This compound belongs to the class of organic compounds known as pyridinecarboxylic acids and derivatives. These are compounds containing a pyridine ring bearing a carboxylic acid group or a derivative thereof.
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
Punto di fusione (°C)
147°C(lit.)
Peso molecolare
139.180 g/mol
XLogP3
0.800
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
139.009 Da
Monoisotopic Mass
139.009 Da
Topological Polar Surface Area
31.000 Ų
Heavy Atom Count
9
Formal Charge
0
Complexity
116.000
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
No validated bioassay/diagnostic protocols are provided for this item in the Product Data. As a small-molecule building block, protocols are inherently application-specific.
General laboratory guidance (non-binding)
Synthetic coupling: See Reaction Conditions for starting points on amide/thioester formation and activation to acyl chlorides.
Sample preparation for analysis: Dissolve in DMSO, DMF, MeOH, or acetonitrile to prepare 10–100 mM stock solutions; filter (0.2 µm PTFE) before LC–MS/UPLC.
Purification: Silica gel chromatography using DCM/MeOH or EtOAc/hexanes gradients; modify with 0.5–1% acetic acid or triethylamine to manage peak tailing.
Quality control checks (suggested)
Identity: 1H/13C NMR (look for thioacid diagnostic C=S region in 13C, and pyridyl resonances), HRMS.
Purity: HPLC or UPLC with diode-array detection; monitor for oxidized (C=O) or desulfurized analogs.
For application-specific SOPs, develop and validate conditions relevant to your synthetic or materials workflow.
Biological Roles
This product is sold strictly for research use only. No medical or clinical claims are made.
General chemical biology perspective (literature-based; not product-specific)
Thionicotinic Acid is a sulfur-substituted analog of nicotinic acid (vitamin B3). While nicotinic acid participates in NAD/NADP biosynthesis, the thio-analog is not a known natural metabolite and is primarily used as a synthetic probe or building block in research settings.
The pyridine nitrogen can engage in noncovalent interactions (hydrogen bonding, cation–π/coordination) with biomolecular targets, while the thiocarboxylic acid can be tuned for prodrug-like derivatization (e.g., thioester masking) in chemical biology tool design. Such uses are exploratory and require case-by-case validation.
Metal-binding: Deprotonated thiocarboxylates and pyridyl nitrogens coordinate transition metals; metal complexes of pyridyl thioacids have been investigated for spectroscopic probes and model systems in bioinorganic research.
ADME/tox surrogacy
Replacement of C=O with C=S modifies hydrogen-bonding patterns and polarizability, often decreasing hydrolytic stability and altering permeability; these qualitative effects are sometimes exploited in SAR campaigns to probe binding interactions.
Caution
Any biological testing must comply with institutional approvals and safety protocols. Stability, reactivity with thiols (e.g., cysteine, glutathione), and potential off-target reactions should be assessed empirically for each application.
Buffer Applications
Thionicotinic Acid is not a standard biological buffer component. As a heteroaromatic thiocarboxylic acid, it lacks a well-defined, narrow buffering range and is not typically used to maintain pH in biochemical assays.
Practical note
If incorporated into aqueous systems (e.g., as a substrate, ligand, or building block), adjust pH using established buffers (HEPES, MOPS, phosphate) and avoid strong oxidants that may convert the thioacid functionality. Generate its soluble thiocarboxylate salt in situ with mild, non-oxidizing bases if enhanced aqueous solubility is required.
Recommendation
Refer to the sections on Solvent Selection and Reaction & Applications for guidance more relevant to this compound’s typical use cases.
Green Alternatives
Greener strategy considerations focus on solvent selection, activation methods, and choice of coupling chemistry when using Thionicotinic Acid to introduce a 3-pyridylcarbonyl motif.
Solvent choices (relative greenness)
Prefer EtOAc, MeTHF, or CPME over chlorinated solvents when solubility allows. DMSO and ethanol are broadly acceptable under many green frameworks; DMF and NMP are higher concern for reproductive toxicity—limit or replace when possible.
