Butane-2-sulfonamide - ≥95% , CAS No.17854-68-1

CAS: 17854-68-1 Cat. No.: B1008446 Formula: C₄H₁₁NO₂S Peso molecolare: 137.200 Numero EC: 841-517-9

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

• Sorrisi canonici: CCC(C)S(=O)(=O)N
• IUPAC Name: butane-2-sulfonamide
• InChIKey: FCWGIFCVCCHGTK-UHFFFAOYSA-N
• INCHI: 1S/C4H11NO2S/c1-3-4(2)8(5,6)7/h4H,3H2,1-2H3,(H2,5,6,7)
• Peso molecolare: 137.200

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Organic sulfonic acids and derivatives
      • Subclass Organosulfonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Organic sulfonic acids and derivatives
• Subclass: Organosulfonic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Organosulfonamides
• Alternative Parents: Organic sulfonamides Aminosulfonyl compounds Organic oxides Organic nitrogen compounds Hydrocarbon derivatives
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Organosulfonic acid amide - Organic sulfonic acid amide - Aminosulfonyl compound - Sulfonyl - Organic nitrogen compound - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organosulfur compound - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as organosulfonamides. These are compounds containing the sulfonamide functional group, an amide of sulfonic acid with the general structure R1S(=O)2N(R2)R3 (R1=alkyl, aryl; R2,R3=H, alkyl, aryl).
• 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

Proprietà chimiche e fisiche

• Peso molecolare: 137.200 g/mol
• XLogP3: 0.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 137.051 Da
• Monoisotopic Mass: 137.051 Da
• Topological Polar Surface Area: 68.500 Ų
• Heavy Atom Count: 8
• Formal Charge: 0
• Complexity: 144.000
• 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 assay or bioanalytical application protocols are provided for this item. For synthetic transformations involving butane-2-sulfonamide, see the Reaction Conditions and Synthetic Utility sections for general procedural guidance and then adapt to your substrate and scale.

Biological Roles

This product is a small organic sulfonamide intended for research and synthesis. No endogenous biological role is known for butane-2-sulfonamide specifically.

• General context (literature; not specific to this item)

  • Sulfonamides as a class are prevalent motifs in bioactive molecules due to strong hydrogen-bonding capacity and metabolic stability; however, simple alkanesulfonamides like butane-2-sulfonamide are most commonly used as building blocks or reference materials rather than as biomolecules.
  • The –SO2–NH– functionality can engage in directed H-bonding interactions with proteins and nucleic acids in designed ligands; such uses require further derivatization (e.g., N-alkylation/acylation) and are beyond the scope of this catalog entry.

• Research Use Note: For research use only. Not for human or veterinary use.

Buffer Applications

Butane-2-sulfonamide is not a buffering agent and is not typically used to prepare biological or analytical buffers. If your workflow requires buffered conditions, select an appropriate buffer system (e.g., phosphate, HEPES, MOPS) and dissolve butane-2-sulfonamide in that buffered medium as solubility permits.

Green Alternatives

• Solvent choices

  • Prefer greener solvents when feasible: 2-MeTHF or CPME can sometimes replace DMF/DMSO for N-alkylations with phase-transfer catalysts. Ethanol or isopropanol may be suitable for certain condensations or crystallizations.

• Comparison (general guidance)

  • DMF/DMSO: excellent solvating power; regulatory scrutiny and challenging workup/disposal.
  • 2-MeTHF/CPME: bio-based or lower environmental impact; improved separations; sometimes reduced solubility may limit reaction rate.
  • Ethanol/iPrOH: renewable, low toxicity; limited basicity window and sometimes insufficient solubility without heating.

• Reagent selection

  • Use milder inorganic bases (K2CO3, Cs2CO3) instead of strong bases when electrophile activation allows.
  • Employ catalytic dehydrating strategies for imine formations (e.g., molecular sieves) instead of stoichiometric reagents when possible.

• Workup and purification

  • Favor aqueous ethanol or EtOAc/water partitions, and crystallization over chromatographic purification to reduce solvent consumption.

These suggestions are general/literature-based sustainability practices and should be validated for your specific transformation involving butane-2-sulfonamide.

