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.
Zertifikate (CoA, COO, BSE/TSE und Analyse-Diagramm)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemische und physikalische Eigenschaften
Molekulargewicht
171.620 g/mol
XLogP3
1.800
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Exact Mass
171.045 Da
Monoisotopic Mass
171.045 Da
Topological Polar Surface Area
22.100 Ų
Heavy Atom Count
11
Formal Charge
0
Complexity
110.000
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
Lösungsrechner
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Application Protocols
Not applicable
No validated bioassay or immunoassay protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block. Application conditions will be highly context-dependent on the synthetic route chosen.
Practical suggestion
For synthetic applications, refer to the Reaction Conditions, Reaction & Applications, and Synthetic Utility sections for starting points, and adapt to your specific substrates, catalysts, and scale.
Biological Roles
Applicability
This compound is a synthetic heteroaromatic building block with no known endogenous biological role.
General context (literature-based; not specific to this item)
Substituted pyridines are ubiquitous motifs in bioactive small molecules due to their tunable basicity and ability to engage in hydrogen bonding and cation–π interactions. Installing diverse substituents at the 2-position via SNAr or cross-coupling enables structure–activity relationship (SAR) exploration.
The 5-(ethoxymethyl) substituent can modulate physicochemical properties (e.g., lipophilicity, solubility, and metabolic soft spots at the benzylic position). Benzylic ethers are often sites for metabolic oxidation in microsomal systems, potentially leading to aldehydes or alcohols; such behavior is a design consideration in medicinal chemistry campaigns.
Pyridine nitrogen basicity (pKa of the conjugate acid typically ~5–6 for unsubstituted pyridine, literature) can be attenuated or enhanced by ring substitution; the 2-chloro is weakly deactivating, while an ether at C5 is mildly electron-donating through resonance/induction.
Note
Any discussion of bioactivity or ADME must be generated from experimental data for the specific analog of interest. No biological data are provided for this item; it is supplied strictly for research use only (per Product Data).
Buffer Applications
Not typically applicable
2-Chloro-5-(ethoxymethyl)pyridine is not used as a buffering agent. It lacks a conjugate acid/base pair with a pKa in a range commonly exploited for laboratory buffers, and it is intended as a synthetic building block.
Practical guidance
For aqueous handling (e.g., extractions or bioconjugation of derived products), standard buffer systems such as phosphate (pH 6–8), acetate (pH 4–5.5), or Tris (pH 7–9) should be selected based on the needs of the target molecule. This substrate itself is generally handled in organic media.
Recommendation
Refer instead to the sections on Reaction & Applications, Synthetic Utility, and Reaction Conditions for relevant, practical information for this compound class.
Green Alternatives
Perspective
As a heteroaryl building block, the “greenness” considerations center on reaction media, catalysts, and process design rather than replacing the substrate itself.
Greener choices around this substrate (literature guidance)
Solvent selection: Replace DMF/NMP with greener polar aprotics such as propylene carbonate, Cyrene, or dimethyl carbonate where compatible. For Suzuki couplings, aqueous ethanol or 2-MeTHF can often substitute for dioxane/THF.
Catalysis: Use highly active ligands/catalysts to reduce catalyst loading and enable lower temperatures (energy savings). Nickel catalysis may allow milder conditions for aryl chlorides.
Bases: Favor inorganic bases with lower EHS impact (K2CO3, K3PO4) over strong, hazardous bases when feasible.
Workup: Minimize halogenated solvent use (e.g., DCM) by adopting EtOAc/Heptane systems and aqueous biphasic extractions.
Illustrative comparison (general)
Polar aprotic solvent: DMF (effective, reproductive toxin) vs Cyrene (bio-based, lower hazard) — tradeoff: solubility and reactivity profiles differ; pilot trials recommended.
Ether solvent: THF (peroxide former, fossil-based) vs 2-MeTHF (bio-based, lower peroxide rate, easier phase splits) — tradeoff: different polarity; may affect rates/selectivity.
Dioxane vs CPME: Dioxane (carcinogenic concerns) vs CPME (safer profile, broad miscibility) — tradeoff: boiling point and catalyst solubility differences.
Process tips
Apply high-solids couplings or flow chemistry to reduce solvent volumes.
Recycle Pd/Ni catalysts where possible; scavenge metals in downstream steps to meet specifications.
Pharmaceutical Uses
Scope and limitations
No pharmacopeial monograph or excipient role is provided for this item. It is supplied for research use only and is best regarded as a synthetic intermediate/building block in medicinal chemistry and process development.
