2-(Ethanesulfinyl)acetic acid - ≥95% , CAS No.57830-38-3

CAS: 57830-38-3 Cat. No.: E1323657 分子式: C₄H₈O₃S 分子量: 136.17 EC番号: 854-966-0

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

仕様と純度

≥95%

保管条件

Room temperature

入荷

Normal

純度

≥95%

名前と識別子

カノニカル・スマイル

CCS(=O)CC(=O)O

IUPAC Name

2-ethylsulfinylacetic acid

InChIKey

KXBITTYZPHWSOO-UHFFFAOYSA-N

INCHI

1S/C4H8O3S/c1-2-8(7)3-4(5)6/h2-3H2,1H3,(H,5,6)

分子量

136.17

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organosulfur compounds
    • 分類 Sulfoxides

• Kingdom: Organic compounds
• Superclass: Organosulfur compounds
• 分類: Sulfoxides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Sulfoxides
• Alternative Parents: Sulfinyl compounds Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Sulfoxide - Sulfinyl compound - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• 説明: This compound belongs to the class of organic compounds known as sulfoxides. These are compounds containing a sulfoxide functional group, with the structure RS(=O)R' (R,R' not H).
• 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

化学的性質と物理的性質

• 分子量: 136.170 g/mol
• XLogP3: -0.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 136.019 Da
• Monoisotopic Mass: 136.019 Da
• Topological Polar Surface Area: 73.600 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 110.000
• 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 item-specific tested bioassay protocols (e.g., WB, IHC, IF, FC) are applicable to this small-molecule building block.

For synthetic use, see Reaction Conditions and Synthetic Utility for representative procedures. For analytical characterization, standard protocols include:

• NMR (1H, 13C; DMSO-d6, CDCl3, or CD3OD),
• IR (C=O ~1700 cm−1; S=O ~1030–1060 cm−1; literature ranges),
• LC–MS (ESI−/ESI+), and HPLC purity assessment with acidified mobile phases.

Always adapt conditions to your specific substrate set and consult the CoA/SDS for item-specific guidance.

Biological Roles

No item-specific biological data are provided for this compound.

General context (literature):

• Organosulfur motifs are prevalent in metabolism; thioethers are often oxidized in vivo to sulfoxides and sulfones by flavin monooxygenases and cytochrome P450s. Conversely, sulfoxides can be enzymatically reduced by methionine sulfoxide reductases in biological systems.
• Carboxylic acids are deprotonated at physiological pH (depending on pKa), influencing membrane transport and protein binding via ionic interactions with basic residues.
• The sulfoxide group is a strong hydrogen-bond acceptor and contributes to polarity and dipole moment; incorporation into small molecules can modulate solubility and target engagement in biochemical assays.

Use constraints:

• This product is supplied strictly for research use only (per Product Data). It is not intended for human or veterinary use, food, drug, cosmetic, or household applications.

Buffer Applications

This compound is not a standard biological buffer component. It is a monocarboxylic acid with an electron-withdrawing sulfoxide substituent, but no validated buffer system is established for routine laboratory buffering.

• Item-specific buffer use: Not applicable/Not specified for this item.
• If a buffering role is explored in research (general guidance):
  • Determine accurate pKa experimentally in the intended medium, as sulfoxide substitution can significantly shift acidity relative to acetic acid.
  • Evaluate ionic strength and compatibility with metals/enzymes; sulfoxides can coordinate or affect redox chemistry.

Recommendation: For routine buffering, use established systems (e.g., acetate, MES, MOPS, phosphate) with known pKa and compatibility profiles. Utilize this compound instead as a synthetic building block; see Reaction & Applications and Synthetic Utility.

Green Alternatives

While 2-(Ethanesulfinyl)acetic acid is a building block rather than a solvent, greener choices concern the media and reagents used with it.

• Prefer greener solvents (literature guidance):
  • Replace DMF/NMP where possible with MeCN, EtOAc, MeTHF, CPME, or water/EtOH systems.
  • For amidations, consider water-compatible coupling or enzyme-mediated couplings to reduce hazardous solvent use.
• Oxidation/reduction at sulfur:
  • Oxidation to sulfone: Use Oxone (aqueous) or hydrogen peroxide with suitable catalysts as alternatives to chlorinated peracids; control exotherm and pH.
  • Reduction to sulfide: Employ catalytic hydrogenation or zinc/acid alternatives where compatible, in EtOH or aqueous media, avoiding halogenated solvents.
• Workup/waste minimization:
  • Choose solid-supported coupling reagents or recyclable coupling auxiliaries to ease purification.
  • Employ in-line scavengers for residual reagents and metals.

