This compound belongs to the class of organic compounds known as indazole-3-carboxamides. These are aromatic compounds containing an indazole ring system that is substituted at the 3-position with a carboxamide group.
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.
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Application Protocols
No antibody/assay application protocols (WB, IHC, IF, FC, etc.) are applicable to this small-molecule building block. For general laboratory use:
• Preparing screening stocks: dissolve in anhydrous DMSO to a convenient concentration (e.g., 10–50 mM), vortex and sonicate if needed, and sterile-filter (0.22 µm PTFE) for cell-free assays as required.
• For synthetic reactions: see Reaction Conditions for representative coupling and N-functionalization setups. Scale, stoichiometry, and workup should be optimized for your substrate set.
Item-specific tested applications and recommended dilutions are not provided for this SKU.
Biological Roles
• Item-specific biological data: Not specified for this item; refer to CoA/Spec Sheet. For research use only (Product Data).
• General/literature context (no medical claims):
Indazole frameworks are bioisosteres of indoles and often occur in probe and tool compounds. The fused N–N heteroaromatic core presents hydrogen-bonding patterns complementary to many protein binding sites (e.g., kinases), while the carboxamide provides additional directional H-bonding and improves polarity for target engagement.
The 5-chloro substituent is a synthetically useful handle for diversification rather than a biological determinant; chloride can modulate lipophilicity and metabolic stability when retained.
As a small heteroaromatic amide, this scaffold is expected to be metabolically stable to some oxidations but susceptible to Phase I aromatic hydroxylation and Phase II conjugation if appropriately substituted (general xenobiotic behavior).
The primary amide may participate in H-bond donor/acceptor interactions; amidases can, in principle, effect hydrolysis in biological systems depending on context, but primary aryl amides are often relatively stable in vitro.
• Use in biology laboratories:
Typically handled as DMSO stock solutions for target-based screening or as synthetic intermediates to prepare more soluble analogs. Ensure final DMSO concentrations are compatible with assay systems.
All statements above are general to the chemotype and are not specific biological claims for this SKU.
Buffer Applications
This compound is not a buffering agent and is not typically used to prepare pH buffer systems. It lacks a suitable conjugate acid/base pair with a useful aqueous pKa in the physiological buffering range as an isolated small molecule. For aqueous handling, prepare DMSO stock solutions and dilute into pre-made buffers (PBS, HEPES, Tris) as needed, monitoring for precipitation. No buffer recipes are applicable to this item.
Green Alternatives
• Greener solvent and process options (literature/general):
Replace dioxane/DMF with 2-MeTHF or CPME for Pd-catalyzed cross-couplings; these ethers offer improved safety and lower environmental impact while maintaining performance with appropriate ligands.
Employ water or water/ethanol with micellar catalysis (e.g., TPGS-750-M, Savie) for Suzuki–Miyaura couplings; enables low Pd loadings and simplified workup.
Explore carbonate bases (K2CO3, Cs2CO3) and room-temperature or flow-enabled couplings to reduce energy input.
Use aqueous crystallizations or antisolvent precipitations (EtOH/H2O) in place of chlorinated solvent workups where feasible.
• Example comparison (general guidance; not item specifications):
Conventional: Pd(dppf)Cl2 in dioxane/H2O (95:5), K3PO4, 80–100 °C → robust but uses problematic solvent.
Greener: Pd/XPhos in 2-MeTHF/H2O or micellar H2O at 40–80 °C → reduced solvent hazard, simpler separations.
• Trade-offs to consider:
Solubility of the heteroaryl amide may limit purely aqueous media; small percentages of bio-derived co-solvents (EtOH, propylene glycol, Cyrene) can help.
Some green solvents may coordinate differently to catalysts, requiring re-optimization of ligand/base and temperature.
• Waste minimization:
Target high atom-economy couplings (Suzuki with pinacol boronates) and recover Pd via scavengers or reusable heterogeneous catalysts.
Pharmaceutical Uses
• Item-specific pharmacopeial status: Not specified for this item; refer to CoA/Spec Sheet. This product is supplied strictly for research use only (Product Data) and is not intended for human or veterinary applications.
• General formulation/CMC context (non-therapeutic):
As a heteroaromatic amide building block, it may serve in medicinal chemistry workflows to generate analog libraries. The 5-chloro group enables late-stage diversification via cross-coupling while the 3-carboxamide contributes polarity and H-bonding.
In pre-formulation research, DMSO or PEG-containing vehicles are commonly used to solubilize comparable scaffolds for in vitro assays. Solid-state screening (polymorph/solvate) can be relevant for related amide solids; no item-specific solid form data are provided here.
