This compound belongs to the class of organic compounds known as pyridazines and derivatives. These are compounds containing a pyridazine ring, which is a six-member aromatic ring containing two nitrogen atoms at positions 1 and 2, and four 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.
Determine the necessary mass, volume, or concentration for preparing a solution.
Dilution Calculator
Determine the dilution needed to prepare a stock solution.
Reconstitution Calculator
Recensioni
Recensioni dei clienti
Application Protocols
Not applicable. This SKU is a chemical building block rather than an antibody, enzyme, or assay kit. There are no WB/IHC/IF/FC protocols or recommended dilutions. For synthetic usage, see the Reaction Conditions, Reaction & Applications, and Synthetic Utility tabs.
Biological Roles
Scope: 4-Bromopyridazine is a synthetic heteroaromatic building block and does not have a known natural biological role.
General notes (literature; not item-specific)
Pyridazine cores are privileged motifs in chemical biology and agrochemical discovery due to their tunable electronics and hydrogen-bond accepting nitrogens.
The 4-bromo substituent acts as a synthetic handle to introduce diverse groups that modulate physicochemical properties (pKa, logD, HBA/HBD counts) of resulting derivatives.
The diazine nitrogens can engage in metal coordination and serve as ligation sites in probe design for enzyme or receptor studies; however, 4-bromopyridazine itself is typically a precursor rather than a probe.
The electron-deficient ring can influence metabolic soft spots in derived compounds (e.g., affecting aromatic oxidation propensities), which is assessed case-by-case in medicinal chemistry research.
Important limitations
No medical or clinical claims are made for this material. It is supplied strictly for research and laboratory use.
Any biological activity arises from derivatives synthesized from this building block; parent compound data are limited and context-dependent.
Buffer Applications
Not typically applicable. 4-Bromopyridazine is a non-buffering, neutral heteroaromatic building block and is not used to formulate pH buffers or electrophoresis running buffers. For aqueous work, choose standard buffering systems (e.g., phosphate, HEPES, acetate) appropriate to your application.
Green Alternatives
Greener choices relate primarily to solvent and coupling methodology; the substrate itself (4-bromopyridazine) is typically fixed by target design.
Solvent substitutions (literature guidance)
Replace DMF/NMP with Cyrene, propylene carbonate, or GBL where compatible.
Use 2-MeTHF or CPME instead of THF/toluene for some Pd couplings; 2-MeTHF offers partial water miscibility to support Suzuki in aqueous systems.
Dioxane alternatives: Consider tert-amyl alcohol, MeTHF, or ethanol/water mixtures for certain Suzuki reactions.
Process intensification
Micellar catalysis (aqueous surfactant media, e.g., TPGS-750-M) for Suzuki/Buchwald–Hartwig can reduce organic solvent usage.
Flow chemistry can reduce solvent volumes and improve heat/mass transfer.
Catalyst/ligand efficiency
Modern biaryl phosphines and NHC–Pd precatalysts often enable ppm-level Pd loadings, decreasing metal footprint.
Concise comparison (general; not item-specific)
Traditional: DMF, dioxane, toluene; 0.5–5 mol% Pd; 80–110 C.
Greener option: 2-MeTHF or aqueous micellar media; 100–1000 ppm Pd (where feasible); 25–80 C.
Trade-offs
Greener solvents may change substrate solubility and base compatibility; initial screening is recommended.
Micellar systems can complicate extraction and may require surfactant recovery protocols.
Pharmaceutical Uses
Context: This compound is a research-grade synthetic intermediate and is not an excipient or finished drug.
Typical roles (literature; not item-specific)
API/intermediate synthesis: Used to construct pyridazine-containing scaffolds by cross-coupling, enabling SAR exploration in medicinal chemistry programs.
Building block in library synthesis for hit-to-lead campaigns.
Regulatory status
No pharmacopeial monograph is expected for this specific building block.
When incorporated into GMP routes, the material specifications, impurity controls, and residual metal limits must be defined in the project-specific quality system.
Formulation/excipient use
None; not used as an excipient.
Note: No therapeutic, diagnostic, or clinical claims are made for this product. It is provided strictly for research and development in laboratory settings.
Physical Properties
Item-specific values (this SKU)
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Grade/Purity: 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 properties (typical for 4-bromopyridazine; for reference only)
Empirical formula: C4H3BrN2 (literature)
Formula weight (average): ~158.99 g/mol (calculated from atomic weights)
Physical state: Commonly reported as a crystalline solid at ambient conditions (literature); specific polymorph/appearance may vary by batch.