Pharmaceutical Uses

No pharmacopeial grade or excipient designation is specified for this item. Sulfonamides broadly feature in pharmaceutical chemistry as functional groups; however, butane-2-sulfonamide itself is offered solely as a research chemical and synthetic building block.

• Item-specific status

  • Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Regulatory/compendial status: Not specified.

• Formulation-relevant notes (general)

  • The hydrogen-bond donor/acceptor profile can influence crystallinity and cocrystal formation when incorporated into drug-like scaffolds.
  • For pre-formulation or salt/cocrystal screening involving derivatives of this sulfonamide, consider evaluating aqueous/biorelevant solubility after N-substitution, as the parent NH often modulates lattice energy and solvation.

This product is not intended for therapeutic, diagnostic, or clinical use.

Physical Properties

• Item-specific physical constants: Not specified for this item; refer to CoA/Spec Sheet.

• General/literature expectations for alkanesulfonamides of similar size (reference only; not specifications)

  • Physical state: typically crystalline solids with comparatively high melting points due to strong intermolecular H-bonding networks.
  • Polarity: polar, protic functionality (–NH) with strong dipole from –SO2–; often exhibits good solubility in polar aprotic media (e.g., DMSO, DMF) and alcohols; water solubility can range from moderate to good depending on alkyl size (C4 sec-alkyl is borderline to moderate).
  • Acid-base: sulfonamide N–H is weakly acidic (literature pKa for simple alkanesulfonamides commonly around 9–11 in water; exact value for butane-2-sulfonamide not confirmed here).
  • Partitioning: logP expected to be modest due to one hydrophobic sec-butyl group countered by a highly polar sulfonamide; exact value not confirmed.
  • Spectroscopic signatures: strong S=O stretches in IR typically near ~1330–1150 cm−1 (asymmetric/symmetric, literature ranges); NH stretch often ~3300–3200 cm−1 (literature).

• Practical notes

  • Drying: hygroscopicity is generally low to moderate, but samples can retain solvent or moisture via H-bonding; vacuum-drying at ambient or mild warmth is commonly effective.
  • Thermal behavior: avoid prolonged overheating to prevent decomposition; exact MP/BP not stated for this item.

Quality and Grades

• Item-specific grade/purity and stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance on grades (context for selection)

  • Research/biochemical grade materials emphasize low inorganic and organic impurities and consistent assay; for chromatographic or spectroscopic applications, additional controls (e.g., low UV-absorbing impurities, water content) may be relevant.
  • For synthetic use, the key determinants are assay/purity, residual solvents, and dryness. Sulfonamides are stable solids but can retain polar solvents; Karl Fischer moisture and residual solvent profiles may be included in high-spec grades.

• Implications for this compound class

  • The presence of a single –NH may lead to minor salt formation with mineral acids or bases; ensure neutral form for reproducible behavior in synthesis.
  • If chiral purity at C2 were ever relevant (not typical for a simple sulfonamide reagent), it would need to be specified explicitly; otherwise expect racemic material.

• Documentation

  • CoA/Spec Sheet will provide assay method, impurity profile, and any applicable limits. For regulated workflows or QC-sensitive contexts, request lot-specific CoA prior to use.

Reaction and Applications

• Representative applications (general, literature-informed)

  • N-Functionalization: Deprotonation of the sulfonamide N–H (e.g., K2CO3, Cs2CO3, NaH) enables N-alkylation or N-acylation to give N-substituted sec-butylsulfonamides. Phase-transfer catalysis can enhance alkylation with alkyl halides or sulfates.
  • Sulfonylurea formation: Reaction with isocyanates or carbamoyl chlorides affords N-(sulfonyl)ureas; such linkages are valuable in materials and as synthetic intermediates (no clinical claims).
  • Imine/imine-like derivatives: Condensation with aldehydes/ketones under dehydrating conditions can form N-sulfonylimines (Schiff-base analogs), useful electrophiles in further transformations (e.g., nucleophilic additions, aza-Mannich-type chemistry).
  • H-bond donor additive: The sulfonamide NH can act as a hydrogen-bond donor in organocatalytic or crystallization contexts, although specialized bis-sulfonamides are more common.

