This compound belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.
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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
162.190 g/mol
XLogP3
-0.300
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Exact Mass
162.079 Da
Monoisotopic Mass
162.079 Da
Topological Polar Surface Area
55.100 Ų
Heavy Atom Count
12
Formal Charge
0
Complexity
193.000
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
Lösungsrechner
Molarity Calculator
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 tested biological assay protocols are specified for this item in the Product Data.
General handling for small-molecule stocks (non-item-specific):
Prepare a concentrated DMSO stock (e.g., 10–50 mM) if solubility permits; filter sterilize (0.22 µm PTFE) for cell-based experiments if required by your SOP.
Store aliquots to minimize freeze–thaw cycles; equilibrate to room temperature before opening to reduce condensation.
When diluting into aqueous media, add the DMSO stock slowly under vortex to prevent precipitation; final DMSO concentration should be validated for your assay system.
Analytical method startup (general):
LC–MS: begin with a C18 gradient (5–95% MeCN in 0.1% formic acid water over 10 min); adjust based on retention and ionization.
NMR: record spectra in DMSO-d6 or CD3OD; add a drop of D2O to confirm exchangeable NH assignments.
For any application-specific settings (WB, IHC, IF, FC), this small molecule is not directly applicable; if used as a probe or ligand, develop custom protocols and controls.
Biological Roles
Item-specific biological data are not provided. No clinical or therapeutic claims are made for this catalog item (for research use only).
General context (literature/non-item-specific):
Isoindoline and related phthalimide/isoindolinone motifs appear in numerous bioactive small molecules and probes, where the bicyclic nitrogen and adjacent aromatic ring provide privileged interactions (cation–π, H-bonding) with protein targets.
The carboxamide group contributes to aqueous compatibility and target engagement via dual H-bond donor/acceptor capability and conformational restraint.
Protonation of the ring nitrogen (if unprotected) can modulate physicochemical properties (permeability, solubility) and may be leveraged in salt formation for tool compounds.
Experimental considerations:
For cell-based assays, prepare concentrated DMSO stocks and verify final DMSO content (≤0.5–1% v/v common) to avoid solvent effects; confirm solubility and stability in assay media to prevent colloidal aggregation or precipitation.
If the scaffold is used as a fragment or lead-like core, determine pKa/logD experimentally to tune binding and ADME profiles. These values are not specified for this item and should not be inferred without measurement.
Buffer Applications
This product is a small-molecule heteroaromatic carboxamide and is not a buffering agent. It is not typically used to prepare laboratory buffers or to control pH.
Practical note (general):
When dissolving small molecules for biochemical assays, prepare stocks in an appropriate organic solvent (commonly DMSO) and dilute into the assay buffer with vigorous mixing. Assess compatibility with the specific buffer system (e.g., PBS, HEPES, Tris) to avoid precipitation. Any buffer-related solubility or stability parameters are not specified for this item and should be determined experimentally for your system.
Green Alternatives
When working with isoindoline carboxamides, greener choices often center on solvent and reagent selection. Item-specific green metrics are not available for this product; the following are general, literature-based recommendations.
Greener solvent substitutions (general):
Replace DMF or NMP with safer polar aprotics where possible: Cyrene (dihydrolevoglucosenone), propylene carbonate, or dimethyl isosorbide for some coupling and N-alkylation reactions.
Swap DCM with EtOAc or 2-MeTHF for extractions and chromatography when compatible with polarity and stability.
Consider 2-MeTHF or CPME in place of THF for base-mediated steps; these offer lower peroxide formation and improved safety profiles.
Comparison (general trends):
2-MeTHF: bio-based, higher bp, good for Grignard-like and base-catalyzed alkylations; reduces solvent use due to easier phase separations.
EtOAc: low toxicity, biodegradable, effective medium for many acylations and workups.
MeCN vs iPrOAc: iPrOAc can sometimes substitute for MeCN in SN2 alkylations with phase-transfer catalysts.
Greener reagents and operations:
Use coupling reagents with improved EHS profiles (e.g., T3P in EtOAc) and minimize excess.
Employ aqueous workups with brine minimization and solvent recovery; monitor PMI/E-factor.
