This compound belongs to the class of organic compounds known as 2-halopyridines. These are organic compounds containing a pyridine ring substituted at the 2-position by a halogen atom.
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 immunoassay or bioassay application protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule reagent. For synthetic use, refer to the Reaction Conditions and Synthetic Utility sections for practical guidance.
Biological Roles
Applicability: This compound is a synthetic halogenated pyridine used as a chemical building block. It has no established physiological role.
General context (literature):
Pyridine is a common heteroaromatic motif found in many bioactive molecules; however, 2-chloro-3-(trichloromethyl)pyridine itself is not known as a metabolite or signaling molecule.
The electron-withdrawing –CCl3 and aryl chloride functionalities are typically introduced for synthetic leverage (tunable reactivity, intermediate formation), not for intrinsic biological function.
Research use only: As stated in the Product Data, this material is for research use only and is not intended for diagnostic, therapeutic, or clinical applications.
Handling in biological experiments:
If used as a small-molecule tool or intermediate en route to bioactive compounds, ensure rigorous removal of residual halogenated reagents and catalysts prior to biological testing.
Solubilization for in vitro assays typically relies on DMSO stock solutions, followed by dilution into assay buffer with attention to final organic content; confirm compound stability under assay conditions as halogenated aromatics may adsorb to plastics or precipitate at low organic percentages.
No claims are made regarding pharmacology, toxicity thresholds, or ADME properties. Any biological experimentation should be preceded by thorough literature review and appropriate safety assessment.
Buffer Applications
Not typically applicable. 2-Chloro-3-(trichloromethyl)pyridine is a neutral, poorly water-soluble halogenated heteroaromatic used as a synthetic intermediate, not a buffering agent. It does not form classical conjugate acid/base pairs in the physiological pH range for controlled buffering capacity.
Practical note: If preparing aqueous assay solutions or extractions, use an appropriate water-miscible organic cosolvent (e.g., DMSO or MeCN) to aid dissolution before dilution into buffer. Verify solubility and stability at the intended pH to avoid precipitation or degradation.
Green Alternatives
Context: This product is a halogenated building block rather than a solvent or consumable. Green considerations focus on solvent choice, catalyst loading, and transformation pathways that minimize hazardous byproducts.
Greener solvent choices (general guidance):
Prefer 2-MeTHF, CPME, Me-THP ether, or toluene over chlorinated solvents when compatible with reactivity and workup.
For polar needs, MeCN or propylene carbonate can sometimes substitute for DMF/DMSO; water/EtOH cosolvent systems are occasionally viable for SNAr with phase-transfer catalysis.
Process considerations:
Cross-couplings: employ ligand-enabled aryl-chloride activation to avoid pre-activation to bromides/iodides; target low Pd/Ni loadings or explore iron/copper catalysis where feasible.
–CCl3 editing: choose methods that avoid stoichiometric tin or strong chlorinated waste. For example, Zn in greener acids/solvents or catalytic hydrogenation (if selectivity permits) can be preferable to SnCl2/HCl. Oxidative conversions to carboxylates using aqueous base/oxygen or peroxide systems can reduce chlorinated waste versus harsh chlorinating reagents.
Comparative trade-offs:
DCM/chloroform offer excellent solubility but pose environmental/health concerns; 2-MeTHF/CPME improve sustainability yet may require longer reaction times or different bases to achieve similar rates.
DMF is effective for SNAr but has regulatory scrutiny; MeCN or solvent blends (MeCN/toluene, 2-MeTHF/water) can be alternatives after optimization.
Waste minimization:
Segregate halogenated streams and employ adsorptive scavengers for residual Pd/Ni.
Design telescoped sequences (e.g., SNAr → oxidation) to limit isolations and solvent exchanges when stability permits.
Pharmaceutical Uses
Scope: For research use only. This compound is not an approved excipient or drug substance.
Role in pharmaceutical R&D (general):
Serves as a synthetic intermediate for the preparation of 2-substituted-3-functionalized pyridines, which are common motifs in medicinal chemistry campaigns (e.g., kinase, GPCR, and enzyme inhibitor scaffolds). The orthogonal handles (C2–Cl and C3–CCl3) allow rapid SAR exploration.
The –CCl3 group can be transformed into aldehydes, carboxylic acids, or reduced alkyls, enabling late-stage polarity and hydrogen-bonding modulations without changing the 2-substituent installed via SNAr/coupling.
