This compound belongs to the class of organic compounds known as indanes. These are compounds containing an indane moiety, which consists of a cyclopentane fused to a benzene ring.
External Descriptors
Not available
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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
197.260 g/mol
XLogP3
1.300
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
197.051 Da
Monoisotopic Mass
197.051 Da
Topological Polar Surface Area
68.500 Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
280.000
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
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Recensioni
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Application Protocols
Not applicable. No validated biological assay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. For chemical use, see the Reaction Conditions and Synthetic Utility sections for representative laboratory procedures.
Biological Roles
General context (literature; no clinical claims)
Functional group behavior: The sulfonamide moiety is a well-known pharmacophore providing a hydrogen-bond donor and two acceptors, often engaging in enzyme active sites and protein binding pockets. Its acidity (pKa ~10–11 for aryl sulfonamides) allows partial ionization in certain biological environments, tuning permeability and binding.
Structural scaffold: The indane ring is a compact hydrophobic bicyclic system that can enhance ligand rigidity and lipophilic contacts. Indane-containing compounds appear across enzyme inhibitors and receptor modulators in the discovery literature.
Metabolic considerations: Aryl sulfonamides are generally metabolically robust toward oxidative de-sulfonylation, but N-alkyl sulfonamides can undergo N-dealkylation; aromatic rings may be hydroxylated (literature trends).
Physicochemical envelope: Combining an indane core with a sulfonamide often yields moderate cLogP and PSA suited to fragment-to-lead exploration. This molecule can serve as a fragment or substructure in library design, or as a reference scaffold in SAR studies.
Note
These are general observations for aryl sulfonamides/indane scaffolds and do not constitute biological activity data for this specific item. Any biological testing must be performed under appropriate approvals and controls.
Buffer Applications
Not typically applicable. Indane-5-sulfonamide is not a conventional buffering agent and lacks a conjugate acid/base pair appropriate for maintaining physiological pH ranges in aqueous solution. For aqueous work, dissolve as a solute (e.g., in DMSO stock) and add to pre-made buffers (phosphate, HEPES, etc.) as needed.
Practical note
Prepare concentrated DMSO or ACN stocks (e.g., 10–100 mM) for dosing into buffered assays; ensure final cosolvent levels are compatible with the system under study.
Green Alternatives
Context: Many transformations of aryl sulfonamides are performed in polar aprotic solvents (DMF, NMP) or chlorinated media (DCM), which have environmental/health concerns. Greener choices can often be adopted without sacrificing performance.
Greener substitutions (literature guidance)
Replace DMF/NMP with safer polar aprotics when feasible:
Alternative: Propylene carbonate or dimethyl carbonate for some SN2/N-alkylations (higher boiling, benign profiles). May require elevated temperature.
Alternative: Cyrene (dihydrolevoglucosenone) or GBL in base-mediated reactions; check base compatibility and solubility.
Replace DCM with ethyl acetate or 2-MeTHF for extractions and chromatography where solubility allows.
Use 2-MeTHF or CPME in place of THF for NaH-mediated deprotonations to reduce peroxide risk and improve safety; dry thoroughly.
Employ aqueous micellar media (e.g., TPGS-750-M) for certain alkylations/acylations; assess sulfonamide solubility and base requirements.
Trade-offs
Propylene carbonate and Cyrene have higher viscosity/boiling points, impacting mass transfer and solvent removal.
2-MeTHF/CPME are less polar than DMF/DMSO; may not dissolve the substrate sufficiently without co-solvents.
Recommendation
Begin with EtOAc/2-MeTHF for workups/purifications and ACN/EtOH/water for analytics. For reactions, screen a greener solvent alongside a conventional control to benchmark conversion/yield.
Pharmaceutical Uses
No pharmacopeial/excipient status is specified for this item; refer to CoA/Spec Sheet. The content below is general background and not a therapeutic claim.
General formulation context (literature)
Role: Aryl sulfonamides are common motifs in small-molecule drug discovery due to favorable hydrogen-bonding and physicochemical properties. Indane-5-sulfonamide can function as a discovery scaffold or intermediate in medicinal chemistry routes.
