Thionicotinamide - 10mM in DMSO , CAS No.4621-66-3

CAS: 4621-66-3 Cat. No.: T661279 分子式: C₆H₆N₂S 分子量: 138.19 EC番号: 225-036-6 PubChem CID: 737155

グレード＆純度 10mM in DMSO

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

仕様

仕様と純度

10mM in DMSO

保管条件

Store at -80°C

入荷

Dry ice packs + Cold packs

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名前と識別子

異性体SMILES

C1=CC(=CN=C1)C(=S)N

RTECS

QS4488000

PubChem CID

737155

分子量

138.19

Reaxy-Rn

109593

化学的性質と物理的性質

• 引火点（°F）: 320°F
• 引火点（°C）: 160℃
• 融点（°C）: 190℃

Application Protocols

No assay-validated protocols are provided for this SKU in the Product Data.

• General laboratory use (illustrative, non-validated):
  • Stock preparation: dissolve thionicotinamide at 10–100 mM in anhydrous DMSO; vortex and, if needed, gently warm (≤40°C). Filter through 0.22 µm PTFE for sterile applications.
  • Working solutions: dilute into assay buffer or reaction medium; keep final DMSO ≤1–2% v/v for biochemical assays. Prepare fresh immediately before use to minimize oxidative changes.
  • Synthetic setup: for electrophilic activation (e.g., SOCl2), dry glassware and inert atmosphere are recommended. Add base or nucleophile after formation of the imidoyl halide intermediate at low temperature.

These steps are general best practices and are not item-specific validated methods. For application-specific guidance, consult primary literature and perform pilot experiments.

Biological Roles

Research-only context: Thionicotinamide is the thioamide isostere of nicotinamide (the amide form of vitamin B3). In biochemical studies, such isosteres are used to probe enzyme active sites and cofactor recognition without making therapeutic claims.

• Conceptual roles in biochemistry (literature/general):

  • Structural mimicry: The pyridine ring mirrors nicotinamide’s heteroaromatic motif, while the thioamide preserves hydrogen-bonding topology but alters sulfur/polarizability, enabling studies of binding energetics and specificity.
  • Enzyme/cofactor model systems: Employed in vitro to interrogate binding pockets that recognize nicotinamide-like motifs (e.g., dehydrogenase cofactor fragments or NAD-related binding elements) to parse out contributions from the amide vs thioamide.
  • Photophysical/chemical differences: Thioamides often display red-shifted UV absorption and enhanced triplet yields vs oxoamides (general property), useful in spectroscopic probing of protein/ligand interactions.

• Limitations and caveats:

  • The sulfur substitution can alter pKa, hydrogen bonding, and reactivity; biochemical outcomes may not extrapolate directly to the oxoamide analogue.
  • Any use must remain within laboratory research settings; not for human or animal administration.

• Practical handling in bioassays:

  • Prepare concentrated DMSO stocks; final DMSO in biochemical assays typically ≤1–2% v/v. Verify solubility and absence of aggregation by light scattering or serial dilution.

Buffer Applications

This compound is not a buffering agent and is not typically used to prepare pH buffer systems. If employed in biochemical assays, it is usually added as a solute in pre-made buffers.

• Practical notes:
  • Dissolve in DMSO or another suitable co-solvent before spiking into assay buffers (e.g., phosphate, HEPES, Tris). Maintain low organic content to avoid perturbing buffer capacity.
  • Confirm that the chosen buffer and pH do not promote undesired reactions at the thioamide (e.g., chlorination in hypochlorite-containing systems).

Green Alternatives

While the compound itself is the research target, process greening can focus on solvent and reagent choices during its synthesis, handling, and downstream transformations.

• Greener solvent choices (literature/general):

  • Replace DMF/NMP with safer polar aprotics where feasible: acetonitrile, ethyl acetate, propylene carbonate, or Cyrene. For dissolution, 2-MeTHF or ethanol can sometimes substitute for DCM/THF.
  • For recrystallization, prefer ethanol/water or isopropanol over chlorinated solvents.

• Reagent alternatives:

  • Thiazole formations: use K2CO3 or organic bases in ethanol rather than strong bases in chlorinated media.
  • Dehydrations to nitriles: switch from POCl3/SOCl2 to catalytic dehydration using tosyl chloride with base or T3P (propylphosphonic anhydride) in greener solvents when compatible.
  • Oxidative desulfurization: employ H2O2 or Oxone under catalytic conditions rather than heavy-metal oxidants, monitoring for over-oxidation.

• Workup/waste minimization:

  • Implement solvent swaps to greener media prior to isolation; use aqueous biphasic extraction with EtOAc/IPA rather than DCM when possible.
  • Capture sulfur-containing off-gases through basic scrubbing solutions; segregate sulfurous wastes for specialized disposal.