Trade-offs: Some green solvents have higher viscosity, lower substrate solubility, or reduced reagent stability; conduct small-scale feasibility studies before scale-up.
Pharmaceutical Uses
No pharmacopeial status, excipient role, or clinical use is specified for this item; it is supplied strictly for research use only.
General, non-item-specific context:
Isoindoline carboxamide scaffolds are common in medicinal chemistry as intermediates or test articles during lead discovery and optimization due to their tunable basicity (ring N) and robust amide functional group.
They may serve as fragments or core structures in structure–activity relationship (SAR) studies, enabling N-alkylation or amide modification to probe binding pockets.
Formulation considerations (research setting):
For in vitro studies, DMSO stock solutions are typical. For in vivo method development in preclinical research, solubilizing vehicles may include co-solvent systems (e.g., PEG400/saline, Captisol, or acidified aqueous solutions) if permitted by protocols—determine compatibility empirically. None of these are item-specific recommendations.
Compliance note:
Do not use this material for human or veterinary applications. For any regulated development work, establish full material control via a detailed specification, CoA review, and stability program; such specifications are not provided here.
Physical Properties
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: 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 specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Solubility: Not specified for this item; refer to CoA/Spec Sheet.
LogP, pKa, refractive index: Not specified for this item; refer to CoA/Spec Sheet.
General/literature expectations for analogous isoindoline carboxamides (non-item-specific):
Physical state: typically off-white to light-colored crystalline solids.
Solubility profile: often sparingly soluble in water; more soluble in polar aprotic organic solvents (e.g., DMSO, DMF, NMP) and moderately in alcohols; exact values vary with substitution.
Acid/base behavior: the ring nitrogen can be weakly basic; the amide is not basic and weakly acidic at the NH, enabling H-bonding.
Important: For specifications, quality control, and release criteria of this specific catalog item, please consult the item’s CoA/Spec Sheet. Do not rely on general or literature trends for method validation or regulatory work.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/antioxidants: Not specified for this item; refer to CoA/Spec Sheet.
UV cutoff/metals/trace specs: Not specified for this item; refer to CoA/Spec Sheet.
How to interpret grades (general guidance):
Research/biochemical grade indicates suitability for most discovery and synthesis workflows. Analytical or HPLC grade (when applicable to solvents) emphasizes low non-volatile residue and low UV background; for solids, additional tests (e.g., HPLC purity, NMR assay, water content by KF) may be defined on the CoA.
If chiral or polymorphic concerns exist, CoAs may include XRPD, DSC, or chiral assay—review before use in regulated studies.
Recommended qualification steps in your lab:
Verify identity by 1H NMR/LC–MS against the reference structure once provided.
Check purity by HPLC/UPLC with orthogonal detection (UV, CAD, MS) and assess residual solvents if critical to your process.
If moisture sensitivity is suspected, perform Karl Fischer on receipt and after opening.
Note: In absence of an explicit grade or purity in the Product Data, treat this material as “for research use only” (as stated) and qualify to fit your internal specifications for discovery or process development.
Reaction and Applications
Manufacturer applications: Not specified in Product Data.
General applications for isoindoline-5-carboxamide–type scaffolds (literature/non-item-specific):
Heteroaromatic amide building block for SAR campaigns in medicinal chemistry and chemical biology tool development.
Precursor for derivatization at the ring nitrogen (N-alkylation, acylation, sulfonylation), enabling rapid generation of analog libraries.
Platform for oxidation to isoindolinone under controlled conditions (e.g., aerobic Cu-catalyzed oxidations), altering H-bonding and conformational properties.
Participation in directed C–H functionalization on the benzene ring when appropriate directing groups are present (amide as a weak DG in certain metal-catalyzed protocols).
Practical tips (general):
N-alkylation: employ mild bases (K2CO3, Cs2CO3) in polar aprotic solvents (DMF/MeCN) with alkyl halides/tosylates; monitor for overalkylation.
Amide coupling (if converting to an amide derivative): utilize modern coupling reagents (HATU, T3P, EDCI) and additive bases (DIPEA) while minimizing epimerization if chiral partners are involved.
Protection strategies: the ring nitrogen can be protected (Boc, Cbz) to control chemoselectivity during acylations elsewhere on the scaffold.