Comparison snapshot (general):

• Task: Amide coupling
  • Conventional: DMF + HATU/DIPEA
  • Greener alternative: EtOAc/MeCN or water/EtOH with EDC·HCl + NHS; enzyme catalysis where applicable
• Task: Oxidation to sulfone
  • Conventional: mCPBA in DCM
  • Greener alternative: Oxone in water/MeOH or H2O2 with acetic acid/catalyst

Trade-offs: Greener media may reduce solubility or rate; optimize by modest heating, phase-transfer catalysis, or salt formation to maintain performance.

Pharmaceutical Uses

• Item-specific pharmacopeial status or excipient role: Not specified for this item; no compendial designation provided.

General formulation/manufacturing context (non-clinical):

• As a functionalized carboxylic acid, 2-(Ethanesulfinyl)acetic acid can serve as an intermediate in multi-step synthesis of pharmaceutical candidates, allowing late-stage modulation of polarity via sulfur oxidation state (sulfide/sulfoxide/sulfone toggling).
• The carboxyl group enables coupling to amines (amide formation) or alcohols (esterification) during prodrug or linker synthesis for research-scale process development.
• Salt formation (e.g., sodium, triethylammonium) can improve handling and crystallinity during isolation and purification in development labs.

Compliance note: This product is for research use only as stated in the Product Data. It is not approved for therapeutic, diagnostic, or veterinary applications.

Physical Properties

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula and mass (literature/computed): C4H8O3S; ~136.17 g/mol
• Acid/base character (general): Brønsted acid (carboxylic acid). The sulfoxide is a Lewis base at oxygen and weakly at sulfur.
• pKa: Not specified for this item. For related sulfoxide-substituted acetic acids, carboxyl pKa is typically lower than acetic acid due to the electron-withdrawing sulfoxide (literature trend; value not assigned).
• Boiling/Melting point: Not specified for this item; refer to CoA/Spec Sheet.
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive index: Not applicable/Not specified for this item; refer to CoA/Spec Sheet.
• Solubility (general expectations from literature):
  • Likely soluble in polar organic solvents (MeOH, EtOH, acetone, acetonitrile) and in water as the carboxylate salt; limited solubility expected in nonpolar solvents (hexanes, toluene).
  • Forms water-soluble salts with bases (Na+, K+, amines).
• Partitioning (general): Increased polarity vs. simple alkanoic acids due to S=O; logP expected to be modest; exact value not specified.

Important: Do not treat the above as specifications. For lot-specific property limits (e.g., MP range, water, UV cutoff), consult the CoA/Spec Sheet.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• What grade implies (general guidance):
  • Analytical/ACS/AR grades typically define assay, water, and trace metal limits; HPLC/spectroscopy grades limit UV-absorbing/fluorescent impurities to minimize chromatographic background.
  • For building blocks, “≥98%” or similar indicates GC/HPLC purity; residual solvent, water content (KF), and identity (NMR/IR/MS) may be provided on CoA.
• Stabilizers: None listed for this item. If present in a given lot, stabilizers/inhibitors will be disclosed on the CoA.
• Practical quality considerations for this compound class:
  • Sulfoxides can slowly oxidize to sulfones or reduce to sulfides under unsuitable storage; monitor by 1H NMR (diagnostic methylene shifts), LC–MS, or HPLC.
  • Carboxylic acids may form dimers; purity assessment by HPLC with acidic mobile phases is recommended.
• Documentation: For assay, residual solvents, water, and spectral data, consult the CoA/Spec Sheet accompanying the shipped lot.

Reaction and Applications

As a sulfoxide-bearing carboxylic acid, 2-(Ethanesulfinyl)acetic acid serves as a versatile building block where both the carboxyl group and the sulfoxide can be chemoselectively manipulated.

• Carboxylate-driven transformations (literature):
  • Amide/ester formation via EDC·HCl/HOBt, HATU, or DIC/DMAP to introduce the –CH2–S(O)–CH2CH3 motif into peptides, peptidomimetics, or polymer backbones.
  • Activation to acid chloride (SOCl2, (COCl)2) or mixed anhydrides for subsequent nucleophilic substitutions.
• Sulfoxide-centered chemistry (literature):
  • Oxidation to sulfone (e.g., mCPBA, Oxone) to increase polarity, acidity of adjacent C–H, and oxidative stability.
  • Reduction to thioether/sulfide (e.g., TiCl3, PCl3, or Mo(CO)6-based methods) to modulate lipophilicity and redox profile of analogs.
  • Pummerer-type activation (Ac2O/Tf2O conditions) enabling alpha-functionalization adjacent to sulfur; can be leveraged for C–C or C–heteroatom bond formation in scaffold elaboration.
• Medicinal/screening chemistry context (general):
  • The –S(O)– linker is a polarity and H-bond accepting handle; toggling S-oxidation state (sulfide/sulfoxide/sulfone) is a common SAR vector in lead optimization.
• Materials/ligand applications (general):
  • Incorporation into monomers or ligands where sulfoxide’s donor ability and carboxyl-derived anchoring provide binding and assembly features.

