This compound belongs to the class of organic compounds known as 2-halopyrimidines. These are aromatic compounds containing a pyrimidine ring substituted at the 2-position with 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.
Prepare a 0.2–0.5 M stock in anhydrous DMF/DMSO under argon for SNAr screening; store aliquots at 2–8 °C, protected from light.
For Pd-catalyzed couplings, pre-dissolve substrate and base in degassed solvent, then add catalyst under inert conditions; monitor by LC–MS/19F NMR.
Refer to peer-reviewed literature or internal SOPs for detailed, validated procedures.
Biological Roles
Intrinsic biological role: None known for this substituted pyrimidine; it is a synthetic small-molecule building block.
Context (general biochemistry): The pyrimidine ring is a core heteroaromatic motif present in nucleobases (cytosine, thymine, uracil). Electron-deficient pyrimidines often engage in hydrogen bonding and π–stacking in biomolecular contexts, but halogenated derivatives like 2-bromo-5-fluoropyrimidine are not natural metabolites.
Research relevance: Fluorinated pyrimidines are widely explored in chemical biology and materials science for probe development, ligand tuning, and as intermediates toward bioactive analogs. However, this product is provided strictly for research and laboratory synthesis; no clinical or in vivo use is intended.
Research Use Note: For research use only.
Buffer Applications
This compound is a neutral, poorly water-soluble heteroaromatic building block and is not used as a buffering agent. It does not form a defined conjugate acid/base pair within physiological pH suitable for buffer preparation.
Practical note:
For aqueous work, prepare stock solutions in DMSO/DMF or co-solvent systems before dilution into buffered media if required for assays. Select buffers based on the biological system rather than this compound’s properties.
Green Alternatives
Greener choices focus on solvent and catalyst systems while maintaining chemoselectivity between C–Br and C–F sites.
Solvent substitutions (literature/general):
Replace DMF/DMAc with 2-MeTHF, CPME, or bio-based solvents (e.g., propylene carbonate) for cross-couplings where compatible with the chosen Pd/Ni system.
Use aqueous micellar catalysis (TPGS-750-M, Savie) enabling room-temperature to moderate-temperature couplings in water-rich media; may reduce organic solvent volumes.
For SNAr, consider sulfolane or propylene carbonate as higher boiling, less regulated alternatives to DMSO/DMF.
Catalyst/base economy:
Nickel catalysis for aryl bromide couplings can reduce reliance on precious metals; requires ligand optimization.
Heterogeneous Pd (Pd/C, Pd on eco-friendly supports) and ppm-level catalysis with Buchwald precatalysts reduce metal burden.
Trade-offs (balanced view):
2-MeTHF/CPME improve workups and EHS profile but can lower solubility of inorganic bases and nucleophiles; phase-transfer or base selection may be needed.
Aqueous micellar systems may demand surfactant removal and can be sensitive to heteroaryl substrates’ solubility.
Propylene carbonate/sulfolane offer high boiling points but can complicate removal; consider solvent swaps.
Recommendation: Screen greener solvent/catalyst matrices early (DoE) to secure both performance and sustainability without compromising selectivity at C-2 vs C-5.
Pharmaceutical Uses
Role: Potential intermediate in the synthesis of drug-like molecules incorporating substituted pyrimidines. It is not an excipient and has no approved therapeutic use.
Formulation status: Not applicable. No pharmacopeial monograph is indicated for this specific substituted pyrimidine.
Process considerations (general):
The orthogonal C–Br and C–F handles allow convergent routes to API intermediates.
Downstream purifications should account for residual palladium/nickel if cross-couplings are employed; plan for metal scavenging and ICH Q3D compliance in API contexts.
Research Use Note: For research use only. Not for human or veterinary use.
Physical Properties
Item-specific specifications are not provided in the Product Data for this SKU.
Appearance: Not specified for this item; refer to CoA/Spec Sheet.
Melting point: Not specified for this item; refer to CoA/Spec Sheet.
Boiling point: Not specified for this item; refer to CoA/Spec Sheet.
Density: Not specified for this item; refer to CoA/Spec Sheet.
Refractive index: Not applicable/unknown for solid; Not specified for this item; refer to CoA/Spec Sheet.
Organic: typically soluble in polar aprotic solvents (DMSO, DMF, DMAc, NMP) and moderately in EtOAc/MeCN; limited solubility in alkanes/alcohols.
Aqueous: very low without cosolvents or pH adjustment.
LogP/logD: Not specified for this item; refer to CoA/Spec Sheet. Electron-deficient heteroaryl halides generally show low-to-moderate lipophilicity (literature trend).
pKa: The pyrimidine ring is weakly basic; conjugate acid pKa for pyrimidines is typically ~1–2 (literature, scaffold-level), but substituents can shift values. No item-specific value is provided.
Always consult the current CoA/SDS for authoritative physico-chemical data required for process design or hazard assessment.
Quality and Grades
Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet for exact assay, impurity profile, and residual solvent limits.