Activation/coupling alternatives
Enabling chemistry: Use catalytic, high-atom-economy coupling (e.g., CDI, propane phosphonic anhydride [T3P]) which often produce benign byproducts and operate in greener solvents (EtOAc, MeOH) compared to traditional DCC/HOBt systems.
Avoid over-activation: Direct thioester or amide formation under mild dehydrative conditions reduces need for acid chlorides (which generate HCl and require chlorinated media).
Oxidant control
If the oxo-analog (nicotinic acid derivatives) is acceptable, aerobic or peroxide-mediated oxidation of the thioacid can convert to the carboxylic acid, potentially simplifying processing and EHS profile; however, weigh against selectivity and waste generation.
Comparison (illustrative)
Route A (traditional): SOCl2 activation in DCM → amide. Pros: high reactivity; Cons: corrosive reagents, chlorinated solvent, HCl/SO2 off-gas.
Route B (greener): T3P in EtOAc or 2-MeTHF with amine nucleophile. Pros: milder, fewer hazards, easier workup (water-soluble byproducts); Cons: may require optimization for thioacids and deliver different selectivity.
Workup/waste
Favor aqueous bicarbonate/Na2CO3 quenches and phase separations; minimize chlorinated waste. Recover and recycle EtOAc/MeTHF where facility permits.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided in the Product Data. This product is offered for research use only and is not intended for human or veterinary use.
Formulation role (general research context)
Thionicotinic Acid may serve as a synthetic intermediate to introduce a 3-pyridylcarbonyl (or thiocarbonyl) functionality into small molecules. Derivatives (amides, esters, thioesters) could be evaluated in discovery programs as part of structure–activity relationship (SAR) studies.
Developability considerations (general)
Salt formation: The acidic thioacid group enables salt screening (e.g., Na+, K+, organic amines) to enhance solubility for in vitro testing. The pyridyl nitrogen can form protonated species in acidic media, influencing solid-state properties.
Chemical stability: Assess susceptibility to oxidation (C=S → C=O conversion) during processing and storage; include antioxidant-free conditions and oxygen control if the thio functionality is critical.
Analytical controls: Use orthogonal methods (NMR, LC–MS, combustion/CHNS for sulfur content) to monitor identity and purity; watch for desulfurized or oxidized impurities.
Regulatory note
There are no claims of compliance with USP/Ph.Eur./JP for this item. Any use in GMP or clinical contexts would require independent qualification, method validation, and sourcing under appropriate quality systems.
Physical Properties
Item-specific specifications are not provided in the Product Data. Always consult the batch CoA/Spec Sheet for definitive values.
Item-specific values
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Purity/grade: Not specified for this item; refer to CoA/Spec Sheet.
Melting point, boiling point, density, UV cutoff, water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.
Physical state: typically a crystalline solid for analogous pyridyl thiocarboxylic acids (literature).
Molecular formula and mass: C6H5NOS; ~139.17 g/mol (literature for thionicotinic acid tautomer).
Solubility profile: expected sparing solubility in water at neutral pH; improved solubility in polar aprotic solvents (DMSO, DMF, NMP) and alcohols; readily soluble in aqueous base due to formation of the thiocarboxylate (general behavior of thiocarboxylic acids).
Acid–base behavior: acidic –OH on the thioacid; deprotonates under mild basic conditions to give a nucleophilic thiocarboxylate; pyridine nitrogen is weakly basic and can be protonated under acidic conditions (general behavior).
Volatility: low; decomposition may precede boiling (typical for heteroaromatic thioacids; literature).
Hygroscopicity: not strongly hygroscopic in general, but salts can be more water-attracting (general trend).
Stability: sensitive to strong oxidants; prolonged exposure to air/oxidizing conditions can lead to oxidation or tautomeric equilibration; store dry and protected from strong oxidizers (general guidance).
Note: Numeric properties (mp, bp, pKa, logP, refractive index) are not specified for this item; refer to CoA/Spec Sheet and primary literature if precise values are required.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet. Aladdin typically provides assay and key impurity controls on the CoA for organic building blocks.
How to interpret common grades (general guidance)
Research Grade: Suitable for most synthetic and analytical workflows; may not include low-UV specifications.