Notes: Always tailor conditions to avoid over-oxidation/reduction if a specific S-oxidation state must be preserved.

Reaction Conditions

The following are general, literature-style conditions for common transformations of sulfoxide-bearing carboxylic acids; optimize per substrate and scale.

• Amide coupling (literature example):
  • Reagents: HATU (1.1–1.5 eq), DIPEA (2–3 eq), amine (1.0–1.5 eq)
  • Solvent: DMF or MeCN; 0–25 °C; 1–16 h
  • Notes: Pre-form carboxylate with base. For greener options, use EDC·HCl/NHS in MeCN/EtOAc or aqueous media.
• Esterification (Steglich, literature):
  • Reagents: DCC (1.1 eq), catalytic DMAP
  • Solvent: DCM or THF; 0–25 °C; 2–18 h
  • Notes: Filter dicyclohexylurea; avoid strong acids that can induce Pummerer chemistry.
• Acid chloride formation (literature):
  • Reagents: SOCl2 (2–4 eq), catalytic DMF
  • Solvent: neat or DCM; reflux or 25–60 °C; 1–3 h
  • Notes: Exclude moisture; subsequent acylations at 0–25 °C.
• Oxidation to sulfone (literature):
  • Reagents: mCPBA (1.1–2.0 eq)
  • Solvent: DCM; 0–25 °C; 1–6 h
  • Alternative: Oxone in MeOH/H2O at 0–25 °C; monitor to avoid over-oxidation of other functions.
• Reduction to sulfide (literature):
  • Reagents: TiCl3 (3–5 eq) or PCl3 (1–2 eq)
  • Solvent: MeOH, THF, or toluene; 0–25 °C; 1–6 h
  • Notes: Quench carefully; verify complete reduction by NMR/LC–MS.

Analytical monitoring: TLC (silica, EtOAc/hexanes with 1% AcOH), HPLC (acidified H2O/MeCN), LC–MS. Typical isolated yields vary with partner and conditions; establish via small-scale optimization.

Safety and Handling

• GHS classification, pictograms, and H-statements: Not specified for this item; refer to the SDS for authoritative hazard information.
• Anticipated hazards (general for carboxylic acid sulfoxides):
  • May cause skin/eye irritation and respiratory tract irritation; carboxylic acids can be corrosive to eyes.
  • Sulfoxides can facilitate dermal penetration; avoid skin contact.
• PPE recommendations (good laboratory practice):
  • Wear lab coat, safety glasses/goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood to avoid inhalation of vapors/aerosols.
• Handling notes:
  • Avoid strong oxidizers (risk of further oxidation to sulfone) and strong reducing agents (may reduce sulfoxide to sulfide).
  • Avoid strong dehydrating acids that can induce Pummerer-type reactivity of sulfoxides.
  • Neutralize to its salt form for aqueous handling if appropriate; avoid aerosol generation.
• First aid (overview; defer to SDS):
  • Skin/eye contact: Rinse with copious water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; seek medical advice if symptoms occur.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Storage incompatibilities: Segregate from strong oxidizers, strong reducing agents, and bases/acylating agents that may trigger sulfoxide rearrangements.
• Waste: Collect as organic acidic waste per institutional and local regulations.

Solvent Selection

This compound is a moderately polar, protic carboxylic acid bearing a polar sulfoxide, favoring polar media.

• Polarity/miscibility (general/literature):
  • Expected good solubility in polar protic (MeOH, EtOH) and polar aprotic solvents (DMF, DMSO, MeCN). Limited solubility in nonpolar solvents (hexane, cyclohexane, toluene).
  • Aqueous solubility increases markedly upon neutralization to its sodium/potassium salt or with amine bases (e.g., triethylamine).
• Selection guidance by task:
  • Amide couplings: DMF, DMAc, NMP, or DCM with coupling reagents; add base to form the carboxylate.
  • Oxidation/reduction at sulfur: DCM, EtOAc, MeOH, or acetonitrile are typical, temperature-controlled.
  • Purification: Reverse-phase prep HPLC (acidified water/MeCN) or normal-phase with polar modifiers; avoid strong bases in silica to limit degradation.
• Comparison (practical):
  • DMSO/DMF maximize solubility of both acid and polar partners; MeCN/EtOAc support cleaner workups and easier removal but may require salt formation to dissolve.
• Drying: For strictly anhydrous transformations (e.g., acid chloride formation), use oven-dried glassware and dry solvents; otherwise ambient moisture is typically tolerable.

