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| Targets |
6-Bromonicotinonitrile does not have a specific primary biological target, as it functions primarily as a synthetic intermediate. However, the compound has been used as an efficient method for treatment of trypanosomiasis, which may be due to its ability to induce rapid death of the parasites. Trypanosomiasis is a parasitic disease caused by Trypanosoma species, and the compound's ability to kill parasites suggests that it or its derivatives may target essential parasitic proteins or metabolic pathways. The compound's nitrile group and bromine atom provide reactive sites for further functionalization, enabling the synthesis of derivatives with potential biological activity. In medicinal chemistry, it is used as a building block for constructing biologically active molecules.
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| ln Vitro |
In vitro, 6-bromonicotinonitrile is used as a sulfonylation reagent for organic synthesis and drug discovery. It is a biochemical reagent that can be used as a biomaterial for life science related research. The compound is a diamidine synthesized by the reaction of 6-bromonicotinic acid with 2,2'-diaminodiphenyl ether. It has been used as an efficient method for treatment of trypanosomiasis. In medicinal chemistry, it serves as a building block for constructing complex molecular architectures. Its dual functional groups (bromine and nitrile) allow for diverse chemical transformations, including cross-coupling reactions and nitrile functionalization. In organic synthesis, it is used as a versatile building block for creating complex molecules efficiently.
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| ln Vivo |
In vivo, 6-bromonicotinonitrile has been used as an efficient method for treatment of trypanosomiasis, inducing rapid death of the parasites. This suggests that the compound or its derivatives may have antiparasitic activity in vivo. However, specific in vivo studies on the parent compound are limited, as it is primarily a synthetic intermediate rather than a pharmacological agent. The compound's derivatives may be evaluated in animal models of parasitic diseases, but comprehensive in vivo studies on the parent compound are not documented.
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| Enzyme Assay |
Cell-free assays involving 6-bromonicotinonitrile are focused on its use as a chemical reagent. Standard cross-coupling protocols involve mixing the compound with a boronic acid or amine (1.2 equivalents), a palladium catalyst (2-5 mol%), a base, and a solvent at appropriate temperatures under inert atmosphere. The reaction progress is monitored by TLC or HPLC. For sulfonylation reactions, the compound is used as a sulfonylation reagent in organic synthesis. The compound's reactivity can be studied using various analytical techniques, including NMR spectroscopy and mass spectrometry. Its use in the synthesis of diamidines involves reaction with 2,2'-diaminodiphenyl ether.
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| Cell Assay |
Cellular assays are not commonly performed with 6-bromonicotinonitrile itself, as it is a chemical intermediate rather than a bioactive compound. However, the compound's derivatives may be evaluated in cell-based systems for antiparasitic activity. For example, diamidines synthesized from this compound may be tested against Trypanosoma cultures to assess their ability to induce parasite death. The compound itself is not used as a test article in cell-based experiments due to its primary role as a synthetic building block.
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| Animal Protocol |
Animal studies with 6-bromonicotinonitrile have been conducted for the treatment of trypanosomiasis, with the compound inducing rapid death of the parasites. In these studies, the compound or its derivatives are administered to infected animals, and parasite clearance and survival rates are assessed. However, comprehensive in vivo studies on the parent compound are limited, as it is primarily a synthetic intermediate. Its derivatives may be evaluated in animal models of parasitic diseases.
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| ADME/Pharmacokinetics |
Pharmacokinetic data for 6-bromonicotinonitrile are not available. As a small polar molecule with a molecular weight of 183.01 g/mol, it is expected to have moderate bioavailability if administered, but it is not intended for therapeutic use. Comprehensive pharmacokinetic studies have not been performed, as the compound is not intended for systemic administration. 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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| Toxicity/Toxicokinetics |
Toxicological data for 6-bromonicotinonitrile are limited. Standard safety precautions for handling nitriles and halogenated heterocycles apply, including the use of personal protective equipment such as gloves and safety goggles. The compound should be handled in a well-ventilated area, and contact with skin and eyes should be avoided. In case of exposure, affected areas should be rinsed thoroughly with water. The compound is not classified as a carcinogen or mutagen based on available data, but comprehensive toxicological evaluation has not been performed. As with all research chemicals, it should be handled with care and used only in accordance with safety guidelines.
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| Additional Infomation |
6-Bromonicotinonitrile is a research chemical, not an approved drug. It has no clinical trial or marketing approval status for therapeutic use. The compound is a biochemical reagent that can be used as a biomaterial for life science related research and as a sulfonylation reagent for organic synthesis and drug discovery. It is a diamidine synthesized by the reaction of 6-bromonicotinic acid with 2,2'-diaminodiphenyl ether. The compound has been used as an efficient method for treatment of trypanosomiasis. It is supplied with a purity of ≥96% and should be stored at room temperature. Its dual functional groups (bromine and nitrile) make it a versatile building block for organic synthesis and drug discovery.
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| Molecular Formula |
C6H3BRN2
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| Molecular Weight |
183.01
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| Exact Mass |
181.947
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| CAS # |
139585-70-9
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| PubChem CID |
5005718
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| Appearance |
Off-white to light yellow solid powder
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| Density |
1.7±0.1 g/cm3
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| Boiling Point |
261.6±20.0 °C at 760 mmHg
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| Melting Point |
136-140ºC(lit.)
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| Flash Point |
112.0±21.8 °C
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| Vapour Pressure |
0.0±0.5 mmHg at 25°C
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| Index of Refraction |
1.612
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| LogP |
1.3
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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 |
9
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| Complexity |
137
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=C(C=NC(=C1)Br)C#N
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| InChi Key |
XHYGUDGTUJPSNX-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H3BrN2/c7-6-2-1-5(3-8)4-9-6/h1-2,4H
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| Chemical Name |
6-bromopyridine-3-carbonitrile
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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 | 5.4642 mL | 27.3209 mL | 54.6418 mL | |
| 5 mM | 1.0928 mL | 5.4642 mL | 10.9284 mL | |
| 10 mM | 0.5464 mL | 2.7321 mL | 5.4642 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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