7-bromothieno[3，2-b]pyridine - ≥95% , CAS No.603305-89-1

CAS: 603305-89-1 Cat. No.: B734596 Formula: C₇H₄BrNS Peso molecolare: 214.08 Numero EC: 810-650-4 PubChem CID: 66721107

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

C1=CN=C2C=CSC2=C1Br

IUPAC Name

7-bromothieno[3,2-b]pyridine

InChIKey

NLHODWKWTMTFEN-UHFFFAOYSA-N

INCHI

1S/C7H4BrNS/c8-5-1-3-9-6-2-4-10-7(5)6/h1-4H

Isomeri SMILES

C1=CN=C2C=CSC2=C1Br

PubChem CID

66721107

Peso molecolare

214.08

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Classe Thienopyridines

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Classe: Thienopyridines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Thienopyridines
• Alternative Parents: Pyridines and derivatives Aryl bromides Thiophenes Heteroaromatic compounds Azacyclic compounds Organonitrogen compounds Organobromides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Thienopyridine - Pyridine - Aryl halide - Aryl bromide - Heteroaromatic compound - Thiophene - Azacycle - Organic nitrogen compound - Hydrocarbon derivative - Organonitrogen compound - Organobromide - Organohalogen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as thienopyridines. These are heterocyclic compounds containing a thiophene ring fused to a pyridine ring. Thiophene is 5-membered ring consisting of four carbon atoms and one sulfur atom. Pyridine is a 6-membered ring consisting of five carbon atoms and one nitrogen center.
• External Descriptors: Not available

Data sources

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.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 214.080 g/mol
• XLogP3: 2.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 212.925 Da
• Monoisotopic Mass: 212.925 Da
• Topological Polar Surface Area: 41.100 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 131.000
• 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

Application Protocols

Not applicable. No tested bioassay protocols (e.g., WB, IHC, IF, FC) or recommended dilutions apply to this small-molecule reagent. For synthetic applications, refer to the Reaction Conditions and Synthetic Utility sections for general laboratory guidance.

Biological Roles

• Item-specific

  • None stated. This product is designated for research use only.

• Literature/general context

  • Thienopyridine is a privileged bicyclic heteroarene motif encountered across medicinal chemistry. While some marketed agents contain thienopyridine cores, those molecules are highly functionalized and differ substantially from this simple aryl bromide building block.
  • The present compound is best considered a synthetic intermediate for assembling functionalized thienopyridines rather than a molecule with intrinsic biological function. Substitution at the 7-position allows tuning of electronics and topology relative to the ring nitrogen and sulfur, which can influence binding profiles in discovery campaigns.
  • Any biochemical evaluation (enzyme panels, receptor binding, cell-based assays) would be entirely user-defined and outside the scope of this catalog listing. No claims are made regarding biological activity, ADME, toxicity, or therapeutic relevance.

• Practical implications for researchers

  • Use this scaffold as an electrophilic handle to build focused libraries by Suzuki/Buchwald couplings, then profile the derived analogs. Maintain strict documentation (CoA, batch identity) so that biological findings can be traced to verified chemical identity and purity.

Reminder: No medical or clinical claims are associated with this item.

Buffer Applications

This compound is a neutral, poorly water-soluble heteroaryl bromide and is not used as a buffering agent.

• Not typically applicable

  • It does not possess acid/base functionalities appropriate for maintaining a defined pH range in aqueous systems at practical concentrations.

• Practical note

  • If aqueous work is required (e.g., bioconjugations on analogs), dissolve the compound in a miscible co-solvent (DMSO or DMF) and add to the buffered system as a concentrated stock, keeping final co-solvent below assay limits.

Green Alternatives

While the substrate itself is a halogenated heteroarene, several greener choices in process design can reduce environmental footprint.

• Greener solvent choices (general)

  • Prefer 2-MeTHF or CPME over THF for many cross-couplings (bio-derived 2-MeTHF; CPME exhibits low peroxide formation and favorable workups).
  • Aqueous micellar catalysis (e.g., TPGS-750-M) can enable Suzuki couplings in water at lower catalyst loadings, reducing organic solvent use.
  • Ethanol or propylene carbonate may replace dioxane/DMF in certain Pd-catalyzed couplings.