Interpretation and guidance:
For cross-coupling applications (Suzuki, Buchwald–Hartwig, Sonogashira), trace metal and halide purity can strongly impact catalyst turnover. When grade is unspecified, review the CoA for:
Assay (% area by HPLC/GC)
Residual halides or regioisomers
Water content (Karl Fischer)
Metal content (ICP) if relevant to downstream needs
If LC/GC/HPLC grades are available, they generally imply lower UV background and tighter limits on non-volatile residues—beneficial for analytical development.
Stabilizer: None is specified. Many heteroaryl halides are shipped without stabilizers; if stabilizers are used, they may subtly affect certain reactions (e.g., base-sensitive SNAr). Always check the CoA.
Recommendation:
For medicinal/process chemistry, verify spectral identity (1H/13C/19F NMR) and assay on receipt. For sensitive catalytic couplings, consider pre-washing or recrystallization if required to remove protic or ionic contaminants.
Reaction and Applications
This bifunctional heteroaryl halide is a versatile building block for constructing functionalized pyrimidines.
Suzuki–Miyaura with aryl/heteroaryl/alkenyl boron reagents to furnish 2-substituted-5-fluoropyrimidines.
Buchwald–Hartwig amination to install anilines or alkyl amines at C-2; BrettPhos/DavePhos-type ligands are often effective on electron-deficient diazines.
Displacement by amines, thiols, or alkoxides under basic conditions (e.g., Cs2CO3/K2CO3 in DMF/DMSO), leveraging the electron-poor ring.
Orthogonal sequences:
Sequence control allows selective C-2 coupling (Br) followed by C-5 SNAr, or vice versa using chemoselective conditions.
Late-stage diversification:
The ring’s innate activation enables rapid SAR expansion for agrochemical and materials leads (no clinical claims), and incorporation into heteroaromatic scaffolds for catalysis ligands or functional materials.
Practical tips:
Use rigorously anhydrous, oxygen-free conditions for Pd-catalyzed steps; degas solvents (sparging or freeze–pump–thaw).
Bases: K3PO4, K2CO3, Cs2CO3 commonly used; tBuONa/tBuOK for challenging couplings.
Monitor by LC–MS; 19F NMR is a sensitive handle to track C-5 substitution.
Protect from light and store under argon (as per Product Data) to preserve integrity between steps.
Reaction Conditions
The following are typical literature/general conditions for pyrimidinyl bromides bearing a C-5 fluoro group; optimize per substrate and scale.
Suzuki–Miyaura (C-2 coupling):
Catalyst: Pd(dppf)Cl2·DCM (1–3 mol%) or Pd-PEPPSI/precatalysts; 0.5–2 mol% on small scale if active ligands used.
Base: K3PO4, K2CO3, or Cs2CO3 (2–3 equiv).
Solvent: 1,4-dioxane/H2O or 2-MeTHF/H2O (degassed).
Temperature/time: 60–100 °C, 2–16 h (literature ranges). Yields often good to excellent with aryl boronates.
Buchwald–Hartwig amination (C-2):
Catalyst/ligand: Pd2(dba)3 with BrettPhos/XPhos, or preformed Pd-BrettPhos precatalyst (1–3 mol%).
Base: NaOtBu or Cs2CO3 (2–3 equiv).
Solvent: Toluene, dioxane, or CPME.
80–110 °C, 4–18 h.
Sonogashira (C-2):
Catalyst: Pd(PPh3)2Cl2 (1–3 mol%) + CuI (5–10 mol%) or copper-free systems.
Hazard classification details are not provided in the Product Data for this item. Defer to the product SDS for authoritative information.
GHS/CLP: Not specified for this item; refer to SDS.
Signal word, H- and P-statements, pictograms: Not specified for this item; refer to SDS.
General laboratory safety for heteroaryl halides (guidance):
PPE: lab coat, chemical-resistant gloves (e.g., nitrile), splash goggles; handle in a fume hood to avoid inhalation of dust/vapors.
Incompatibilities: Strong bases/acids may promote decomposition or reaction; avoid strong nucleophiles unless intended. Keep away from oxidizers and reducing agents incompatible with organohalides.
Special risks: Aromatic bromides can be irritants; pyrimidine derivatives may be harmful if swallowed/inhaled. Avoid dust formation. No known tendency for peroxide formation.
First aid (overview; see SDS):
Inhalation: move to fresh air; seek medical attention if symptoms persist.
Skin/eye: rinse with water for several minutes; remove contaminated clothing; obtain medical advice if irritation continues.
Ingestion: rinse mouth; do not induce vomiting; seek medical attention.
Storage/handling per Product Data:
Store at 2–8°C, protected from light, under argon.
Shipped on wet ice.
Handle under inert atmosphere for moisture/air-sensitive transformations. Keep container tightly closed. Use dry techniques for coupling chemistry.
Solvent Selection
Profile and practical selection for a heteroaryl bromofluoropyrimidine:
Polarity/miscibility (general):
Best solubility in polar aprotic media: DMSO, DMF, DMAc, NMP, acetonitrile.
