1-(3-bromo-2-pyridyl)ethanol - ≥97% , CAS No.1383734-83-5

CAS: 1383734-83-5 Cat. No.: E628787 Formula: C₇H₈NOBr Peso molecolare: 202.05 PubChem CID: 68041060

GRADE & PURITY ≥97%

Synonyms

1-(3-bromopyridin-2-yl)ethanol | 1383734-83-5 | 1-(3-bromopyridin-2-yl)ethan-1-ol | MFCD26860013 | (S)-1-(3-Bromo-2-pyridyl)ethanol | SCHEMBL10124296 | AKOS026738433 | PB42529 | SY289336 | F85949

Storage

Room temperature

Shipped In

Normal

Specifications

Sinonimi

1-(3-bromopyridin-2-yl)ethanol | 1383734-83-5 | 1-(3-bromopyridin-2-yl)ethan-1-ol | MFCD26860013 | (S)-1-(3-Bromo-2-pyridyl)ethanol | SCHEMBL10124296 | AKOS026738433 | PB42529 | SY289336 | F85949

Specifiche e purezza

≥97%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥97%

Nomi e identificatori

• Sorrisi canonici: CC(C1=C(C=CC=N1)Br)O
• IUPAC Name: 1-(3-bromopyridin-2-yl)ethanol
• InChIKey: XEBDEXIOOONSJK-UHFFFAOYSA-N
• INCHI: 1S/C7H8BrNO/c1-5(10)7-6(8)3-2-4-9-7/h2-5,10H,1H3
• Isomeri SMILES: CC(C1=C(C=CC=N1)Br)O
• PubChem CID: 68041060
• Peso molecolare: 202.05

Proprietà chimiche e fisiche

• Peso molecolare: 202.050 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 200.979 Da
• Monoisotopic Mass: 200.979 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

Application Protocols

No validated bioanalytical protocols (e.g., WB, IHC, IF, FC) are associated with this small-molecule building block.

• General usage guidance for chemistry workflows:
  • For stock solutions, dissolve in dry DMSO, DMF, MeCN, or DCM to desired concentration. Filter if necessary (0.2 µm PTFE) to remove particulates.
  • For cross-coupling screens, set up small-scale (0.05–0.2 mmol) reactions with ligand/base/solvent matrices to identify active conditions tolerant of pyridine coordination.
  • For analytical characterization, typical methods include 1H/13C NMR (CDCl3, DMSO-d6), LC–MS, and HPLC/UPLC purity assessment.

For application-specific, itemized conditions, refer to your internal methods or contact technical support with your intended transformation.

Biological Roles

This compound is a synthetic heteroaromatic building block and does not have an established endogenous biological role.

• General context (literature):

  • Pyridine rings are common motifs in bioactive molecules due to their capacity for hydrogen bonding and modulation of basicity/lipophilicity. The ring nitrogen can participate in ligand–protein interactions or metal coordination in metalloenzymes.
  • Benzylic alcohols can alter solubility and metabolic profiles when incorporated into larger drug-like structures; oxidation to ketones or further derivatization is common in medicinal chemistry workflows.
  • Aryl bromides serve as precursors to diversified analogs through biorthogonal late-stage functionalization (e.g., C–C/C–N couplings), enabling rapid structure–activity relationship exploration.

• Caution:

  • No clinical, pharmacological, or therapeutic claims are made for this item. It is supplied strictly for research use as noted in the Product Data.

For any biological testing, prepare solutions in appropriate vehicles (e.g., DMSO) and confirm compatibility with assay buffers to avoid precipitation or nonspecific effects.

Buffer Applications

Not typically applicable. 1-(3-bromo-2-pyridyl)ethanol is a small-molecule building block, not a buffering agent.

• Practical note: If used in biochemical assays, dissolve in DMSO or another compatible cosolvent and dilute into the assay buffer while monitoring for precipitation. The compound itself does not provide pH buffering capacity in physiological ranges.

Green Alternatives

As a substrate (not a solvent), greenness considerations focus on solvent/catalyst choices and step economy rather than on substituting the reagent itself.

• Greener solvent options (general guidance):

  • Replace DMF/DMAc with Me-THF, 2-MeTHF, CPME, propylene carbonate, or EtOAc where compatible.
  • Favor water/EtOH or water/2-MeTHF biphasic systems for Suzuki couplings when suitable bases/ligands are used.
  • Prefer MeCN or EtOAc over DCM when oxidation protocols allow.

• Catalysis and stoichiometry:

  • Use highly active Pd catalysts at ppm–low mol% loadings or nickel catalysis for aryl amination/coupling to reduce precious metal usage.
  • Employ aqueous micellar catalysis for cross-couplings where feasible to minimize organic solvent volumes.

