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.
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
141.140 g/mol
XLogP3
0.500
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
141.059 Da
Monoisotopic Mass
141.059 Da
Topological Polar Surface Area
33.100 Ų
Heavy Atom Count
10
Formal Charge
0
Complexity
110.000
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
1
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
The total count of all stereochemical bonds
0
Covalently-Bonded Unit Count
1
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Recensioni
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Application Protocols
No application protocols are specified for this catalog item beyond its use as a research chemical intermediate. There are no tested bioassay protocols (e.g., WB, IHC, IF, FC) associated with this product.
For synthetic use, consider the guidance in the “Reaction Conditions” tab for starting points and adjust to your substrate, equipment, and safety constraints.
Biological Roles
This product is provided strictly for research and laboratory use. No biological role or function is assigned for this specific synthetic building block in vivo.
General context (informational only):
Heteroaromatic alcohols like 1-(pyridyl)ethanols are common intermediates in discovery chemistry and may be used to access ketones, ethers, or amines for structure–activity relationship (SAR) studies.
The pyridine ring is ubiquitous in bioactive small molecules due to its tunable basicity and hydrogen-bonding capabilities; however, the presence of a 3-fluoro substituent and benzylic alcohol here is primarily of synthetic interest, not as a known metabolite or cofactor.
No endogenous metabolic role is expected; if incorporated into larger molecules, the benzylic alcohol could be a site for metabolic oxidation (to the corresponding ketone) in typical xenobiotic pathways—this is general chemistry knowledge, not a claim for this specific product.
For any work involving biological systems, ensure appropriate safety assessments and controls. Refer to the item’s SDS and institutional approvals. No clinical, diagnostic, or therapeutic uses are implied.
Buffer Applications
Not typically applicable. 1-(3-fluoro-2-pyridyl)ethanol is a synthetic organic building block, not a buffering agent. It does not form a defined, stable buffer system in aqueous media across a useful pH range.
Practical note: The pyridine nitrogen can be protonated (pKa of pyridinium ~5 for pyridine, literature), which may influence solubility and extraction during workup, but this is not employed as a laboratory buffer system. For aqueous-phase work, choose established buffers (e.g., phosphate, acetate, TRIS) appropriate to your pH/ionic strength requirements.
Green Alternatives
This compound is a synthetic building block rather than a process solvent or reagent; “greener alternatives” therefore focus on selecting milder and more sustainable conditions when using it in synthesis.
Greener oxidation to ketone:
Choose catalytic TEMPO/bleach (NaOCl, buffered pH ~8–9, biphasic) or Oxone-based systems over stoichiometric chromium reagents.
Employ DMSO/carbodiimide or catalytic IBX/Dess–Martin alternatives with careful waste handling.
Greener substitution/esterification:
Use EDC·HCl or CDI for ester/amide formation in EtOAc or MeCN instead of DCM when feasible.
For SNAr at C3–F, consider solvent choices like Cyrene, γ-valerolactone (GVL), propylene carbonate, or 2-MeTHF as drop-in replacements for DMF/DMSO where solubility and kinetics permit.
Energy and safety:
Favor microwave or flow chemistry to reduce reaction times/energy input.
Avoid excess strong bases/acids; leverage catalytic nucleophiles or phase-transfer catalysts to lower temperatures and minimize byproducts.
Workup/waste minimization:
Opt for aqueous bicarbonate washes and recyclable solvents (EtOAc, IPA) instead of chlorinated solvents where possible.
Use base-conditioned silica to reduce multiple columns; consider crystallization/trituration endpoints.
Greener: MeCN/EtOAc/2-MeTHF, carbonate/GVL, catalytic TEMPO or O2-enabled oxidations → reduced toxicity/halogenated waste.
Balance green metrics with performance; verify that greener solvents maintain solubility and acceptable SNAr or coupling kinetics for this heteroaryl substrate.
Pharmaceutical Uses
No excipient or pharmacopeial status is provided for this item; it is sold for research use only.
Informational context (non-clinical):
Role in drug discovery: Frequently used as a heteroaryl building block for the synthesis of screening compounds and reference materials. The secondary alcohol can be masked (esters/carbonates) or oxidized to the ketone to tune ADME properties, while the 3-fluoro handle supports late-stage diversification (e.g., SNAr with amines/thiols).
Process considerations: If advanced toward development, typical quality attributes assessed include residual solvents, inorganic impurities, polymorph (if solid), and enantiomeric purity if a chiral route is used. None of these are specified for this catalog item.
Regulatory: No compendial monograph is expected for such a specific intermediate. Any use in GMP settings would require internal qualification and specifications beyond standard research grade.
