfur solvents/intermediates can present odor and EHS burdens. Depending on the task (solvation vs. synthetic intermediate), greener replacements may exist.

Potential alternatives (literature/general)

• 2‑Methyltetrahydrofuran (2‑MeTHF): bio-based, higher hydrophobicity than THF; good for Grignard and many catalytic reactions; forms peroxides but typically more stable and easier to dry.
• Cyclopentyl methyl ether (CPME): low peroxide formation tendency, high boiling point, wide liquid range, good for water-tolerant processes; often favored in process chemistry.
• Dimethyl carbonate (DMC): greener polar aprotic solvent in certain SN2/oxidation systems; biodegradable and low toxicity relative to many carbonates.
• Propylene carbonate/ethylene carbonate: high-permittivity, low-volatility media for electrochemistry and certain catalyses (not suitable where sulfur ligation is specifically required).

Trade-offs

• Replacing a thioether-containing medium may reduce odor and metal-poisoning risk but can alter coordination environment and reaction rates.
• In oxidizing systems, sulfur-free ethers minimize side oxidations.

Recommendation

• Match solvent choice to the key driver (EHS, catalysis, separations). For essential sulfur coordination, consider lower-odor thioethers (e.g., sulfoxides like DMSO) if compatible; otherwise prefer 2‑MeTHF/CPME for general ether needs.

Item-specific note

• No solvent grade is specified for this item; if using it as a solvent, confirm batch-specific impurities and odor profile on the CoA.

Pharmaceutical Uses

Item-specific pharmacopeial/excipient status

• Not specified for this item; refer to CoA/Spec Sheet.

General considerations (no therapeutic claims)

• Ether–thioethers are not common excipients due to odor and potential reactivity (oxidation at sulfur). However, related materials may appear as process intermediates or specialty solvents in route scouting.
• If evaluated as a process solvent or reagent, assess extractables/leachables, residual limits in final API, and robustness under oxidative manufacturing conditions.
• Regulatory note: absence from major pharmacopeias typically necessitates full toxicological justification and strict purge arguments for any residual presence in drug substance manufacturing.

Physical Properties

Item-specific values

• Not specified for this item; refer to CoA/Spec Sheet.

Literature/typical data for 1-methoxy-2-(methylthio)ethane (reference only)

• Physical state: expected colorless liquid (typical for low–molecular weight ether–thioethers).
• Estimated molecular weight: ~106.18 g/mol (from C4H10OS; literature).
• Polarity: moderately polar aprotic; higher polarizability due to sulfur; miscible with many organic solvents; limited water solubility expected.
• Volatility: low-to-moderate; anticipate a modest vapor pressure akin to other C4 ether–sulfides.
• Odor: organosulfur-like (literature expectation for thioethers).

Discussion and practical implications (general chemistry knowledge)

• The combination of ether and thioether often gives good solvating power for soft cations and organometallics relative to purely hydrocarbon media.
• Sulfur’s high polarizability can increase refractive index and UV background versus common ethers; verify suitability for spectroscopic applications before chromatographic use.
• If exact BP/MP, density, refractive index, UV cutoff, water content, or metal content are critical, obtain them from your specific batch documentation (CoA) and do not rely on generic estimates.

Quality and Grades

Item-specific grade/purity

• 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 best practices (general guidance)

• In the absence of a stated grade (e.g., AR, HPLC, anhydrous), assume general laboratory grade and qualify the material in-process for critical applications (e.g., trace-metal sensitive catalysis, low-UV chromatography).
• If using for moisture- or air-sensitive transformations, consider on-receipt testing of Karl Fischer water, or pre-drying over molecular sieves, followed by GC assay to verify composition and absence of oxidized sulfur species.
• Stabilizers: None stated. Etheric materials are sometimes shipped with inhibitors or under inert gas for stability. Check the CoA for inhibitor status and remove if necessary prior to use (e.g., alumina pass-through) while understanding potential impact on sulfur functionality.
• Documentation: For regulated workflows, retain batch CoA/SDS and record any in-house conditioning (drying, filtration) as part of your quality file.

Reaction and Applications

General reactivity (literature)

• Thioether functionality is nucleophilic and readily oxidized to sulfoxides/sulfones (m-CPBA, Oxone, H2O2/Ti or WO catalysts). The ether moiety is relatively inert under neutral/basic conditions but cleavable by strong acids (HI/HBr).