Solubility profile: Expected to be moderately soluble in polar aprotic organic solvents (e.g., DMSO, DMF, NMP) and in chlorinated/aromatic solvents (e.g., dichloromethane, chloroform, toluene); low aqueous solubility (literature, qualitative).
Volatility: Low; typical of halo-diazines (literature, qualitative).
Spectral identifiers: 1H/13C NMR and HRMS are routinely used; ring nitrogens and aryl bromide influence characteristic chemical shifts and isotopic patterns (literature, qualitative).
Notes
Do not treat literature values as specifications. For regulated or precision work, confirm all parameters on the product-specific CoA and SDS.
Actual handling properties (clumping, flow, hygroscopicity) can depend on storage history and particle size; check the container immediately upon receipt.
Quality and Grades
Item-specific grade/purity
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.
Guidance on grades (general; not item-specific)
Research grade: Suitable for general synthetic use. Trace impurities (e.g., residual halides, inorganic salts, or regioisomers) can influence catalytic reactions.
High-purity/99%+: Preferred for sensitive cross-couplings, C–H activations, and SAR studies where impurity carryover complicates interpretation.
HPLC grade (solvents) vs reagent grade (solids): For solid building blocks like 4-bromopyridazine, “HPLC grade” is not applicable; instead, look for assay by qNMR/GC, residual solvent profile, and metal content if relevant.
What to check on the CoA/Spec Sheet for this compound
Residual solvents and water (KF): Not specified for this item; refer to CoA/Spec Sheet.
Inorganic impurities/halide content or metal traces: Not specified for this item; refer to CoA/Spec Sheet.
Stabilizers/additives: Typically none for halo-diazines; any present should be declared on the CoA.
Practical note
For Pd-catalyzed couplings, low halide contaminants and well-defined purity improve reproducibility and catalyst turnover. If reactions are sluggish, check substrate purity and consider re-crystallization or silica plug before use.
Reaction and Applications
General use-cases (literature; building-block context)
Cross-coupling handle: The aryl bromide enables Suzuki–Miyaura (C–C), Buchwald–Hartwig (C–N), Sonogashira (C(sp2)–C(sp)) and Stille couplings to elaborate the pyridazine core with diverse substituents.
Regioselective functionalization: The diazine nitrogens direct metalation and can influence site-selectivity in subsequent C–H activation.
Nucleophilic aromatic substitution: Although aryl bromides are typically poor SNAr substrates, the electron-deficient pyridazine ring can engage in SNAr with strong nucleophiles under forcing conditions, especially when additional ring activation is present.
Heteroaryl diversification: Useful for preparing libraries of pyridazine derivatives for agrochemical and materials research.
Practical tips
Catalyst choice: Electron-poor heteroaryl bromides often couple efficiently with Pd(0/II) catalysts bearing bulky, electron-rich ligands (e.g., SPhos, XPhos, RuPhos) to accelerate oxidative addition and suppress deactivation by ring nitrogens.
Base/system: K2CO3, Cs2CO3, or NaOtBu are common; aqueous bases enable biphasic dioxane/H2O Suzuki conditions.
Additives: Use of phase-transfer agents or water co-solvent can improve Suzuki rates with boronic acids/esters.
Deactivation control: Free ring nitrogens can bind Pd and slow turnover. Consider protonation (acidic additives), ligand tuning, or increased catalyst loading.
Workup/purification: Residual Pd/Cu may coordinate to the diazine; charcoal treatment or metal scavengers can simplify isolation.
General literature conditions (typical ranges; verify experimentally for your system)
Suzuki–Miyaura coupling
Catalyst: Pd(PPh3)4 (1–3 mol%) or Pd2(dba)3 (0.5–2 mol%) with XPhos/SPhos (1–4 mol% ligand).
Base: K2CO3, Cs2CO3, or K3PO4 (2–3 equiv); aqueous base in dioxane/H2O (3:1 to 1:1) or 2-MeTHF/H2O.
Temperature/time: 60–100 C, 2–16 h.
Buchwald–Hartwig amination
Catalyst/ligand: Pd2(dba)3 (1 mol% Pd) + BrettPhos or RuPhos; or precatalysts (e.g., XPhos Pd G3 at 0.5–1 mol%).
