GRADE & PURITYReagent Grade?General reagent-grade purity suitable for most laboratory work. Use as a dependable default when no specific higher grade is required.
This compound belongs to the class of organic compounds known as indoles and derivatives. These are organic compounds containing an indole, which is a bicyclic ring system made up of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole 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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Bewertungen
Kundenbewertungen
Application Protocols
No assay or bioanalytical protocols are specified for this small-molecule reagent in the Product Data. Typical use involves synthetic organic chemistry procedures as outlined in the Reaction & Applications and Reaction Conditions sections.
For handling in screening assays:
Prepare concentrated stock solutions in DMSO (e.g., 10–100 mM), filter if needed (0.22 µm PTFE), and dilute into assay buffers with attention to final DMSO percentage.
Verify solubility and stability under assay conditions by a quick LC-MS check before full screening.
Biological Roles
This product is offered strictly for research and laboratory use (per Product Data: For research use only). Indoline-1-carbothioamide is a synthetic small-molecule building block rather than a native metabolite.
General context (literature):
Indoline scaffolds appear in numerous bioactive molecules; the N1 position is frequently derivatized. The carbothioamide group is a versatile convertible handle for generating amides, amidines, or heterocycles in lead optimization.
Thioamides can engage in strong hydrogen bonding and different tautomeric forms versus oxoamides, which medicinal chemists exploit to modulate physicochemical properties during SAR.
No intrinsic biological role is assigned to indoline-1-carbothioamide itself. Any biological activity would be context- and derivative-dependent and must be determined empirically.
Caution: No medical, diagnostic, or therapeutic use is intended or implied. Do not use in vivo or in clinical applications.
Buffer Applications
Not typically applicable. Indoline-1-carbothioamide is a synthetic organic building block rather than a buffering reagent. It does not constitute a standard buffer system with defined pKa windows used in biochemical buffering.
For work in aqueous media (e.g., bioassays), dissolve in suitable co-solvents (DMSO, DMF) and dilute into buffered solutions as required; verify compatibility and solubility experimentally.
Green Alternatives
Selecting greener options involves both solvent choices and, where chemistry permits, functional-group surrogates to minimize hazardous reagents and waste.
Greener solvent choices (literature/guidance):
Prefer low-toxicity, high-boiling polar solvents like Cyrene or propylene carbonate over DMF/NMP where compatible.
Use bio-based 2-MeTHF or CPME over chlorinated solvents for workups or extractions when solubility allows.
Favor aqueous-organic systems (EtOH/H2O) for S-alkylation of activated substrates when feasible.
Reagent/reaction alternatives:
Oxidative conversions of thioamides to amides: choose H2O2 in alcohols or urea–hydrogen peroxide adduct over heavy-metal oxidants to reduce EHS burden.
Desulfurization: consider catalytic hydrogenation (Raney Ni or Pd/C under H2) instead of stoichiometric phosphines or tin hydrides.
Heterocycle formation: Employ organocatalytic or enzyme-mimetic conditions when possible; avoid excess halogenating agents by using green electrophiles (e.g., carbonate leaving groups) for cyclizations.
Trade-offs (balanced view):
Cyrene and propylene carbonate may reduce rate or change selectivity versus DMF/DMSO and can be harder to remove.
2-MeTHF/CPME improve safety and phase separations but may lower solubility for polar thioamides, requiring higher temperatures or co-solvents.
Operational green practices:
Minimize solvent volumes via high-solids charging and telescoped steps.
Implement in-process controls to avoid over-oxidation of C=S, limiting byproducts and rework.
These suggestions are general and should be validated on small scale for this specific substrate.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided in the Product Data. This item is intended for research use only and is not for use in human or veterinary drug products.
General R&D context (literature):
Employed as an intermediate for N1-functionalized indoline derivatives during medicinal chemistry campaigns.
The thioamide group can be transformed into amides, amidines, and heterocycles, enabling rapid exploration of N1 substitution patterns on indoline-containing scaffolds.
Any GMP, ICH, or compendial requirements are outside the scope of this research-grade material. For process development or clinical manufacturing, source GMP-grade material and establish full impurity, residual solvent, and elemental impurity profiles per applicable guidelines.
Physical Properties
Item-specific physico-chemical specifications (melting point, water content, residual metals, UV cutoff, etc.) are not provided in the Product Data for SKU I479185.
