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| Targets |
2-Bromo-5-fluoropyridine is a precursor for the synthesis of mGluR5 antagonists for the treatment of neuropathic pain. mGluR5 (metabotropic glutamate receptor 5) is a G protein-coupled receptor that plays a critical role in the modulation of synaptic transmission and plasticity. mGluR5 antagonists are being investigated for the treatment of various neurological and psychiatric disorders including neuropathic pain, anxiety, depression, and addiction. The compound serves as a building block for the construction of mGluR5 antagonists that target the receptor's orthosteric or allosteric binding sites. The compound's bromine atom allows for cross-coupling reactions to introduce various substituents, while the fluorine atom can influence pharmacokinetic properties and binding affinity. The compound is also a key intermediate in the synthesis of various pyridine-containing pharmaceuticals.
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| ln Vitro |
In vitro, 2-bromo-5-fluoropyridine is used in the synthesis of mGluR5 antagonists for the treatment of neuropathic pain. It can be used in the synthesis of 5-fluoro-2-phenylpyridine via Suzuki coupling reaction with phenylboronic acid and 5-fluoro-2-(p-tolyl)pyridine. It is a key intermediate in the synthesis of many pyridine compounds and is an important starting material for the synthesis of various pharmaceuticals. In medicinal chemistry, it serves as a versatile building block for constructing biologically active molecules, particularly mGluR5 antagonists and other pyridine-containing drugs. Its bromine atom allows for cross-coupling reactions such as Suzuki, Heck, and Buchwald-Hartwig couplings, enabling the introduction of various substituents. The fluorine atom can enhance metabolic stability and modulate lipophilicity. In organic synthesis, it is used as a building block for creating complex molecules efficiently.
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| ln Vivo |
In vivo activity is mediated through the derivatives of 2-bromo-5-fluoropyridine rather than the parent compound itself. mGluR5 antagonists synthesized from this compound are evaluated in animal models of neuropathic pain and other neurological disorders. In these studies, compounds are typically administered orally or intraperitoneally to rodents, and pain thresholds, behavioral responses, and other parameters are assessed. The parent compound itself is not administered in vivo, as it is a synthetic intermediate rather than a pharmacological agent.
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| Enzyme Assay |
Cell-free assays for 2-bromo-5-fluoropyridine are focused on its use as a chemical reagent. Standard protocols for Suzuki coupling involve mixing the compound with a boronic acid (1.2 equivalents), a palladium catalyst (2-5 mol%), a base (e.g., K2CO3 or Cs2CO3), and a solvent (e.g., toluene, dioxane, or DMF) at elevated temperatures (80-120°C) under an inert atmosphere for 12-24 hours. The reaction progress is monitored by TLC, GC, or HPLC, and the products are purified by column chromatography. For the synthesis of mGluR5 antagonists, the compound is used as a starting material in multi-step synthetic routes. The compound's reactivity can be studied using various analytical techniques including NMR spectroscopy, mass spectrometry, and HPLC.
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| Cell Assay |
Cellular assays are not performed with the parent compound 2-bromo-5-fluoropyridine. Instead, its derivatives, such as mGluR5 antagonists, are evaluated in cell-based systems. For mGluR5 antagonists, cell lines expressing mGluR5 are treated with the derivatives, and receptor binding, calcium flux, or other signaling endpoints are measured. The parent compound itself is not used as a test article in cell-based experiments due to its role as a synthetic building block.
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| Animal Protocol |
Animal studies are not conducted with the parent compound 2-bromo-5-fluoropyridine. Its derivatives, such as mGluR5 antagonists, are evaluated in animal models of neuropathic pain and other neurological disorders. The parent compound itself is not administered to animals, as it is a synthetic intermediate. Toxicity and pharmacological profiles for the parent compound are inferred from related halogenated pyridine derivatives.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 2-bromo-5-fluoropyridine are not available, as the compound is primarily a chemical intermediate rather than a drug candidate. With a molecular weight of 175.99 g/mol and appearing as a light yellow crystalline solid, the compound would be expected to have moderate lipophilicity and membrane permeability if administered. However, comprehensive pharmacokinetic studies including absorption, distribution, metabolism, and excretion have not been performed, as the compound is not intended for therapeutic use. For research purposes, the compound is typically handled as a neat chemical and not administered to living organisms for pharmacokinetic profiling.
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| Additional Infomation |
2-Bromo-5-fluoropyridine is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is used in the synthesis of mGluR5 antagonists for the treatment of neuropathic pain. It can be used in the synthesis of 5-fluoro-2-phenylpyridine via Suzuki coupling reaction with phenylboronic acid and 5-fluoro-2-(p-tolyl)pyridine. It is a key intermediate in the synthesis of many pyridine compounds and is an important starting material for the synthesis of various pharmaceuticals. The compound has a molecular weight of 175.99 g/mol and appears as a light yellow crystalline solid. It should be stored under cold conditions.
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| Molecular Formula |
C5H3BRFN
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| Molecular Weight |
175.99
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| Exact Mass |
174.943
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| CAS # |
41404-58-4
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| PubChem CID |
2783171
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| Appearance |
Colorless to off-white <30°C powder,>31°C liquid
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
171.6±20.0 °C at 760 mmHg
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| Melting Point |
30-31ºC
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| Flash Point |
57.6±21.8 °C
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| Vapour Pressure |
1.8±0.3 mmHg at 25°C
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| Index of Refraction |
1.534
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| LogP |
1.51
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
8
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| Complexity |
78.8
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(C=NC(=C1)Br)F
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| InChi Key |
UODINHBLNPPDPD-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C5H3BrFN/c6-5-2-1-4(7)3-8-5/h1-3H
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| Chemical Name |
2-bromo-5-fluoropyridine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.6821 mL | 28.4107 mL | 56.8214 mL | |
| 5 mM | 1.1364 mL | 5.6821 mL | 11.3643 mL | |
| 10 mM | 0.5682 mL | 2.8411 mL | 5.6821 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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