Salt formation: As a weak acid (sulfonamide N–H), it can form salts with strong organic bases (e.g., TBA, DBU) for solubility manipulation; however, such salts are typically research intermediates rather than formulated products.
Solid-state behavior: Sulfonamides frequently crystallize well and may offer polymorphism; screening different solvents can tailor particle size for processing (literature observation).
Compliance reminder
This product is supplied strictly for research use only (non-GMP). It is not intended for diagnostic, therapeutic, or human/animal consumption applications.
Physical Properties
Item-specific specifications
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: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed (general reference; not item specifications)
Empirical formula (computed from structure): C9H11NO2S
Formula weight (computed): ~197.26 g/mol
Physical state: Typically an organic solid for aryl sulfonamides of this size (literature expectation).
Acid–base: Primary aryl sulfonamides are weak acids; pKa(NH) typically ~10–11 in water for benzenesulfonamide analogs (literature).
Polarity/solubility (qualitative, literature): Moderately polar; usually sparingly soluble in water but soluble in polar aprotic organic solvents (e.g., DMSO, DMF) and often in hot alcohols or chlorinated solvents.
LogP: Aryl sulfonamides of similar size commonly show moderate lipophilicity (logP ca. 1–2.5; literature trend), modulated by the indane ring.
Boiling/melting point, density, refractive index, UV cutoff: Not located in reliable literature sources specific to indane-5-sulfonamide.
Notes
Use the product’s Certificate of Analysis for definitive item-specific values (mp, assay, water, residual solvents, etc.).
Quality and Grades
Item-specific details
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 interpreting grades (context for small-molecule building blocks)
Research grade: Suitable for general synthetic and discovery chemistry. Typical controls include identity (NMR/HRMS/IR) and purity by HPLC/GC. UV-absorbing impurities are usually acceptable unless chromatography or photophysical studies are intended.
High-purity or HPLC grade (if applicable): Emphasizes low nonvolatile residue and low UV absorbance; useful when compound will be analyzed by LC-UV or used as an analytical standard.
Metal content/residual solvent/water: When relevant to sensitive catalysis (e.g., Pd-catalyzed couplings) or solid-state characterization, consult the CoA for trace metals, residual solvents, and KF water. If values are not listed, these are “Not specified for this item; refer to CoA/Spec Sheet.”
What matters for indane-5-sulfonamide
Identity confirmation: 1H/13C NMR typically shows characteristic sulfonamide NH (often broad) and indane aromatic/aliphatic signatures; IR shows strong S=O stretches (~1150–1350 cm−1, literature).
Purity considerations: Aryl sulfonamides often crystallize well, allowing high chemical purity; however, hydration/solvent of crystallization can affect assay—verify by drying/weighing and CoA data.
Reaction and Applications
General applications (literature; research use only)
Building block: Aryl sulfonamides are privileged motifs in discovery chemistry for hydrogen-bond-donor/acceptor profiles and metabolic stability. The indane scaffold adds hydrophobic bulk and conformational constraint.
N-functionalization: The sulfonamide N–H (pKa ~10–11, literature) can be selectively alkylated or acylated. Typical conditions include K2CO3 or Cs2CO3 with alkyl halides in DMF/MeCN, or NaH in THF/DMF at 0–25 °C, to give N-alkyl sulfonamides.
Protecting-group chemistry: The –SO2NH– can act as a directing/anchoring group; conversion to N-sulfonyl derivatives enables subsequent transformations and can be removed under robust conditions (e.g., reductive or strongly basic methods depending on substituents; consult specific literature).
Cross-coupling adjacency: While the sulfonamide itself is not a coupling handle, installing halogens on the ring (from suitable precursors) allows Suzuki/Negishi/etc. elaboration of the indane core while retaining the sulfonamide.
Hydrogen bonding and crystal engineering: Useful in co-crystal formation and solid-state studies owing to strong S=O···H–N motifs (literature).