For process development studies (non-GMP), crystallization from alcohols or alcohol/water mixtures is a frequent approach for aromatic amides; exact solvent systems must be determined experimentally.
• Regulatory note: Absent explicit GMP or pharmacopeial designation, materials of this type should not be used in manufacturing drug substances or products without appropriate qualification and quality agreements.
Physical Properties
• Item-specific values: Not specified for this item; refer to CoA/Spec Sheet for melting point, purity, elemental analysis, residual solvents, and related specifications.
• Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
• Storage: Store at 2–8 °C (Product Data). Shipped on wet ice (Product Data).
• General/literature expectations for this class of compound (indazole carboxamides; for context only):
Physical state: typically a crystalline solid due to strong intermolecular hydrogen bonding via the primary amide.
Solubility profile: low aqueous solubility; good solubility in polar aprotic organic solvents (DMSO, DMF, NMP). Often sparingly soluble to moderately soluble in alcohols; limited solubility in nonpolar hydrocarbons.
Acid/base behavior: the 1H-indazole N1 is mildly acidic (pKa of conjugate acid of indazoles typically ~1–2; ring N basicity is low); the primary amide is neutral (weakly acidic N–H).
Lipophilicity: aryl chloride and fused ring increase hydrophobicity; amide lowers logP relative to halogenated arenes. Overall moderate lipophilicity (qualitative).
UV absorption: expected strong absorption in UV region due to fused aromatic system; amide introduces an n→π* band; exact λmax not provided here.
• Refractive index, density, vapor pressure, and thermal transitions: Not specified for this item; refer to CoA/Spec Sheet.
Note: Literature descriptors above are provided for planning purposes and are not specifications for this SKU.
Quality and Grades
• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
• What “research grade” implies (general): Products designated for research and laboratory use are manufactured and quality-checked to support synthetic chemistry and analytical workflows. They are not certified for human or veterinary use and are not produced under GMP unless explicitly stated.
• Typical characterization package (general description; check the specific CoA for this lot):
Identity confirmation by NMR and/or HRMS; optional IR.
Purity by HPLC/UPLC or GC where applicable.
Water and residual solvents by Karl Fischer and GC headspace where applicable.
Appearance and melting range for solids.
• Stabilizers/inhibitors: None specified for this item; refer to CoA/Spec Sheet. Aromatic amides typically do not require added stabilizers.
• Lot-to-lot consistency: For structure-sensitive medicinal chemistry and library synthesis, verify the lot CoA for exact assay (%), impurity profile, and any residual inorganic content if relevant to downstream catalysis.
• Documentation: If your workflow demands specific attributes (e.g., low-metal content for cross-coupling, trace halide quantitation, or tight UV cutoff for analytical methods), request the CoA/Spec Sheet prior to use. Do not assume unspecified limits.
Reaction and Applications
• Functional handles present:
Aryl chloride at the 5-position enables cross-coupling (C–C and C–N) via Pd-catalyzed transformations.
Indazole N1 (1H tautomer) can be deprotonated for N-alkylation/acylation under basic conditions.
The 3-carboxamide can be further derivatized at the amide nitrogen (e.g., N-acylation, sulfonylation) or used as an H-bonding motif in molecular recognition studies.
• Representative reaction families (literature/general):
Suzuki–Miyaura coupling with aryl/heteroaryl boronic acids or esters to replace the 5-chloro group; useful for rapid SAR diversification on the benzene ring.
Buchwald–Hartwig amination with primary/secondary amines to install anilines or diarylamines at C5.
Ullmann-type couplings (Cu) under elevated temperatures for cost-sensitive processes.
N1-alkylation with alkyl halides or sulfate esters using NaH/K2CO3 in polar aprotic solvents; protecting-group strategies may be required to control selectivity vs amide N.
Electrophilic aromatic substitution is relatively deactivated on the indazole ring; directed ortho-metalation is uncommon without additional directing groups.
• Application contexts (non-clinical):
Discovery chemistry scaffold: the indazole–carboxamide core is a common heteroaromatic pharmacophore mimic; C5 diversification via the aryl chloride streamlines library synthesis.
Supramolecular chemistry: amide H-bonding and planar heteroaromatic stacking make it a candidate motif in crystal engineering and host–guest studies.
• Practical tips:
For couplings on aryl chlorides, use modern ligands (e.g., SPhos/XPhos/XantPhos) and optimized bases; monitor for potential N-arylation of the amide under strongly basic, high-temperature conditions.