Item-specific values:
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not applicable (decomposes before boiling typically for thioamides); item-specific value not specified.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable to solids.
Literature/general guidance (for planning only; not item specifications):
Physical state: typically a crystalline solid for analogous N-carbothioamide indoline derivatives.
Polarity/H-bonding: contains a thioamide (strong H-bond donor/acceptor) and a tertiary ring nitrogen bound to the thiocarbonyl carbon; overall polar protic functionality with aromatic character from the indoline.
Solubility tendencies: better solubility expected in polar aprotic solvents (DMSO, DMF, NMP) and polar protic alcohols (MeOH, EtOH) than in nonpolar hydrocarbons; limited aqueous solubility unless protonated (acidic media) or with co-solvent.
Ionization: the exocyclic thioamide NH2 can be deprotonated under strong basic conditions; the ring nitrogen is amide-like in this linkage and significantly less basic than in free indoline.
Always confirm any numerical property for your lot on the CoA/Spec Sheet before method development or scale-up.
Suitable for most synthetic and analytical laboratory procedures where high purity is needed but ultra-trace impurity limits (e.g., for semiconductor or LC-MS trace analysis) are not mandated.
Typically controlled for identity and assay, with limits on common inorganic/organic impurities appropriate for research use. Exact impurity limits, if any (water, peroxides, metals, UV absorbance), are Not specified for this item; refer to CoA/Spec Sheet.
Implications for use:
Adequate for route scouting, heterocycle construction, S-alkylation/N-acylation studies, and library synthesis.
If your application is impurity-sensitive (e.g., catalysis poisoned by sulfur/trace metals, bioassays), verify impurity profile on the CoA or consider a higher grade if available.
Stabilizers/additives:
Not specified for this item; refer to CoA/Spec Sheet. Thioamide solids are generally offered neat without stabilizers, but confirm per lot documentation.
Lot-specific documentation:
For method development, regulatory support, or reproducibility, request and retain the Certificate of Analysis (CoA) and Spec Sheet for this SKU to confirm identity (NMR/IR/HRMS), assay, and residual solvent content where applicable.
Reaction and Applications
As an N-carbothioamide of indoline, this reagent is a versatile synthon for constructing diverse nitrogen- and sulfur-containing frameworks and for N1-functionalization of the indoline core.
Representative application families (literature; expand as suitable to your route):
S-Alkylation/S-Acylation: Thioamide sulfur is nucleophilic; reaction with alkyl halides or acyl chlorides affords thioimidates or thioimides. Subsequent transformations can give amidines, imidates, or heterocycles.
Thiazole/Thiazoline formation: Condensation with α-halo carbonyls (Hantzsch-type) or 1,2-dicarbonyls under basic conditions cyclizes to thiazol(in)e motifs tethered to indoline N.
Desulfurization/Amide conversion: Oxidants (e.g., m-CPBA, H2O2) or desulfurizing agents (Raney Ni, PPh3/DEAD variants) convert thioamide to corresponding amide or amine derivatives at N1.
Guanidinylation/Amidine synthesis: Through S-activation (e.g., S-methylation) followed by amine substitution, access to N1-amidines/guanidines of indoline.
Imidoyl halide formation: Treatment with halogenating agents (e.g., SOCl2, oxalyl chloride with activators) can generate imidoyl halides for further coupling.
Indoline N1 diversification:
The carbothioamide serves as a traceless or convertible handle at N1; after C–S chemistry and installation of substituents, sulfur removal can unveil amide/amine targets without over-alkylating the ring nitrogen during earlier steps.
Practical notes:
Control chemoselectivity (S- vs N-alkylation) by solvent, base, and temperature; S-alkylation is generally favored under kinetic control in polar aprotic solvents with mild base.
Exclude strong oxidants unless desired; thioamide C=S is sensitive.
For library synthesis, pre-form DMSO stocks and dispense under inert atmosphere to limit adventitious oxidation.
Reaction Conditions
The following are general, literature-informed conditions for thioamide chemistry applied to an indoline-1-carbothioamide scaffold. They are guidelines only and must be optimized for your substrate and scale.
S-alkylation (to thioimidates/isothioureas):
Solvent: DMF, MeCN, or acetone.
Base: K2CO3, Cs2CO3, or DIPEA (1.2–2.0 equiv).