Purification: strong H-bonding can cause tailing on silica; use 1–5% MeOH in DCM/EtOAc or add 0.1–1% Et3N to the eluent.
Applications in materials and coordination (general):
The amide and amine donors can coordinate to metals; such chelation can be leveraged in catalytic ligand exploration or crystallographic derivatization.
Reaction Conditions
Item-specific optimal conditions are not provided. Below are general, literature-based conditions for common transformations on isoindoline carboxamide scaffolds; adapt based on your substrate and pilot screens.
N-Alkylation (general):
Substrate: isoindoline N–H.
Base: K2CO3 or Cs2CO3 (1.5–2.0 equiv).
Electrophile: primary alkyl bromide/iodide, benzyl halide, or mesylate (1.2–1.5 equiv).
Solvent: DMF or MeCN (0.1–0.5 M).
Temperature/time: 25–60°C, 2–16 h.
Notes: minimize over-alkylation by limiting equivalents and monitoring by TLC/LC–MS.
N-Acylation/Sulfonylation (general):
Base: DIPEA or Et3N (2–3 equiv).
Reagent: acyl chloride or sulfonyl chloride (1.1–1.5 equiv).
Solvent: DCM, THF, or 2-MeTHF.
Temperature: 0°C to rt.
Additives: catalytic DMAP for acylations.
Oxidation to isoindolinone (general):
Catalyst: Cu(OAc)2 (5–10 mol%).
Oxidant: O2/air or TBHP.
Solvent: toluene, DMSO, or 2-MeTHF.
Temperature: 60–110°C.
Directed C–H functionalization (case-dependent):
Catalyst: Pd(II)/Ru(II) systems with carboxamide as DG.
Additives: Ag(I) salts, acetate bases.
Solvent: AcOH, HFIP, or DMA.
Expected yields vary widely (40–90%) depending on substitution and conditions; confirm on small scale. Always verify compatibility with the specific compound and avoid conditions that could hydrolyze the amide.
Safety and Handling
GHS classification and hazard statements: Not specified for this item; refer to the SDS for authoritative safety data.
General laboratory safety (non-item-specific best practice):
PPE: wear appropriate lab coat, safety glasses/goggles, and suitable chemically resistant gloves (e.g., nitrile). Use in a fume hood to avoid inhalation of dust or aerosols.
Inhalation/ingestion/skin contact: avoid creating dust; wash thoroughly after handling; do not eat, drink, or smoke in work area. If exposure occurs, follow standard first-aid: move to fresh air, rinse skin/eyes with water for ≥15 min, seek medical attention as needed.
Fire safety: aromatic amide solids are typically combustible. Use CO2, dry chemical, or foam for small fires. Prevent dust accumulation near ignition sources.
Reactivity/incompatibilities (general): avoid strong oxidizers and strong acids/bases during storage. Amides are generally stable, but prolonged heating can induce decomposition.
Environmental precautions: prevent uncontrolled release to drains; collect spills with inert absorbent. Dispose of waste according to institutional and local regulations.
Storage per Product Data:
Storage conditions: Room temperature (store tightly closed in a dry, well-ventilated place; protect from moisture and prolonged light exposure).
Always defer to the product-specific SDS and institutional risk assessments for definitive hazard classification, exposure limits, and emergency procedures.
Solvent Selection
Item-specific solubility data: Not specified for this item; refer to CoA/Spec Sheet.
General, literature-based guidance for isoindoline carboxamides (non-item-specific):
Polar aprotic solvents (DMSO, DMF, NMP) typically provide the highest solubility for sample preparation and screening assays.
Alcohols (MeOH, EtOH, i-PrOH) often afford moderate solubility and are useful for recrystallization with co-solvents.
Water solubility is usually limited unless the amide is ionized or additional polar substituents are present; dissolution may improve with minimal base (e.g., dilute NaOH) if compatible with the amide stability.
Selection scenarios:
Analytical stock solutions: DMSO at 10–50 mg/mL is commonly feasible for related scaffolds; dilute into assay buffer with vigorous mixing to avoid precipitation (confirm compatibility).
Purification/crystallization: EtOAc/hexanes or EtOAc/MeOH gradients can be effective; for more polar analogs, MeOH/DCM or MeOH/EtOAc.