Reaction Conditions
General literature guidance for aryl chloride couplings and N-functionalizations of indazoles (not item-specific specifications):
• Suzuki–Miyaura at C5 (aryl chloride):
Catalyst: Pd(dppf)Cl2·DCM (1–3 mol%) or Pd2(dba)3 (0.5–1 mol%) with SPhos/XPhos (2–4 mol%).
Base: K3PO4 (2–3 equiv) or K2CO3; aqueous inorganic bases often effective.
Solvent: dioxane/H2O (4:1), 2-MeTHF/H2O, or DMF/H2O.
Temperature/time: 70–100 °C, 2–12 h. Inert atmosphere recommended.
• Buchwald–Hartwig amination at C5:
Catalyst/ligand: Pd2(dba)3 (1 mol%) with XantPhos or BrettPhos; or Pd(OAc)2 with RuPhos.
Base: NaOtBu or Cs2CO3 (2–3 equiv).
Solvent: toluene, 1,4-dioxane, or CPME.
Temperature/time: 90–120 °C, 4–16 h.
• N1-alkylation of indazole:
Base: NaH (1.1–1.5 equiv) or K2CO3 (excess) depending on electrophile reactivity.
Solvent: DMF, DMSO, or acetonitrile.
Temperature: 0–25 °C for reactive benzyl/allyl halides; 40–80 °C for less reactive alkyl halides.
• Amide transformations (general):
Dehydration to nitrile: SOCl2/POCl3 or T3P/Et3N under controlled conditions.
Hydrolysis to acid: aqueous NaOH or HCl under reflux (monitor to avoid ring degradation).
Notes:
Optimize ligand/base for heteroaryl chlorides, which can be less reactive than bromides.
Competing N-arylation can occur; suppress with appropriate ligands and milder bases.
Always verify compatibility of conditions with the amide functionality.
Safety and Handling
• Product-specific hazard information (GHS/CLP):
Signal Word: Not specified for this item; refer to SDS.
Hazard Statements (H-phrases): Not specified for this item; refer to SDS.
Pictograms/GHS Classification: Not specified for this item; refer to SDS.
• General safety guidance for heteroaromatic amides (informational, not a substitute for the SDS):
Likely low volatility; handle as a fine solid to minimize dust generation and inhalation. Use local exhaust ventilation when weighing/dispensing.
Avoid contact with skin and eyes; wear suitable PPE: lab coat, nitrile gloves, and splash goggles. Change gloves regularly when working in DMSO/DMF, which can enhance dermal absorption of solutes.
Incompatibilities: strong oxidizers and strong bases may affect stability (base-promoted ring N-alkylation is possible under forcing conditions). Avoid prolonged exposure to strong acids/bases that could hydrolyze the amide under harsh conditions.
Thermal hazards: aromatic amides are generally thermally stable but avoid overheating and open flames; decompose on strong heating.
First aid (overview): in case of skin contact, wash with soap and water; eye contact, rinse thoroughly with water for several minutes; inhalation, move to fresh air; ingestion, rinse mouth. Seek medical attention as appropriate. Always follow site SOPs.
• Storage and handling notes (Product Data): Store at 2–8 °C. Keep container tightly closed, protected from moisture. Shipments are on wet ice to maintain cool chain.
Always consult the official SDS for authoritative hazard, exposure, and disposal guidance.
Solvent Selection
• Polarity and solubility considerations (general guidance for indazole carboxamides):
Preferred dissolution solvents: DMSO, DMF, NMP offer strong solubility via H-bond accepting ability and polarity. Hot ethanol or isopropanol may dissolve moderate amounts; water solubility is typically poor.
For reactions: polar aprotic solvents (DMSO, DMF, DMAc, NMP) or mixed aqueous-organic systems (dioxane/H2O, THF/H2O) are commonly employed for cross-couplings on the aryl chloride.
• Miscibility profile (literature/general):
DMSO, DMF, NMP: miscible with water and most organics; facilitate high-temperature couplings.
Alcohols: can assist crystallization and purification; methanol/ethanol mixtures often used for recrystallization.
Nonpolar solvents (toluene, xylene): sometimes suitable for Buchwald–Hartwig amination with strong bases and bulky ligands; solubility may be limiting.
• When to choose alternatives:
If downstream bioassays are planned, prepare concentrated DMSO stocks (e.g., 10–50 mM) and dilute into aqueous buffers with surfactants or co-solvents to avoid precipitation.
For greener operations, consider 2-MeTHF, CPME, propylene carbonate, or water/ethanol blends with micellar surfactants in catalytic cross-couplings (see Green Alternatives).