Base/solvent: NaOtBu or Cs2CO3 in toluene, dioxane, or t-AmOH; 60–110 C, 4–18 h.
Sonogashira coupling
Catalyst: PdCl2(PPh3)2 (1–2 mol%) with CuI (2–5 mol%).
Base/solvent: Et3N, DIPEA, or i-Pr2NH in DMF, MeCN, or toluene; 25–80 C, 2–12 h.
Stille coupling
Catalyst: Pd(PPh3)4 (1–3 mol%); solvent toluene/dioxane; 80–110 C.
Tips for heteroaryl bromides
Ligand choice matters: Electron-rich bulky phosphines (XPhos/SPhos/BrettPhos) or NHCs can accelerate oxidative addition into electron-poor aryl–Br bonds.
Nitrogen coordination: Free diazine nitrogens can bind Pd; adjust ligand loading or add mild acid (e.g., 1–5 mol% MsOH) if deactivation is suspected.
Workup: Charcoal and metal scavengers (e.g., Si-TMT) help remove residual Pd/Cu.
These conditions are literature-style guidelines and not specifications for this SKU. Optimize for your substrates and scale.
Safety and Handling
Item-specific hazard data
GHS Classification: Not specified for this item; refer to SDS.
Signal Word / Pictograms / H-Statements: Not specified for this item; refer to SDS.
General safety considerations for aryl bromides and diazines (literature; not item-specific)
Likely hazards: May cause irritation to skin, eyes, and respiratory tract. Avoid inhalation of dust and contact with skin/eyes. Some halogenated heteroaromatics may be harmful if swallowed.
PPE: Use lab coat, safety glasses or splash goggles, and appropriate chemical-resistant gloves (e.g., nitrile). Handle in a fume hood to minimize exposure.
Incompatibilities: Strong bases and nucleophiles can react with aryl bromides under forcing conditions. Strong oxidizers should be avoided. Copper/metal powders may catalyze undesired reactions.
Thermal stability: Avoid excessive heat; decomposition can release hydrogen bromide and nitrogen-containing irritants.
Spill/accidental release: Avoid dust formation. Collect solids by gentle sweeping with inert absorbent. Dispose according to local regulations.
First aid (overview; defer to SDS):
Inhalation: Move to fresh air; seek medical attention if symptoms persist.
Skin contact: Wash with soap and water; remove contaminated clothing.
Eye contact: Rinse cautiously with water for several minutes; remove contact lenses if present and easy to do.
Ingestion: Rinse mouth; do not induce vomiting; seek medical advice.
Always consult the product-specific SDS for authoritative hazard classifications and response procedures.
Solvent Selection
Applicability: 4-Bromopyridazine is a polar, heteroaromatic aryl bromide. Solvent choice primarily concerns its role as a coupling substrate and its dissolution during synthesis and purification.
Polarity/miscibility (literature, qualitative)
Soluble in polar aprotic solvents: DMSO, DMF, NMP, DMAc.
Generally soluble in moderately polar organics: acetonitrile, ethyl acetate.
Often dissolves in chlorinated and aromatic solvents: dichloromethane, chloroform, toluene; solubility can be temperature-dependent.
Poorly soluble in water.
Choosing solvents by application
Pd-catalyzed cross-coupling (Suzuki/Buchwald–Hartwig/Sonogashira): 1,4-dioxane, toluene, anisole, tert-amyl alcohol, or mixed dioxane/water systems are common. For green alternatives, see the Green Alternatives tab.
SNAr or metalation chemistry: DMF, DMSO, or THF/Et2O with strong bases. Monitor for ring metallation near N atoms.
Crystallization/purification: Ethyl acetate/hexanes or toluene/hexanes systems often give good control of precipitation; DCM/MeOH can be used for trituration.
Comparison snapshot (general)
DMF/DMSO: Excellent solubility; high-boiling—harder to remove.
1,4-Dioxane/toluene: Coupling-friendly; balance between solubility and volatility.
MeCN/EtOAc: Lower boiling; may require heating for complete dissolution.
Note: Verify actual solubility and compatibility with your catalyst/base system at lab scale before scale-up.
Storage and Reconstitution
Item-specific storage
Storage Conditions: Room temperature (per Product Data).
Shipped In: Not specified for this item; refer to CoA/Spec Sheet.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
General handling guidance (literature; not item-specific)
Container: Store tightly closed in an inert atmosphere (nitrogen/argon) if long-term storage is anticipated, to minimize moisture uptake and potential hydrolysis.