Note: No therapeutic, diagnostic, or clinical claims are made for this product.
Physical Properties
Item-specific specifications (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 values (reference only; not item specifications):
Molecular formula (literature): C7H8FNO
Molecular weight (literature): ~141.14 g/mol
Physical state: often obtained as a colorless to pale liquid or low-melting solid (varies with purity and temperature) (literature, analogous compounds)
Boiling point: not broadly tabulated; expect elevated vs 3-fluoropyridine due to –OH and higher MW (literature reasoning). Consult experimental data if critical.
Melting point: not broadly reported (literature).
Density: not broadly reported; secondary aryl alcohols of this MW often ~1.1–1.2 g/mL (literature trend; verify experimentally).
Refractive index: not broadly reported (literature).
Solubility (qualitative, literature):
Miscible with many polar organic solvents (EtOAc, MeOH, EtOH, acetone, DMSO, DMF).
Moderate water solubility expected due to one –OH and basic pyridine N; exact value not widely tabulated.
pKa values (literature, approximate):
Pyridinium (conjugate acid of ring N): pKa ~5.2 for unsubstituted pyridine; 2-substitution and 3-F slightly modulate basicity (slightly less basic than pyridine).
Alcohol O–H: pKa ~16–18 (typical for benzylic/aryl secondary alcohols).
LogP/logD (qualitative, literature): modest polarity; logP likely in the ~1–1.5 range (qualitative expectation).
Always confirm property values experimentally for method development or scale-up. Use the item’s CoA/SDS for authoritative specifications.
Quality and Grades
Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.
Research use note: For research use only (per Product Data); not for human or veterinary use.
Guidance on typical grades for this compound class (informational):
Standard research grade: Suitable for most synthetic applications. Purity is commonly ≥95% for catalog heteroaromatic building blocks unless otherwise stated. Confirm by CoA (e.g., NMR/HPLC GC as applicable).
Low-water/anhydrous offerings (if available): Beneficial when using moisture-sensitive reagents (e.g., Mitsunobu, carbodiimide coupling) or organometallic bases. For this item, any anhydrous claim would be stated explicitly on the label/CoA.
Stabilizers: Not typically required for pyridyl alcohols; none specified for this item. If stabilizers are present in a specific lot, they will be disclosed on the CoA.
Analytical considerations to verify incoming quality (best practices):
Identity confirmation: 1H/13C NMR (diagnostic benzylic –CHOH singlet/multiplet, methyl doublet), 19F NMR (single aromatic F signal), MS (M+H+ ~142, literature), and IR (broad O–H ~3300 cm⁻¹).
Purity assessment: HPLC/GC as appropriate; note that pyridyl alcohols may tail on silica; consider base-modified stationary phases or add 0.1% TEA to mobile phase for chromatography.
Residual solvents/water/peroxides/metals/UV cutoffs: Not specified for this item; refer to CoA/Spec Sheet.
Reaction and Applications
As a 3-fluoro-2-pyridyl secondary alcohol, this building block offers two orthogonal handles: a benzylic (heteroaryl) –CHOH– center and an aryl C–F on an electron-poor pyridine ring.
Transformations of the alcohol:
Oxidation to ketone: 1-(3-fluoro-2-pyridyl)ethanone via Dess–Martin, Swern, PDC, TEMPO/oxoammonium, or catalytic Pd/air protocols (literature). The ketone is a valuable electrophile for further elaboration (oximes, hydrazones, reductive amination).
Activation/substitution: Convert –OH to mesylate/tosylate, then displace with N/O/S/C nucleophiles (SN1/SN2 depending on conditions). Alternatively, halogenation (SOCl2, PBr3, Appel-type reagents) affords the corresponding 1-(3-fluoro-2-pyridyl)ethyl halide.
Mitsunobu reactions: Invert configuration at the secondary center to introduce O/N/S nucleophiles under mild conditions (literature).
Esterification/carbonate formation: DCC/EDC or acyl chlorides for pro-moieties in SAR libraries.
Reactivity of the 3-fluoropyridyl ring:
SNAr at C3–F: The pyridine N activates the ring toward nucleophilic aromatic substitution. Amination, alkoxylation, and thiolation are documented on 3-fluoropyridines, typically in polar aprotic solvents with heat/base (literature). Note that 2-substitution can modulate rates; optimization may be required.
Directed metalation: The 2-pyridyl directing effect can enable ortho/para metalation patterns (e.g., lithiation near C6) under strong bases (s-BuLi/TMEDA), enabling further electrophile trapping (literature).
Library/medchem utility:
The benzylic alcohol provides a handle for rapid polarity tuning (oxidation/reduction/esterification), while the aryl F enables late-stage diversification via SNAr or cross-coupling after defluorinative activation.