Formulation/excipient status:
No pharmacopeial excipient status is known for this compound. It is generally incompatible with pharmaceutical excipient use due to reactivity and halogen content.
Process chemistry considerations:
If used in an API route as an intermediate, ensure robust purge of residual compound and chlorinated byproducts. Analytical controls could include GC/HPLC assay, residual solvent analysis, and targeted halide quantification.
Choice of coupling conditions at C2 should account for scale-up constraints (catalyst loading, ligand cost, halogenated waste), and transformations of –CCl3 should avoid tin reagents where possible for greener, regulatory-friendly processes.
No therapeutic or clinical claims are made or implied.
Physical Properties
Item-specific specs (from Product Data):
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/computed (for context; not product specifications):
Empirical formula (literature): C6H3Cl4N
Formula weight (literature): ~230.90 g/mol (C=12.011, H=1.008, N=14.007, Cl=35.45)
Physical state: Halogenated pyridines of this size often present as low-melting solids or high-boiling liquids; the exact state for this item is not specified here.
Solubility (qualitative, literature):
Water: expected low solubility due to multiple chlorines and limited H-bonding capacity.
Organic solvents: typically soluble in chlorinated solvents (DCM, chloroform), aromatics (toluene), ethers (THF), and polar aprotics (DMF, DMSO, MeCN).
Polarity/partitioning (literature expectation): relatively lipophilic aryl chloride bearing a polarizable heteroatom (pyridine N); logP anticipated in the moderate-to-high range for halopyridines of similar substitution.
Boiling point, melting point, density, refractive index, pKa/logP: Not specified for this item; refer to CoA/Spec Sheet. If needed for method development, consult primary databases (e.g., PubChem CID 606698) and confirm against the supplied CoA.
Practical notes:
The –CCl3 substituent and ring N significantly withdraw electron density, which can affect chromatographic retention (often longer on nonpolar phases) and UV absorbance (pyridine chromophore). Confirm exact values experimentally under your method conditions.
Quality and Grades
Item-specific quality data:
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.
Interpretation and guidance (general):
Without an explicit grade (e.g., AR, >98%, HPLC, anhydrous), users should rely on the accompanying CoA/Spec Sheet for assay, GC/HPLC purity, and impurity profile. For moisture-/air-sensitive handling (argon-charged storage), verify water content (Karl Fischer) and halide content as needed for sensitive transformations.
For cross-coupling and SNAr chemistry, trace metal and base-sensitive impurities can influence reactivity. If your application is catalytic (Pd, Ni, Cu), consider running a small test reaction and, if necessary, pre-purifying (short silica plug) to remove adventitious acids or colored impurities.
UV/LC considerations: If using for analytical method development, low-UV-absorbing solvents and high-purity reagents are typically preferred; confirm this material’s UV cutoff and impurity baselines if it will be used as a standard.
Batch-to-batch control: Check the CoA for identity confirmation (1H/13C NMR, MS, IR), residual solvents, and water content if applicable. If rigorous dryness is needed, briefly dry under vacuum with inert backfill, mindful of potential volatility.
If a specialized grade is required (e.g., anhydrous, metal-scavenged), contact us for availability or custom specifications.
Reaction and Applications
Overview: 2-Chloro-3-(trichloromethyl)pyridine is a bifunctional electrophile combining an activated aryl chloride (C2) with a strongly electron-withdrawing –CCl3 at C3. This enables orthogonal transformations for rapid diversification of the pyridine core.
Reactions at the 2-chloro position:
Nucleophilic aromatic substitution (SNAr): facilitated by the ring nitrogen and additional deactivation from –CCl3. N-, O-, S- and certain C-nucleophiles can be installed under basic conditions.
Cross-coupling: Suzuki–Miyaura, Buchwald–Hartwig amination, Negishi, Stille, and Kumada couplings from the 2-chloro handle to forge C–C or C–N bonds. Ligand/catalyst selection tailored to aryl chlorides (e.g., bulky/electron-rich phosphines or NHCs).
Transformations of the –CCl3 group (literature strategies):
Reduction to methyl or dichloromethyl: Zn/AcOH, SnCl2, or catalytic hydrogenolysis under controlled conditions.
