This compound belongs to the class of organic compounds known as nitroaromatic compounds. These are c-nitro compounds where the nitro group is C-substituted with an aromatic 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.
Certificati (CoA, COO, BSE/TSE e tabella di analisi)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Proprietà chimiche e fisiche
Peso molecolare
235.060 g/mol
XLogP3
1.300
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
0
Exact Mass
233.91 Da
Monoisotopic Mass
233.91 Da
Topological Polar Surface Area
89.900 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
279.000
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
Calcolatori di soluzioni
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Recensioni
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Application Protocols
Not applicable. No tested bioassay or immunoassay protocols (WB, IHC, IF, FC, etc.) are provided for this small-molecule building block. For synthetic procedures, see the Reaction Conditions and Synthetic Utility sections for general, literature-based guidance.
Biological Roles
This product is intended strictly for research use (per Product Data). No biological role or activity is specified for this item; the following are general, literature-based considerations for related chemotypes and must not be construed as product-specific claims.
Heteroaryl thiols such as 2-mercaptopyridines are known to chelate transition metals via N,S-coordination, a feature leveraged in probe design and materials coordination chemistry (literature). The presence of a nitro group can modulate electronic properties and redox behavior.
Potential utility in chemical biology (general):
As a scaffold for installing reporter groups via the thiol (S-alkylation) while retaining a heteroaromatic recognition element.
As a precursor to amine-functionalized analogs after nitro reduction, enabling conjugation to biomolecules through amide or urea linkages.
As part of affinity ligands or resins where pyridine N and sulfur serve as binding motifs for soft metal centers.
Cautions:
Many nitroaromatics and thiols exhibit cytotoxic or irritating properties; handle exclusively in vitro/in chemico. No suitability for in vivo use is implied.
No specific pathways, targets, or bioactivities are defined for this catalog item. For biological testing, users should establish appropriate controls, dose–response ranges, and analytical verification of identity/purity with their own methods.
Buffer Applications
This compound is not a buffering reagent and is not typically used to prepare biological buffers or electrophoresis running solutions.
If dissolution in aqueous media is needed for assays, consider:
Preparing stock solutions in DMSO or acetonitrile, then diluting into buffer with vigorous mixing while keeping final organic content low (≤1–2%) to avoid precipitation.
Generating the thiolate salt with a compatible base for temporary aqueous solubility, noting increased oxidation risk and potential assay interference.
Sustainability considerations arise primarily from solvent and catalyst choices; the substrate itself is fixed. Greener process design can substantially reduce EHS impact.
Solvent substitution (literature/guidance):
Replace DMF/DMAc/NMP with 2-MeTHF, CPME, propylene carbonate, Me-THF/H2O biphasic, or EtOAc when solubility and reaction kinetics permit.
Use aqueous ethanol or iPrOH for catalytic hydrogenations (nitro → amine) when compatible with the thiol.
Employ dioxane alternatives (e.g., 2-MeTHF, tert-amyl alcohol) in Suzuki couplings.
Catalyst and base:
Use ligand-optimized low-Pd loadings or Ni catalysis for cross-coupling to reduce precious metal usage.
Solid-supported catalysts and recyclable Pd on benign supports can simplify metal removal.
Bases with lower EHS footprint (K2CO3, Na2CO3) in water-containing media are preferred over strong inorganic bases when feasible.
Workup/waste minimization:
Telescoping protection–coupling–deprotection sequences to avoid isolating air-sensitive thiols.
Use microencapsulated oxidants (or air) for disulfide formations to limit halogenated waste.
Comparison snapshot (general):
Conventional: DMF, dioxane, high Pd loading, halogenated extraction (DCM).
Greener: 2-MeTHF or CPME, aqueous ethanol/EtOAc systems, low/ppm-level Pd or Ni, non-chlorinated extractions (EtOAc/MTBE).
Trade-offs: Greener solvents may reduce solubility; mild bases can slow couplings. Conduct small DoE screens to balance E-factor and throughput without compromising chemoselectivity around the thiol/nitro groups.
Pharmaceutical Uses
No pharmacopeial grade or excipient role is specified for this item. It is offered for research use only (per Product Data) and is best regarded as a synthetic intermediate/building block.
General, non-item-specific context:
Substituted pyridines are common intermediates in small-molecule discovery and process chemistry. The orthogonal handles (Br, NO2, SH) enable late-stage diversification for SAR.
