Ethanesulfinyl chloride - ≥95% , CAS No.1718-44-1

CAS: 1718-44-1 Cat. No.: E1007935 Fórmula: C₂H₅ClOS Peso molecular: 112.580 Número CE: 988-093-2

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Especificações e pureza

≥95%

Condições de armazenamento de armazenamento

Room temperature

Pureza

≥95%

Nomes e identificadores

• Sorrisos canónicos: CCS(=O)Cl
• IUPAC Name: ethanesulfinyl chloride
• InChIKey: CXAVWUXAKZJEBR-UHFFFAOYSA-N
• INCHI: 1S/C2H5ClOS/c1-2-5(3)4/h2H2,1H3
• Peso molecular: 112.580

Taxonomic Classification

Taxonomy Tree

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

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Sulfinic acids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Sulfinic acids and derivatives
• Alternative Parents: Sulfinyl halides Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Sulfinyl halide - Sulfinic acid derivative - Sulfinyl compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Aliphatic acyclic compound
• Descrição: This compound belongs to the class of organic compounds known as sulfinic acids and derivatives. These are compounds derived from sulfinic acid, with the general formula RS(=O)R' ( R not H, R'=any heteroatom).
• 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

• Peso molecular: 112.580 g/mol
• XLogP3: 0.700
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 111.975 Da
• Monoisotopic Mass: 111.975 Da
• Topological Polar Surface Area: 36.300 Ų
• Heavy Atom Count: 5
• Formal Charge: 0
• Complexity: 44.900
• 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 bioanalytical application protocols are provided for this reagent. As a moisture-sensitive electrophile, it is used in synthetic organic transformations rather than direct analytical/biological assays.

For synthetic use, typical protocols are outlined under Reaction Conditions and Synthetic Utility. Refer to peer‑reviewed procedures for your specific substrate class, and confirm stoichiometry, base, solvent, and temperature by small-scale trials.

Biological Roles

This product is an organosulfur reagent intended for chemical synthesis and has no established physiological or biochemical role.

Literature/general context

• Small sulfinyl chlorides are not endogenous metabolites and are generally too reactive to persist in biological systems. They hydrolyze rapidly in aqueous environments to release HCl and form sulfinic derivatives.
• Organosulfur functionalities such as sulfoxides and sulfones do occur in bioactive molecules, but their preparation typically avoids direct handling of sulfinyl chlorides in biological media.

Implications for researchers

• Use only in anhydrous, non-aqueous synthetic steps outside of biological matrices.
• If ultimate targets are biological, thoroughly remove residual reagent and HCl byproducts before any biochemical testing.

No biological activity, receptor binding, or pathway interactions are claimed or implied for this product. For research and laboratory chemical synthesis only.

Buffer Applications

Not typically applicable. Ethanesulfinyl chloride is highly moisture- and hydrolysis-sensitive and is incompatible with aqueous buffers. If your workflow involves buffered media, perform all sulfinylation steps in anhydrous organic solvents, then quench and purify fully before introducing products into any aqueous buffer system.

Green Alternatives

Context

• Ethanesulfinyl chloride is corrosive, moisture-sensitive, and releases HCl. While effective, it poses handling and waste challenges. Consider alternative sulfinylations or routes that limit acid chloride use.

Potential alternatives (literature/generic)

• Sulfinate salts (e.g., sodium aryl/alkyl sulfinates): Can be coupled or oxidized to access sulfoxides/sulfones without handling acid chlorides; milder but may require transition metals.
• SO2 surrogates (e.g., DABSO): Enable in situ sulfinate generation from organometallics or aryl halides under catalytic conditions; reduces corrosive byproducts.
• Sulfinyl imines/sulfinamides from alternative sulfinyl chlorides: tert-Butanesulfinyl chloride (Ellman reagent) offers stereocontrol for chiral auxiliaries; however, it shares corrosivity.
• Oxidation of thioethers: Build the C–S bond first, then selectively oxidize to sulfoxide (e.g., with H2O2, Oxone, t‑BuOOH) to avoid acid chloride stage.

Trade-offs

• Reagent greenness vs step-count: Alternatives may increase steps or require catalysts/solvents with their own EHS burdens.
• Selectivity: Direct sulfinyl chloride methods can be more chemoselective for N‑sulfinylation; alternatives may affect stereochemical or functional group tolerance.

Quick comparison (qualitative)

• Ethanesulfinyl chloride: High atom efficiency for direct sulfinylation; generates HCl; moisture sensitive; corrosive.
• Sulfinate salts/DABSO routes: Safer handling, often catalytic; may need metals/bases and have larger inorganic waste streams.

Recommendation

• For scale-up or EHS-sensitive labs, evaluate sulfinate or SO2-surrogate approaches and greener solvents (e.g., 2-MeTHF, EtOAc) where compatible.

