4-Bromo-2-hydroxypyridine
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4-Bromo-2-hydroxypyridine (4-Bromo-2-pyridone) is a brominated pyridine/pyridone chemical building block. 4-Bromo-2-hydroxypyridine exists in tautomeric forms between 2-hydroxypyridine and pyridin-2 (1H)-one. 4-Bromo-2-hydroxypyridine is used for the synthesis of bromopyridone nucleoside analogs, phosphoramidite intermediates, and 4-phenylpyridin-2-one derivatives. 4-Bromo-2-hydroxypyridine is applied in studies on heterocyclic synthesis and oligonucleotide modification chemistry.
For research use only. We do not sell to patients.
- Purity: 99.04%
- CAS No.: 36953-37-4
- Formula: C5H4BrNO
- Molecular Weight:174.00
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Storage:Powder -20°C, 3 years , 4°C, 2 years ; In solvent -80°C, 6 months , -20°C, 1 month
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Biological Activity
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Chemical Information
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Solvent & Solubility
- Purity & Documentation
- References
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Help & FAQs
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Biological Activity
4-Bromo-2-hydroxypyridine (440 mg; MeCN; room temperature; overnight) undergoes Lewis acid-mediated glycosylation with α-chloro sugar to produce β-isomer 10a (38%) and α-isomer 11a (37%); β-isomer 10a is converted into bromopyridone nucleoside analogue 7 (81%) via methanolysis, followed by further preparation of phosphoramidite 12a and nucleotide triphosphate 15[1].
Reaction of 4-Bromo-2-hydroxypyridine (10.0 g; 120 °C; 4 h) with 1,2-cyclohexene oxide and K2CO3 yields 2-alkoxypyridine 4a (7%) and N-alkylpyridin-2-one 4b (77%); this product distribution is associated with the 2-hydroxypyridine/pyridin-2 (1H)-one tautomerism of 4-Bromo-2-hydroxypyridine[2].
Reaction of 4-Bromo-2-hydroxypyridine (500 mg; 120 °C; 5 days) with bromocyclohexane and K2CO3 yields 4-bromo-1-cyclohexylpyridin-2 (1H)-one 11b (16%)[3].
4-Bromo-2-hydroxypyridine (300 mg; room temperature; 24 h) reacts with 2-bromo-N,N-dimethylacetamide, K2CO3, and KI to yield 2-(4-bromo-2-oxopyridin-1 (2H)-yl)-N,N-dimethylacetamide 11c[3].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS No. 36953-37-4
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Appearance Solid
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Molecular Weight 174.00
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Formula C5H4BrNO
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Color White to light brown
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SMILES
OC1=NC=CC(Br)=C1
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Synonyms
4-Bromo-2-pyridone
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Solvent & Solubility
DMSO : 100 mg/mL (574.71 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Select the appropriate dissolution method based on your experimental animal and administration route.
- For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
- To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for In Vivo experiments, it is recommended to prepare freshly and use it on the same day.
- The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.
Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (14.37 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (14.37 mM); Clear solution
This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Please enter the basic information of animal experiments:
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Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Please enter your animal formula composition:
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%DMSO +
Recommended: Keep the proportion of DMSO in working solution below 2% if your animal is weak.
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%+
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+%Tween-80 + +
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%Saline +
The co-solvents required include: DMSO, . All of co-solvents are available by MedChemExpress (MCE). , Tween 80. All of co-solvents are available by MedChemExpress (MCE).
Working solution concentration: 0.22 mg/mL
Method for preparing stock solution: mg drug dissolved in μL DMSO. Stock solution concentration: mg/mL.
1. Take μL DMSO stock solution;
2. Add μL .
μL , mix evenly;
3. Then add μL Tween 80, mix evenly;
4. Then add μL
Please ensure that the stock solution in the first step is dissolved to a clear state, and add co-solvents in sequence. You can use ultrasonic heating (ultrasonic cleaner, recommended frequency 20-40 kHz), vortexing, etc. to assist dissolution.
Purity & Documentation
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Data Sheet (273 KB)
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SDS (393 KB)
- English - EN (393 KB)
- Français - FR (393 KB)
- Deutsch - DE (393 KB)
- Norwegian - NO (393 KB)
- Español - ES (393 KB)
- Swedish - SV (393 KB)
- Italian - IT (393 KB)
- Korean - KR (393 KB)
- Portuguese - PT (393 KB)
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Handling Instructions (2659 KB)
References
[2]. Mistry SN, et al. 4-Phenylpyridin-2-one Derivatives: A Novel Class of Positive Allosteric Modulator of the M1 Muscarinic Acetylcholine Receptor. Journal of medicinal chemistry. 2016 Jan 14;59(1):388-409. [Content Brief]
[3]. Jörg M, et al. Development of Novel 4-Arylpyridin-2-one and 6-Arylpyrimidin-4-one Positive Allosteric Modulators of the M Muscarinic Acetylcholine Receptor. ChemMedChem. 2021 Jan 08;16(1):216-233. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 5.7471 mL | 28.7356 mL | 57.4713 mL | 143.6782 mL |
| 5 mM | 1.1494 mL | 5.7471 mL | 11.4943 mL | 28.7356 mL | |
| 10 mM | 0.5747 mL | 2.8736 mL | 5.7471 mL | 14.3678 mL | |
| 15 mM | 0.3831 mL | 1.9157 mL | 3.8314 mL | 9.5785 mL | |
| 20 mM | 0.2874 mL | 1.4368 mL | 2.8736 mL | 7.1839 mL | |
| 25 mM | 0.2299 mL | 1.1494 mL | 2.2989 mL | 5.7471 mL | |
| 30 mM | 0.1916 mL | 0.9579 mL | 1.9157 mL | 4.7893 mL | |
| 40 mM | 0.1437 mL | 0.7184 mL | 1.4368 mL | 3.5920 mL | |
| 50 mM | 0.1149 mL | 0.5747 mL | 1.1494 mL | 2.8736 mL | |
| 60 mM | 0.0958 mL | 0.4789 mL | 0.9579 mL | 2.3946 mL | |
| 80 mM | 0.0718 mL | 0.3592 mL | 0.7184 mL | 1.7960 mL | |
| 100 mM | 0.0575 mL | 0.2874 mL | 0.5747 mL | 1.4368 mL |
4-Bromo-2-hydroxypyridine Related Classifications
HY-65036 Related Classifications
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- 4-Bromo-2-hydroxypyridine
- 36953-37-4
- 4-Bromo-2-pyridone
- Biochemical Assay Reagents
- DNA/RNA Synthesis
- human deoxycytidine kinase
- PCR products
- DNA polymerases
- DNA interstrand cross-links
- Klenow (exo-)
- DU145 prostate cancer cells
- p53 gene
- prostate cancer
- Suzuki coupling
- M1 muscarinic acetylcholine receptor
- Inhibitor
- inhibitor
- inhibit