Storage and Reconstitution

• Storage (from Product Data): Room temperature. Ship under Normal conditions.
• Container: Keep tightly closed in a dry, inert atmosphere. Use amber glass if prolonged light exposure is anticipated (general good practice for organosulfur compounds).
• Stability considerations (general):
  • Avoid prolonged exposure to strong oxidizers or reducers which may change the S-oxidation state.
  • Avoid strong acids under dehydrating conditions that could trigger Pummerer-type reactions.
• Reconstitution/dissolution:
  • For stock solutions, dissolve in MeOH, EtOH, DMSO, DMF, or MeCN. For aqueous work, prepare salts with NaHCO3/Na2CO3 or amines to enhance solubility.
  • Filter sterilize solutions for biological assays if needed (0.22 µm PTFE/nylon) and use freshly or store aliquots at 2–8 °C or −20 °C depending on solvent stability (general guidance). Avoid repeated freeze–thaw.
• Shelf life: Not specified for this item; refer to CoA/Spec Sheet.

Research Use Note: For research use only (per Product Data).

Structure and Identity

2-(Ethanesulfinyl)acetic acid is a sulfur-oxygen functionalized carboxylic acid featuring a sulfoxide (S=O) linker between an ethyl group and an acetic acid moiety.

• Item-specific identifiers (from Product Data):
  • SKU: E1323657
  • Product Name: 2-(Ethanesulfinyl)acetic acid
  • CAS: 57830-38-3
  • CID: 19105823
  • InChIKey: 191950 (as provided)
  • Storage: Room temperature; Shipped: Normal
• Structure description (literature/computed):
  • 2D connectivity: HOOC–CH2–S(=O)–CH2–CH3 (carboxylate-bearing methylene linked to a sulfoxide, which is bonded to an ethyl group)
  • Functional groups: carboxylic acid; sulfoxide (S(IV), one S=O and two single bonds to carbon)
  • Ring systems: none (acyclic)
  • Stereochemistry: sulfoxide sulfur is a stereogenic center; material is typically racemic unless specified
• Formula and formula mass (literature/computed):
  • Molecular formula: C4H8O3S (literature/computed)
  • Molecular weight: ~136.17 g/mol (literature/computed)
• SMILES (literature/computed): CCSCH2C(=O)O

Notes: The provided InChIKey is non-standard length; consult the CoA/SDS for canonical identifiers used for this catalog lot.

Synthetic Utility

2-(Ethanesulfinyl)acetic acid is a bifunctional building block. Its carboxyl group supports classical acyl chemistry, while the sulfoxide offers orthogonal redox and rearrangement handles.

• Carboxyl functionality:
  • Amide formation (EDC/HOBt, HATU, DIC/DMAP) to introduce the –CH2–S(O)–CH2CH3 motif into amides/peptides; subsequent S-oxidation widens polarity range for SAR.
  • Esterification (Fischer, Steglich) to generate protected derivatives or pro-moieties for further transformations.
  • Conversion to acid chloride (SOCl2, (COCl)2) enabling acylations and assembly of mixed anhydrides.
• Sulfoxide functionality:
  • Oxidation to sulfone (mCPBA, Oxone) to increase electron-withdrawing character and activate adjacent C–H for alpha-functionalization (e.g., enolate chemistry of sulfone derivatives).
  • Reduction to sulfide (e.g., TiCl3, PCl3, or catalytic hydrogenation in select systems) to access 2-(ethylthio)acetic acid congeners.
  • Pummerer rearrangement pathways (Ac2O/Tf2O) enabling construction of C–C and C–heteroatom bonds at the carbon alpha to sulfur.
• Orthogonality:
  • The carboxyl group can be protected (as esters) while manipulating S-oxidation state, allowing stepwise diversification.

Analytical control: Monitor reactions by LC–MS (m/z ~136 for acid; higher for esters/amides; literature/computed) and 1H/13C NMR; sulfur oxidation shifts are diagnostic.

Target Specificity

Not applicable. This product is a small-molecule reagent/building block, not a biological targeting reagent (e.g., antibody, ligand with defined target panel). No antigen/epitope, species reactivity, clone, or isotype information applies.

よくある質問

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). 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 57830-38-3, the molecular formula is C4H8O3S, and the molecular weight is 136.17 g/mol. InChIKey KXBITTYZPHWSOO-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.