• Practical tips:
Warm and sonicate to aid dissolution; avoid strong base during stock preparation unless purposeful (can induce N1-alkylation or amide hydrolysis under harsh conditions).
Filter stock solutions (0.22 µm PTFE) to remove particulates before sensitive applications.
Storage and Reconstitution
• Storage conditions (Product Data): Store at 2–8 °C in a tightly closed container. Shipments are on wet ice to maintain a cool chain.
• Stability/shelf life: Not specified for this item; refer to CoA/Spec Sheet. As a general practice, protect from moisture and prolonged exposure to light and heat.
• Handling:
Allow container to equilibrate to room temperature before opening to minimize condensation.
Reseal promptly under dry air or inert gas if available; include a desiccant in secondary containment for long-term storage.
• Preparing stock solutions (general guidance):
Solvents: Use anhydrous DMSO, DMF, or NMP for concentrated stocks. Typical laboratory stocks are 10–50 mM in DMSO for screening or 0.1–0.5 M in DMF/DMSO for synthesis.
Procedure: Weigh accurately, add solvent, vortex/sonicate to dissolve. If necessary, gently warm (<40 °C). Filter through 0.22 µm PTFE before sensitive applications.
Aliquoting: Divide into single-use portions to avoid repeated freeze–thaw and moisture uptake.
• Storage of solutions:
DMSO/DMF solutions: store at 2–8 °C for short term; for longer-term storage, freeze at −20 °C. Monitor for precipitation upon cooling; redissolve by warming and mixing.
• Reconstitution buffer: Not applicable; this product is not supplied lyophilized in an aqueous buffer.
Always consult the CoA/SDS for any item-specific precautions or incompatibilities.
Structure and Identity
• Item-specific identifiers (Product Data):
SKU: C192535
Product Name: 5-Chloro-1H-indazole-3-carboxamide
CAS: 28751-70-4
InChIKey: 197083 (as provided)
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 description (from chemical name; general/literature-based):
Core scaffold: an indazole (benzopyrazole) fused bicyclic heteroaromatic system consisting of a benzene ring fused to a pyrazole (N–N-containing five-membered ring). The “1H” designation indicates the predominant tautomer bears a proton on N1 of the pyrazole.
Substituents: a chloro substituent at the 5-position on the benzene ring; a carboxamide (–C(=O)NH2) at the 3-position of the indazole.
Stereochemistry: none (achiral); planar polycyclic aromatic framework with conjugation across the indazole core and into the amide carbonyl by resonance.
Tautomerism: indazoles can exhibit 1H/2H tautomers; 1H-indazole is usually favored in neutral conditions. The amide typically adopts trans (anti) conformation with partial C–N double-bond character.
• Computed/depicted structure: For exact coordinates and connectivity (SMILES/InChI), consult the product CoA/Spec Sheet; do not infer without vendor documentation.
Synthetic Utility
• Strategic roles of 5-chloro-1H-indazole-3-carboxamide (general/literature):
Diversifiable aryl chloride: serves as a linchpin for installing diverse aryl, heteroaryl, vinyl, or amine substituents at C5 via Pd-catalyzed cross-couplings (Suzuki, Buchwald–Hartwig, Negishi, Stille).
Bifunctional scaffold: orthogonal reactivity between the aryl chloride and the N1–H allows sequential modifications (e.g., first perform Suzuki on C5, then N-alkylate N1; or vice versa with appropriate protection strategies).
Amide handle: the primary amide can be converted to other functionalities—e.g., to nitrile (via dehydration), to acid (hydrolysis), or to ureas/sulfonamides (N-functionalization). It can also direct H-bonding in crystal engineering.
• Retrosynthetic value:
Enables convergent routes where the indazole core is constructed early, leaving C5 diversification for late-stage SAR escalation.
Readily couples with commercially available boronic acids/esters or amines to access analogs without re-synthesizing the heterocycle.
• Selectivity considerations:
Under basic conditions, competition between C5 coupling and N1-arylation/alkylation can occur. Ligand/base choice and temperature govern selectivity. Protecting the amide N (if modified) may be necessary to avoid undesired N-acylation.
• Workup/purification:
Products often purify by silica gel chromatography (polar eluents) or crystallization from alcohols. The amide may cause tailing on silica; adding 0.1–1% Et3N to eluents can improve band shape.
Target Specificity
No biological target specificity, antigen, clone, or isotype information is applicable to this small-molecule reagent. This product is a heteroaromatic building block for chemical synthesis and research. Item-specific target data are not provided; refer to CoA/Spec Sheet if needed.
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