S,S'-Diethyl Dithiocarbonate - ≥98%(GC) , CAS No.623-80-3

CAS: 623-80-3 Cat. No.: S161294 Fórmula: C₅H₁₀OS₂ Peso molecular: 150.25 Beilstein Registry Number: 3(3)339 PubChem CID: 12196

GRAU & PUREZA ≥98%

Synonyms

Carbonodithioic acid, S,S-diethyl ester | Carbonic acid, dithio-, S,S-diethyl ester | S,S-DIETHYL CARBAMODITHIOATE | S,S-DIETHYL CARBONODITHIOATE | S,S'-Diethyl Dithiocarbonate | S,S-Diethyl dithiocarbonate | ETHYLTRIFLUOROMETHYLETHER | bis(ethylsulfanyl)

Storage

Room temperature

Shipped In

Normal

Especificações

Sinónimos

Carbonodithioic acid, S,S-diethyl ester | Carbonic acid, dithio-, S,S-diethyl ester | S,S-DIETHYL CARBAMODITHIOATE | S,S-DIETHYL CARBONODITHIOATE | S,S'-Diethyl Dithiocarbonate | S,S-Diethyl dithiocarbonate | ETHYLTRIFLUOROMETHYLETHER | bis(ethylsulfanyl)

Especificações e pureza

≥98%

Condições de armazenamento de armazenamento

Room temperature

Enviado em

Normal

Pureza

≥98%

Product Line

S161294-250mg

Nomes e identificadores

Sorrisos canónicos

CCSC(=O)SCC

IUPAC Name

bis(ethylsulfanyl)methanone

InChIKey

MBUCFVKJCBBWRI-UHFFFAOYSA-N

INCHI

1S/C5H10OS2/c1-3-7-5(6)8-4-2/h3-4H2,1-2H3

SMILES isoméricas

CCSC(=O)SCC

PubChem CID

12196

Peso molecular

150.25

Beilstein

3(3)339

Reaxy-Rn

1744980

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Organic carbonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Organic carbonic acids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Organic carbonic acids and derivatives
• Alternative Parents: Sulfenyl compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Carbonic acid derivative - Sulfenyl compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Descrição: This compound belongs to the class of organic compounds known as organic carbonic acids and derivatives. These are compounds comprising the organic carbonic acid or a derivative thereof.
• 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

Propriedades químicas e físicas

• Índice de refração: 1.52
• Ponto de inflamação (°C): 71 °C
• Ponto de ebulição (°C): 168°C(lit.)
• Peso molecular: 150.300 g/mol
• XLogP3: 2.300
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 150.017 Da
• Monoisotopic Mass: 150.017 Da
• Topological Polar Surface Area: 67.700 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 64.800
• 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

No assay or bioanalytical application protocols are provided for this small-molecule reagent.

• For synthetic use, follow substrate- or monomer-specific literature procedures (e.g., RAFT/MADIX polymerizations or radical xanthate transformations) and adapt stoichiometry, solvent, and temperature accordingly.
• Always verify identity and purity by appropriate analytical methods (NMR, GC/GC–MS, IR) prior to use in critical applications.

Biological Roles

This material is a synthetic organic reagent/monomer modifier and does not have established physiological roles.

• Not typically a metabolite, cofactor, or signaling molecule in biological systems.
• In biochemical research, xanthate motifs may be used as hydrophobic or sulfur-rich handles for derivatization, polymer conjugation, or as reversible radical control groups, but these are chemical utilities rather than biological functions.
• Any interactions with biomacromolecules (e.g., proteins, membranes) are generally nonspecific hydrophobic/thiocarbonyl contacts and are not leveraged for targeted biological activity.

Note: For research use only. No medical or clinical applications are claimed or supported.

Buffer Applications

Not typically applicable. S,S'-Diethyl Dithiocarbonate is a neutral, water-immiscible organic reagent susceptible to hydrolysis in aqueous buffers, and it is not used to prepare buffer systems or as a buffering component.