Practical tips
Drying: Sulfonamides can hold trace solvent; dry under high vacuum at ambient to 40 °C before weighing for stoichiometric accuracy.
Base choice: Start with K2CO3 for N-alkylation; escalate to NaH for sluggish substrates. Avoid over-alkylation by limiting electrophile and monitoring.
Workup: After base-mediated reactions, quench carefully (ice/water), extract with EtOAc/DCM, then wash organic layers with brine. Sulfonamides often crystallize from EtOAc/hexanes.
Reaction Conditions
General literature conditions (guidance; optimize empirically)
N-alkylation of the sulfonamide
Base: K2CO3 (2–3 equiv) or Cs2CO3 in DMF/MeCN; or NaH (1.1–1.5 equiv) in THF/DMF for less reactive electrophiles.
Electrophiles: Primary alkyl bromides/iodides, benzyl halides, epoxides (via ring opening), or activated sulfates/carbonates.
Temperature/time: 20–80 °C, 2–16 h depending on substrate.
Workup: Aqueous quench, extract with EtOAc/DCM, wash, dry, and crystallize or chromatograph.
N-acylation to form sulfonyl ureas/carbamates
Reagents: Acid chlorides or anhydrides with base (Et3N, DIPEA) in DCM or ACN at 0–25 °C; or CDI-activated acids in DMF/ACN.
Protection/deprotection
Temporary N-protection (e.g., Boc, Cbz on nitrogen of related amines) is not typically required for sulfonamides; the sulfonamide itself is often the protecting group on nitrogen in multistep syntheses.
Metalation on the arene (when pursuing substituted indanes)
Directed lithiation requires appropriate directing groups; indane-5-sulfonamide can sometimes assist under strong base/low temperature, but consult specific protocols.
Expected outcomes
Yields for straightforward N-alkylations of aryl sulfonamides commonly range 60–95% (literature), influenced by base, solvent, and sterics. Monitor by TLC/LC-MS.
Safety note
Control exotherms when adding NaH; rigorously dry solvents and maintain inert atmosphere as needed.
Safety and Handling
Item-specific hazard information
Signal word: Not specified for this item; refer to SDS.
GHS hazard statements/classification/pictograms: Not specified for this item; refer to SDS.
General safety guidance for aryl sulfonamides (literature/typical practices)
Hazards: Many sulfonamides are of low volatility but may cause skin/eye irritation and respiratory irritation as dusts. Avoid inhalation of particulates and contact with skin/eyes.
PPE: Use lab coat, safety glasses or splash goggles, and suitable gloves (e.g., nitrile). Employ dust control and local exhaust when weighing.
Handling: Minimize dust generation. Avoid strong bases/acids when not intended, as the sulfonamide N–H can be deprotonated under strong basic conditions. Keep away from strong oxidizers and reducing agents as a general precaution.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin: Wash with soap and water. Remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contacts if present and easy.
Ingestion: Rinse mouth; seek medical advice.
Fire safety: Use CO2, dry chemical, or foam. Combustion may produce SOx and NOx; firefighters should wear self-contained breathing apparatus.
Spill response: Avoid dust; collect mechanically and place in suitable container for disposal per local regulations.
Always consult the product-specific SDS for authoritative hazard and first-aid information.
Solvent Selection
Applicability: Indane-5-sulfonamide is a moderately polar, largely non-ionized organic solid at neutral pH. Solvent choice is primarily for dissolution during reactions or analytical work.
General miscibility and polarity (literature expectations)
Good solvents: DMSO, DMF, NMP, acetonitrile, dichloromethane, chloroform, hot ethanol/isopropanol, and ethyl acetate.
Limited/poor solubility: Water (at neutral pH), alkanes (hexanes, heptane). Solubility in alcohols increases with temperature.
Ionization leverage: Deprotonation (strong base) enhances solubility in water/alcohols as the sulfonamide anion but alters reactivity; use only if compatible.