• Catalysis and conditions (general)

  • Use ligand-enabled low-Pd loadings or Ni-catalysis where feasible; consider flow chemistry to minimize solvent volume and improve heat/mass transfer.
  • Room-temperature or base-optimized protocols (e.g., K3PO4 in water/ethanol) can cut energy consumption.

• Comparative snapshot (general)

  • Traditional: Dioxane or DMF, 1–2 mol% Pd, 80–110 °C, inert atmosphere.
  • Greener variant: Water/EtOH + micelles, 0.1–0.5 mol% Pd or Ni, 25–60 °C, air-tolerant ligands.

• Waste minimization

  • Replace stannanes (Stille) with boronates (Suzuki) to avoid organotin waste.
  • Employ borylation–Suzuki sequences to streamline convergent routes and reduce protecting-group operations.

Note: Feasibility depends on coupling partner and substitution pattern on the thienopyridine. Validate on small scale before scale-up.

Pharmaceutical Uses

This product is not an excipient and is not supplied under any pharmacopeial monograph.

• Not typically applicable

  • 7-bromothieno[3,2-b]pyridine serves as a research intermediate for synthesis of more complex molecules. It is not intended for human or veterinary use, nor for formulation as a drug substance or excipient.

• Process chemistry context (general)

  • In pharmaceutical discovery, heteroaryl bromides such as this are frequently employed to access SAR around a heteroaromatic core via Pd-catalyzed couplings, enabling rapid generation of lead-like analogs. Any GMP-related specifications (residual solvents, elemental impurities) would be project-specific and are not provided here.

Physical Properties

• Item-specific (from Product Data)

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
  • Storage conditions: Room temperature
  • Shipped in: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/general properties (typical of heteroaryl bromides; for guidance only)

  • Physical state: Usually a crystalline solid (off-white to light tan is common for heteroaryl bromides), but confirm with the item’s CoA.
  • Solubility: Poorly soluble in water; generally soluble in polar aprotic organics (DMSO, DMF, NMP) and chlorinated solvents (DCM, chloroform). Limited solubility in alcohols; variable in ethers and toluene.
  • Volatility: Low; negligible vapor pressure at ambient conditions typical for aryl bromides.
  • Photostability: Aromatic bromides can undergo slow photolysis; minimize prolonged light exposure during storage and handling.
  • Thermal behavior: Stable under normal lab conditions; avoid prolonged heating above typical coupling temperatures to prevent decomposition.
  • Partitioning: Expected to be moderately lipophilic due to aryl bromide; exact logP not established here.

• Characterization suggestions (general)

  • NMR: Aromatic 1H signals typically span δ ~7.0–9.0 ppm with distinctive downfield pyridine protons; 13C shows deshielded C–Br signal.
  • MS: Prominent M and M+2 isotopic peaks (79Br/81Br) assist confirmation.
  • HPLC/GC: Reverse-phase HPLC with UV (254–300 nm) commonly effective; confirm UV cutoff/absorbance empirically.

Note: Where a specific numerical value is not provided above, it is not established for this item; refer to CoA/Spec Sheet.

Quality and Grades

• Item-specific (from Product Data)

  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• How to interpret grade/purity (general guidance)

  • Research grade heteroaryl halides are commonly supplied at ≥95% purity by HPLC/GC unless otherwise stated. If your application is sensitive (e.g., medicinal chemistry SAR or high-throughput synthesis), verify the exact assay purity, residual solvents, and halide content from the CoA.
  • Spectroscopic characterization: 1H/13C NMR, HRMS, and HPLC trace are typical. For cross-couplings, trace metal contaminants are usually acceptable at ppm levels, but certain catalytic screens may be metal-sensitive; review elemental analysis/ICP if provided.
  • Stabilizers: None are typically added to aryl bromides; if any stabilizer or inhibitor is present, it will be declared on the CoA. Absence of stabilizers is advantageous for catalysis.

