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 pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
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
Not applicable. No validated bioassay or immunoassay protocols (WB, IHC, IF, FC) are associated with this small‑molecule reagent. For synthetic applications, refer to the Reaction & Applications and Reaction Conditions sections.
Biological Roles
This compound is a synthetic heteroaromatic thiol. It is not a natural metabolite and does not have established endogenous biological roles.
General biochemical considerations (literature/general)
The thiol group can engage in redox transformations (thiol/disulfide exchange) and covalent modification of electrophilic biomolecules in model studies, but such uses are typically confined to chemical biology experiments in vitro.
The pyridine ring confers basicity (protonation near physiological pH is limited; pKaH of pyridinium ~5.2 for unsubstituted pyridine) and potential metal binding; these features can be exploited in probe design or immobilization on metal surfaces.
Any biological or cellular applications should be designed and interpreted strictly as research use; consult institutional biosafety guidelines.
Buffer Applications
Not typically used as a buffering agent. As a heteroaromatic thiol, it lacks the conjugate acid/base pairs and pKa placements needed for conventional biological buffer systems.
Practical note
If used in aqueous systems (e.g., model thiol chemistry), select an appropriate external buffer (HEPES, phosphate, acetate) and account for thiol oxidation. Degas solutions and consider adding a reducing agent if compatible with the experiment.
Green Alternatives
Working with low‑molecular‑weight thiols often entails odor, air oxidation, and waste handling challenges. Consider process and reagent substitutions that reduce hazard and environmental footprint (literature/general guidance).
Strategy 1: Use protected thiol surrogates
Thioacetates or S‑thiocarbonates can be installed under milder/less odorous conditions and then hydrolyzed to unveil the free thiol late in the sequence, minimizing odor and oxidation losses.
Strategy 2: In situ generation and immediate consumption
Generate the thiolate under inert atmosphere and feed directly into the electrophile stream (flow chemistry) to reduce handling and headspace emissions.
Strategy 3: Solvent selection
Prefer greener solvents (2‑MeTHF, CPME, propylene carbonate, EtOAc) over chlorinated solvents where compatible with reactivity and separation.
Strategy 4: Oxidation control and recovery
Capture off‑odors using activated carbon/permanganate scrubbers; oxidize aqueous residues to disulfides (less odorous) before disposal per local regulations.
Comparison (illustrative; literature)
Free thiol vs thioacetate: free thiol is more reactive but odorous/air‑sensitive; thioacetate is less odorous, more stable, requires deprotection step (additional reagent/energy). Balance EHS with step economy.
Pharmaceutical Uses
No pharmacopeial or excipient status is specified for this item; refer to CoA/Spec Sheet. This compound is generally used as a synthetic building block or ligand in research.
Formulation/manufacturing context (general)
Free thiols are rarely used directly in dosage forms due to odor, instability (air oxidation), and reactivity. When incorporated into research prototypes, protection (e.g., thioesters/disulfides) or polymer attachment may be preferred to mitigate volatility and odor.
Regulatory note
For any cGMP or clinical manufacturing considerations, a different grade and full compendial characterization would be required; this product is labeled for research use only.
Physical Properties
Item-specific specifications
Appearance: 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/general properties (for reference; not item-specific specs)
Empirical formula (literature): C7H9NS
Formula weight (literature): ~139.22 g/mol
Expected physical state: liquid or low‑melting solid; many low‑MW thiols are liquids with strong odor (literature trend)
Acidity/basicity: thiol pKa typically ~10–11 in water; pyridine conjugate acid pKaH ~5.2 (unsubstituted pyridine; substitution can shift values)
Partitioning: moderate hydrophobicity anticipated; protonation of pyridine under acidic conditions can enhance aqueous solubility (literature reasoning)
Solubility profile (qualitative, literature): miscible with many organic solvents (EtOAc, alcohols, chlorinated solvents, ethers); sparing to moderate in water unless protonated
Practical notes (general)
Air sensitivity: thiols can oxidize to disulfides on exposure to air/oxidants; inert‑gas storage minimizes this.
Odor: characteristic thiol odor; handle in fume hood.
Quality and Grades
Item-specific
Grade: Reagent Grade (as provided). No additional assay, stabilizer, or impurity limits are specified for this item; refer to CoA/Spec Sheet.
What “Reagent Grade” typically signifies (general guidance)
Suitable for routine synthetic and analytical laboratory work where ultra‑trace impurities and ultra‑low UV background are not critical. Typical intent is reliability in general reactions and sample prep.
Not equivalent to HPLC/GC/ACS/Ph. Eur. grades unless explicitly stated. If applications require low nonvolatile residue, low UV cutoff, or metal‑trace control, verify via CoA or choose a higher grade.
Stabilizers and additives
None specified for this item; refer to CoA/Spec Sheet. In general, free thiols are sometimes supplied under inert gas to limit oxidation; this product is argon‑charged.