Literature-based context (non-clinical)
Substituted 2-chloropyridines are common starting points for constructing heteroaryl amines, ethers, thioethers, and C–C coupled products used in small-molecule discovery. The ethoxymethyl group at C5 provides a handle to tune lipophilicity and solid-state properties during lead optimization.
In process chemistry, aryl chlorides are attractive due to cost and availability; with appropriate ligands, they participate efficiently in Pd/Ni-catalyzed couplings, offering scalable routes to candidate drug intermediates.
Manufacturing considerations
Downstream purity requirements typically include control of residual palladium/nickel, aryl chloride residuals, and genotoxic impurities as per ICH guidelines for drug substance intermediates. If this compound is used in a route to a regulated substance, ensure appropriate specification setting and analytical method validation.
Note
No therapeutic/clinical claims are made or implied. Any use in pharmaceutical contexts should be limited to non-clinical research and development.
Physical Properties
Item-specific (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 values (for context; not item specifications)
Calculated molecular formula (from name): C8H10ClNO (literature deduction)
Calculated molecular weight: ~171.62 g/mol
Expected physical state: low-molecular-weight heteroaromatic; commonly encountered as a liquid or low-melting solid depending on purity and temperature (literature generalization for similar chloro-pyridines).
Volatility: moderate; 2-chloropyridines often have measurable vapor pressure—use in a fume hood.
Polarity/solubility (qualitative): anticipated good solubility in common organic solvents (e.g., dichloromethane, ethyl acetate, THF, acetonitrile) and limited solubility in water, in line with substituted pyridines (literature expectation).
Not provided for this specific item (consult CoA/Spec Sheet)
Boiling point, melting point
Density, refractive index
Water/peroxide/metal content limits
UV-Vis cutoff, pKa, logP/logD
Notes
Because this material is shipped on wet ice and recommended for argon storage at 2–8 °C (Product Data), plan handling to minimize headspace oxygen and moisture, and allow the container to equilibrate to room temperature before opening to prevent condensation.
Quality and Grades
Item-specific (Product 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)
In the absence of a stated grade, consult the CoA for assay, GC/HPLC area %, and impurity profile (e.g., isomeric pyridines, hydrolysis/oxidation products). For heteroaryl chlorides used in cross-coupling, trace metal content and halide identity can influence catalyst performance; review ICP/MS or related metal screening where available.
Low UV background is not usually critical for use as a building block, but if the compound is intended for use as a reference standard or in analytical method development, consider requesting chromatographic grade material with stated UV cutoffs and residual solvent limits.
Water content: If moisture sensitivity is a concern for the planned reaction (e.g., air/moisture-sensitive metalation), Karl Fischer water content can be decisive. If not specified, perform an in-house KF check upon receipt.
Stabilizer implications: None are listed for this item. If your process indicates instability (e.g., peroxide formation is not typical for this class, but benzylic ether oxidation could occur), store under argon as directed and maintain cold chain to preserve assay.
Batch-to-batch reproducibility: For scale-up or regulated environments, retain CoA, lot traceability, and any available spectral data (1H/13C NMR, LCMS, GCMS) to document identity and purity.
Reaction and Applications
Role in synthesis (general, literature-based)
Electrophilic handle: The 2-chloro substituent on a pyridine activated by ring nitrogen is a reliable site for nucleophilic aromatic substitution (SNAr) with amines, alkoxides, and thiolates to form 2-substituted pyridines.
Cross-coupling partner: Functions as an aryl (heteroaryl) chloride in Pd- or Ni-catalyzed couplings (e.g., Suzuki–Miyaura with boronic acids/esters, Buchwald–Hartwig amination, Negishi/Kumada/Stille for C–C formation), enabling rapid diversification at C2.
Benzylic ether manipulation: The 5-(ethoxymethyl) side chain can serve as a latent functionality—subject to oxidative transformations (e.g., benzylic oxidation to an aldehyde or acid under suitable conditions) or cleavage to unmask a hydroxymethyl substituent.
Applications and strategy
Medicinal chemistry: Heteroaryl chlorides like this are frequently used to build libraries by varying the C2 substituent while retaining a polarity-modulating ether at C5. The –CH2–OEt group can tune lipophilicity and solubility.
Materials/ligands: Substituted pyridines are precursors to N,N-chelating ligands; modifying C2 while preserving the ring nitrogen allows fine control of donor strength and sterics.
Practical tips
For SNAr, use strong bases (NaH, t-BuOK) to generate nucleophiles and polar aprotic solvents (DMF/DMSO); heating (80–120 °C) may be required depending on nucleophile hardness.
For Pd-catalyzed couplings, consider Buchwald ligands that accelerate aryl chloride activation (e.g., XPhos, SPhos, RuPhos). Control moisture and oxygen as per inert storage recommendations.