• Fit-for-purpose selection (practical tips)

  • For Pd-catalyzed couplings, low peroxide/acid content is not usually critical, but dryness and absence of protic impurities help reproducibility.
  • For lithiation/metal–halogen exchange, trace moisture/oxygen are more detrimental; consider freshly drying the solid in vacuo at ambient/mild temperature and handling under inert gas.

Note: When specific numeric limits (water, heavy metals, residual solvents, UV) are required, they must be taken from the item’s CoA/Spec Sheet; they are not specified here.

Reaction and Applications

As an aryl bromide on a thienopyridine core, this compound is a versatile electrophile for C–C and C–N/C–O bond formations in heteroaromatic synthesis.

• Cross-couplings (literature/general)

  • Suzuki–Miyaura: Couples with (hetero)aryl- or vinyl-boronic acids/esters to access diverse 7-substituted thieno[3,2-b]pyridines. Typical Pd catalysts: Pd(PPh3)4, Pd2(dba)3/XPhos or SPhos; bases K2CO3, Cs2CO3, K3PO4; solvents dioxane/H2O or toluene/EtOH/H2O; 60–110 °C.
  • Buchwald–Hartwig amination: Installation of anilines/alkylamines using Pd2(dba)3 or Pd(OAc)2 with BrettPhos, XPhos, or RuPhos; bases NaOtBu/KOtBu; 60–120 °C.
  • Stille/Negishi/Kumada: Vinyl/aryl stannanes, zinc, or Grignard reagents provide rapid access to C–C coupled products; THF or toluene, 0–80 °C.

• Halogen–metal exchange and directed metalation (general)

  • Bromine–lithium exchange (e.g., n-BuLi, sec-BuLi) at −78 to −30 °C in anhydrous THF affords lithiated thienopyridine for formylation, borylation, or electrophile trapping. The ring nitrogen can influence regioselectivity; rigorous low-temperature control is advised.

• Late-stage diversification (general)

  • Borylation (via Miyaura) to the pinacol boronate enables iterative Suzuki couplings.
  • Carbonylation (Pd-catalyzed, CO atmosphere) yields esters/amides/acids at C-7.
  • C–O coupling: Aryloxylation with phenols under Pd or Cu catalysis.

• Use context

  • Ideal for medicinal chemistry SAR around the thienopyridine core and for materials-oriented heteroarene synthesis. No medical/clinical use implied; research use only.

Practical tip: Dry substrate and degas solvents to improve reproducibility in Pd-catalyzed transformations.

Reaction Conditions

The following are literature/general guidelines for aryl bromides on heteroaromatic systems; optimize for your substrates and scale.

• Suzuki–Miyaura biaryl formation (general)

  • Catalyst: 1–3 mol% Pd(PPh3)4 or Pd2(dba)3 (1 mol% Pd) + SPhos/XPhos (2–4 mol%).
  • Base: K3PO4 (2–3 equiv) or Cs2CO3 (2 equiv); aqueous conditions often beneficial.
  • Solvent: 1,4-dioxane/H2O (4:1) or toluene/EtOH/H2O.
  • Temperature/time: 70–100 °C, 2–12 h.
  • Notes: Degas solvents; add a phase transfer agent (TBAB) if using less polar media.

• Buchwald–Hartwig amination (general)

  • Catalyst/ligand: Pd2(dba)3 (0.5–1 mol% Pd) + BrettPhos/XPhos (1–2 mol% ligand) or Pd(OAc)2 + RuPhos.
  • Base: NaOtBu or KOtBu (2–3 equiv).
  • Solvent: Toluene, dioxane, CPME; sometimes DMAc for difficult partners.
  • Temperature/time: 80–110 °C, 4–18 h.
  • Notes: For aliphatic amines, stronger bases and bulky ligands enhance rates.

• Sonogashira alkynylation (general)

  • Catalyst: Pd(PPh3)2Cl2 (1–2 mol%) + CuI (2–5 mol%).
  • Base: Et3N, i-Pr2NH, or K2CO3.
  • Solvent: THF, toluene, or Et3N as solvent; 25–80 °C.