• If used near aqueous media (e.g., emulsion polymerization), maintain neutral pH and minimize residence time in water to reduce hydrolysis.
• For actual buffer preparation, consult dedicated buffering agents (e.g., phosphate, HEPES, Tris).

Green Alternatives

• Solvent considerations (greener media; literature guidance)

  • Replace chlorinated solvents with greener options where feasible: use toluene, 2-MeTHF, CPME, anisole, or propylene carbonate depending on solubility and temperature needs.
  • For RAFT/MADIX, bulk or emulsion polymerizations in water/mini-emulsions can reduce VOC footprint when monomer compatibility allows; protect against hydrolysis by pH control and short residence times.

• Reagent/CT agent alternatives (functional equivalents; literature)

  • Dithiobenzoates and trithiocarbonates are alternative RAFT agents that may offer higher stability and lower odor while retaining control over more activated monomers; tradeoff is different transfer constants and possible color (purple/pink) due to aromatic C=S.
  • Xanthates bearing renewable Z-groups (e.g., alkoxy segments derived from bioalcohols) can align with green sourcing goals.

• Comparative notes (qualitative)

  • Xanthate (this product): good for less activated monomers; susceptible to hydrolysis; odor management required; typically metal-free processes.
  • Trithiocarbonate: greater hydrolytic robustness; broader monomer scope; sometimes more persistent chromophores in product.
  • 2-MeTHF vs THF as solvent: 2-MeTHF from biomass, higher bp, better phase separation, lower peroxide tendency; however, it can retain water and may extract differently.

• Waste and EHS

  • Limit exposure to air/moisture to reduce formation of malodorous volatile sulfur species, minimizing odor emissions.
  • Implement closed transfers and cold traps for off-gases in thermal reactions.

Select alternatives balancing performance, safety, and sustainability for your specific process.

Pharmaceutical Uses

This product is not an excipient or pharmacopeial buffer component and is not typically used in finished pharmaceutical formulations.

• Potential roles in a pharma R&D context (general)
  • As a synthetic reagent or chain-transfer agent during preparation of specialty polymers (e.g., for excipient research or controlled-release matrices) under process-development settings.
  • As a sulfur-containing intermediate in route scouting for API synthesis where a dithiocarbonate mask/handle is transiently installed.

No medical or therapeutic claims are made. Use is restricted to research and laboratory applications.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Storage & shipping (from Product Data)

  • Storage conditions: Room temperature
  • Shipped in: Normal

• Literature/typical values (for reference; not item-specific specs)

  • Physical state: typically a colorless to pale-yellow liquid with characteristic sulfurous odor.
  • Miscibility/solubility: sparingly soluble in water; miscible with common organic solvents (e.g., alcohols, ethers, esters, aromatics, chlorinated solvents).
  • Polarity/logP: nonpolar-to-weakly polar thioester-like; expected high organic phase affinity (qualitative).
  • Hydrolytic sensitivity: susceptible to slow hydrolysis, especially under acidic/basic conditions, potentially releasing CS2/ethanethiol—handle under dry, neutral conditions.
  • Volatility: lower volatility than light ethers; can still produce vapors—use in fume hood.

• Computed/literature identifiers (for reference)

  • Typical molecular formula: C5H10OS2 (literature)
  • Typical formula weight: ~150.26 g/mol (literature)

Note: Exact numeric values for boiling point, melting point, density, refractive index, UV cutoff, water/peroxide/metal limits are not specified for this item; refer to the CoA/Spec Sheet and SDS.