Monitor reactions by LCMS/HPLC; typical byproducts include dehalogenation and over-alkylation at benzylic positions under strongly basic conditions.
Reaction Conditions
General literature guidance (not item specifications)
Temperature: 60–120 °C depending on nucleophile strength.
Time: 2–24 h; monitor by LCMS.
Notes: Avoid over-alkylation at the benzylic –CH2–OEt under very strong basic conditions.
Buchwald–Hartwig amination (aryl chloride):
Catalyst: Pd2(dba)3 (0.5–2 mol% Pd) or Pd(OAc)2 with ligand (1–4 mol% ligand).
Ligands: XPhos, SPhos, RuPhos, BrettPhos; use bulky/electron-rich ligands for aryl chlorides.
Base: NaOtBu, K3PO4, or Cs2CO3.
Solvent: Toluene, dioxane, CPME, or 2-MeTHF.
Temperature: 60–110 °C; inert atmosphere.
Suzuki–Miyaura coupling:
Catalyst: Pd(PPh3)4 or Pd(dppf)Cl2 (0.5–2 mol% Pd), or precatalysts with Buchwald ligands.
Base: K2CO3, K3PO4, or Na2CO3 in aqueous-organic mixtures (dioxane/H2O, THF/H2O, 2-MeTHF/H2O).
Temperature: 50–100 °C.
Benzylic oxidation (–CH2–OEt):
Reagents: MnO2 (ambient to reflux in DCM/toluene), TEMPO/NaOCl (biphasic), or IBX/DMSO.
Caution: Control conditions to avoid ether cleavage or over-oxidation.
Workup/purification
Typical quench with water/brine; extract with EtOAc or MTBE. Remove Pd/Ni residues with scavengers (e.g., silica–thiol) and polish by silica gel chromatography. Maintain low temperature and inert handling consistent with the product’s argon storage guidance.
Safety and Handling
Item-specific (Product Data)
Storage: Store at 2–8 °C, argon charged.
Shipping: Shipped on wet ice.
GHS signal word/H-statements/pictograms: Not specified for this item; refer to SDS.
General safety guidance (literature/standard practice; defer to SDS for authoritative data)
Likely hazards for chloro-pyridines include irritation to skin/eyes/respiratory tract and toxicity if swallowed or inhaled. Avoid aerosol formation and direct contact. Use only in a chemical fume hood.
Personal protective equipment: lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles; consider using a face shield for bulk transfers.
Incompatibilities: Strong oxidizers and strong bases/acids may lead to decomposition or side reactions; avoid prolonged exposure to moisture/air if the product is purged with argon.
Handling under inert atmosphere: Given the argon-charged storage instruction, purge headspace with inert gas after each use. For transfers, use dry glassware and minimize exposure time with septum/syringe or Schlenk techniques when practical.
First aid (overview): In case of skin contact, wash with soap and water. For eye exposure, rinse cautiously with water for several minutes and seek medical attention. If inhaled, move to fresh air; if ingested, rinse mouth—do not induce vomiting; seek medical attention. Consult the SDS for detailed instructions.
Spill/cleanup: Absorb small spills with inert material (e.g., vermiculite), place in chemical waste. Prevent entry into drains. Dispose in accordance with local regulations.
Fire safety: Use CO2, dry chemical, or foam as appropriate for organics. Thermal decomposition may release irritant fumes (e.g., HCl, NOx)—firefighters should wear SCBA.
Solvent Selection
Applicability
This product is an organic building block, not a process solvent. Solvent selection here refers to dissolving it for reactions, workups, and analyses.
General solubility and polarity (literature-based expectations)
Polarity: Moderately polar heteroaromatic due to ring nitrogen; presence of a benzylic ether increases organic solvent compatibility.
Aqueous solubility: Expected to be low at neutral pH; modestly higher in acidic media where the pyridine can be protonated. For extractions, manipulate pH to partition between organic and aqueous phases.
Choosing a solvent by application
Nucleophilic aromatic substitution (SNAr): Polar aprotic solvents (DMF, DMSO, NMP) often accelerate reactions with amines/thiols/alkoxides at the 2-chloro position.
Cross-coupling (Suzuki/Buchwald–Hartwig): Aqueous-organic mixtures such as toluene/H2O, dioxane/H2O, or THF/H2O under basic conditions are common. MeCN or CPME can also be effective with suitable catalysts/ligands.
Analytical: For HPLC/UPLC, MeCN or MeOH with aqueous modifiers; ensure UV transparency if UV detection is used. For GC, DCM or ethyl acetate are typical sample solvents.
Practical tips
If crystallization is desired for purification, test EtOAc/hexane or toluene/hexane systems; the ether side chain may favor oiling out—seed as needed.