• Comparison snapshot (general; illustrative):

  • THF vs 2-MeTHF: similar polarity; 2-MeTHF offers renewable sourcing and higher boiling point, easing water removal.
  • DCM vs EtOAc: EtOAc is less toxic and has preferable environmental metrics, though DCM can offer higher substrate solubility.

• Step economy:

  • Leverage the orthogonality of the aryl bromide and the alcohol to minimize protecting-group operations (e.g., one-pot oxidation–coupling sequences).

These are general recommendations; optimize conditions case-by-case.

Pharmaceutical Uses

No excipient or pharmacopoeial role is specified for this item; it is provided for research and synthesis only (Product Data: For research use only).

• Typical role in pharmaceutical R&D (general):

  • Heteroaryl building block for the preparation of screening compounds, lead optimization analogs, and reference materials.
  • The aryl bromide enables rapid diversification via cross-coupling to access chemical space around a pyridine core; the secondary alcohol can be oxidized, esterified, or converted to other functionalities to adjust physicochemical properties.

• Manufacturing/formulation note:

  • If carried forward into pre-formulation research samples, prepare DMSO or ethanol stock solutions and evaluate stability under accelerated conditions (light, heat, humidity). No pharmacopeial monograph is known for this specific compound.

All uses must remain within laboratory research contexts; no clinical or therapeutic claims are made or implied.

Physical Properties

• Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general expectations (for structural analogs; not item specs):

  • Physical state: typically a solid or low-melting solid/oil for benzylic pyridyl alcohols with halo substituents.
  • Polarity: polar, hydrogen-bond donor/acceptor (secondary alcohol; pyridine N acceptor).
  • Acid-base behavior: pyridine nitrogen is basic (conjugate acid pKa ~5.2, literature for pyridines); benzylic alcohol pKa of O–H typically ~16–18 (literature), enabling deprotonation with strong base when required.
  • Solubility profile: good solubility in polar organics (DMSO, DMF, MeOH, EtOH, acetone, acetonitrile, dichloromethane, ethyl acetate); limited aqueous solubility expected due to hydrophobic ring and aryl bromide.
  • Partitioning: moderate lipophilicity is expected relative to non-halogenated analogs (qualitative).

• Practical handling implications:

  • The secondary alcohol can engage in hydrogen bonding; drying prior to moisture-sensitive transformations may be required.
  • The aryl bromide facilitates transition-metal catalysis; residual water can impact cross-coupling rates—use dry, degassed solvents where relevant.

Note: For definitive values (mp, bp, density, refractive index, water/peroxide/metal content, UV cutoff), consult the product-specific CoA/SDS.

Quality and Grades

• Item-specific grade/purity: Not specified for this item; refer to CoA/Spec Sheet.

• General guidance on grades (context for synthetic building blocks):

  • Research grade: Suitable for discovery chemistry and method development; typical assays include NMR, HPLC/GC, and MS. Trace water, residual solvents, and metal content are uncontrolled unless stated.
  • High-purity or HPLC grade (when specified): Tight control of organic and inorganic impurities; often accompanied by low UV background data—useful for analytical development.
  • Metal content: For cross-coupling programs, low residual metals (e.g., Pd, Cu) and halide identity confirmation are important. If critical, request ICP or specific impurity data.
  • Stabilizers: None specified for this item. If stabilizers were added (e.g., BHT, amines), they can affect reactivity and analytical baselines; check the CoA.

• Release documentation:

  • CoA typically includes identity (NMR/HRMS), purity assay, and appearance. For regulated work or reproducibility-critical synthesis, request exact test methods and limits.

• Batch-to-batch considerations:

  • Heteroaryl bromides can exhibit light sensitivity or trace debromination. Store properly and confirm identity/purity prior to scale-up.

Reaction and Applications

The 3-bromopyridyl motif and benzylic secondary alcohol provide orthogonal handles for diversification in discovery and library synthesis.

• Aryl bromide chemistry:

  • Suzuki–Miyaura coupling with boronic acids/esters to access 3-substituted 2-(1-hydroxyethyl)pyridines.
  • Buchwald–Hartwig amination to introduce anilines or alkyl amines at C-3.
  • Stille/Negishi/Kumada couplings for diverse carbon–carbon bond formations.
  • Lithiation/halogen–metal exchange (iPrMgCl·LiCl, tBuLi) followed by electrophile trapping; control temperature to protect the alcohol functionality.

• Alcohol functional group manipulations:

  • Oxidation to the corresponding ketone (2-acetyl-3-bromopyridine) via Dess–Martin, Swern, or TEMPO-based protocols.
  • Activation as sulfonate (mesylate/tosylate) enabling SN2 substitution or intramolecular cyclizations.
  • Dehydration to generate the vinyl derivative (1-(3-bromopyridyl)ethene) using acid or POCl3/pyridine conditions.
  • Mitsunobu reactions to invert configuration (if enantioenriched) or to install oxygen/nitrogen nucleophiles.