HPLC Grade (for solvents/solubles): Low UV absorbance background and particulates; not generally applicable to solid building blocks like this compound unless explicitly stated.
Stabilizers/additives
Not specified for this item; refer to CoA/Spec Sheet. Thiocarboxylic acids are typically provided neat without stabilizers. If present, stabilizers will be declared on the label/CoA.
What to check on receipt (practical tips)
Verify assay and identity (NMR/HRMS/LC–MS). Inspect for discoloration (possible oxidation) and unusual odors.
If using in moisture- or air-sensitive transformations (e.g., conversion to acyl chlorides or thioesters), consider drying under vacuum and handling under inert atmosphere.
Trace analysis
Specific limits for water, peroxides, metals, UV cutoff: Not specified for this item; refer to CoA/Spec Sheet.
Documentation
Lot-specific CoA and, if requested, additional QA documents (e.g., TDS/SDS) should be consulted for acceptance criteria and testing methods.
Reaction and Applications
Thionicotinic Acid serves as a versatile heteroaromatic acyl/thiocarbonyl synthon. Key application domains leverage the reactivity of the thiocarboxylic acid and the coordinating pyridine nitrogen.
Amide formation: Activation (e.g., via carbodiimides, Mukaiyama-type reagents, or conversion to acid chlorides) to install the 3-pyridylcarbonyl motif onto amines. Thioacids can be converted to the corresponding carboxy derivatives under oxidative conditions; choose conditions that preserve the C=S when desired.
Thioester synthesis: Direct coupling with alcohols/thiols under activating conditions affords 3-pyridyl thioesters—useful acyl-transfer intermediates.
Acyl chloride/thioanhydride formation: Treatment with chlorinating agents (e.g., oxalyl chloride, SOCl2) can furnish activated derivatives enabling subsequent esterification, amidation, or coupling.
Metal–ligand and materials chemistry: The pyridine N and the thiocarboxylate (upon deprotonation) can chelate transition metals, enabling coordination polymers, MOF-like constructs, or catalytic complexes.
Cross-coupling from halogenated congeners: While the parent compound lacks a halogen handle, its 3-pyridyl framework aligns with literature methods where carboxyl(thiocarbonyl) directing effects are leveraged in C–H functionalization; derivatization of Thionicotinic Acid can thus serve as a handle for late-stage diversification.
Practical tips
Dry, oxygen-limited conditions favor retention of the thio functionality; trace oxidants (e.g., adventitious peroxides) can drive conversion toward the oxo-analog.
For base-mediated steps, moderate bases (DIPEA, DBU) often suffice; very strong bases can induce side reactions (e.g., thio-Michael additions or ring activation) in sensitive systems.
Monitor by LC–MS; the C=S chromophore may shift UV absorbance relative to the C=O analog (longer wavelength).
Reaction Conditions
The following are general, literature-informed conditions for typical transformations involving heteroaromatic thiocarboxylic acids like Thionicotinic Acid. Optimize for your system and verify on small scale.
Amide coupling (from thioacid)
Solvent: DMF, DCM, or EtOAc.
Activation: T3P (50% in EtOAc) or CDI (1.0–1.5 equiv) at 0–25 °C; add amine (1.1–1.5 equiv) and base (DIPEA 2–3 equiv). Stir 1–12 h. Typical literature yields for analogous systems: 60–90% (literature; substrate dependent).
Conversion to acid chloride
Reagent: SOCl2 (3–5 equiv) with catalytic DMF.
Solvent: neat SOCl2 or DCM.
Temperature: reflux in SOCl2 (60–80 °C) for 1–3 h; remove volatiles, use crude acyl chloride in situ for esterification/amidation. Exercise strict moisture control.
Thioester formation
Reagents: EDC·HCl or DIC with catalytic DMAP; nucleophile: RSH (1.2–2.0 equiv).
Solvent: DCM or DMF; Temperature: 0–25 °C; Time: 2–16 h. Purify by silica chromatography (add 0.5–1% Et3N to mobile phase if tailing).
Oxidation to oxo-analog (nicotinic acid derivatives)
Mild oxidants: mCPBA (≤1 equiv) or Oxone in MeCN/H2O; Temperature: 0–25 °C; Monitor by LC–MS; avoid over-oxidation.