Given argon storage, pre-sparge high-oxygen-solubility solvents (e.g., toluene, DCM) with inert gas when preparing sensitive reaction solutions.
Storage and Reconstitution
Item-specific (Product Data)
Storage conditions: Store at 2–8 °C, argon charged.
Shipping: Shipped on wet ice.
Practical handling guidance
Upon receipt: Keep cold. Allow container to warm to ambient temperature before opening to minimize moisture condensation. Open under inert atmosphere if possible (glovebox or Schlenk line) to maintain the argon blanket.
In-use management: Reseal promptly after dispensing. If septum-capped, backfill with inert gas. For repeated use, consider aliquoting into dry, inert-gas-purged vials to limit headspace exposure.
Container: Use airtight, chemically compatible containers (e.g., amber glass) to limit light exposure and oxidative processes. Label with open date and number of freeze–thaw/temperature cycles.
Reconstitution
Not applicable: This product is supplied neat (no reconstitution buffer specified). If preparing stock solutions for reactions or analytics, use anhydrous, oxygen-free organic solvents appropriate to your application (e.g., DCM, THF, MeCN, DMF). Record solvent, concentration, and date of preparation.
Stability notes
No shelf-life data are provided. Maintain cold-chain storage and inert atmosphere as directed to preserve assay and limit benzylic oxidation or hydrolysis. For long-term projects, verify integrity periodically by GC/HPLC and NMR.
Disposal
Dispose of waste and contaminated materials according to institutional and local regulations for halogenated organic chemicals.
Structure and Identity
Item-specific (Product Data)
SKU: C729484
Product name: 2-Chloro-5-(ethoxymethyl)pyridine
CAS: 871829-50-4
CID: 19010916
InChIKey: 183759 (as provided)
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed information (general identification)
Expected molecular formula (from name): C8H10ClNO (literature deduction)
Calculated molecular weight: ~171.62 g/mol (literature/computed from formula)
Core scaffold: a substituted pyridine (six-membered aromatic ring with one ring nitrogen at position 1).
Substituents and regiochemistry: chlorine at the 2-position (ortho to the ring nitrogen) and an ethoxymethyl substituent [–CH2–O–CH2–CH3] at the 5-position (meta to the ring nitrogen).
Functional groups: heteroaromatic ring (pyridine), aryl chloride (activated by ring N for SNAr), and a benzylic ether side chain (ethoxymethyl).
2D description: The planar pyridine ring bears N at position 1; C2 carries Cl; C5 carries a –CH2–O–CH2–CH3 substituent extending out of plane. No stereocenters are present.
Notes
Structural features enable orthogonal reactivity: the 2-chloro is a typical handle for SNAr or Pd-catalyzed cross-coupling; the benzylic –CH2–OEt can be manipulated via oxidation or cleavage under appropriate conditions. Always verify final identity against the CoA/SDS for the supplied lot.
Synthetic Utility
Key reactive elements
Activated aryl chloride: The 2-chloro substituent on pyridine is predisposed to substitution due to the ring nitrogen’s –I effect, enabling SNAr with a variety of nucleophiles.
Benzylic ether: The 5-(ethoxymethyl) group can undergo transformations at the benzylic position (oxidation, halogenation) or at oxygen (cleavage, exchange) to access hydroxymethyl, aldehyde, or other functionalities.
SNAr amination: Reaction with primary/secondary amines (e.g., morpholine, anilines) in DMF/DMSO with base yields 2-aminated products.
Buchwald–Hartwig amination: Pd2(dba)3 or Pd(OAc)2 with bulky phosphines (XPhos, RuPhos) couples amines at C2 under mild conditions.
Suzuki–Miyaura: Cross-coupling with boronic acids/esters installs aryl/alkenyl groups at C2; bases like K2CO3/K3PO4 in dioxane/H2O or 2-MeTHF/H2O are common.
Benzylic oxidation: Conversion of –CH2–OEt to the corresponding aldehyde or acid can be achieved using TEMPO/bleach, MnO2, or chromium-free oxidants; conditions must be tuned to avoid ether cleavage.
Ether cleavage/functionalization: Acid-promoted cleavage can reveal a hydroxymethyl group; alternatively, convert the benzylic position into a leaving group (e.g., via halogenation) for further diversification.
Strategic value
Orthogonal handles at C2 and C5 enable two-direction diversification—rapidly building molecular libraries while maintaining a consistent heteroaromatic core.
Target Specificity
Not applicable
This product is a small-molecule building block, not a biological reagent with defined binding specificity (e.g., antibody, enzyme inhibitor standard). No antigen, epitope, clone, or species reactivity information is relevant or provided in the Product Data.
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