• Practical tips

  • Base choice: For simple N-alkylations, inorganic bases (K2CO3/Cs2CO3) in DMF/MeCN are often sufficient; stronger bases (NaH) enable less activated electrophiles but require rigorous anhydrous conditions.
  • Selectivity: Over-alkylation is typically not an issue (single NH). Steric hindrance at sulfur-bound sec-butyl has little effect on N-alkylation but may influence crystallinity and solubility.
  • Protecting-group logic: The sulfonyl group strongly deactivates nitrogen; N-sulfonyl derivatives are stable toward many conditions yet can be cleaved reductively or under strong nucleophilic conditions (method depends on N-substituent and sulfonyl type; for alkanesulfonyl, harsh conditions may be required).

Reaction Conditions

The following are literature-style, general conditions for reactions involving alkanesulfonamides; optimize for your substrate and scale.

• N-Alkylation

  • Base: K2CO3 or Cs2CO3 (1.5–2.5 equiv) in DMF or MeCN; optional phase-transfer catalyst (e.g., TBAB) when using less polar media.
  • Electrophiles: primary alkyl bromides/iodides, alkyl tosylates/mesylates; for chlorides or hindered substrates, stronger base (NaH) or iodide catalysis may be needed.
  • Temperature/time: ambient to 60 °C, 2–18 h depending on substrate reactivity.

• N-Acylation

  • Reagents: acyl chlorides or anhydrides with base (Et3N, DIPEA) in DCM, THF, or MeCN; alternatively, EDCI/HOBt or CDI in MeCN/THF for milder coupling to carboxylic acids.
  • Temperature: 0 °C to room temperature; monitor to minimize overacylation of adventitious impurities.

• N-Sulfonylimine formation

  • Conditions: aldehyde (1.0–1.5 equiv) with molecular sieves (3 Å/4 Å) in toluene, MeCN, or 2-MeTHF; catalytic acid/base as needed.
  • Water removal is key; Dean–Stark (for higher-boiling solvent) or sieves for lower-boiling media.

• Workup/purification

  • Neutralization and liquid–liquid extraction (EtOAc/water). Crystallization from alcohols/EtOAc-hexanes is often effective for sulfonamide derivatives.

All parameters above are general guidance from literature precedent and should be verified experimentally.

Safety and Handling

• GHS classification, signal word, pictograms, and H-statements: Not specified for this item; consult the SDS for authoritative information.

• Likely hazards (general guidance for simple alkanesulfonamides; not product-specific)

  • May cause skin and eye irritation; dust may irritate respiratory tract. Low volatility reduces inhalation exposure compared to solvents, but powdered solids can become airborne.
  • Combustible as organic solid; not known for self-reactivity or peroxide formation.

• PPE and handling

  • Wear lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation. Avoid contact with strong oxidizers and strong bases/acids that could induce decomposition or hydrolysis.
  • Good hygiene: avoid ingestion/inhalation; wash thoroughly after handling.

• First-aid overview (general)

  • Skin/eye contact: rinse with water for several 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 unless directed by medical personnel.

Always refer to the product’s SDS for definitive hazard classification, exposure limits, and spill/firefighting procedures.

Solvent Selection

This product is a solid building block, not a solvent. The following guidance addresses solvents suitable for dissolving and reacting butane-2-sulfonamide.

• Polarity and solubility tendencies (general)

  • Favored solvents: polar aprotic media such as DMSO, DMF, NMP, and acetonitrile often dissolve alkanesulfonamides well. Alcohols (MeOH, EtOH, iPrOH) can also be effective. Water solubility is variable; small alkyl sulfonamides may be moderately soluble.

• Choosing among common options

  • DMSO/DMF: maximize solubility for N-alkylation/acylation; compatible with strong bases at controlled temperatures.
  • Alcohols: useful for crystallizations and for reactions with isocyanates to form sulfonylureas (often with base catalysts).
  • Acetonitrile/2-MeTHF/ethyl acetate: suitable for milder reactions or extractions where limited hydrogen bonding is desired.