Quality and Grades

• Item-specific (from Product Data)

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grades for this compound class (general guidance)

  • Research grade: suitable for general synthetic use; typical focus on purity by GC/NMR; stabilizers generally not required but dryness/peroxide content may be relevant for radical chemistry.
  • HPLC/UV grade (if offered): controlled UV absorbance profile and lower trace metals, useful if applying as RAFT/MADIX CT agent in kinetic studies by UV.
  • Anhydrous/anhydrous-sealed (if offered): reduced water content to minimize hydrolysis; recommended for moisture-sensitive transformations.
  • Inhibitors/stabilizers: xanthate esters are not typically supplied with radical inhibitors; verify if any stabilizer is present on the CoA and consider removal if it interferes with radical chemistry.

• What to check on receipt (practical tips)

  • Verify identity by 1H/13C NMR (characteristic thiocarbonyl carbon near 210–220 ppm, literature) and IR (νC=S ~1050–1200 cm−1, literature).
  • Assess purity by GC or GC–MS; monitor for hydrolysis products (CS2, ethanethiol, diethyl carbonate byproducts, literature guidance).
  • Inspect water content (Karl Fischer) if employing moisture-sensitive protocols.

For any item-specific specifications (UV cutoff, metal limits, water content), consult the CoA/Spec Sheet; do not infer values.

Reaction and Applications

• General roles (literature; expand-your-use ideas)

  • Xanthate ester chemistry: S,S'-Diethyl dithiocarbonate is a prototypical O-alkyl S-alkyl dithiocarbonate (xanthate-type) useful as a sulfur-transfer and radical chain-transfer reagent.
  • RAFT/MADIX polymerization: Xanthate-based chain transfer agents control radical polymerization of less activated monomers (e.g., vinyl acetate, N-vinyl amides). Diethyl dithiocarbonate and related xanthates have served as Z-group frameworks in MADIX systems.
  • Radical deoxygenation (Barton–McCombie context): While classical protocols use xanthates derived from alcohols, preformed dialkyl dithiocarbonates serve as models and can participate in radical sulfur transfer under AIBN/thermal initiation.
  • Thionation/sulfurization: Dithiocarbonates can act as mild sulfur donors in transformations of electrophilic centers under Lewis acid or radical conditions.

• Practical considerations (literature)

  • Oxygen sensitivity: Radical applications require rigorous deoxygenation (freeze–pump–thaw or inert gas sparging) to suppress inhibition.
  • Moisture control: Hydrolysis generates CS2 and thiols; keep reaction media dry and neutral. Employ freshly dried solvents and glassware.
  • Initiators: AIBN or peroxides for radical processes; azo loadings typically 0.1–2 mol% relative to xanthate or monomer in RAFT/MADIX (optimize per system).
  • Monitoring: IR (C=S band), 13C NMR (C=S ~210–220 ppm) and GC/GC–MS are convenient for tracking consumption and byproducts.

• Downstream handling

  • Workup often benefits from washing with dilute sodium bicarbonate to remove acidic/byproduct species and drying organic layers over MgSO4/Na2SO4.

These uses are presented as general literature guidance; adapt conditions to your substrate/monomer set and consult primary sources.

Reaction Conditions

The following are general, literature-based conditions for chemistries involving dialkyl dithiocarbonate (xanthate-type) esters and are not item-specific specifications.

• RAFT/MADIX polymerization (xanthate CT agent)

  • Typical solvents/medium: bulk monomer, toluene, anisole, dioxane, or alcohols (dry); aqueous emulsion possible with surfactants and pH control.
  • Initiators: AIBN (60–80 °C), ACVA/VA-044 (water-borne, 40–70 °C), peroxides for higher temperatures. Typical initiator 0.1–1 mol% vs chain transfer agent; CTA 0.05–1 mol% vs monomer depending on target DP.
  • Temperature: 50–120 °C depending on initiator and monomer activation.
  • Oxygen removal: thorough deoxygenation (sparging or freeze–pump–thaw) essential for control.

• Radical xanthate transfer/deoxygenation (Barton–McCombie-type workflows)

  • Solvent: toluene, benzene, xylene, or refluxing chlorinated solvents (dry).
  • Initiation: AIBN or peroxide; radical mediators sometimes added.
  • Temperature: reflux of chosen solvent; adjust to maintain steady radical flux.