When to choose what
Reaction setup: DMF, DMSO, or NMP for SN2 or N-alkylation chemistry; THF/DMF blends when using strong bases (NaH, K2CO3) to manage solubility and reactivity.
Purification: Often crystallizable from ethyl acetate/hexanes or ethanol/water mixtures (optimize empirically). For flash chromatography, use EtOAc/hexanes or DCM/MeOH gradients.
Analytics: For LC-MS/LC-UV, dissolve in ACN/H2O with a small amount of DMSO if needed; add 0.1% formic acid for better peak shape when appropriate.
Small comparison (literature trends)
DMSO vs DMF: DMSO maximizes solubility for polar sulfonamides but can be harder to remove; DMF offers similar solubilization with easier workup by aqueous washes. ACN provides faster evaporation but may limit solubility.
Storage and Reconstitution
Item-specific storage/shipping
Storage conditions: Room temperature (as provided in Product Data). Protect from moisture and strong light. Keep container tightly closed.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance
Solid handling: If clumping or residual solvent is suspected, dry under high vacuum at ambient to 40 °C before accurate weighing.
Solution preparation: Prepare stock solutions in DMSO, DMF, ACN, or other suitable organic solvents. Filter (0.2 µm PTFE) if particulate matter is present.
Reconstitution: Not applicable to lyophilized biologics; dissolve to desired concentration in compatible solvent. Record solvent, concentration, and date.
Stability of solutions: Aryl sulfonamide solutions in dry organic solvents are typically stable for weeks at 2–8 °C in amber vials. For aqueous or basic solutions, use promptly and monitor for hydrolysis or discoloration.
Research use note
For research use only. Consult the SDS and CoA for definitive guidance on stability, incompatibilities, and recommended storage limits.
Structure and Identity
Item-specific (from Product Data)
SKU: I1071319
Product name: Indane-5-sulfonamide
CAS: 35203-93-1
PubChem CID: 96876
InChIKey: 428476 (as listed in product data)
Storage: Room temperature
Literature/computed structural information (for reference; not item specifications)
Molecular formula (computed from structure): C9H11NO2S
Core scaffold: Indane (benzocyclopentane) fused bicyclic system bearing a para/meso ring sulfonamide substituent at the 5-position on the aromatic ring.
Functional groups/features: Aromatic ring, saturated cyclopentane fused ring (indan), aryl sulfonamide (–SO2–NH2) providing one H-bond donor (NH) and two H-bond acceptors (sulfonyl oxygens).
2D description in words: A benzene ring fused to a cyclopentane ring (indane). At the 5-position of the benzene ring, a sulfonyl group (S(=O)2) is attached, terminating in a primary sulfonamide (–NH2). No stereogenic centers are present; the molecule is overall rigid around the aromatic portion with limited conformational flexibility from the saturated ring.
Synthetic Utility
Functional group leverage (literature)
N–H acidity: Enables selective N-alkylation/acylation to diversify the scaffold rapidly. Indane-5-sulfonamide can serve as a nucleophile upon deprotonation (K2CO3, Cs2CO3, NaH) toward alkyl halides, epoxides, or activated carbonates.
Hydrogen bonding/auxiliary: The sulfonamide can direct or stabilize transition states, and participates in supramolecular assembly—useful in crystallization-driven purifications or co-crystal engineering.
Orthogonal elaboration: The aromatic ring of the indane allows electrophilic substitution or, if pre-halogenated, cross-coupling to append substituents without disturbing the sulfonamide.
Late-stage diversification: Convert to N-sulfonyl carbamates/ureas via reaction with phosgene equivalents or CDI-activated carboxamides; or to sulfamides via chlorosulfonylation on related derivatives (route-dependent; consult primary literature).
Retrosynthetic perspective
Accessible from indane precursors via sulfonyl chloride formation on the arene (chlorosulfonation) followed by ammonolysis to the sulfonamide. Conversely, the sulfonamide can be a convergence point for fragment coupling strategies in library synthesis.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent or antibody. No antigen/epitope, clone, isotype, or species reactivity information applies.
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