Comparison snapshot (general):

• DMF/NMP: excellent solvating power; reproductive toxicity concerns; challenging EHS profile.
• Ethanol/2-MeTHF/EtOAc: renewable or lower-toxicity options; may require higher temperatures or longer times to match rates/solubility.

Pharmaceutical Uses

No pharmacopeial or excipient status is provided for this item, and it is sold strictly for research use only.

• Not specified for this item; refer to CoA/Spec Sheet if any compendial references exist.

• Research/formulation context (general):

  • As a small-molecule research tool or synthetic intermediate, thionicotinamide may be formulated short-term in DMSO or ethanol for in vitro testing. It is not intended for clinical or diagnostic use.
  • If used in preformulation research, characterize solubility across pH and co-solvent systems and assess chemical stability (oxidation/desulfurization) under storage and assay conditions.

Physical Properties

Only limited item-specific physical data are provided for this catalog entry. Where values are included below, they are labeled by source.

• Item-specific values (from Product Data):

  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general reference values (non-binding, for planning only):

  • Empirical formula (literature): C6H6N2S (thioamide analogue of nicotinamide)
  • Formula weight (literature): ~138.19 g/mol
  • Physical state: typically a crystalline solid (thioamides of this class are solids at ambient temperature)
  • Solubility profile (qualitative, literature/general):
    • Water: low to moderate solubility typical for small heteroaromatic thioamides
    • Polar aprotic: good solubility in DMSO and DMF; moderate in acetonitrile
    • Protic: soluble in hot ethanol/methanol; sparingly to moderately soluble at RT
  • Acid–base behavior: neutral thioamide; the –NH is weakly acidic (thioamide N–H pKa often ~10–12, literature-general)
  • LogP: expected low to moderate due to heteroatoms; exact value not confirmed (literature not cited here)

• Practical handling implications:

  • Readily dissolves for analytical prep in DMSO or DMF; aqueous work may require co-solvent or pH adjustment.
  • Solid-state stability is generally good when protected from light and moisture; follow the Storage section for this specific item.

Always consult the item’s CoA/Spec Sheet for definitive, batch-specific physical data.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grades for small-molecule research reagents (general guidance):

  • Research/biochemical grade materials are typically suitable for synthetic, analytical, and exploratory biological research where precise impurity profiles are not as stringent as GMP. If UV-transparency, low water, or trace metals are critical, specify HPLC grade solvents/reagents or request extended CoA parameters.
  • For heteroaromatic thioamides, common quality differentiators include: residual solvents (e.g., DMF/DMSO from workup), sulfur-containing byproducts, inorganic salts, and oxidation products. Confirm by 1H/13C NMR and HRMS; optional: elemental analysis to verify S content and confirm absence of oxygenated analogs.

• Stabilizers/additives:

  • None are listed for this item. If stabilizers are present in a batch, they will be disclosed on the CoA.

• Documentation:

  • Request the batch CoA for: assay method and result, residual solvent profile, water content (Karl Fischer), and any chromatographic purity assessments (HPLC/GC). Where application-specific thresholds exist (e.g., for photochemistry or metal-catalyzed cross-couplings), communicate your needs to Technical Support for lot selection.

Reaction and Applications

As a 3-pyridinecarbothioamide (thioamide), thionicotinamide is a versatile building block and functional handle in heterocycle synthesis and functional-group interconversions.

• Representative transformations (literature/general):

  • Cyclization to thiazoles/thiazolines: condensation with α-haloketones or α-haloesters (Hantzsch-type) affords 2-substituted thiazoles; bases such as K2CO3 or Et3N in EtOH/MeCN, 20–80°C.
  • Formation of thioimidates/imidoyl halides: activation with SOCl2, PCl5, or oxalyl chloride converts the thioamide to reactive intermediates for subsequent nucleophilic substitution (alcohols/thiols/amines → thioimidates/amidines).
  • Desulfurization/oxidation:
    • To amide: oxidative desulfurization with H2O2 in the presence of catalysts, or via electrophilic activation followed by hydrolysis (literature variants exist); milder routes use metal-mediated oxygen transfer.
    • To nitrile: dehydrating agents (POCl3, SOCl2, P2O5) can convert thioamides to nitriles via imidoyl halide intermediates.
  • Reduction/Desulfurization to amines: Raney Ni can remove sulfur from thioamides to give amines under hydrogenative conditions (often via imine intermediates, then hydrolysis).
  • N-Functionalization at sulfur/nitrogen: alkylation at sulfur gives thioimidate salts; N-acylation and N-alkylation furnished under basic conditions.

• Applications:

  • Precursor for sulfur-containing heterocycles and ligands where a pyridyl donor is advantageous.
  • Analog tool compound for biochemical studies replacing nicotinamide with the thioamide isostere (research only; see Biological Roles).