• Halogen–lithium exchange (general)

  • Reagent: n-BuLi or sec-BuLi (1.1–1.5 equiv) at −78 to −30 °C in dry THF.
  • Trap with: DMF (aldehyde), CO2 (acid), B(OMe)3 (boronate), MeI (methylation).

• Carbonylative coupling (general)

  • Pd catalyst + CO (1–10 bar) with alcohols/amines; dioxane/DMF, 60–90 °C.

Reported yields for well-behaved partners commonly range 60–95% under optimized conditions; heteroaryl partners may require ligand tuning.

Safety and Handling

• Item-specific (from Product Data)

  • GHS classification: Not specified for this item; refer to SDS.
  • Signal word / H-statements / Pictograms: Not specified for this item; refer to SDS.
  • Research use note: For research use only
  • Storage conditions: Room temperature

• General safety guidance for heteroaryl bromides (literature/practice; defer to SDS as authoritative)

  • Likely hazards: May cause skin/eye irritation and respiratory irritation; harmful if swallowed or inhaled. Avoid dust generation. Exact classification requires the SDS for this product.
  • PPE: Wear lab coat, safety glasses or splash goggles, and appropriate chemically resistant gloves (e.g., nitrile). Use in a fume hood to limit inhalation exposure.
  • Incompatibilities: Strong bases can induce metal–halogen exchange; strong nucleophiles may cause substitution under forcing conditions. Avoid strong oxidants and reducing agents unless intended. Keep away from ignition sources when using flammable solvents during handling.
  • First aid overview: Skin—wash with soap/water. Eyes—rinse with water for 15 minutes; remove contacts. Inhalation—move to fresh air. Ingestion—rinse mouth; seek medical advice. Always follow site SOPs and consult the SDS.
  • Spill/accidental release: Avoid dust, ventilate area, collect mechanically and place in compatible waste containers. Decontaminate surfaces with suitable solvent while observing flammability and waste rules.
  • Waste: Halogenated organic waste stream unless your facility directs otherwise.

Special notes: Unlike dialkyl ethers, aryl bromides do not form peroxides. However, photosensitivity is possible—store in amber containers if feasible.

Solvent Selection

This product is a neutral, fused heteroaryl bromide. Solvent choice is dictated by reaction type and solubility needs rather than buffering or proticity.

• General polarity/solubility profile (literature/general)

  • Water: Expected to be sparingly soluble to insoluble.
  • Polar aprotic: Typically soluble in DMSO, DMF, NMP, and DMAc—useful for coupling and SNAr.
  • Chlorinated: Good solubility in DCM and chloroform; moderate in 1,2-dichloroethane.
  • Ethers/aromatics: Variable in THF, 2-MeTHF, dioxane; often soluble in toluene/xylene at elevated temperature.

• Selection by use case (general guidance)

  • Suzuki–Miyaura: 1,4-dioxane/water, THF/water, or toluene/EtOH/water with phase transfer/base present.
  • Buchwald–Hartwig amination: Toluene, dioxane, CPME, or tert-amyl alcohol with strong inorganic base (NaOtBu, KOtBu); polar aprotics for more challenging substrates.
  • Stille/Negishi/Kumada: THF, toluene, or diethyl ether alternatives depending on organometallic partner stability.
  • Metal–halogen exchange/lithiation: Anhydrous THF or Et2O at low temperature under inert gas.

• Small comparison (general)

  • DMSO/DMF: High solubility; challenging workup and removal.
  • 2-MeTHF/CPME: Greener ethers; good for couplings; easier separation; lower peroxide tendency (CPME) than THF.
  • Toluene: Good for high-temperature couplings; hydrophobic.

Always match solvent choice to base, catalyst, and downstream isolation strategy. Verify actual solubility empirically for your lot.

Storage and Reconstitution

• Item-specific (from Product Data)

  • Storage conditions: Room temperature

• General storage guidance for heteroaryl bromides

  • Keep container tightly closed in a dry, well-ventilated place. Protect from prolonged light exposure; use amber bottles if possible.
  • Handle under inert atmosphere for air/moisture-sensitive operations (e.g., prior to lithiation). For routine storage, ambient air is typically acceptable if kept dry.
  • Avoid high humidity; include desiccant in secondary containment where practical.