Batch documentation
For method development or regulated workflows, retain the specific batch CoA with assay, appearance, and relevant test results (e.g., identity by NMR/IR/GC‑MS).
Reaction and Applications
Nucleophilic substitution (literature)
Formation of thioethers via SN2 on primary alkyl halides/mesylates/tosylates. The pyridine N can modulate solubility and can be selectively protected by protonation if needed.
Typical setup: base (K2CO3/Cs2CO3) in DMF/MeCN at rt–60 °C; inert atmosphere to prevent oxidation. Workup with dilute acid can protonate pyridine, aiding separation.
Conjugate (Michael) addition (literature)
Addition to acrylates, acrylamides, maleimides, vinyl sulfones gives β‑thio carbonyls/sulfones. Base‑catalyzed (DBU/Et3N) or thiolate generated with NaH. Useful for appending a 2‑pyridylethyl thioether handle to acceptors.
Thiol–ene/thiol–yne “click” (literature)
Radical or photoinitiated addition to alkenes/alkynes (AIBN, peroxides, or UV with photoinitiators). Solvents: toluene, MeCN, or bulk polymerizations. The pyridyl group offers post‑functionalization or metal binding.
Thioester and thiocarbonyl formation (literature)
Activation of carboxylic acids (DCC, DIC, EDC/HOBt) affords thioesters; can serve as acyl transfer intermediates.
Coordination/chelation (literature)
Bidentate/ambident ligand behavior via pyridine N and thiolate S enables formation of metal complexes (e.g., late transition metals), useful in materials, sensing, or as catalytic precursors.
Oxidation chemistry (literature)
Controlled oxidation to the corresponding disulfide provides a protected, less odorous intermediate; reversible under reducing conditions (DTT/TCEP/NaBH4).
Practical notes
Maintain inert atmosphere, especially in base. Monitor for disulfide by GC/LC. Add base portionwise to avoid over‑deprotonation of acidic co‑substrates. Masking of pyridine (e.g., N‑oxide formation or protonation) can be leveraged when interference with catalysts is observed.
Reaction Conditions
General literature guidance for common transformations; optimize per substrate.
SN2 thioether formation
Solvent: DMF, MeCN, or acetone (dry). Base: K2CO3/Cs2CO3 (2–3 equiv) or NaH (1.1–1.5 equiv) for hindered electrophiles.
Temperature: rt to 60 °C; time: 2–16 h. Inert atmosphere recommended. Typical isolated yields for unhindered primary halides: 70–95% (literature reports across analogs).
Michael addition to acrylates/maleimides
Solvent: MeCN, THF, or MeOH; Base: Et3N/DBU or catalytic TMEDA. rt to 40 °C, 1–6 h. Often near‑quantitative conversions under mild conditions.
Thiol–ene click
Initiation: AIBN (thermal, 60–80 °C) or photoinitiators (365–405 nm). Solvents: toluene, MeCN, bulk polymerization. Typical times: 0.5–4 h.
Thioester formation (carbodiimide coupling)
Reagents: DCC or DIC with catalytic DMAP; solvent: DCM/DMF; 0–25 °C, 1–12 h. Filter dicyclohexylurea byproduct where applicable.
Oxidation to disulfide
Conditions: I2, air/O2 with base, or H2O2 (careful control). Monitor to avoid over‑oxidation to sulfinic/sulfonic acids.
Practical controls
Degas solvents; backfill with argon. If pyridine coordination inhibits certain catalysts, transient protonation (e.g., HBF4·Et2O, then adjust pH) can suppress binding during key steps.
Safety and Handling
GHS/SDS
Signal word, H‑statements, pictograms, and classification: Not specified for this item; refer to SDS for authoritative information.
General hazard profile (literature/general for low‑MW thiols and pyridyl thiols)
May cause skin/eye/respiratory irritation; strong odor typical of thiols. Avoid inhalation and contact; use in a certified fume hood.
Thiols can oxidize to disulfides generating heat; avoid strong oxidizers. Some thiols may form malodorous, persistent residues.
PPE and engineering controls
Wear lab coat, safety goggles/face shield, and appropriate chemical‑resistant gloves (e.g., nitrile). Employ local exhaust ventilation or fume hood.
Incompatibilities and reactivity
Avoid: strong oxidizers (peroxides, hypochlorites), strong acids/bases (uncontrolled reactions), and soft‑metal salts that may form complexes.
Metals: copper and silver can catalyze thiol oxidation and cause surface staining.
First‑aid overview (general)
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye contact: rinse with water for ≥15 minutes; remove contaminated clothing; seek medical advice.
Ingestion: rinse mouth; do not induce vomiting; obtain medical attention.
Storage and handling practices
Follow item-specific guidance: store at 2–8 °C under argon; keep tightly closed; minimize headspace; dispense with inert‑gas backfill. Protect from light and air to reduce disulfide formation. Consult SDS before use.