Pharmaceutical Uses

Formulation/excipient role

• None. Ethanesulfinyl chloride is not used as a pharmaceutical excipient due to its reactivity and corrosivity.

Relevance to pharmaceutical process chemistry (literature/general)

• It can serve as a transient reagent to access sulfinamides, sulfoxides, and sulfinate esters as intermediates in API or fragment synthesis. Such steps are conducted in dry, non-aqueous media with stringent controls.
• Regulatory considerations: Residual acid chlorides and HCl must be controlled; demonstrate clearance by appropriate analytical methods (e.g., GC headspace for volatiles, chloride assays, titration for residual acidity).

Manufacturing notes

• Choose scalable solvents with acceptable EHS profiles (e.g., toluene, EtOAc, 2-MeTHF) when compatible, and implement controlled addition and robust scrubbing of off-gases (HCl).
• Ensure materials of construction resist HCl and sulfur oxides (e.g., glass-lined reactors).

No therapeutic or clinical claims are made. This product is offered strictly for research and development use in synthetic chemistry.

Physical Properties

Item-specific specifications

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
• Density, refractive index, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties (non-spec; for planning only)

• State: Typically a colorless to pale liquid; may fume in moist air due to HCl liberation (literature).
• Volatility: Low-to-moderate volatility expected for small sulfinyl chlorides; distillation commonly performed under reduced pressure to limit decomposition (literature).
• Solubility: Miscible with many aprotic organic solvents (e.g., dichloromethane, toluene, ether, acetonitrile). Reacts with protic solvents (alcohols, water) (literature).
• Hydrolytic sensitivity: Rapidly hydrolyzes with moisture to ethanesulfinic acid derivatives and HCl; avoid ambient humidity (literature).
• Odor: Pungent, lachrymatory character typical of acid chlorides/sulfur chlorides (literature).

Discussion and practical implications

• Dry handling is critical; material performance in sulfinylations is strongly impacted by trace water.
• For analytical characterization, GC or GC–MS may be used with short residence times and cool injectors; NMR should be performed in rigorously dry deuterated solvents (e.g., CD2Cl2) with sealed tubes.
• If distillation is necessary, employ short-path at reduced pressure and inert atmosphere. Avoid prolonged heating near the normal boiling range to minimize decomposition.

Always verify exact numerical physical constants from primary literature or the item’s CoA; values are not specified for this product listing.

Quality and Grades

Item-specific status

• 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 for this class of reagent

• Typical offerings: Research grade or ≥95–98% assay are often provided for sulfinyl chlorides, with Karl Fischer moisture and acid chloride content sometimes reported (literature/generic). Low moisture is essential due to rapid hydrolysis to sulfinic species and HCl.
• UV/Chromatography: When used as a reagent rather than an analyte, low-UV grade is less relevant than dryness and low hydrolyzable chloride/acid content. If employing in photochemical settings or UV detection, request UV-Vis baseline data from the CoA.
• Stabilization: Many acyl/sulfinyl chlorides are shipped in amber or with headspace inert gas to mitigate hydrolysis. No stabilizer is ideal; purity is best preserved by dryness and minimal headspace.

What to check on the CoA for your lot

• Assay by titration or NMR/GC, free HCl content, hydrolyzable chloride, water by KF, color (APHA), and residues after distillation.
• If your application is moisture-sensitive (e.g., sulfinamide synthesis), specify maximum water (ppm) and acceptable acidity. If you require low metals (e.g., for catalytic screening), request an elemental impurities profile.

Conclusion

• Use the CoA to align the reagent’s fitness-for-use with your reaction sensitivity. This listing does not specify numerical quality attributes.

Reaction and Applications

Overview

• Ethanesulfinyl chloride is a versatile sulfinylating electrophile. It transfers the ethylsulfinyl [–S(=O)–Et] group to nucleophiles, enabling access to sulfinamides, sulfinate esters, and related organosulfur intermediates (literature/general).

Representative transformations (literature)

• Sulfinamide formation: Reaction with amines (R2NH) in an aprotic solvent and a base (e.g., Et3N, pyridine) affords N-ethanesulfinamides. These can serve as protecting groups or intermediates toward thioamides, sulfonamides, or sulfoxides.
• Sulfinate esters: Alcohols (ROH) react under basic conditions to give ethylsulfinate esters (R–O–S(=O)–Et), useful as radical precursors or for further oxidation to sulfones.
• Organometallic additions: Grignard or organolithium reagents can attack sulfur, forming sulfoxide derivatives after workup. Stoichiometric control and low temperature improve chemoselectivity.
• Halide substitution: Reaction with halide salts (e.g., NaCl, NaBr) is typically unproductive; the S–Cl is the leaving group, not a substitution target under standard conditions.