Electrophile: primary alkyl halide or mesylate (1.1–1.5 equiv).
Temperature/time: 20–60 °C, 1–12 h.
Notes: S-alkylation typically outcompetes N-alkylation; work under dry conditions.
Thiazole formation with α-haloketones:
Solvent: DMF or DMSO.
Base/catalyst: K2CO3 or NaHCO3; optionally Cu(I) catalysts for certain annulations.
Temperature: 60–100 °C.
Notes: Control stoichiometry to limit bis-alkylation.
Oxidation to amide (desulfurization):
Reagent: m-CPBA (1.2–1.5 equiv) or 30% H2O2 (excess) in MeOH/CH2Cl2.
Temperature: 0–25 °C.
Notes: Quench carefully; avoid over-oxidation to sulfinyl/sulfonyl byproducts.
Raney Ni desulfurization to amine:
Solvent: EtOH or i-PrOH.
Conditions: H2 atmosphere (1–5 bar) or catalytic transfer hydrogenation, 25–60 °C.
Notes: Filter catalyst thoroughly; sulfur poisons many catalysts—fresh Raney Ni recommended.
Imidoyl halide formation:
Reagent: SOCl2 or oxalyl chloride with catalytic DMF.
Solvent: CH2Cl2 or toluene.
Temperature: 0–25 °C.
Notes: Exclude moisture; capture HCl; subsequent coupling with amines/alcohols.
These ranges are illustrative; verify on small scale and consult primary literature for closely related substrates.
Safety and Handling
GHS/CLP information (item-specific): Not specified for this item; refer to the SDS for SKU I479185 for authoritative hazard classification, pictograms, signal word, and H/P statements.
General safety considerations for thioamides and indoline derivatives (literature/good practice; not a substitute for SDS):
Likely hazards: may cause irritation to skin, eyes, and respiratory tract; harmful if swallowed. Some thioamides can be sensitizers. Avoid dust formation.
PPE: use lab coat, safety glasses or goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to avoid inhalation of dust or vapors from reagents used with it.
Hygiene: wash hands thoroughly after handling; avoid contact with skin and eyes; do not eat/drink in the lab.
Incompatibilities: strong oxidizers (risk of exothermic oxidation of thioamide sulfur), strong bases (can cause decomposition or anionic reactions), and strong electrophiles (rapid S/N alkylation or acylation). Separate from acids/bases and oxidizing agents.
Thermal stability: thioamides may decompose on strong heating; avoid unnecessary thermal stress.
First aid (overview):
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 attention if symptoms occur.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Storage per Product Data: store at room temperature. Keep in a tightly closed container, dry, and protected from light/oxidants. Always consult the SDS for definitive guidance.
Solvent Selection
Indoline-1-carbothioamide is a polar, H-bonding-capable aromatic heterocycle bearing a thioamide. Solvent choice strongly affects dissolution, reactivity at the C=S bond, and handling.
Aqueous media: limited solubility at neutral pH; solubility can increase in acidic media via protonation of the exocyclic nitrogen and/or with co-solvents.
When to choose which solvent:
High-concentration stock solutions for screening or derivatization: DMSO or DMF.
S-alkylation/acylation reactions: polar aprotic solvents (DMF, MeCN, acetone) often favor SN2/SNAc pathways; ensure base compatibility.
Oxidations or desulfurization: mixed MeOH/CH2Cl2 or MeCN systems are common; control water content.
Cyclizations to thiazoles/thiazolines with α-halo carbonyls: polar aprotic media (DMF, DMSO) with a non-nucleophilic base.
Practical tips:
Dry solvents prior to strong-base or moisture-sensitive transformations; thioamides can hydrolyze/oxidize under harsh conditions.
If crystallization is desired, use a polar aprotic solvent for dissolution and an anti-solvent like toluene/hexanes for crash-out.
Comparison (general):
DMSO vs DMF: DMSO dissolves more but may participate in side reactions under strong activation; DMF offers lower nucleophilicity and easier removal under vacuum at reduced pressure with co-evaporation.
General best practices for this class of compounds:
Store tightly closed in a dry, inert atmosphere (desiccator or with desiccant). Thioamides can slowly oxidize; protect from prolonged exposure to air and light.
For longer-term storage, consider subdivision into small vials to minimize repeated headspace oxygen/moisture exposure.