• General tips

  • Maintain neutral to slightly acidic conditions to limit hydrolysis; avoid strong base.
  • Use dry glassware/solvents; include molecular sieves if necessary.
  • Monitor by GC or NMR; quench and work up promptly to reduce odor and side reactions.

Expected yields and kinetics are system-dependent; consult monomer/substrate-specific literature for transfer constants and optimization.

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 and pictograms: Not specified for this item; refer to SDS.

• General safety considerations for dithiocarbonate (xanthate) esters (literature/good practice)

  • Likely hazards: irritant to skin/eyes; harmful if inhaled/ingested; may release malodorous/toxic sulfur compounds upon decomposition (e.g., CS2, ethanethiol, H2S). Avoid heat, sparks, open flames, and strong oxidizers. Work in a fume hood.
  • Personal protective equipment (PPE): lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles. For bulk handling, consider face shield and butyl/laminated gloves.
  • Incompatibilities: strong acids/bases (promote hydrolysis/transesterification), strong oxidants (risk of exothermic oxidation), and active metals. Avoid prolonged contact with moisture.
  • First-aid overview (consult SDS for definitive instructions):
    • Inhalation: move to fresh air; seek medical attention if symptoms persist.
    • Skin contact: remove contaminated clothing; wash with soap/water ≥15 min.
    • Eye contact: rinse cautiously with water for several minutes; remove contacts; seek medical attention.
    • Ingestion: rinse mouth; do not induce vomiting; get medical attention.
  • Spill/response: contain and absorb with inert material; avoid release to drains; ventilate area; dispose according to local regulations.
  • Fire-fighting: use dry chemical, CO2, or foam; combustion may produce SOx and COx; firefighters wear SCBA.

Always defer to the product-specific SDS and local institutional safety procedures.

Solvent Selection

This product is a neutral, weakly polar sulfur-containing ester that dissolves readily in many organic solvents but poorly in water.

• Solubility/miscibility profile (literature/generic)

  • Miscible: dichloromethane, chloroform, toluene, ethyl acetate, THF, diethyl ether, acetonitrile, lower alcohols.
  • Limited/low: water and highly protic aqueous buffers (hydrolysis risk).

• Polarity and handling

  • Functions well both as reagent and as a component in nonpolar to moderately polar organic media. Avoid strongly basic alcoholic media for long durations to minimize transesterification/hydrolysis.

• Choosing solvents by application (general)

  • Radical chemistry (e.g., RAFT/MADIX): use inhibited, peroxide-free solvents such as toluene, dioxane, anisole, or bulk monomer; remove oxygen by sparging (N2/Ar).
  • Nucleophilic substitution or sulfurization steps: polar aprotic solvents (DCM, MeCN, THF) under dry, neutral conditions aid reactivity while limiting side hydrolysis.
  • Extraction/partition: prefer nonpolar solvents (hexanes/toluene) to drive separation from aqueous phases and to remove residual CS2 or thiols under reduced pressure.

• Quick comparison (literature)

  • DCM vs toluene: DCM offers faster extractions and lower viscosity; toluene is higher-boiling for thermal radical reactions.
  • MeCN vs THF: MeCN affords low nucleophilicity and easy removal; THF increases solubility of polar cocatalysts but may require peroxide control.

Confirm solvent quality and dryness according to your method; no item-specific solvent recommendations are provided with this product.

Storage and Reconstitution

• Item-specific storage (from Product Data)

  • Storage conditions: Room temperature
  • Shipped in: Normal

• General storage guidance for dithiocarbonate esters (literature/good practice)

  • Keep tightly closed under inert gas (N2/Ar) to minimize oxidation and hydrolysis; store in a cool, dry, well-ventilated place away from light and moisture.
  • Avoid contact with acids, bases, and oxidizers. Use PTFE-lined caps to reduce permeation/odor.
  • If long-term storage is anticipated, refrigeration (2–8 °C) under inert gas can improve stability; allow to warm to room temperature before opening to avoid condensation.