Moderate in ethyl acetate, dioxane, THF; limited in toluene/hexanes.
Selection by transformation:
Pd-catalyzed cross-coupling at C-2 (Br): dioxane/H2O, THF/H2O, toluene, MeCN, or green alternatives like 2-MeTHF/CPME depending on catalyst/base.
SNAr at C-5 (F): DMF/DMSO/DMAc or NMP to solubilize nucleophiles and withstand elevated temperatures; alcohols for alkoxide SNAr.
Dual functionalization sequences: Begin with solvent compatible with first step (e.g., dioxane for Suzuki), then switch to high-boiling polar aprotic for SNAr if required.
Dryness/inertness: Air/moisture exclusion improves cross-coupling reliability; use anhydrous grades and degassed solvent.
Comparison (general):
DMSO/DMF: maximize solubility and SNAr rates; challenging removal and regulatory burden.
2-MeTHF/CPME: greener, easier workup; may need higher temperature or tailored ligands for couplings.
MeCN: good for many Pd couplings; limited high-temperature headroom (bp ~82 °C, literature).
Choose solvent based on catalytic system, base solubility, and downstream isolation constraints.
Storage and Reconstitution
From Product Data:
Storage conditions: Store at 2–8 °C, protected from light, under argon (argon-charged).
Shipping: On wet ice.
Practical guidance:
Keep container tightly closed; purge headspace with inert gas after each use. Minimize exposure to ambient moisture and light to preserve assay and limit hydrolytic side reactions.
Reconstitution/stock solutions:
Prepare solutions in anhydrous solvents such as DMSO, DMF, DMAc, NMP, or MeCN under inert atmosphere.
Typical screening concentrations: 0.1–0.5 M for cross-coupling or SNAr libraries (adjust to solubility).
Filter (PTFE, 0.2 µm) if particulates are present before use in automated platforms.
Stability: Item-specific stability data are not provided; refer to CoA/Spec Sheet. As a general practice, store solutions at 2–8 °C protected from light; use fresh solutions for sensitive catalytic reactions.
Avoid repeated freeze–thaw of stock solutions; dispense single-use aliquots when possible.
Always consult the current CoA/SDS for definitive storage limits and handling recommendations.
Structure and Identity
A heteroaryl halide building block featuring a pyrimidine core bearing bromine at C-2 and fluorine at C-5. The scaffold provides orthogonal handles for cross-coupling (C–Br) and SNAr (C–F) chemistry.
SKU: B178446
Product name: 2-bromo-5-fluoropyrimidine
CAS: 947533-45-1
CID: 26344048
InChIKey (as provided): 10267
SMILES: Not specified for this item; refer to CoA/Spec Sheet.
Molecular formula: C4H2BrFN2 (literature)
Molecular weight: ~176.97 g/mol (literature)
Structural features (descriptive):
Core: six-membered aromatic diazine (pyrimidine) ring with ring nitrogens at positions 1 and 3.
Substituents: bromine at the 2-position (activated for Pd-catalyzed cross-coupling) and fluorine at the 5-position (activated toward SNAr by ring nitrogens).
Planar, electron-deficient heteroaromatic system enhancing susceptibility to nucleophilic aromatic substitution at C-5 and facilitating oxidative addition at C-2.
Note: Identity strings (SMILES/InChIKey) above should be verified against the current CoA/Spec Sheet before regulatory documentation or database registration.
Synthetic Utility
Functional group and reactivity highlights enabling efficient synthesis planning:
Orthogonal handles:
C–Br at C-2: Pd/Ni-catalyzed cross-couplings (Suzuki, Negishi, Kumada, Stille, Sonogashira; Buchwald–Hartwig amination) proceed readily due to the electron-deficient ring that accelerates oxidative addition.
C–F at C-5: Activated toward SNAr by ring nitrogens; displacement by N/O/S nucleophiles enables rapid library build-out.
Retrosynthetic value:
Serves as a node for late-stage diversification: assemble the core early, then introduce diverse aryl/alkyl/alkynyl groups at C-2 and heteroatom substituents at C-5.
Enables regioselective construction of 2,5-disubstituted pyrimidines without protecting groups.
Chemo-/regioselectivity control:
Typical order: C-2 coupling (Br) first, then C-5 SNAr. In special cases, strongly nucleophilic conditions can target C-5 first while preserving C–Br for a subsequent coupling.
Further elaboration:
Lithiation at C-4 (with careful control) followed by electrophile trapping can access 4-substituted derivatives (advanced use; consult literature).
Halogen–metal exchange on C-2 (Br) is possible at low temperature but less common than cross-coupling for this electron-poor system.
Overall, the substrate streamlines access to medicinally relevant pyrimidine architectures and functional materials.
Target Specificity
Not applicable. This product is a small-molecule chemical building block, not a biological reagent (e.g., antibody/ligand) with defined biological targets. No antigen/epitope, clone, isotype, or species reactivity applies.
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