Solvent Selection
As a heteroaromatic thiol reagent (not a solvent), solvent choice focuses on maximizing nucleophilicity, controlling odor/volatility, and solubility of all reactants.
Good solubility in common organics: THF, Et2O, MeCN, DMF/DMSO, alcohols, toluene, chlorinated solvents. Limited water solubility in neutral media; increases in acidic media due to pyridinium formation.
For SN2 and Michael additions, polar aprotic solvents (DMF, DMSO, MeCN) enhance thiolate nucleophilicity. For radical thiol–ene reactions, nonpolar (toluene) to moderately polar (acetone) media are common.
Choosing conditions
Base‑promoted reactions: Use dry polar aprotics with non‑nucleophilic base (e.g., K2CO3, Cs2CO3, DBU) to generate the thiolate in situ.
Metal‑mediated couplings/ligations: Consider coordinating solvents (MeCN) or weakly coordinating media (toluene, EtOAc) depending on catalyst tolerance to pyridine N.
Avoid strongly oxidizing media and prolonged exposure to air; add antioxidants or perform under inert gas when feasible.
Practical tips
Degas solvent and maintain inert atmosphere to curb disulfide formation.
If thiolate precipitation occurs with inorganic bases, switch to phase‑transfer conditions or more polar solvent.
Storage and Reconstitution
Item-specific storage guidance
Store at 2–8 °C under argon (as provided). Shipments are on wet ice. Keep container tightly closed to limit air ingress and oxidation.
General handling
Minimize headspace and air exposure; backfill with argon or nitrogen after each use. Use septum‑cap vials for repeated dispensing. If solidification occurs at low temperature, warm gently to ambient and mix thoroughly under inert gas.
Stability
Free thiols can oxidize to disulfides upon air/light exposure; maintain inert atmosphere and consider storing in amber containers. Do not add stabilizers unless validated for your use; none are specified for this item.
Solution preparation (general)
Prepare solutions in dry, oxygen‑free solvent immediately before use. For stock solutions in DMF/MeCN, degas and store under inert gas at 2–8 °C; use within a few days, monitoring for disulfide formation by LC/GC.
Disposal
Collect thiol‑containing waste separately due to odor and potential reactivity. Oxidation to disulfides prior to disposal can reduce odor; follow institutional and local regulations.
Structure and Identity
Short description: 2‑pyridylethylmercaptan is a bifunctional heteroaromatic thiol featuring a pyridine ring (2‑pyridyl) connected through an ethylene spacer to a terminal thiol (–SH). This motif enables both Lewis basic (pyridine N) and soft‑nucleophilic/ligating (thiol/thiolate) behavior.
Item-specific (from Product Data)
SKU: P478817
Product name: 2‑pyridylethylmercaptan
CAS: 2044‑28‑2
Grade/Purity: Reagent Grade
Storage: Store at 2–8 °C, Argon charged; shipped on wet ice
InChIKey (as provided): 240377
Research Use: For research use only
Literature/Computed identity (general reference values; not item-specific specs)
Example SMILES: n1ccccc1CCS (aromatic pyridine attached at C2 via –CH2–CH2–SH) (literature)
2D structural description (general chemistry)
A six‑membered aromatic pyridine ring bearing nitrogen at position 1; at the adjacent 2‑position, an ethylene chain (–CH2–CH2–) terminates in a thiol group (–SH). No stereocenters are present; the molecule is achiral. The electron pair on pyridine N and the polarizable sulfur confer ambident coordination to metals and diverse reactivity in synthesis.
Synthetic Utility
Functional group leverage
Soft nucleophile: S–H deprotonation affords a thiolate that reacts readily with primary alkyl electrophiles to form thioethers.
Bifunctional handle: the pyridine nitrogen enables secondary coordination, directional effects, or subsequent N‑functionalization (N‑oxide, N‑alkylation) orthogonal to S‑chemistry.
Named/typical transformations (literature)
SN2 thioetherification of alkyl halides/tosylates; Mitsunobu‑type conversion of alcohols to thioethers via inversion.
Michael additions to α,β‑unsaturated carbonyls; thiol–ene click additions to terminal alkenes (AIBN/UV initiated).
Formation of thioesters using carbodiimide coupling (DCC/DIC/EDC), setting up for native‑like chemical ligations or acyl transfers in small‑molecule synthesis.
Oxidation to disulfide “protecting group” and subsequent reduction (DTT/TCEP/NaBH4) for redox‑switchable systems.
Coordination chemistry and materials (literature)
Anchoring to metal surfaces (Au, Ag) via thiolate with the pyridyl group providing additional interaction or functionality; potential in monolayer or sensor construction.
Retrosynthetic role
As a masked sulfur nucleophile enabling late‑stage introduction of a 2‑pyridylethyl thioether, which can impart metal affinity or adjust electronics of target scaffolds.
Target Specificity
Not applicable. This product is a small‑molecule reagent and has no antibody/biologic target attributes. No antigen, epitope, species reactivity, clone, or isotype information applies.
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