Metal complexation
Generate thiocarboxylate salt in situ with NaHCO3/Na2CO3 in H2O/MeOH, then add metal salt (e.g., Cu(II), Zn(II)) under inert atmosphere; isolate complexes by slow evaporation or diffusion.
Note: These are literature-style guidelines for related substrates and not product-specific specifications. Always consult safety data and conduct controls.
Safety and Handling
Authoritative safety information must come from the product-specific SDS. The following are general handling considerations for heteroaromatic thiocarboxylic acids.
Product Data (item-specific)
GHS classification, signal word, pictograms, and H-statements: Not specified for this item; refer to SDS.
Storage: Room temperature; ship under normal conditions.
General hazards and precautions (literature/good practice)
Irritation: Thiocarboxylic acids and pyridine derivatives may cause skin, eye, and respiratory irritation. Avoid dust formation and inhalation.
Odor: Sulfur-containing compounds can possess strong odors; work in a fume hood.
Oxidation sensitivity: Avoid contact with strong oxidizers (e.g., peroxides, nitric acid). Keep container tightly closed and dry.
PPE: Laboratory coat, nitrile gloves, and splash goggles as minimum. Consider double-gloving for extended handling.
Engineering controls: Use in a chemical fume hood with local exhaust. Avoid aerosolization during weighing and transfers.
First aid overview (consult SDS for details)
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water. Remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present; obtain medical advice.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Incompatibilities and storage notes
Incompatible with strong oxidizers and strong bases/acids for prolonged periods (can cause decomposition). Store in a cool, dry place in the original, tightly sealed container.
Waste disposal: Collect as organic sulfur-containing waste; follow institutional and local regulations.
Solvent Selection
As a heteroaromatic thiocarboxylic acid, Thionicotinic Acid displays dual behavior: acidic (thiocarboxyl group) and weakly basic (pyridine N). Solvent choice should balance solubility, stability, and downstream reaction compatibility.
Polarity/miscibility (literature/general)
Polar aprotic solvents (DMSO, DMF, NMP): Typically offer excellent solubility and maintain the neutral thioacid/tautomeric mixture; useful for coupling or activation steps.
Alcohols (MeOH, EtOH, i-PrOH): Moderate solubility; can participate in esterification under activation; useful for recrystallization when appropriate.
Water: Generally low solubility at neutral pH; solubility increases markedly in basic aqueous media (thiocarboxylate salt formation).
Chlorinated/ether solvents (DCM, THF, EtOAc): Variable solubility; often suitable for extractions and workups.
Selection guidance
For amide coupling or thioester formation: DMF or DCM with appropriate coupling agents; add base (e.g., DIPEA) judiciously to minimize over-deprotonation/side reactions.
For salt formation or metal coordination studies: Aqueous/MeOH mixtures with controlled pH to generate the thiocarboxylate; buffer pH with non-oxidizing bases.
For purification: EtOAc/hexanes or DCM/MeOH gradients on silica; mind potential adsorption via hydrogen bonding—add a small % of acetic acid or triethylamine to modify silica if tailing occurs.
Comparison (typical)
DMSO vs DMF: DMSO maximizes solubility but is higher boiling and harder to remove; DMF balances solubility and workup ease.
Aqueous base vs neat organic: Aqueous base simplifies deprotonation/salt formation; neat organic preferred for moisture-sensitive activations.
Keep tightly closed in a dry, well-ventilated place away from strong oxidizers. Protect from prolonged exposure to air and moisture to minimize oxidation of the thio functionality.
If long-term storage is planned, consider inert-gas backfilling (nitrogen or argon) after each use. Store in amber glass if using under strong light conditions to avoid photochemical effects.
Reconstitution and solution preparation
Solubility: Readily dissolved for stock solutions in DMSO or DMF; soluble to moderately soluble in MeOH/EtOH. Solubility in water is low at neutral pH but increases upon basification (thiocarboxylate formation).