Practical tips

• Dose ethanesulfinyl chloride slowly at 0–5 °C into a solution of the nucleophile and base to manage exotherm and HCl capture.
• Employ 1.0–1.2 equivalents for clean conversions; excess can lead to over-sulfinylation or side reactions.
• Exclude moisture rigorously; even trace water generates ethanesulfinic acid and HCl, reducing yield.
• Workup: Quench residual acid chloride at low temperature (e.g., with methanol/base) before aqueous separation; buffered washes help retain sensitive sulfinyl products.

Reaction Conditions

General guidance (literature; adjust per substrate and scale)

• N‑Sulfinylation (amines → sulfinamides)

  • Solvent: DCM, THF, or EtOAc (anhydrous).
  • Base: Triethylamine or pyridine (1.1–2.0 equiv) to capture HCl.
  • Temperature: 0–5 °C during addition; then 0–25 °C for 0.5–4 h.
  • Stoichiometry: 1.0–1.2 equiv ethanesulfinyl chloride to amine.
  • Workup: Quench residual acid chloride at 0 °C (e.g., MeOH + base), aqueous bicarbonate wash, then standard purification.

• O‑Sulfinylation (alcohols/phenols → ethylsulfinates)

  • Solvent: DCM or toluene; optionally DMAP catalysis for hindered phenols.
  • Base: Et3N or DIPEA (1.5–2.5 equiv).
  • Temp/time: 0 °C addition, then rt for 1–6 h; monitor by TLC/GC.

• Formation of sulfoxides via organometallics

  • Reagents: RLi or RMgX generated in situ.
  • Solvent: Ether/THF, rigorously dry.
  • Temperature: −78 to −20 °C to favor clean addition.
  • Quench: Controlled, at low temp with electrophile or buffered aqueous workup to set oxidation state.

• Typical yields (literature ranges)

  • Sulfinamides/sulfinates: Often 60–90% depending on sterics and electronics; sensitive to moisture and base choice.

Process and safety notes

• Add ethanesulfinyl chloride last, via syringe pump, to a cooled, stirred mixture containing nucleophile and base.
• Maintain inert atmosphere and use acid gas scrubbers for HCl.
• Validate on small scale to define exotherm and induction periods; calorimetry recommended for scale-up.

Safety and Handling

Regulatory/GHS (item-specific)

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

General safety profile (literature/generic for sulfinyl chlorides)

• Hazards: Corrosive; severe skin/eye irritation or burns possible. Strong lachrymator. Reacts exothermically with water, alcohols, amines, and bases, releasing HCl.
• Incompatibilities: Moisture, protic solvents, strong bases, strong nucleophiles, oxidants/reductants (depending on conditions), and amines without temperature control. Avoid glass joints contaminated with amines (can gum up via sulfinamide formation).
• Special risks: Hydrolysis can be vigorous; pressure buildup possible in sealed moist containers. Thermal decomposition may release HCl and sulfur oxides.

PPE and engineering controls

• Wear chemical splash goggles/face shield, acid-resistant gloves (e.g., butyl, Viton), lab coat; handle in a certified fume hood.
• Keep scrupulously dry; use inert gas blanketing and septum transfers for small-scale dispensing.

First aid (summary; defer to SDS)

• Inhalation: Move to fresh air, seek medical attention. Provide oxygen if trained.
• Skin/eye contact: Immediate 15+ min water rinse; remove contaminated clothing; obtain medical attention.
• Ingestion: Rinse mouth; do not induce vomiting; get medical aid.

Spill/response

• Small spills: Absorb with dry, inert material (avoid water-based absorbents). Quench cautiously with anhydrous alcohol in a controlled, ice-cooled setup if trained.
• Waste: Collect as halogenated/acid chloride-containing organosulfur waste per institutional and local regulations.

Always consult the official SDS for authoritative guidance.

Solvent Selection

Role and polarity

• Ethanesulfinyl chloride is an electrophilic, moisture-sensitive reagent rather than a solvent. Choose process solvents that dissolve substrates while controlling reactivity and heat.

Preferred media (literature guidance)

• Halogenated aprotics: Dichloromethane (DCM) and chloroform provide good solubility and heat removal for sulfinylations; DCM is most common.
• Aromatic hydrocarbons: Toluene and chlorobenzene for higher-temperature operations with careful control.
• Ethers: MTBE, diethyl ether, or THF can be used, especially for reactions with organometallics; ensure absolute dryness.
• Polar aprotics: Acetonitrile can be suitable for certain nucleophiles; confirm compatibility.

Avoid

• Protic solvents (water, alcohols) unless deliberately performing sulfinylation to make sulfinates; uncontrolled reaction and HCl evolution can occur.
• Strongly basic media that may induce side reactions or decomposition.