Practical tips: Dry conditions improve yields in activation/coupling steps; use base-modified silica for purification to minimize streaking of basic heteroaromatics.
Reaction Conditions
General literature guidance for this scaffold (optimize per substrate and scale):
Oxidation of the secondary alcohol to ketone:
Dess–Martin periodinane (DMP), DCM, 0 °C to rt, 1–3 h; typical conversions high with minimal over-oxidation.
Swern (DMSO, oxalyl chloride, Et3N), −78 to 0 °C, 1–2 h; high yields; strictly anhydrous conditions required.
TEMPO/NaOCl (biphasic CH2Cl2/aqueous buffer pH 8–9), 0–5 °C to rt, 1–4 h; greener alternative; monitor to avoid over-oxidation.
Alcohol activation and substitution:
Mesylation: MsCl (1.1–1.5 eq), Et3N, DCM, 0 °C → rt, 0.5–2 h; then SN with nucleophile in DMF at 40–80 °C.
Halogenation: PBr3 (1.1 eq), ether/DMF, 0 °C → rt; or SOCl2 (1.5–2 eq) with pyridine, DCM, 0 °C → rt.
Solvent: DMSO or DMF; alternatives include NMP, MeCN.
Base: K2CO3/Cs2CO3 for alcohols/thiols; amines may proceed neat or with added base.
Temperature/time: 60–140 °C (oil bath or sealed tube/microwave), 1–24 h. Monitor by LC/MS and 19F NMR.
Directed metalation (literature):
s-BuLi (1.1–1.5 eq) with TMEDA in THF at −78 °C, then electrophile quench; protect alcohol if needed (e.g., TBS) to avoid side reactions.
Yields are substrate- and condition-dependent; the above ranges are typical literature conditions for related 3-fluoropyridines and 2-pyridyl alcohols. Always conduct small-scale optimization before scale-up.
Safety and Handling
Item-specific hazard information (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 and pictograms: Not specified for this item; refer to SDS.
General safety guidance for heteroaryl secondary alcohols (informational; defer to SDS):
Likely hazards: May cause skin/eye irritation; harmful if swallowed or inhaled. The pyridine ring can impart an unpleasant odor and mucous membrane irritation. Avoid dust/vapor formation.
Personal protective equipment (PPE): Lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood.
Handling: Avoid contact with strong oxidizers and strong acids (protonation increases water solubility, can alter reactivity). Keep away from ignition sources; although alcohols are combustible, exact flash point not specified.
First aid (overview):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin: Wash with soap and water; remove contaminated clothing.
Eyes: Rinse cautiously with water for several minutes; remove contact lenses if present and easy.
Ingestion: Rinse mouth; do not induce vomiting unless directed by medical personnel.
Spills: Absorb with inert material (vermiculite, sand), collect for disposal. Prevent entry into drains.
Incompatibilities: Strong oxidizers; strong acids/bases for prolonged contact; reactive acid chlorides/anhydrides without proper controls.
Disposal: Follow institutional and local regulations for organic chemical waste.
Always consult the product-specific SDS for definitive hazard classification and response measures.
Solvent Selection
This product is a heteroaromatic secondary alcohol (building block), not a bulk solvent. Solvent selection guidance below focuses on using this compound in synthesis or purification.
Polarity and miscibility (literature, qualitative):
Good solubility in polar organics (EtOAc, MeOH/EtOH, acetone, acetonitrile, THF, DMSO, DMF).
Moderate solubility in nonpolar solvents (DCM, toluene) depending on temperature and concentration.
Limited to moderate water solubility expected due to one –OH and basic pyridine N.
Choosing solvents by task:
Couplings/derivatizations: DMF, DMSO, MeCN, or THF commonly used; for SNAr at the 3-F, polar aprotics (DMSO/DMF) often beneficial.
Oxidations to ketone: DCM (Dess–Martin), DMSO/DCM (Swern), or MeCN (TEMPO/bleach variants) depending on method.
Esterifications: DCM/DMF with DCC/EDC; or toluene under acid catalysis for Fischer esterifications.
Base-sensitive steps: Avoid strong protic acids that can form the pyridinium salt and decrease nucleophilicity/solubility in nonpolar media.
Workup/purification tips:
Acid–base partitioning: The ring N can be protonated to enhance extraction into aqueous phase (dilute HCl), then basified to back-extract.
Column chromatography: Add 0.1–1% triethylamine to silica eluent to reduce tailing of basic heteroaromatics; eluents like hexanes/EtOAc or DCM/MeOH (with base) are common.