After nitro-to-amine reduction, the scaffold can be elaborated into amide/urea derivatives typical of medicinal chemistry libraries.
The thiol can be protected or converted to thioethers as sulfur-containing motifs are prevalent in drug-like space.
Compliance note: No therapeutic, diagnostic, or clinical application is implied. This material is not an API, nor is any pharmacopeial monograph indicated. For GMP or regulatory applications, obtain appropriate grades and documentation.
Physical Properties
Item-specific physicochemical specifications (bp/mp, density, solubility, etc.) are not provided in the Product Data. Do not treat the following as specifications; these are literature/general expectations for this scaffold to aid planning only.
Molecular formula: C5H3BrN2O2S (computed from name)
Molecular weight: ~235.06 g/mol (computed)
Physical state: typically a crystalline solid for comparable substituted pyridine thiols (literature, indicative).
Acid–base: thiol pKa for related 2-mercaptopyridines ~4–7 depending on substitution; nitro and ring N further acidify the thiol (literature trend).
Lipophilicity: presence of Br and nitro increases polarizability; expected moderate logP; exact value not established here (literature expectation).
Solubility profile (qualitative, literature):
Good: DMSO, DMF, NMP, acetone, acetonitrile.
Moderate: ethyl acetate, alcohols (MeOH/EtOH) depending on salt/neutral form.
Low: alkanes; limited in water unless deprotonated to thiolate.
UV–vis: pyridine/nitro chromophores absorb in UV; exact ε/λmax not established (literature expectation).
Not provided for this item; refer to CoA/Spec Sheet: melting point, boiling point, density, refractive index, water content, residual metals, stabilizers, and any chromatographic cutoffs.
Always confirm solubility and stability experimentally at small scale before preparative work.
Quality and Grades
Item-specific status:
Grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Storage: Room temperature (per Product Data). Shipped under normal conditions.
How to interpret common grades for heteroaromatic building blocks (general guidance):
Research grade: Suitable for routine synthesis and screening; may have broader impurity limits.
95% or >98% purity (when specified): Facilitates reproducible cross-couplings and downstream transformations; reduces byproduct formation.
Low-residual-metal or “catalyst-screened” variants: Beneficial for sensitive medicinal chemistry workflows and analytical clarity.
Typical QC elements you may find on the CoA (general):
Identity confirmation: 1H/13C NMR, HRMS/ESI-MS, IR; sometimes HPLC purity assay with UV traces.
Residual solvents and water: Karl Fischer, GC headspace.
Inorganic halide/acid content, and assay by qNMR or HPLC.
Stabilizers/additives:
None are indicated in the Product Data. If present, stabilizer identity and level would be listed on the CoA; otherwise, assume neat solid. Absence/presence of antioxidants can affect thiol oxidation rate.
For regulated or analytical applications, request the current CoA/specification sheet for definitive limits and test methods.
Reaction and Applications
With three orthogonal handles on a pyridine core, 5-bromo-3-nitropyridine-2-thiol is a versatile building block for heteroaromatic diversification.
Aryl bromide at C-5:
Cross-couplings: Suzuki–Miyaura (to aryl/heteroaryl/alkenyl), Stille, Negishi, and Kumada couplings to elaborate the 5-position. Use standard Pd(0/II) systems; the ring N and nitro group can modulate oxidative addition rates.
Metal–halogen exchange/Lithiation: Enables further functionalization (formylation, borylation), with careful control to avoid thiol/NO2 side reactions.
Thiol at C-2:
S-Alkylation and S-arylation: Generate thioethers; copper- or palladium-mediated couplings form C–S bonds. Base-promoted alkylation (e.g., with RX) affords sulfides.
Disulfide formation/oxidation: Controlled oxidation (I2, air, DMSO) to disulfides; subsequent transformations or use as ligands.
Protection: Convert to thioesters or thioethers if the free thiol interferes with metal catalysis.
Nitro at C-3:
Reductive transformations: Reduce to an aniline (Pd/C–H2, Fe/AcOH, SnCl2/HCl), unlocking diazotization, acylation, or intramolecular cyclizations.
Nucleophilic aromatic substitution (SNAr): Nitro and ring N increase ring activation; nucleophiles may substitute at positions activated by the pyridine N (reaction site control should be validated experimentally).