Conversion to formyl (–CHO) or carboxyl (–CO2H): stepwise reduction/oxidation sequences or alkaline hydrolysis/oxidation protocols are reported for aryl–CCl3 systems; outcome depends on reagent and temperature.
Radical or carbene pathways: under strong basic or photochemical conditions, –CCl3 can engage in dehalogenative processes, enabling further functionalization.
Applications:
Synthesis of 2-substituted-3-functionalized pyridines relevant to agrochemical and materials leads.
Divergent libraries: install at C2 (via SNAr/coupling), then edit C3 (–CCl3) to tune polarity and electronics (CHO/CO2H/CH3), or vice versa.
Practical tips:
Maintain anhydrous, oxygen-free conditions (argon) for air-/base-sensitive catalytic systems and to preserve –CCl3 when desired.
For selectivity, perform C2 substitution first, then adjust –CCl3; many –CCl3 conversions tolerate the newly formed C2 bond.
Reaction Conditions
General literature guidance for aryl-chloride pyridines bearing strong EWGs; adapt to your substrate and scale. Values below are typical ranges, not specifications for this item.
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd(dppf)Cl2 (1–2 mol%).
Base/solvent: K2CO3 or Cs2CO3 in toluene/H2O or dioxane/H2O; 70–100 °C; 4–12 h.
Notes: For challenging partners, use more active ligands (SPhos, XPhos) and higher temperatures.
Editing –CCl3 (aryl–CCl3 systems):
Reduction to –CHCl2/–CH3: Zn (3–6 equiv) in AcOH or EtOH/AcOH, reflux, 2–8 h; or catalytic hydrogenation under mild pressures (substrate dependent).
Conversion to –CHO/–CO2H: stepwise hydrodechlorination/oxidation or alkaline hydrolysis/oxidation (e.g., NaOH, H2O2, 50–90 °C) have precedents; carefully optimize to avoid over-conversion.
Always confirm conditions on small scale and consult primary literature for aryl–CCl3 selectivity controls.
Safety and Handling
Item-specific hazards (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 and shipping (from Product Data):
Storage: Store at 2–8 °C, under argon (inert gas).
Shipping: Wet ice.
General safety guidance (literature/Good Laboratory Practice; not a substitute for the SDS):
Likely hazards: Halogenated heteroaromatics may cause skin/eye irritation and may be harmful if swallowed or inhaled. Avoid generation of vapors/aerosols. Handle in a fume hood.
Personal protective equipment: lab coat, safety glasses or face shield, and suitable chemical-resistant gloves (e.g., nitrile). Use splash protection when charging or transferring.
Handling: Minimize exposure to air/moisture per argon-storage guidance. Keep containers tightly closed. Purge headspace with inert gas after each use.
Incompatibilities: Strong nucleophiles/bases (can induce substitution/elimination), strong reducing agents (may reduce CCl3), and strong oxidizers. Avoid prolonged contact with reactive metals and finely divided metals.
Spill/first aid (overview):
Skin/eye contact: rinse with water for several minutes; remove contaminated clothing; seek medical attention according to SDS.
Inhalation: move to fresh air; monitor for respiratory irritation.
Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
Waste: Treat as halogenated organic waste. Use segregated containers consistent with institutional and regulatory requirements.
Always consult the product’s SDS for authoritative hazard classification, exposure limits, and emergency procedures.
Solvent Selection
Applicability: This compound is a halogenated heteroaromatic reagent, not a solvent. This section discusses solvent choices for dissolving it and for reactions where it participates.
Polarity class and miscibility (general):
Expected to dissolve well in moderately polar aprotic media (DCM, THF, MeCN, DMF, DMSO) and aromatic solvents (toluene). Sparingly soluble in water.
Choosing a solvent for reactivity:
SNAr or base-mediated substitutions at C2: DMF, DMSO, NMP, or MeCN are typical to solubilize inorganic bases (K2CO3, Cs2CO3, NaOtBu). THF can be used with soluble bases.
Pd-catalyzed couplings at C2 (Suzuki, Buchwald–Hartwig): toluene, dioxane, THF, or MeCN with aqueous base; DMF/ DMAc for higher-temperature protocols.
Transformations of the –CCl3 group (reduction, hydrolysis, formylation): select solvents compatible with the reagent system (e.g., acetic acid for Zn-mediated reductions; alcoholic or aqueous base for hydrolysis/oxidation).
