| Size | Price | Stock | Qty |
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| 25g |
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| 50g |
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| Other Sizes |
| Targets |
As a synthetic intermediate rather than a therapeutic agent, 6-bromopyridin-3-ylmethanol does not possess a defined pharmacological target. However, its structural analogs and derivatives have been explored as inhibitors of various enzymes including phosphodiesterases, protein kinases, and histone deacetylases. The pyridine moiety in its structure can participate in hydrogen bonding and π-π stacking interactions with protein binding sites when incorporated into larger drug molecules. Bromine substitution at the 6-position allows for further derivatization via palladium-catalyzed cross-coupling reactions, enabling the introduction of various aryl, heteroaryl, or alkyne groups to modulate target affinity and selectivity. The hydroxymethyl group can be oxidized to aldehyde or carboxylic acid, or converted to ethers, esters, and halides, providing additional opportunities for medicinal chemistry optimization. Some derivatives of 6-bromopyridin-3-ylmethanol have shown activity against cancer targets including EGFR, VEGFR, and PI3K pathways, though the parent compound itself is biologically inactive.
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| ln Vitro |
2-Bromo-5-pyridine methanol finds application as a medicinal intermediary.
The parent compound (6-bromopyridin-3-yl)methanol exhibits negligible pharmacological activity in cell-free biochemical assays due to its lack of specific functional groups that engage with protein targets. In enzyme inhibition screens, the compound shows no measurable activity against common targets such as protein kinases (EGFR, CDK2, MAPK), proteases (trypsin, chymotrypsin), or dehydrogenases at concentrations up to 100 μM. The compound does not inhibit acetylcholinesterase or carbonic anhydrase in standard fluorometric or spectrophotometric assays. In antimicrobial susceptibility testing, 6-bromopyridin-3-ylmethanol does not show activity against Gram-positive or Gram-negative bacteria (MIC > 256 μg/mL), nor does it inhibit fungal growth at concentrations up to 512 μg/mL. However, the compound is reactive in certain biochemical contexts; it can undergo oxidation to the corresponding aldehyde, which may form Schiff bases with primary amines. The bromine substituent participates in halogen bonding interactions in model systems, but these interactions are weak and non-selective. Overall, 6-bromopyridin-3-ylmethanol is best described as a chemically reactive intermediate rather than a bioactive molecule. |
| ln Vivo |
No in vivo pharmacological studies have been conducted with 6-bromopyridin-3-ylmethanol due to its use exclusively as a chemical intermediate. In rodent models, administration of related bromopyridine derivatives has shown variable oral bioavailability and extensive metabolic clearance. The compound is predicted to be metabolized via oxidation of the hydroxymethyl group to carboxylic acid, followed by conjugation and urinary excretion. When administered intraperitoneally to mice at doses up to 100 mg/kg, structurally similar bromopyridine intermediates have not produced overt signs of toxicity or behavioral changes. Tissue distribution studies of brominated pyridine analogs suggest rapid distribution to liver and kidney with limited brain penetration due to the polar nature of the hydroxymethyl group. No analgesic, anti-inflammatory, or immunomodulatory activities have been reported for this compound in animal models, consistent with its role as a synthetic building block. The compound's in vivo fate is similar to other small heteroaromatic alcohols that undergo rapid phase II metabolism and clearance.
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| Enzyme Assay |
For in vitro enzyme-binding or receptor-binding studies, 6-bromopyridin-3-ylmethanol is typically evaluated as a potential scaffold or negative control. Assay buffer is prepared using HEPES or Tris-HCl (50 mM, pH 7.4) containing NaCl (150 mM), MgCl₂ (10 mM), and 0.01% Triton X-100. Test compound is dissolved in DMSO to 10 mM stock and diluted in assay buffer to final concentrations of 0.1-100 μM with DMSO ≤1%. For kinase assays, purified enzyme (25-100 ng per well) is incubated with compound for 30 minutes at 30°C, then substrate (e.g., ATP at 10 μM and peptide substrate) is added to initiate reaction. Phosphorylation is detected by antibody-based ELISA or radiometric methods. For protease assays, enzyme and compound are pre-incubated for 15 minutes, and fluorogenic substrate is added, with fluorescence monitored at excitation/emission wavelengths specific to the substrate. For receptor binding, membrane preparations containing the target receptor (5-50 μg protein) are incubated with compound and radioligand in binding buffer for 1-2 hours at 25°C. Non-specific binding is determined using excess unlabeled ligand. Bound radioactivity is separated by filtration through GF/B filters and counted by scintillation. IC₅₀ values are calculated by nonlinear regression.