• Practical notes

  • For base-mediated N-functionalization, ensure anhydrous solvents to avoid quenching strong bases (e.g., NaH, K2CO3 in DMF).
  • For workups, partition in EtOAc/water systems is often favorable; adjust pH to move the compound between phases via deprotonation/protonation of the sulfonamide N–H.
  • If using green chemistry approaches, consider 2-MeTHF, CPME, or water-lean alcohol mixtures where compatible with reactivity.

Storage and Reconstitution

• Storage conditions (item-specific): Room temperature (per Product Data). Protect from moisture and strong oxidizers. Keep container tightly closed when not in use.

• Reconstitution/solution preparation (general guidance)

  • Prepare stock solutions in DMSO, DMF, MeOH, or EtOH as needed for reactions or assays. For maximum stability, use anhydrous solvents and store solutions in sealed vials under inert gas where practical.
  • Aqueous solutions: solubility may be limited; if required, adjust pH or use co-solvents (e.g., water/alcohol mixtures). Prepare fresh to minimize hydrolysis/contamination.

• Stability notes (general)

  • Neat solid sulfonamides are typically stable at ambient conditions for extended periods. Avoid prolonged exposure to heat and light. If clumping occurs due to ambient humidity, gently dry under vacuum at room temperature.

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

Always consult the product label and CoA/SDS for lot-specific storage recommendations.

Structure and Identity

Butane-2-sulfonamide is a secondary-alkyl sulfonamide in which the sulfonyl group (–SO2–) bears an NH2 and is bonded to the C2 position of a butyl chain (sec-butyl). The molecule features a tetrahedral sulfur(VI) center doubly bonded to oxygen atoms and single-bonded to nitrogen and carbon.

• Item-specific identifiers (from Product Data)

  • CAS: 17854-68-1
  • CID: 20482438
  • InChIKey: 79433 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature identifiers and composition (for reference; not item specifications)

  • Preferred name: Butane-2-sulfonamide (sec-Butylsulfonamide)
  • Molecular formula (literature): C4H11NO2S
  • Molecular weight (literature): ~137.19 g/mol
  • Example SMILES (literature): CC(C)CS(=O)(=O)N

• Structural features (general description)

  • Functional groups: sulfonamide (–SO2–NH2), secondary alkyl substituent at sulfur.
  • 2D description: a four-carbon chain with the sulfonamide substituent at the second carbon; sulfur double-bonded to two oxygens and single-bonded to nitrogen and carbon. The C2 center is a stereogenic carbon when substituted as sec-butyl; commercial material is typically racemic unless specified.
  • Hydrogen-bonding: one H-bond donor (NH) and two strong H-bond acceptors (sulfonyl oxygens).

Synthetic Utility

• Functional group leverage

  • N–H acidity: The sulfonamide NH is sufficiently acidic to be deprotonated by common bases, enabling N-alkylation, N-acylation, and formation of N-sulfonyl derivatives. The sulfonyl group strongly withdraws electron density, rendering the nitrogen a relatively poor nucleophile until deprotonated.
  • Leaving-group strategy: N-sulfonyl imines (from condensation with carbonyls) are versatile electrophiles in aza-Mannich and nucleophilic addition chemistry.

• Retrosynthetic role

  • As a nucleophile equivalent at nitrogen after deprotonation, butane-2-sulfonamide provides access to libraries of N-substituted sec-butylsulfonamides (SAR variations by changing the N-substituent while holding the alkanesulfonyl constant).
  • The sec-butyl sulfonyl fragment can modulate lipophilicity and steric profile relative to more common arylsulfonyl (e.g., tosyl) groups, offering alternative physicochemical properties in target molecules.

• Transformations (literature-general)

  • Alkylation with alkyl halides/sulfates under phase-transfer or polar aprotic conditions.
  • Coupling with acid chlorides/anhydrides to give N-acyl sulfonamides; further elaboration to ureas via isocyanates or carbamoyl reagents.
  • Reductive or nucleophilic N–S bond cleavage methods exist for sulfonamides but often require forcing conditions for alkanesulfonyl systems; plan deprotection routes accordingly if temporary protection is intended.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological targeting reagent (e.g., antibody, ligand with defined biomolecular specificity). No target specificity data are provided for this item.