Workup and isolation:
Halogenated aromatics often extract cleanly into nonpolar or moderately polar organics (EtOAc, MTBE, DCM). Avoid prolonged basic aqueous exposure if the objective is to retain the –CCl3 functionality.
Small comparison (general tendencies):
DCM: excellent solubility and volatility; limited base solubility.
MeCN: good balance of polarity and volatility; supports many catalytic couplings.
DMF/DMSO: strong solubilizers for salts; higher boiling, more challenging removal.
Toluene/dioxane: favored for Pd catalysis; lower polarity may limit SNAr rates without phase transfer or higher temperature.
Storage and Reconstitution
Item-specific storage (from Product Data):
Store at 2–8 °C, argon charged.
Shipped on wet ice.
Handling guidance:
This compound is supplied neat; no reconstitution is typically required. If a solution is desired for dosing or parallel synthesis, prepare under inert atmosphere in a dry, oxygen-free solvent (e.g., anhydrous DCM, THF, toluene, or MeCN). Use oven-dried glassware and inert-gas sparging.
After opening, promptly recap, purge the headspace with argon, and return to cold storage. Minimize freeze–thaw and temperature cycling.
Solution stability (general):
In dry, oxygen-free organic solvents at 0–5 °C, halogenated pyridine solutions are typically stable for days to weeks; however, verify by LC/GC before critical uses. Avoid prolonged exposure to strong bases or nucleophiles in stock solutions if preservation of the –CCl3 functionality is required.
Container compatibility:
Use fluoropolymer-lined caps; avoid reactive metals. Amber glass is recommended to limit photolysis of chlorinated moieties.
If exact shelf-life, permissible water content, or stabilizers are required, consult the CoA/Spec Sheet and the SDS. Research use only.
Structure and Identity
Brief overview: 2-Chloro-3-(trichloromethyl)pyridine is a halogenated heteroaromatic building block featuring an electron-withdrawing trichloromethyl group ortho to a ring nitrogen and a chloro leaving group at the 2-position.
Notes: Where specific structural identifiers (e.g., exact SMILES or standardized InChIKey) are required, please verify using the cited CAS or PubChem CID and refer to the product’s CoA/Spec Sheet.
Synthetic Utility
Functional handles and reactivity:
2-Chloro (aryl chloride):
Activated toward SNAr by the pyridine N and further deactivated ring electronics from the –CCl3 group. Enables displacement with amines, alkoxides/phenoxides, thiolates, and certain carbon nucleophiles.
Amenable to cross-coupling to forge C–C and C–N bonds. For aryl chlorides, electron-rich bulky phosphine or NHC ligands (e.g., XPhos, SPhos, tBuBrettPhos; IPr) typically enhance oxidative addition.
3-(Trichloromethyl):
A versatile latent functionality. Literature precedents allow conversion to:
Dichloromethyl (–CHCl2) or formyl (–CHO) by controlled reduction or hydrodechlorination sequences.
Carboxyl (–CO2H) or derivatives via oxidative or hydrolytic conditions on aryl–CCl3 systems.
Methyl (–CH3) under strong reducing conditions (e.g., Zn/AcOH, catalytic hydrogenation on suitably robust scaffolds).
Strategic applications:
Sequential diversification: install a substituent at C2 (SNAr/coupling), then tune the C3 functionality (–CCl3 → CHO/CO2H/CH3) to modulate acidity, polarity, and binding profiles in lead optimization.
Convergent routes: use the C2 chloride for cross-coupling with boronic acids/esters (Suzuki) or amines (Buchwald–Hartwig), keeping –CCl3 intact as a placeholder for late-stage oxidation/reduction.
Practical guidance:
Control moisture and oxygen to improve reproducibility in catalytic steps and to preserve –CCl3.
When targeting SNAr, choose bases that balance nucleophile generation with control of side reactions (e.g., E2 or over-reduction). Cs2CO3 and NaOtBu are common choices; phase-transfer catalysis can assist with poorer nucleophiles.
Monitor –CCl3 transformations carefully; small temperature or reagent stoichiometry changes can shift selectivity between –CHCl2, –CHO, –CO2H, and –CH3 endpoints.
Target Specificity
Not applicable. This product is a small-molecule chemical building block and has no antibody/biological target specificity parameters such as antigen, clone, isotype, or species reactivity.
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