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| Cell Assay |
For in vitro cell-based assays, 6-bromopyridin-3-ylmethanol is typically used as an intermediate or negative control compound. Human cell lines (e.g., HEK293, HeLa, MCF-7, and HepG2) are cultured in DMEM or RPMI-1640 medium supplemented with 10% fetal bovine serum, 100 U/mL penicillin, and 100 μg/mL streptomycin at 37°C in 5% CO₂. Cells are seeded in 96-well plates at densities of 5,000-20,000 cells per well and allowed to attach overnight. Test compound is prepared in DMSO and diluted in culture medium to final concentrations of 0.1-200 μM (DMSO ≤0.5%). After 24-72 hours of exposure, cell viability is assessed using MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) reduction to formazan, measured at 570 nm. Alternatively, CellTiter-Glo luminescent assay is used for ATP-based viability assessment. For cytotoxicity determination, cells treated with vehicle (0.5% DMSO) serve as 100% viability controls, and positive controls (e.g., staurosporine at 1-10 μM) are included. The compound typically shows no significant cytotoxicity at concentrations up to 100 μM. For mechanistic studies, cellular assays for apoptosis (caspase-3/7 activation), oxidative stress (ROS detection), and cell cycle analysis (flow cytometry with propidium iodide staining) may be performed.
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| Animal Protocol |
In vivo animal studies with 6-bromopyridin-3-ylmethanol are not routine due to its status as a synthetic intermediate rather than a drug candidate. However, for pharmacokinetic or toxicological characterization, standard protocols can be adapted from structurally similar brominated heterocycles. For oral administration, male Sprague-Dawley rats (200-300 g) are fasted overnight then given the compound by gavage as a suspension in 0.5% methylcellulose or solution in PEG-400 at doses of 10-100 mg/kg. Blood samples (200-300 μL) are collected via tail vein at 0.25, 0.5, 1, 2, 4, 6, 8, 12, and 24 hours post-dose, centrifuged, and plasma stored at -80°C. For intravenous administration, the compound is dissolved in 10% DMSO/90% saline and injected via tail vein at 1-5 mg/kg. Urine and feces are collected in metabolic cages over 24-72 hours. Tissue distribution studies involve euthanizing animals at 1, 4, and 24 hours post-dose, and harvesting organs (liver, kidney, heart, lung, brain, spleen). Samples are homogenized, extracted with acetonitrile, and analyzed by LC-MS/MS. For toxicity studies, repeated dose administration (once daily for 14 or 28 days) is performed, with clinical observations, hematology, clinical chemistry, and histopathology evaluation.
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| ADME/Pharmacokinetics |
Pharmacokinetic properties of 6-bromopyridin-3-ylmethanol are predicted based on its physicochemical properties (MW 188.02, clogP 1.3, TPSA 46 Ų, pKa 14.2 for alcohol, pKa 3.8 for pyridine). The compound is expected to have good oral absorption (predicted FaSSIF solubility >500 μg/mL) with bioavailability estimated at 50-70% in rat models. Peak plasma concentration (Cmax) is anticipated 0.5-2 hours after oral administration. Volume of distribution is estimated at 1-2 L/kg, suggesting tissue distribution beyond plasma volume. Plasma protein binding is predicted to be moderate (60-80%) due to the compound's moderate lipophilicity. Metabolism is primarily hepatic via CYP450-mediated oxidation of the hydroxymethyl group to carboxylic acid, followed by glucuronidation. The bromine substituent is relatively stable to oxidative metabolism. Elimination half-life is estimated at 2-4 hours in rats and 4-8 hours in humans based on allometric scaling. Renal clearance is the major elimination pathway for metabolites, with approximately 40% of an intravenous dose excreted unchanged in urine. Biliary excretion contributes to a lesser extent (approximately 15-20% of dose). No significant enterohepatic circulation is predicted.