• Coordination/chelation effects:

  • The pyridine nitrogen can coordinate to metals, influencing cross-coupling rates and selectivity; catalyst/ligand choice (e.g., BrettPhos/XPhos systems) can mitigate catalyst inhibition.

• Applications:

  • Fragment growth and SAR exploration in medicinal chemistry.
  • Assembly of N-heteroaryl scaffolds, bidentate ligands (post-functionalization), and advanced intermediates via site-selective C–C/C–N coupling.

Reaction Conditions

General literature conditions for closely related substrates (optimize per project; not item specifications):

• Suzuki–Miyaura coupling:

  • Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd-precatalyst with XPhos/BrettPhos (0.5–2 mol%).
  • Base: K2CO3 or K3PO4 (2–3 equiv); aqueous Na2CO3 also common.
  • Solvent: 1,4-dioxane/H2O (3:1), THF/H2O, or toluene/H2O.
  • Temperature: 60–100 °C; time: 2–12 h under N2 or Ar; degas solvents.

• Buchwald–Hartwig amination:

  • Catalyst/ligand: Pd2(dba)3 (1 mol% Pd) with BrettPhos or RuPhos; or Pd-PEPPSI-type systems.
  • Base: NaOtBu or Cs2CO3; Solvent: toluene, dioxane, or tBuOH.
  • 80–110 °C, 4–18 h. Pyridine N coordination may necessitate stronger ligands/excess base.

• Oxidation of secondary alcohol to ketone:

  • Dess–Martin periodinane (1.3 equiv), DCM, 0 °C to rt, 1–3 h.
  • Swern oxidation (oxalyl chloride/DMSO, −78 °C, then Et3N) in DCM.
  • TEMPO/NaOCl with NaHCO3 buffer in biphasic CH2Cl2/H2O, 0–5 °C to rt.

• Dehydration to alkene:

  • POCl3/pyridine or SOCl2/pyridine, 0 °C to reflux; or acid-catalyzed (p-TsOH) in toluene with Dean–Stark.

• Halogen–metal exchange:

  • iPrMgCl·LiCl or nBuLi at −78 to −40 °C in THF; quench with electrophiles. Protect/consider compatibility of the alcohol (e.g., silylation) if necessary.

Safety and Handling

• Item-specific hazard information (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.

• General laboratory precautions (for heteroaryl bromides and pyridyl alcohols; not a substitute for SDS):

  • Potential hazards: May cause irritation to skin/eyes/respiratory tract. Avoid inhalation of dust/vapors and contact with skin/eyes.
  • PPE: Lab coat, safety glasses, and suitable gloves (e.g., nitrile). Use in a chemical fume hood.
  • Incompatibilities: Strong oxidizers (may over-oxidize), strong acids (protonate pyridine nitrogen; possible exotherm), and strong bases at elevated temperature (risk of elimination/substitution on activated positions). Avoid halide-reactive metals without appropriate control.
  • Fire safety: Organic combustible solid/liquid; keep away from ignition sources. Use CO2, dry chemical, or foam for small fires.
  • First aid (overview): In case of skin/eye contact, rinse with water for ≥15 minutes; remove contaminated clothing. If inhaled, move to fresh air. If ingested, rinse mouth; do not induce vomiting—seek medical attention. Always follow SDS instructions.
  • Waste: Collect halogenated organic waste separately per institutional and regulatory guidelines.

Always consult the product SDS for authoritative hazard, exposure limits, and first-aid details.

Solvent Selection

This compound is a polar, heteroaromatic secondary alcohol with an aryl bromide. Solvent choice depends on task (analytical dissolution vs. synthesis vs. catalysis).

• Dissolution/stock solutions (general):

  • Highly soluble in DMSO and DMF; good solubility in MeOH, EtOH, acetone, MeCN, DCM, and EtOAc (literature/general). Limited water solubility expected.
  • For bioassays, prepare concentrated DMSO stocks, then dilute into aqueous buffers with cosolvent to prevent precipitation.

• Synthesis and transformations:

  • Cross-coupling: Polar aprotic solvents (1,4-dioxane, THF, toluene, MeCN, DMAc/DMF) often used; inclusion of water can accelerate Suzuki reactions.
  • Oxidations of the secondary alcohol: DCM, EtOAc, or MeCN under Dess–Martin; DMSO/acid chloride for Swern; MeCN or EtOAc for TEMPO systems.
  • Nucleophilic substitutions on the alcohol derivative (e.g., tosylate/mesylate): Polar aprotic solvents (DMF, DMSO, MeCN) promote SN2 at benzylic positions.