Reaction media: For N-alkylation or coupling transformations on this scaffold, DMF, DMSO, MeCN, or toluene are frequently employed depending on base and electrophile.
Comparison (general):
DMSO vs DMF: DMSO offers broader solubility and is less volatile; DMF is easier to remove but can form dimethylamine on storage and may interfere in couplings.
MeCN: lower solubility than DMF/DMSO but easy workup and high volatility—good for SN1/SN2 alkylations when solubility permits.
Storage and Reconstitution
Item-specific storage/shipping:
Storage conditions: Room temperature (per Product Data). Store in a tightly sealed container, in a dry place, away from direct light.
Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Reconstitution and solution handling (general, non-item-specific):
Solubility screening: Test a small amount in DMSO, DMF, MeOH, and EtOH to identify a suitable vehicle; gently warm (≤40°C) and sonicate if needed. Item-specific solubility is not provided.
Stock solutions: Prepare concentrated DMSO stocks (e.g., 10–50 mM) where feasible. Filter through 0.22 µm PTFE if particulate persists.
Storage of solutions: Aliquot and store at −20°C to −80°C for long-term stability, protected from light; minimize freeze–thaw. Label with concentration, solvent, and date.
Stability monitoring: Periodically check by LC–MS/HPLC for degradation; avoid prolonged exposure to elevated temperatures and moisture.
Note: All quantitative specifications (water content, residual solvents, purity, specific stability) are Not specified for this item; refer to CoA/Spec Sheet and SDS for authoritative guidance.
Structure and Identity
Isoindoline-5-carboxamide is an aromatic heterocycle-based carboxamide presumed to feature an isoindoline core (a benzene ring fused to a saturated five-membered ring bearing a secondary amine) with a carboxamide substituent at the 5-position of the benzofused ring.
SKU: I1013375
CAS: 137453-25-9
PubChem CID: 45084625 (catalog reference)
InChIKey: 76548 (as provided in Product Data; note this is not a standard-length InChIKey)
SMILES: 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.
Structural features (general description, literature):
Core scaffold: isoindoline (benzannulated 2,3-dihydroindole with ring nitrogen).
Functional groups: anilide-type carboxamide on the aromatic ring; secondary amine in the isoindoline ring (if N–H is unsubstituted).
2D description: a bicyclic system (six-membered benzene fused to a five-membered N-containing ring). The carboxamide (–C(=O)NH2) at the 5-position lies on the benzene portion; the ring nitrogen is adjacent to the fusion juncture.
Stereochemistry: none expected for the parent scaffold (achiral), absent additional substituents (literature/general).
Synthetic Utility
Isoindoline-5-carboxamide offers two complementary reactive handles (general literature perspective):
Ring nitrogen (isoindoline N): amenable to alkylation (SN2 with alkyl halides/tosylates), acylation (anhydrides/acid chlorides), sulfonylation (sulfonyl chlorides), and carbamoylation. Protection (Boc, Cbz) can be used to control selectivity.
Aromatic amide: while the amide itself is typically robust, it can participate in coupling sequences if transformed to activated derivatives (e.g., conversion to acid chloride from the corresponding acid or via CDI/EDCI activation when synthesizing analogs). The amide acts as a weak directing group in certain C–H activation protocols on the benzene ring.
Strategy in medicinal chemistry (general):
Rapid diversification through N-alkyl libraries to explore basicity and solubility. Choice of alkyl group tunes pKa/logD.
Oxidative manipulation to isoindolinone alters the H-bond pattern and ring planarity, often impacting potency/selectivity trends.
Late-stage functionalization: metal-catalyzed C–H arylation/amination adjacent to the amide has precedent with appropriate catalysts and additives; feasibility depends on substitution pattern.
Workup/purification tips:
Add small percentages of MeOH or Et3N to chromatography solvents to reduce adsorption.
For polar analogs, reverse-phase prep-LC can outperform normal-phase silica.
All reactivity notes are general and should be validated for this specific compound.
Target Specificity
Not applicable. This product is a small-molecule chemical and not a biological targeting reagent (e.g., antibody, ligand-standardized probe). No antigen, epitope, clone, isotype, or species reactivity applies to this catalog item.
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.