Multistep design:
Typical sequences include (i) protect/derivatize thiol, (ii) cross-couple at C-5, (iii) reduce/functionalize the nitro. Order can be inverted depending on catalyst tolerance.
Applications: Synthesis of sulfur-containing heteroaryl intermediates, chelating ligands, and medicinal chemistry scaffolds where orthogonal diversification is desired.
Handle under inert atmosphere when free thiol reactivity or oxidation is a concern; employ freshly degassed solvents and base drying where applicable.
Reaction Conditions
The following are literature-style general conditions for analogous substrates. They are not product specifications; optimize for your system.
Base: K2CO3 or Cs2CO3 (2–3 equiv), often in H2O or 2 M aq. solution.
Solvent: 1,4-dioxane/H2O (3:1), 2-MeTHF/H2O, or toluene/H2O; 60–90°C, 2–12 h.
Notes: Protect/temporarily mask the thiol if catalyst inhibition is observed (e.g., S-benzyl protection). Degas thoroughly.
S-Alkylation (thiol → thioether):
Base: K2CO3, Cs2CO3, or NaH (0.5–1.0 equiv depending on RX).
Electrophile: Primary alkyl halides or activated secondary halides (1.1–1.5 equiv).
Solvent/Temp: Dry DMF or MeCN, 0–25°C, 1–4 h.
Tip: Minimize air exposure; antioxidant trace (e.g., BHT) can suppress oxidation if compatible.
Nitro reduction (to aniline):
Catalytic hydrogenation: Pd/C (5–10 wt%), H2 (1–3 bar), EtOH or iPrOH, rt–40°C, 2–6 h.
Metal/acid: Fe powder (3–5 equiv) in AcOH or Fe/NH4Cl in EtOH/H2O, 50–80°C.
Chemoselectivity: Monitor to avoid over-reduction of other functionalities; thiol may require protection to prevent catalyst poisoning.
Disulfide formation:
Reagents: I2 (0.5 equiv), air/O2, or mild oxidants (DMSO) in MeOH/CH2Cl2, rt.
Yields for these transformations typically range 60–90% in the literature for well-optimized systems; actual outcomes depend on substrate substitutions, protection strategy, and catalyst choice.
Safety and Handling
Item-specific hazard details 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/pictograms: Not specified for this item; refer to SDS.
Storage conditions: Room temperature (per Product Data).
Shipped in: Normal (per Product Data).
General safety considerations for nitro- and halo-substituted pyridine thiols (literature/good practice; not a substitute for the SDS):
Hazards: May cause skin/eye irritation; harmful if swallowed or inhaled. Thiols often have strong odor and can cause sensitization in some individuals. Nitroaromatics can be harmful; avoid prolonged exposure.
PPE: Lab coat, nitrile gloves, splash goggles; handle powders in a fume hood to minimize inhalation and odor.
Incompatibilities: Strong oxidizers (thiol → disulfide or sulfonyl derivatives), strong bases/acids (can promote decomposition or undesired reactions), and soft metal salts (thiolates complex strongly with metals).
Stability: Aromatic thiols can slowly oxidize to disulfides on air exposure; limit air/light exposure and keep containers tightly closed. If high thiol integrity is critical, work under inert atmosphere and use freshly opened material.
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; obtain medical advice if irritation continues.
Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
Always consult the product-specific SDS for authoritative hazard, response, and disposal guidance.
Solvent Selection
This compound is a polar, multifunctional aromatic solid. Solvent choice should balance solubility, reaction compatibility (thiol, nitro, aryl bromide), and downstream handling.
Polarity/miscibility (literature expectations):
Polar aprotic solvents (DMSO, DMF, NMP, acetonitrile) generally offer the highest solubility due to the pyridine N and nitro group.
Moderately polar organics (ethyl acetate, acetone, 2-MeTHF) may dissolve it at useful concentrations for reactions or chromatography.
Aqueous solubility is limited in the neutral thiol form; deprotonation to thiolate (pH > pKa) increases water miscibility, albeit with oxidation risk.
Practical choices by task:
Cross-coupling at C-5 (Br): 1,4-dioxane/H2O, toluene, 2-MeTHF, or CPME; add a small amount of polar cosolvent (DMF) if needed to dissolve substrate.
Thiol alkylation/acylation: Dry DMF, MeCN, or acetone with a non-nucleophilic base (e.g., K2CO3, Cs2CO3) to minimize side reactions.