• Stock solutions (general)

  • Prepare concentrated stocks in dry DMSO, DMF, or acetonitrile for screening; filter if particulates are present. Record solvent and concentration on the vial.
  • Store solutions at 2–8 °C or −20 °C depending on solvent stability and project needs; minimize freeze–thaw cycles by aliquoting.

• Reconstitution

  • No aqueous reconstitution is recommended due to low water solubility. Dissolve in anhydrous organic solvent compatible with the intended reaction or assay.

Always follow your institution’s SOPs. For definitive stability data (shelf life, degradation pathways), consult the CoA/Spec Sheet and the product SDS.

Structure and Identity

Brief overview: 7-bromothieno[3,2-b]pyridine is a fused N,S-heteroaromatic bearing a bromine substituent at the 7-position of the bicyclic scaffold; it serves as a versatile heteroaryl halide building block.

• Item-specific (from Product Data)

  • SKU: B734596
  • Product name: 7-bromothieno[3,2-b]pyridine
  • CAS: 603305-89-1
  • InChIKey: 241484 (truncated as provided)
  • SMILES: 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/general identity (for reference only; verify against CoA before use)

  • Typical molecular formula (literature): C7H4BrNS (for 7-bromo derivative of thieno[3,2-b]pyridine)
  • Typical molecular weight (literature): ~214.08 g/mol
  • Core scaffold: Thieno[3,2-b]pyridine = thiophene ring annulated to a pyridine ring (two fused five- and six-membered aromatics containing S and N, respectively)
  • Key functional group: Aryl bromide (activated for cross-coupling and substitution chemistry)
  • Positional annotation: “7-bromo” denotes substitution on the pyridine ring portion opposite the ring fusion juncture.

• 2D structure described in words (general)

  • A bicyclic, planar aromatic system where a thiophene (C4H2S) shares an edge with a pyridine (C5H3N). The bromine atom is attached to the perimeter carbon corresponding to position 7 by standard thienopyridine numbering. No stereocenters are present; the molecule is achiral and fully conjugated.

Synthetic Utility

• Electrophile versatility (general)

  • The aryl bromide at C-7 renders the scaffold primed for Pd/Ni-catalyzed cross-couplings, enabling installation of (hetero)aryl, vinyl, alkynyl, and amine/alkoxy substituents. This single handle allows late-stage diversification without perturbing the fused heteroaromatic core.

• Regiochemical implications (general)

  • Substitution at the 7-position situates new functionality para to the ring nitrogen within the pyridine portion and meta/para to the sulfur across the fused framework. This arrangement can modulate basicity and H-bonding vectors in derived analogs.

• Common transformations (examples)

  • Suzuki–Miyaura to form biaryl libraries; subsequent oxidation/reduction on appended groups is straightforward.
  • Buchwald–Hartwig to access anilines and alkylamines; intramolecular variants can form N-bridged frameworks.
  • Sonogashira to append alkynes for further cycloadditions (e.g., click chemistry after azidation of the partner fragment).
  • Carbonylative couplings under CO to form amides/esters/acids.
  • Borylation (Miyaura) to the pinacol boronate; iterative coupling expands accessible chemical space.
  • Halogen–lithium exchange followed by electrophile capture (CHO, CO2, B(OR)3, Me3SiCl) for swift derivatization.

• Retrosynthetic value

  • Serves as a convergent linchpin: assemble the thienopyridine core early, then diversify at C-7 to explore vectors without reinvesting in core synthesis.

Target Specificity

Not applicable. This product is a small-molecule building block, not a biological reagent (e.g., antibody, enzyme, or probe) with defined biomolecular target specificity. No antigen/epitope, clone, isotype, or species reactivity information applies.

Domande frequenti

What is the purity of this product?

This product is supplied at ≥95% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 603305-89-1, the molecular formula is C7H4BrNS, and the molecular weight is 214.08 g/mol. InChIKey NLHODWKWTMTFEN-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.