• Practical considerations:

  • Maintain anhydrous conditions when generating reactive intermediates (imidoyl halides); quench cautiously.
  • The pyridine nitrogen can coordinate metals and influence reaction pathways—consider protonation (HBF4, HCl) to modulate reactivity.

Reaction Conditions

General literature guidance for common transformations of heteroaryl thioamides like thionicotinamide (parameters are indicative, not item specifications):

• Thiazole formation (Hantzsch-type):

  • Reagents: α-haloketone or α-haloester (1.0–1.2 eq), base (K2CO3, Et3N, or NaOAc, 1–2 eq).
  • Solvent: EtOH, MeOH, or MeCN.
  • Temperature/time: 25–80°C, 2–16 h.
  • Notes: Monitor by TLC/HPLC; base selection modulates S- vs N-attack.

• Conversion to nitrile:

  • Reagents: POCl3 or SOCl2 (3–6 eq) with catalytic DMF (Vilsmeier-type activation) or neat.
  • Solvent: DCM, toluene, or neat reagent.
  • Temperature/time: 0°C to reflux, 1–6 h.
  • Workup: cautious quench onto ice; neutralize acid; isolate nitrile after extraction.

• Formation of imidoyl chlorides/thioimidates:

  • Reagents: SOCl2 or (COCl)2, then alcohol/thiol/amine trapping.
  • Conditions: anhydrous, 0–25°C initial activation; subsequent substitution at 0–40°C.

• Oxidative desulfurization to amide:

  • Reagents: H2O2 (30%) with catalytic tungstate or peracid (mCPBA) in MeOH/MeCN.
  • Temperature/time: 0–25°C, 0.5–4 h.
  • Notes: Control equivalents to prevent over-oxidation of the pyridine.

• Raney Ni desulfurization (to amine under hydrogenation):

  • Reagents: Raney Ni (slurry), H2 (1–5 bar) or transfer hydrogenation.
  • Solvent: EtOH/MeOH or THF.
  • Temperature/time: RT–50°C, 2–12 h.
  • Caution: sulfur poisons catalysts; ensure adequate catalyst activity and gas handling.

Always perform small-scale optimization and consult primary literature for your specific substrate set.

Safety and Handling

• Item-specific hazard data (from Product Data):

  • Signal Word: Not specified for this item; refer to SDS.
  • H-Statements: Not specified for this item; refer to SDS.
  • GHS Classification: Not specified for this item; refer to SDS.
  • Pictograms: Not specified for this item; refer to SDS.

• General safety guidance for thioamides and pyridine derivatives (literature/general; not a substitute for SDS):

  • Likely hazards: may cause irritation to skin, eyes, and respiratory tract upon contact or inhalation. Thioamides can release malodorous sulfur species on decomposition.
  • PPE: wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Handle powders in a fume hood to minimize dust inhalation.
  • Incompatibilities: strong oxidizers (risk of exotherm/oxidation); strong acids/chlorinating agents (possible formation of reactive imidoyl halides); strong bases may induce decomposition or tautomerization.
  • Thermal decomposition: sulfur-containing compounds can generate SOx or H2S under severe heating; ensure adequate ventilation.
  • First aid (overview; defer to SDS):
    • 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 and easy to do.
    • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
  • Spill response: avoid dust generation; sweep up carefully, transfer to a suitable container for disposal; ventilate area.

Always review the Aladdin Scientific SDS for this SKU prior to use and follow institutional EHS protocols.

Solvent Selection

Thionicotinamide is a neutral, polarizable heteroaromatic thioamide. Solvent choice affects solubility, reaction rate, and selectivity.

• Polarity/miscibility (literature/general):

  • Highly soluble: DMSO, DMF, NMP
  • Moderate: acetonitrile, acetone, ethyl acetate, hot alcohols
  • Limited: water at ambient conditions; solubility can improve with co-solvent or slight base to form thioenolate-derived species (not generally recommended for storage)

• Selection by use case:

  • Analytical stock solutions: DMSO (anhydrous) affords stable, concentrated stocks; dilute into aqueous buffers with vigorous mixing.
  • Nucleophilic/electrophilic transformations at the thioamide: polar aprotics (DMF, DCM with additives, MeCN) often maximize rates and control.
  • Cyclizations to thiazoles/thiazolines (with α-haloketones/esters): EtOH, MeOH, or MeCN commonly used; base and temperature tuned to suppress side reactions.
  • Metal-catalyzed steps on the ring (e.g., N-oxidation or cross-coupling if suitably prefunctionalized): choose dry, degassed polar aprotics.

• Brief comparison (general):

  • DMSO vs DMF: DMSO gives superior solubility and thermal stability; DMF is easier to remove and compatible with many reagents. For moisture-sensitive reagents, acetonitrile provides lower coordinating ability at some loss of solubility.