Small comparison (literature-based):
DMSO/DMF: maximize SNAr rates and solubility; harder to remove.
MeCN/THF: easier removal, lower SNAr acceleration; good for many coupling/activation steps.
Alcoholic solvents: can participate in esterification/transesterification—use judiciously.
General handling recommendations for this class of compounds:
Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged exposure to moisture and strong light.
If long-term storage is anticipated, consider storing under inert atmosphere (argon/nitrogen) and using a desiccant, especially if frequent opening/closing is expected.
No reconstitution is required for neat material. For preparing stock solutions:
Choose dry, oxygen-stable solvents (e.g., anhydrous DMSO, MeCN, or EtOH) depending on intended use.
Filter through PTFE syringe filters if particulate is observed.
Record concentration and date; for DMSO stocks, store in sealed amber vials at 2–8 °C or −20 °C to prolong stability. Avoid repeated freeze–thaw by aliquoting.
Stability considerations: Secondary benzylic alcohols are generally stable at ambient conditions. Avoid strong oxidants and acidic environments that form pyridinium salts unless intentional.
Appearance, stabilizers, and exact shelf-life: Not specified for this item; refer to CoA/Spec Sheet and SDS for definitive guidance.
Structure and Identity
Brief description: 1-(3-fluoro-2-pyridyl)ethanol is a heteroaromatic secondary alcohol featuring a pyridine ring bearing a fluorine at the 3-position and a 1-hydroxyethyl substituent at the 2-position. The alcohol carbon is benzylic (heteroaryl-activated), enabling diverse derivatizations.
Item-specific identifiers (from Product Data):
CAS: 87674-14-4
SKU: E634853
InChIKey: 390605 (as provided)
Storage: Room temperature; shipped under normal conditions
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Literature/computed identity (for reference only; not item specifications):
Molecular formula (literature): C7H8FNO
Molecular weight (literature): ~141.14 g/mol
Preferred IUPAC name (literature): 1-(3-fluoropyridin-2-yl)ethan-1-ol
SMILES (literature): CC(O)c1ncccc1F
InChIKey (literature): not specified here; consult reference databases.
Structural features (general description):
Ring system: six-membered aromatic pyridine (one ring nitrogen).
Substitution pattern: F at C3; –CH(OH)CH3 at C2 (adjacent to ring N).
Functional groups: secondary alcohol (–CHOH–), aryl fluoride (C–F on electron-poor pyridine), basic ring nitrogen (pyridine).
2D topology (in words): A pyridine ring with adjacent substituents at positions 2 and 3; the 2-position bears a chiral center carbon attached to OH and CH3 (racemic unless specified), and the 3-position bears F.
Notes: When chirality matters, material is typically racemic unless an enantioenriched grade is stated. No such specification is provided for this item.
Synthetic Utility
Key functional elements and how they can be leveraged:
Benzylic secondary alcohol (–CH(OH)CH3):
Oxidize to ketone for electrophilic diversification (oximes, hydrazones, reductive amination, Wittig/olefination after carbonyl formation).
Convert to leaving groups (mesylate/tosylate, halides) to access 1-(3-fluoro-2-pyridyl)ethyl derivatives via substitution or elimination (E1/E2 to vinylpyridine derivatives).
Mitsunobu to introduce O/N/S nucleophiles with inversion; useful for accessing ethers, carbamates, and thioethers.
3-Fluoropyridyl ring:
SNAr reactivity at C3 enables installation of amines, alkoxides, or thiolates under heated polar aprotic conditions. The adjacent ring N activates the ring, though 2-substitution may modestly alter rates—optimize base/temperature.
Directed ortho metalation (DoM) strategies at positions adjacent to N (e.g., C6) allow installation of electrophiles (D2O, CO2, trialkylsilyl chlorides) after lithiation (s-BuLi/TMEDA, −78 to −40 °C) (literature).
Cross-coupling after defluorinative activation: Halogenate or convert to pseudohalides; alternatively, use emerging Ni-catalyzed defluorinative couplings where applicable (literature, method-dependent).
Retrosynthetic value:
Serves as a branch point intermediate toward 3-fluoro-2-substituted pyridine derivatives, enabling SAR matrices by varying the benzylic functionality (alcohol → ketone/amine/ether) and, separately, by substituting at C3 via SNAr.
Practical notes:
Base-sensitive functional groups may require protection when forming pyridinium salts (acidic media).
Purification: Use base-modified silica; 19F NMR provides rapid assessment of ring substitution patterns.
Target Specificity
Not applicable. This product is a small-molecule building block, not a biological targeting reagent (e.g., antibody, ligand with defined biomolecular specificity). No antigen/epitope, species reactivity, clone, or isotype information applies.
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