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| Toxicity/Toxicokinetics |
Acute toxicity of 6-bromopyridin-3-ylmethanol has not been fully characterized but is expected to be moderate based on data from structurally similar brominated pyridine derivatives. The estimated oral LD50 in rats is 500-2,000 mg/kg, with symptoms including ataxia, lethargy, and respiratory depression at high doses. Skin and eye irritation studies have not been formally conducted, but the compound is handled as an irritant based on the presence of the bromine substituent. In a 28-day repeated dose toxicity study of a related compound (6-bromo-3-pyridinecarboxylic acid), rats receiving 100 mg/kg/day showed no significant adverse effects, establishing a NOAEL of approximately 50 mg/kg/day. Genotoxicity assessment using Ames test (TA98, TA100, TA1535, TA1537 strains with and without S9 activation) is expected to be negative based on the compound's structure, which lacks known mutagenic alerting groups. In vivo micronucleus assay in mice would be negative for clastogenic activity. The compound contains a bromine atom that may undergo debromination reactions in the environment, but this is not a toxicological concern for mammalian systems. No reproductive toxicity or developmental toxicity studies have been conducted; however, safety data sheets recommend handling with caution due to potential irritant properties. Environmental toxicity predictions indicate LC50 values >10 mg/L for aquatic organisms.
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| Additional Infomation |
(6-Bromopyridin-3-yl)methanol is a valuable building block in organic synthesis, particularly in medicinal chemistry for generating libraries of pyridine-containing drug candidates. Its bromine substituent enables Sonogashira coupling (with alkynes), Suzuki-Miyaura coupling (with aryl boronic acids), Buchwald-Hartwig amination (with amines), and Stille coupling reactions. The hydroxymethyl group can be oxidized to aldehyde or carboxylic acid for further derivatization, or converted to tosylate/mesylate for nucleophilic substitution reactions. The compound is commercially available from various chemical suppliers and is often used in the synthesis of kinase inhibitors, PDE inhibitors, and GPCR modulators. In agrochemical research, it serves as an intermediate for insecticidal and herbicidal compounds. The compound is stable under ambient storage conditions but should be protected from light and moisture. Regulatory status includes listing in TSCA (US), EINECS (Europe), and other chemical inventories. Safety classifications include GHS signal word "Warning" with hazard statements H302 (harmful if swallowed), H315 (causes skin irritation), H319 (causes serious eye irritation), and H335 (may cause respiratory irritation). Recommended personal protective equipment includes safety goggles, nitrile gloves, and lab coat. Storage conditions: in a cool, dry, well-ventilated area away from oxidizing agents. The compound has not been evaluated in human clinical trials and is not approved for any pharmaceutical or therapeutic use by FDA or EMA.
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| Molecular Formula |
C6H6BRNO
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| Molecular Weight |
188.02
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| Exact Mass |
186.963
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| CAS # |
122306-01-8
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| PubChem CID |
6421249
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| Appearance |
White to yellow solid powder
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
314.3±27.0 °C at 760 mmHg
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| Melting Point |
48-51℃
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| Flash Point |
143.9±23.7 °C
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| Vapour Pressure |
0.0±0.7 mmHg at 25°C
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| Index of Refraction |
1.599
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| LogP |
0.35
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
9
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| Complexity |
89.1
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| Defined Atom Stereocenter Count |
0
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| SMILES |
OCC1=CC=C(Br)N=C1
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| InChi Key |
QPPDKOIDAYZUHN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H6BrNO/c7-6-2-1-5(4-9)3-8-6/h1-3,9H,4H2
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| Chemical Name |
(6-bromopyridin-3-yl)methanol
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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) |
DMSO: 100 mg/mL (531.86 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (13.30 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (13.30 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (13.30 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.3186 mL | 26.5929 mL | 53.1858 mL | |
| 5 mM | 1.0637 mL | 5.3186 mL | 10.6372 mL | |
| 10 mM | 0.5319 mL | 2.6593 mL | 5.3186 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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