• Practical tips:

  • Filter solutions before use to remove particulates; pre-warm to 30–40°C to aid dissolution. Avoid prolonged aqueous storage; prepare fresh working solutions.

Storage and Reconstitution

• Item-specific storage and shipping (from Product Data):

  • Storage Conditions: Store at -80°C.
  • Shipped In: Dry ice packs + Cold packs.

• Handling and in-use stability (general best practices for small-molecule solids):

  • Store in original, tightly closed container under dry, inert atmosphere if available. Allow vial to equilibrate to room temperature before opening to prevent condensation.
  • Protect from moisture and prolonged light exposure; thioamides can undergo slow oxidative changes.

• Solution preparation and storage (general guidance):

  • Reconstitution solvents: anhydrous DMSO or DMF for concentrated stocks; ethanol or acetonitrile for moderate concentrations.
  • Aliquoting: prepare single-use aliquots (e.g., 50–200 µL) to avoid repeated freeze–thaw. Store aliquots at -80°C in amber vials.
  • Stability: monitor solutions by HPLC or NMR if stored >1 week; discard if discoloration or precipitate forms after thawing.
  • Thawing: warm to room temperature and vortex to fully dissolve; avoid repeated freeze–thaw cycles.

• Shelf life: Not specified for this item; refer to CoA/Spec Sheet. Adhere to -80°C storage to maximize long-term integrity.

• Research Use Note: For research use only.

Structure and Identity

Thionicotinamide is the thioamide analogue of nicotinamide, featuring a pyridine ring (nicotinoyl position) bearing a carbothioamide (–C(=S)NH2) at the 3-position.

• Item-specific identifiers from Product Data:

  • CAS: 4621-66-3
  • SKU: T661279
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature identity (for reference; not item-specific specifications):

  • Synonyms: 3-pyridinecarbothioamide; thio-nicotinamide; nicotinamide thioamide analog
  • Molecular formula (literature): C6H6N2S
  • Molecular weight (literature): ~138.19 g/mol
  • Representative SMILES (literature): NC(=S)c1ccncc1 (3-carbothioamide on a pyridine ring)

• Structural features (general description):

  • Aromatic heteroaromatic core: a six-membered pyridine ring (one ring nitrogen).
  • One thioamide functional group: planar C(=S)–NH2 conjugated to the aromatic ring, capable of thione–thiol tautomerism in strongly donating environments.
  • No stereocenters; achiral compound.

• 2D description in words:

  • A pyridine ring with the ring nitrogen at position 1; at the 3-position relative to N, the ring carbon is bonded to a carbonyl sulfur (C=S) bearing an exocyclic primary amide nitrogen (–NH2). The thioamide is conjugated with the ring, increasing electron donation to the carbonyl carbon and enabling nucleophilic and electrophilic reaction manifolds characteristic of thioamides.

Synthetic Utility

Thionicotinamide combines a pyridinic nitrogen (Lewis basic site) with a conjugated thioamide (ambident nucleophile/electrophile), giving rise to rich synthetic behavior.

• Functional-group reactivity (literature/general):

  • Thioamide moiety:
    • Electrophilic activation (SOCl2, oxalyl chloride) → imidoyl halides → access to thioimidates, amidines, and nitriles.
    • Sulfur alkylation → thioimidate salts; subsequent nucleophilic substitutions.
    • Condensation with α-haloketones/esters → thiazoles/thiazolines (Hantzsch-type cyclizations).
    • Oxidative desulfurization → amide (via oxygen transfer) or further oxidation to sulfinyl/sulfonyl derivatives in related systems.
  • Pyridine ring:
    • Acts as a directing/chelating group in metal-catalyzed C–H functionalization (if compatible with thioamide).
    • Can be N-oxidized (mCPBA, H2O2/AcOH) to the N-oxide, adjusting electronic properties for downstream substitutions.

• Retrosynthetic value:

  • Serves as a masked imidoyl equivalent, enabling convergent assembly of amidines and heteroaryl thioethers.
  • The thioamide allows access to sulfur-containing heterocycles while preserving a pyridyl handle for coordination chemistry or further elaboration.

• Practical tips:

  • Control chemoselectivity by transiently protonating the pyridine nitrogen when activating the thioamide, limiting off-target N-acylation.
  • Consider protecting strategies (e.g., N-oxide formation) to tune ring electronics before cross-coupling on suitably halo-functionalized analogues.

Target Specificity

Not applicable to this product category. This item is a small-molecule research reagent, not an antibody, protein, or nucleic acid probe with defined biological target specificity in our catalog listing.

• Item-specific target/epitope/isotype data: Not specified for this item; refer to CoA/Spec Sheet if any target-binding characterization was performed in your application.