• Handling after opening

  • Minimize headspace and reseal promptly. If feasible, aliquot into smaller vials under inert gas.
  • No reconstitution is required; supplied as a neat liquid (appearance for this item is not specified—consult CoA). If solidification/crystallization is observed at low temperature, gently warm to dissolve and homogenize before use.

Refer to the product’s CoA and SDS for definitive storage limitations and stability information. For research use only.

Structure and Identity

S,S'-Diethyl Dithiocarbonate is a neutral xanthate-type dithiocarbonate ester commonly encountered as EtO–C(=S)–SEt (O-ethyl S-ethyl dithiocarbonate), i.e., a dialkyl dithiocarbonate.

• Item-specific (from Product Data)

  • Product name: S,S'-Diethyl Dithiocarbonate
  • SKU: S161294
  • CAS: 623-80-3
  • InChIKey: 215001 (as listed; verify against CoA/SDS)
  • 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/typical identity data (for reference only; not item-specific specs)

  • Common structural description: O-alkyl S-alkyl dithiocarbonate (xanthate ester)
  • Typical formula (literature): C5H10OS2
  • Typical exact mass (literature): ~150.26 g/mol
  • Typical SMILES (one representation, literature): CCOC(=S)SCC

• Structural features (general)

  • Functional groups: dithiocarbonyl (C(=S)–S–), alkoxy (–OR), thioether (–S–R)
  • 2D description in words: a central thiocarbonyl carbon doubly bonded to sulfur and single-bonded to an ethoxy oxygen and a thioethyl sulfur, with both substituents ethyl groups.
  • No stereocenters; conformationally flexible about C–O and C–S bonds.

Synthetic Utility

• Functional handle (literature)

  • The dithiocarbonate (xanthate) group serves as a versatile masked functionality enabling radical-based transformations, sulfur transfer, and controlled radical polymerizations.

• Key transformations

  • Radical chain transfer: In RAFT/MADIX, xanthates govern molecular weight and dispersity for less activated monomers. Diethyl dithiocarbonate-type structures can function as Z-group frameworks, with ethyl as the leaving radical (R-group).
  • Group-transfer/substitution: Under nucleophilic conditions, transesterification/exchange at O or S may be achieved to install dithiocarbonate onto alcohols/thiols (often via CS2 routes; this reagent can provide a dithiocarbonate source in stepwise strategies).
  • Thioacyl equivalents: The C(=S) moiety participates in additions to soft nucleophiles and can be elaborated to thiocarbonyl derivatives (e.g., conversion to trithiocarbonates or xanthate-derived radical precursors).

• Strategic advantages

  • Orthogonality: Xanthate esters are stable to many neutral conditions, allowing late-stage radical modifications without affecting common protecting groups.
  • Cleavability: The xanthate can be removed or converted under mild radical or reductive conditions, enabling traceless transformations.

• Characterization pointers (literature)

  • IR: C=S stretching in the 1050–1200 cm−1 region; strong C–O–C bands around 1000–1100 cm−1.
  • 13C NMR: Thiocarbonyl carbon typically appears near 210–220 ppm; ethoxy/thioethyl carbons in the 10–70 ppm range depending on substitution.

Use these insights as general guidance; tailor to your substrate and consult primary methods.

Target Specificity

Not applicable. This product is a small-molecule reagent and does not have biological target specificity (no antigen/epitope, clone, or isotype).

Perguntas frequentes

What is the purity of this product, and how is it determined?

This product is supplied at ≥98% purity, determined by gas chromatography (GC). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 623-80-3, the molecular formula is C5H10OS2, and the molecular weight is 150.25 g/mol. InChIKey MBUCFVKJCBBWRI-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.