Representative transformations and uses

• Selective sulfur oxidation: stepwise S→O oxidation allows access to the corresponding sulfoxide and sulfone, useful polarity handles for purification or further functionalization.
• Sulfonium salt formation: alkylation at sulfur with MeOTf, EtI, or similar electrophiles to give sulfonium salts; these can undergo [2,3]-sigmatropic rearrangements or serve as phase-transfer catalysts in some systems.
• Metal coordination: thioethers act as soft donors to late-transition metals (Pd, Pt, Au, Ag), enabling temporary ligation or acting as a modulator in catalytic systems. Verify compatibility—sulfur can inhibit certain catalysts (e.g., Pd cross-couplings) unless intentionally utilized.
• Ether cleavage under acidic conditions: HI/HBr can cleave the methyl ether to generate 2-(methylthio)ethanol and the corresponding methyl halide—useful for accessing the alcohol while preserving sulfur.
• Alpha-deprotonation next to sulfur: the –CH2–SMe site is mildly acidified; strong bases (e.g., LDA) can generate carbanions for further alkylation (case-dependent; control over competing O/S chemistry is required).

Practical tips

• Exclude strong oxidants unless oxidation is desired. For oxidations, monitor by TLC/GC; sulfoxide formation is typically faster than sulfone.
• If employing as co-solvent, pre-test catalyst tolerance to thioethers.

Reaction Conditions

General literature guidance (not item-specific specifications)

• Sulfur oxidation to sulfoxide: m‑CPBA (1.0–1.2 equiv) in DCM or EtOAc, 0–25 °C, 0.5–4 h; monitor to avoid over-oxidation.
• Sulfone formation: Oxone (2–3 equiv) in MeOH/H2O or acetone/H2O, rt–50 °C, 2–12 h; or H2O2 (30%) with tungstate/molybdate catalysts; typical good to excellent conversions.
• Ether cleavage (to 2‑(methylthio)ethanol): conc. HI or HBr, reflux (50–100 °C depending on acid/solvent), hours; yields vary; ensure appropriate quench and halide handling.
• Sulfonium salt formation: MeOTf or EtI (1.1–2.0 equiv) in acetonitrile/ether, 0–25 °C, 0.5–2 h; isolate as the corresponding salt; strictly anhydrous conditions recommended.
• Alpha‑deprotonation next to sulfur: strong base (e.g., LDA, LiTMP) in THF or ether at −78 to −20 °C, then electrophile; compete with elimination/over-alkylation—optimize stoichiometry and temperature.

Practical notes

• Thioethers can coordinate metals and poison some catalysts; pre-test with Pd/Cu/Ni systems. If inhibition occurs, oxidize to sulfoxide/sulfone or switch solvent.
• Control oxidations carefully; exotherms possible with peracids/peroxides. Use incremental oxidant addition and cooling.
• For acidic cleavages, glassware compatibility and corrosion should be considered; employ proper acid-resistant setups and scrubbing for volatile alkyl halides.

Safety and Handling

Item-specific hazard data

• GHS classification, signal word, pictograms, and H‑statements: Not specified for this item; refer to SDS.

General safety information for ether–thioethers (literature/generic guidance)

• Likely hazards: combustible liquid; vapors may be irritating; organosulfur compounds may have strong odor. Avoid inhalation and skin contact.
• PPE: safety glasses, lab coat, and suitable chemical-resistant gloves (e.g., nitrile). Work in a fume hood.
• Incompatibilities: strong oxidizers (may oxidize thioether to sulfoxide/sulfone); strong acids/HI/HBr can cleave alkyl ethers; halogens and peracids can rapidly oxidize sulfur.
• Peroxide formation: simple dialkyl ethers readily form peroxides on storage; for mixed ether–thioethers, formation is generally less pronounced but possible—periodically test if stored for extended periods and avoid concentrating to dryness without checks.
• First aid (summary; defer to SDS): move to fresh air if inhaled; rinse skin with water upon contact; flush eyes with water for several minutes and seek medical attention if irritation persists; if swallowed, rinse mouth—do not induce vomiting—seek medical advice.
• Spill/Fire response: contain with inert absorbent; eliminate ignition sources. For fire, use CO2, dry chemical, or foam. Vapors may travel to a source of ignition.

Always consult the product’s SDS for authoritative, item-specific safety instructions.

Solvent Selection

Applicability

• This substance is primarily an organic intermediate; however, its mixed ether–thioether structure imparts useful solvent/co-solvent characteristics in specialized contexts.