Comparison and selection tips

• DCM vs toluene: DCM offers better heat sinking and lower bp for easier removal; toluene tolerates slightly higher temperatures but slows some nucleophilic substitutions.
• Ether vs DCM: Ethers promote organometallic reactivity but can increase exotherm risk; dose slowly and maintain low temperature.

Practical notes

• Dry solvent thoroughly (molecular sieves, distillation) and maintain inert atmosphere.
• When forming sulfinamides/sulfinates, include a base (e.g., triethylamine, pyridine) to scavenge HCl and improve selectivity.

Storage and Reconstitution

Item-specific storage

• Storage conditions: Room temperature (per Product Data).
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General handling/storage guidance (literature)

• Keep tightly closed in original container under inert gas (nitrogen or argon). Store in a dry place away from moisture, bases, amines, and nucleophiles. Amber glass is preferred to minimize photolysis.
• After each use, purge headspace with inert gas, recap promptly, and store in a desiccator or dry cabinet.
• Do not refrigerate if crystallization/viscosity may hinder accurate dosing; room temperature is typically suitable if dry. Avoid heat sources.

Reconstitution

• Not applicable; supplied neat as a reagent. If dilution is needed, prepare stock solutions in dry, aprotic solvents (e.g., DCM, toluene, THF) under inert atmosphere. Use within the working day; long-term stock solutions are discouraged due to hydrolysis risk.

Stability notes

• Hydrolyzes upon exposure to moisture, liberating HCl and forming sulfinic derivatives. Monitor by NMR/GC if stored for extended periods.

Research use only

• For research use only (per Product Data). Not for human or animal therapeutic use.

Structure and Identity

Brief description: Ethanesulfinyl chloride is a low‑molecular‑weight organosulfur acid chloride bearing a sulfinyl functionality [S(=O)Cl] attached to an ethyl group. It is the ethanesulfinyl analog used as a sulfinylating electrophile.

• Item-specific (from Product Data):
  • CAS: 1718-44-1
  • SKU: E1007935
  • Storage conditions: Room temperature
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet. (Product Data lists "55951", which is incomplete.)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Literature/computed identifiers (for reference; not product specifications):
  • Common name: Ethylsulfinyl chloride; Ethanesulfinyl chloride
  • Molecular formula (literature): C2H5OSCl
  • Molecular weight (literature): ~112.58 g/mol
  • Representative SMILES (literature): CCSCl
  • Core functional groups: sulfinyl chloride [S(=O)–Cl], ethyl substituent
  • 2D structural description: An ethyl chain (–CH3–CH2–) bonded to a tetravalent sulfur that bears a doubly bonded oxygen (sulfinyl, S=O) and a chloride leaving group (–Cl). The sulfur is chiral-at-sulfur only when bearing two different carbon substituents; here it is not stereogenic.

Notes

• The above literature identifiers are provided for general reference only; consult the product’s CoA/SDS for definitive identifiers associated with this specific lot.

Synthetic Utility

Functional group logic

• The S(=O)–Cl moiety is a potent electrophile; nucleophilic attack at sulfur with concomitant chloride departure forms S–Nu bonds while retaining the sulfoxide oxidation state.

Key transformations (literature)

• N‑Sulfinylation: Amines → N‑ethanesulfinamides (R2N–S(=O)–Et). These can direct stereoselective additions (less so than tert‑butanesulfinamides) or serve as transient protecting groups convertible to sulfonamides or amides.
• O‑Sulfinylation: Alcohols/phenols → ethylsulfinate esters (RO–S(=O)–Et), useful as radical precursors or intermediates to sulfones via oxidation or to thioethers via substitution.
• C‑S bond construction via organometallics: RM (M = Li, MgX) addition at sulfur yields sulfinyl carbanion equivalents that, upon workup, provide sulfoxides (R–S(=O)–Et). Careful temp control prevents overreduction or elimination.
• Halogen–sulfur interconversions are generally unfavorable; S–Cl behaves as the leaving group, not a site for SNAr/SN1 at carbon.

Strategic uses

• Temporary sulfinyl handle: Facilitates downstream oxidation to sulfones or reduction to thioethers, enabling oxidation-state editing on sulfur.
• Chemoselectivity: Sulfinyl chloride reacts faster with hard nucleophiles (amines, alkoxides) than many neutral functionalities, allowing late-stage S-functionalization.

Caveats

• Competes with adventitious water; include base to neutralize HCl and prevent substrate salt formation.
• Sensitive substrates may require hindered bases (e.g., DIPEA) or non-nucleophilic bases to avoid N/O overacylation elsewhere.

Target Specificity

Not applicable. This product is a small-molecule synthetic reagent and is not an antibody, enzyme, or affinity reagent. No antigen/epitope or biological target specificity is associated with ethanesulfinyl chloride.