Nitro reduction: Alcoholic solvents (EtOH, iPrOH) or EtOAc under hydrogenation; for chemoselective reductions, consider MeOH/THF blends.
2-MeTHF/CPME: greener, easy separations; may require heating or co-solvent.
Acetonitrile: good balance of polarity and volatility; generally compatible with bases and Pd catalysis.
Confirm solvent compatibility with your specific catalysts/reagents and evaluate stability of the thiol toward oxidation in chosen media.
Storage and Reconstitution
Item-specific storage and shipping:
Storage conditions: Room temperature (per Product Data).
Shipped in: Normal conditions (per Product Data).
Research Use: For research use only.
General handling guidance for aromatic thiols (literature/best practice):
Keep container tightly closed in a dry place; store under inert gas (N2/Ar) if possible to minimize air oxidation to disulfides.
Protect from prolonged exposure to light and moisture; use a desiccator. Open only in a fume hood due to potential thiol odor.
Reconstitution/stock solutions (guidance; not a specification):
Prepare concentrated stocks in dry DMSO, DMF, or acetonitrile (e.g., 10–100 mM) depending on intended use.
Filter through a PTFE syringe filter if particulates are present. For moisture-sensitive work, pre-dry solvents and glassware.
For aqueous assays, dilute organic stocks into buffer with vigorous mixing; keep final organic content low (≤1–2%). Avoid strong base unless thiolate formation is desired.
Stability notes:
Monitor for discoloration or odor changes indicative of oxidation; if necessary, assay by HPLC or 1H NMR to confirm thiol integrity.
If disulfide forms during storage and the free thiol is required, reduce with DTT/TCEP (in suitable solvent system) or with catalytic thiol–disulfide exchange under inert conditions.
Refer to the product’s CoA/SDS for any additional, item-specific storage precautions.
Structure and Identity
A multifunctional heteroaromatic building block combining a pyridine core with bromo, nitro, and thiol functionalities.
Item-specific identifiers (from Product Data):
SKU: B187736
Product Name: 5-Bromo-3-nitropyridine-2-thiol
CAS: 886372-86-7
InChIKey: 438213 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity (for general reference; not item specifications):
Common name interpretation: pyridine ring substituted with Br at C-5, NO2 at C-3, and –SH at C-2 (adjacent to ring N).
Functional groups: aromatic heterocycle (pyridine), aryl bromide, nitro group (strongly electron-withdrawing), aromatic thiol (mercapto). No stereocenters.
Molecular formula (computed from the name): C5H3BrN2O2S (literature)
Note: Where exact identifiers are not provided in Product Data, consult the product CoA/Spec Sheet for definitive structural metadata.
Synthetic Utility
Key functional elements confer broad versatility in synthesis:
Functional group portfolio:
Aryl bromide (C-5): ideal for Pd/Ni-catalyzed cross-couplings to install aryl, heteroaryl, vinyl, or alkyl fragments.
Nitro group (C-3): convertible handle to an aniline; serves as a strong deactivator directing reactivity and can participate in Meisenheimer intermediates under SNAr conditions.
Thiol (C-2): nucleophilic sulfur for S-alkylation/arylation, disulfide assembly, and metal-binding site; can be protected as thioethers or thioesters.
Orthogonality and sequencing:
Typical approach protects/derivatizes the thiol first (e.g., as a thioether) to prevent catalyst poisoning, then performs cross-coupling at C-5, followed by nitro reduction and further N-functionalization.
Alternatively, conduct nitro reduction first with catalyst systems tolerant to thiols or after transient thiol protection.
Retrosynthetic value:
Enables rapid assembly of N,S-bidentate ligands, bicyclic heteroaromatics via intramolecular cyclizations, and libraries where electronic tuning through the nitro/amine switch is critical.
Selectivity considerations:
The ring nitrogen and nitro group modulate oxidative addition rates; electron-poor aryl bromides often couple efficiently under mild conditions.
Free thiol can bind Pd/Ni; use catalyst/ligand excess or temporary protection to maintain activity.
Purification:
Avoid prolonged exposure to basic alumina/silica which can promote oxidation; include 0.1–1% TEA in eluent or use neutral silica. Store fractions under inert gas when possible.
Target Specificity
Not applicable. This product is a small-molecule building block and is not an antibody, enzyme, or affinity reagent. No target specificity, clone, isotype, antigen, or species reactivity is defined in the Product Data.
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