Reconstitution/solution preparation:
Solvents: DMSO or DMF for concentrated stocks; MeOH/EtOH for moderate concentrations. Water solubility is limited; use co-solvents if aqueous use is required.
Filtration: If particulate is present, sterile-filter through PTFE or PES membranes; avoid cellulose acetate with DMSO.
Stability: Solutions in DMSO/DMF are generally stable short-term at room temperature; for extended periods, store at 2–8 °C or −20 °C in amber vials and allow to warm to room temperature before opening to prevent moisture ingress.
Shipping: Not specified for this item; refer to CoA/Spec Sheet. Given room-temperature storage, ambient shipment is typically acceptable unless otherwise stated.
Always defer to the product’s SDS and lot-specific documentation for definitive storage and handling requirements.
Structure and Identity
Indoline-1-carbothioamide is a thioamide-functionalized indoline, where the indoline ring nitrogen bears a carbothioamide moiety (–C(=S)NH2).
Item-specific identifiers (Product Data):
SKU: I479185
Product Name: Indoline-1-carbothioamide
CAS: 56632-37-2
Grade/Purity: Reagent Grade
Storage: Room temperature
InChIKey (as provided): 321748 (note: non-standard format as provided in Product Data)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identifiers and features (for reference; not item-specific specifications):
Common structural description: bicyclic indoline (benzofused 5-membered saturated N-heterocycle) with N1-substituted carbothioamide (thiourea-like) group.
Key functional groups: secondary cyclic amine (as part of indoline, N substituted), thioamide C(=S)–NH2.
Stereochemistry: none (achiral as drawn).
2D structural features in words:
A benzene ring fused to a saturated ethylene bridge (–CH2–CH2–) completing the indoline system.
The ring nitrogen (position 1) is bonded to the thioamide carbon of a –C(=S)NH2 group, making an N-acyl(thiocarbonyl) linkage.
The exocyclic –NH2 on the thioamide is available for hydrogen bonding and derivatization.
Notes:
Where the Product Data differ or are incomplete (e.g., SMILES, InChIKey format), consult the CoA/Spec Sheet and SDS for the definitive identifiers for this specific lot/item.
Synthetic Utility
Key reactivity stems from the thioamide C(=S)–NH2 linked to the indoline N. This dual character (soft nucleophilic sulfur and electrophilic thiocarbonyl carbon) enables diverse transformations.
Functional group behavior (literature):
Soft nucleophile (S): preferential S-alkylation with primary halides under SN2 conditions; subsequent substitution by amines can yield amidines/guanidines.
Electrophile (C=S): activation affords imidoyl halides or thioimidates that couple with O-, N-, or C-nucleophiles.
Hydrogen-bond donor/acceptor: facilitates directed metalation or intramolecular cyclizations in presence of adjacent nucleophiles/electrophiles.
Named/typical transformations:
Hantzsch-type thiazole formations from thioamides and α-haloketones.
Pinner-like amidine syntheses via S-activated thioimidates followed by amine trapping.
Desulfurization to amides (e.g., with peracids or H2O2) or to amines (Raney Ni) at N1, enabling traceless protection/activation strategies.
Retrosynthetic value:
Serves as a convertible N1 handle on indoline: delayed installation of final N1 substituent after ring-functionalization minimizes over-alkylation of indoline nitrogen early in routes.
Practical guidance:
Control S vs N selectivity with solvent/base; S-alkylation favored in polar aprotic solvents with mild bases (K2CO3, Cs2CO3), while stronger bases/less polar media can increase N-attack.
Monitor reactions by IR (ν(C=S) ~ thioamide region) or LC-MS; oxidation shifts to ν(C=O) upon amide formation.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting agent (e.g., antibody, ligand with defined biomolecular target), and no such information is provided in the Product Data.
Need help choosing the grade?
Our grade selection guide covers purity, stabilizer status, and application suitability for all variants in our catalog.
Wir verwenden Cookies, um die ordnungsgemäße Funktion der Website sicherzustellen und, soweit zulässig, Ihr Nutzererlebnis zu verbessern. Sie können Ihre Einstellungen jederzeit unter „Einstellungen“ verwalten. Weitere Informationen finden Sie in unserer Cookie-Richtlinie.
Shall we send you a message when we have discounts available?
Remind me later
Thank you! Please check your email inbox to confirm.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