• Practical considerations:

  • The pyridine nitrogen can coordinate catalysts; solvent/catalyst systems tolerant to Lewis basic substrates are preferred (e.g., Pd with dialkylbiaryl phosphines).
  • If water sensitivity is a concern (e.g., metal–halogen exchange), rigorously dry etheric solvents (THF, Et2O) and glassware.

• Comparison (general):

  • DMSO/DMF: maximal solubility; harder to remove.
  • MeCN/EtOAc/DCM: balanced solubility and ease of removal; compatibility depends on reaction.

Storage and Reconstitution

• Storage (Product Data): Room temperature; ship normal. Store tightly closed in a dry, well-ventilated place.

• Best practices (general):

  • Protect from prolonged light exposure to minimize potential debromination or discoloration.
  • Keep container tightly sealed with desiccant to limit moisture uptake; the secondary alcohol is hygroscopic to a limited extent via hydrogen bonding.
  • If long-term storage is planned (>12 months), consider 2–8 °C in amber glass to further preserve integrity (general guidance).

• Reconstitution/preparation of solutions:

  • Solvents: DMSO, DMF, MeOH, EtOH, MeCN, DCM, or EtOAc are typically suitable. Aqueous solubility is limited; use cosolvent strategies for water-based systems.
  • Typical stock concentrations: 10–100 mM in DMSO for screening; filter-sterilize if required for biological assays.
  • Stability: Organic solutions are generally stable for days at 2–8 °C; for longer periods, aliquot and store at −20 °C to avoid repeated freeze–thaw. Allow solutions to equilibrate to room temperature before opening to minimize condensation.

• Inspection: Prior to use, check for precipitation, discoloration, or particulates. If observed, re-verify purity by NMR/LC–MS.

Note: For item-specific limits (water content, residual solvents, metal impurities), consult the CoA/Spec Sheet.

Structure and Identity

A heteroaromatic secondary alcohol combining a 3-bromopyridyl electrophile with a 1-hydroxyethyl substituent for diversification.

• Item-specific identifiers (Product Data):

  • CAS: 1383734-83-5
  • SKU: E628787
  • Storage: Room temperature (Product Data)
  • Shipped: Normal (Product Data)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/computed identity (verify against CoA):

  • Preferred name: 1-(3-bromo-2-pyridyl)ethanol (a.k.a. 3-bromo-2-(1-hydroxyethyl)pyridine)
  • Molecular formula (structural count): C7H8BrNO (literature/computed)
  • Molecular weight: ~202.05 g/mol (literature/computed)
  • Example structural string (literature depiction): CC(O)-c1ncc(Br)cc1 (proposed SMILES; verify)

• Structural features (general description):

  • Aromatic six-membered pyridine ring with ring nitrogen (sp2 N) at position 1.
  • Bromine at the 3-position (para to C4, ortho to C2), providing a competent aryl–Br handle for cross-coupling and metal–halogen exchange.
  • Secondary alcohol side chain (–CH(OH)CH3) attached at the 2-position (adjacent to the ring nitrogen), offering redox, substitution, and dehydration chemistry.
  • One stereogenic center at the benzylic alcohol carbon; supplied as racemate unless otherwise specified (grade not specified for this item; refer to CoA).

Synthetic Utility

Dual-functional handle enables convergent synthesis:

• Electrophilic aryl bromide at C-3:

  • Carbon–carbon formation via Suzuki, Negishi, Stille, Kumada, and Sonogashira (with precautions) to introduce aryl, alkyl, alkenyl, or alkynyl groups.
  • Carbon–heteroatom formation via Buchwald–Hartwig amination or etherifications after suitable activation.
  • Halogen–metal exchange affording 3-metalated pyridyl species for direct trapping with electrophiles.

• Benzylic secondary alcohol at C-2:

  • Oxidation to 2-acetyl-3-bromopyridine (useful pivot intermediate) with DMP, Swern, or TEMPO/bleach-like systems (compatibility-driven choice).
  • Conversion to leaving groups (mesylate/tosylate) enabling SN2 substitution, azide installation, or intramolecular cyclizations.
  • Dehydration to the vinyl derivative followed by hydrofunctionalizations (e.g., hydroboration–oxidation, epoxidation after halovinyl formation).
  • Mitsunobu coupling to install N/O nucleophiles with inversion (applicable if enantioenriched material is used).

• Orthogonality and protection:

  • The pyridine nitrogen may coordinate catalysts; appropriate ligands or temporary N-oxides can be leveraged to modulate reactivity/selectivity in some methodologies (literature strategy).

• Retrosynthetic value:

  • Readily participates in late-stage diversification of pyridine-containing scaffolds, serving as a modular node for parallel synthesis.

Target Specificity

Not applicable. This product is a small-molecule chemical building block and is not an antibody, enzyme, or biological probe with defined target specificity. No target, epitope, or isotype information is associated with this item.