Light/moisture: Protect from excessive moisture; store in a dry place. Light sensitivity is typically low for aryl bromides, but amber glass is prudent.
Stability: Halo-diazines are generally stable at ambient conditions. Avoid prolonged exposure to strong bases/acids during storage.
Reconstitution/solution prep
Solvents: Prepare stock solutions in dry DMSO, DMF, MeCN, or DCM depending on planned use. Filter through a PTFE syringe filter (0.2 µm) for sensitive applications.
Concentrations: Common lab stocks are 0.1–1.0 M in dry solvent for coupling screens; verify solubility before preparing concentrated solutions.
Freeze–thaw: For solutions, aliquot and store at low temperature (e.g., −20 C) to avoid repeated freeze–thaw; equilibrate to room temperature before opening to reduce condensation.
Always consult the product’s CoA and SDS for definitive guidance on storage, shelf life, and safe handling.
Structure and Identity
Brief overview: 4-Bromopyridazine is a halogenated diazine (pyridazine) bearing a bromine substituent at the 4-position, widely used as a cross-coupling handle on a nitrogen-rich aromatic scaffold.
Item-specific (from Product Data)
CAS: 115514-66-4
InChIKey: 38239 (as provided; truncated/atypical formatting in source)
Storage Conditions: Room temperature
Research Use Note: For research use only
Literature/computed (general reference; not item-specific)
Molecular formula (expected for 4-bromopyridazine): C4H3BrN2
InChI (not provided here); consult primary databases for the full string
Structural features (general chemistry description)
Ring system: Six-membered aromatic ring (pyridazine) with adjacent ring nitrogens at positions 1 and 2 (ortho-diazine).
Substitution pattern: Bromine at the 4-position (para to N1 across the ring), providing a good leaving group for Pd-catalyzed cross-couplings and enabling directed metalation strategies.
Functional groups: Aromatic C–Br (aryl bromide); two ring nitrogens that modulate electron density and coordination behavior.
2D structure in words: A benzene-like hexagon containing two neighboring nitrogens; counting from N at position 1 clockwise as N(1)–N(2)–C(3)–C(4)(Br)–C(5)–C(6).
Synthetic Utility
Functional elements and reactivity (literature; not item-specific)
Aryl bromide at C4: Serves as a versatile leaving group for Pd-catalyzed couplings (Suzuki, Buchwald–Hartwig, Sonogashira, Stille) and Ni-catalyzed transformations.
Diazine core: Electron-deficient and coordinating; influences oxidative addition rates and catalyst speciation. Nitrogen lone pairs can bind metals, sometimes necessitating stronger or more electron-rich ligands.
Directing ability: Ring nitrogens may direct ortho-metalation at C3/C5 under strong base/metal amide conditions, enabling sequential functionalization.
Retrosynthetic value
4-Bromopyridazine acts as a linchpin that convergently couples with boronic acids/esters, amines, alkynes, or stannanes to access a diverse array of 4-substituted pyridazines.
Can be elaborated first at C4 via cross-coupling, then further modified at other ring positions by electrophilic substitution, N-oxidation/reduction, or lithiation–quench sequences.
Representative transformations
Suzuki–Miyaura: Installation of aryl/heteroaryl moieties using bases such as K2CO3/Cs2CO3 in dioxane/H2O or MeTHF/H2O.
Buchwald–Hartwig amination: C–N coupling to give primary/secondary/tertiary anilines on the pyridazine ring using bulky biaryl phosphines.
Sonogashira: Formation of alkynyl derivatives that can undergo subsequent cycloadditions or reductions.
Halogen–lithium exchange at low temperature (careful control) to access 4-lithiopyridazine for electrophile trapping.
Target Specificity
Not applicable. This product is a small-molecule building block and not a biological affinity reagent. No antigen/epitope, species reactivity, clone, or isotype information applies.
Utilizziamo i cookie per garantire il corretto funzionamento del sito web e, ove consentito, per migliorare la tua esperienza. Puoi gestire le tue preferenze in qualsiasi momento nelle Impostazioni. Per saperne di più, consulta la nostra Cookie Policy.
Desidera che le inviamo un messaggio quando avremo sconti disponibili?
Ricordamelo più tardi
Grazie! Controlli la sua casella di posta per confermare.
Products are supplied to verified businesses, institutions, and qualified professionals for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