Polarity and miscibility (general chemistry knowledge)

• Class: polar, aprotic, sulfur-containing ether.
• Expected miscibility: good with common organic solvents (ethers, aromatics, chlorinateds, esters); limited with water. The sulfur increases polarizability and can enhance solubility of soft organometallic species relative to purely oxygenated ethers.

When to choose it

• As a coordinating co-solvent to tune solvation of soft Lewis acids/late-transition-metal catalysts where standard ethers are insufficient.
• For sulfur-tolerant transformations where a thioether cosolvent is advantageous (recognizing sulfur can poison some catalysts—evaluate case-by-case).

Comparison to common ethers (literature-based qualitative trends)

• THF: higher polarity, widely used; forms peroxides; fully oxygenated—less risk of catalyst poisoning but different coordination profile.
• 2-MeTHF/CPME: greener options, more hydrophobic, good for extractions; often better EHS profile than sulfurous ethers.
• DMSO: much higher polarity and boiling point; strong ligand/oxidant compatibility but can over-coordinate or participate in side reactions.

Note

• If using as a solvent, confirm key parameters (water, UV background, inhibitor content, and purity) from the specific batch CoA.

Storage and Reconstitution

Item-specific guidance (from Product Data)

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

General handling recommendations (literature/generic)

• Store tightly closed in a well-ventilated area away from oxidizers and strong acids. Consider amber or opaque containers to minimize light exposure if long-term storage is expected.
• To maintain low moisture and suppress potential peroxide formation, keep under inert gas after opening; optionally add peroxide stabilizer only if compatible with intended use (verify CoA/SDS).
• No reconstitution is required; use as supplied. If drying is necessary, pass through activated alumina/silica or store over 3 Å molecular sieves (verify no acid sites that could promote cleavage under your conditions).
• Inspect periodically for discoloration or odor changes indicative of oxidation; confirm by GC/GC–MS or peroxide test strips before concentrating to dryness.

Research use

• For research use only. Not for human or veterinary use.

Structure and Identity

Item-specific (from Product Data)

• SKU: E991366
• Product name: Ethane, 1-methoxy-2-(methylthio)-
• CAS: 35332-09-3
• PubChem CID: 4431608
• InChIKey: 83895 (as provided)
• Storage: Room temperature

Literature/computed structural information (for reference; not item-specific specifications)

• Common description: a mixed ether–thioether (alkyl methyl ether and alkyl methyl thioether) on a 2‑carbon backbone; also described as 2‑methoxyethyl methyl sulfide.
• Functional groups: one ether (–CH2–O–CH3) and one thioether (–CH2–S–CH3); no rings; no stereocenters.
• Suggested SMILES (literature): COCCSC
• Approximate molecular formula (literature): C4H10OS
• Approximate molecular weight (literature): ~106.18 g/mol
• 2D structural description in words: an ethane chain where C1 bears a methoxy substituent (–O–CH3) and C2 bears a methylthio substituent (–S–CH3); both backbone carbons are methylenes (–CH2–).

Notes

• Where exact identifiers (e.g., definitive InChI, elemental analysis) are required for regulatory or analytical purposes, consult the item-specific CoA/Spec Sheet.

Synthetic Utility

Functional group leverage (literature)

• Dual functionality provides orthogonal handles: the ether is generally inert under basic conditions, while the thioether is nucleophilic and readily oxidized.
• Oxidation series: rapid access to sulfoxide/sulfone increases polarity and can enable subsequent SN2 displacements at activated carbons or facilitate crystallization-based purifications.
• Sulfonium chemistry: quaternization at sulfur (e.g., with MeOTf) yields sulfonium salts that can serve as electrophiles or transient leaving groups, enabling rearrangements or C–C bond formation.
• Backbone manipulations: cleavage of the methyl ether under HI/HBr gives 2‑(methylthio)ethanol, a useful intermediate for further derivatization (tosylation → SN2, oxidation to aldehyde/acid, etc.).
• Alpha-functionalization: deprotonation alpha to sulfur allows C‑alkylation or addition to electrophiles; control conditions to avoid O-alkylation or elimination.

Retrosynthetic value

• Serves as a masked 2‑mercaptoethanol equivalent where methylation at sulfur prevents disulfide formation until deprotection/oxidation.
• Useful as a sulfur-containing polarity modulator in fragment libraries to probe soft-metal coordination in catalytic method development.

Target Specificity

Not applicable to this product.

• This listing is a small-molecule chemical, not a biological affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.