Typical stock solutions (research use): Prepare 10–200 mM in DMSO or DMF; filter through 0.2 µm PTFE syringe filters for analytical use. For aqueous work, dissolve in minimal DMSO/DMF and dilute with buffer immediately before use.
Stability of solutions: Organic solvent stocks are generally stable short-term at room temperature during use; for longer storage, keep at 2–8 °C or −20 °C under inert atmosphere and protect from light. Monitor for precipitation or discoloration.
Specifications
Appearance, assay, water/metal/peroxide content, and other item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.
Safety note
Open and handle inside a fume hood. Cap promptly after use to reduce oxidation and solvent uptake.
Structure and Identity
Thionicotinic Acid is the thio-analog of nicotinic acid (pyridine-3-carboxylic acid), in which the carbonyl oxygen of the carboxyl group is replaced by sulfur to give a thiocarboxylic acid attached at the 3-position of a pyridine ring.
Product Data (item-specific)
SKU: T161551
Product Name: Thionicotinic Acid
CAS: 51087-03-7
PubChem CID: 571572 (per Product Data)
Storage: Room temperature; shipped under normal conditions
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
InChIKey: 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 identifiers (for reference; confirm prior to use)
Common structural description: pyridine ring (positions 1 N, 3 substituent) bearing a thiocarboxylic acid group (–C(=S)–OH) at C-3.
Typical literature SMILES for the neutral thioacid tautomer: OC(=S)c1cccnc1 (literature)
Heteroaromatic pyridine core (sp2 N) capable of coordination and hydrogen bonding.
Thiocarboxylic acid functionality with thione (C=S) and acidic OH; exists as tautomeric thioacid/thiolactim forms depending on medium.
Planar aromatic system; no stereocenters.
Functional handles: ring nitrogen (basic/ligating), acidic thioacid OH (deprotonation, salt formation), electrophilic C(=S) center (acyl/thiocarbonyl transfer).
Synthetic Utility
Thionicotinic Acid is a convenient handle for installing the 3-pyridylcarbonyl motif with control over the oxo/thio state. Its dual functionality enables diverse derivatizations.
Functional group reactivity (general)
Thiocarboxylic acid: Can be activated to acylating species (acid chlorides via SOCl2/oxalyl chloride; mixed anhydrides; T3P/CDI adducts). Reacts with nucleophiles (amines, alcohols, thiols) to furnish amides, esters, and thioesters.
Thio-specific chemistry: The C=S bond participates in thioacyl transfer and can undergo selective oxidation (to C=O) or sulfur extrusion under forcing conditions, enabling access to the oxo-analog (nicotinic acid derivatives).
Pyridine nitrogen: Enables coordination to metals, directional effects in C–H activation strategies, and tuning of electronic properties in conjugated systems.
Retrosynthetic value
Serves as a bench-stable alternative to 3-pyridinecarbonyl chloride, which is moisture sensitive and corrosive. Generation in situ of activated intermediates from the thioacid can improve operational simplicity.
Thioesters derived from Thionicotinic Acid act as powerful acyl donors in native chemical ligation-like reactions (in model systems) and as masked acyl fragments in multistep sequences.
Representative downstream products
3-Pyridyl amides (pharmacophore motifs), esters (probes/precursors), metal–organic frameworks (pyridyl–thiocarboxylate linkers), and heteroaryl acylating agents for cross-coupling after further functionalization.
Practical notes
Maintain anhydrous, oxygen-limited conditions during activation to preserve C=S. Use mild bases (DIPEA, lutidine) to control chemoselectivity, and monitor for over-oxidation or desulfurization.
Target Specificity
Not applicable. This product is a small-molecule chemical reagent, not a biological targeting reagent (e.g., antibody, probe with defined biomolecular target), and the Product Data include no target specificity information.
Domande frequenti
How should this product be stored?
Store at room temperature.
How is this product shipped?
This product ships under standard ambient conditions. No temperature-controlled packaging is required.
What are the CAS number, molecular formula and molecular weight?
The CAS Number is 51087-03-7, the molecular formula is C6H5NOS, and the molecular weight is 139.17 g/mol. InChIKey OWDHSOUPMJJTFN-UHFFFAOYSA-N.
What documentation is provided?
Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.
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