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| 25g |
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| 100g |
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| 500g |
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| Targets |
2-(2-Bromoethyl)-1,3-dioxane does not have a specific biological target (receptor/enzyme) as it is a chemical synthetic intermediate and not a pharmacological agent. Its mechanism of action is chemical rather than biological: it acts as an alkylating agent via the bromoethyl group, which can undergo nucleophilic substitution (SN2) reactions with various nucleophiles (amines, thiols, carboxylates). The dioxane ring is stable under basic conditions but can be hydrolyzed under acidic conditions to regenerate the parent aldehyde (3-hydroxypropionaldehyde equivalent). Thus, the compound serves as a protected bifunctional linker (electrophile + masked aldehyde) for the synthesis of various drug molecules, natural product analogs, and chemical biology probes.
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| ln Vitro |
As a chemical building block, 2-(2-Bromoethyl)-1,3-dioxane is not designed to have direct in vitro pharmacological activity (e.g., cell viability inhibition or receptor binding). Instead, it is used in vitro as an alkylating reagent for the modification of proteins, peptides, or small molecules. In a typical biochemical assay, the compound can be added to a solution containing a thiol-containing biomolecule (e.g., cysteine residue on a protein) in aqueous buffer at pH 7-8. The bromoethyl group undergoes nucleophilic substitution with the thiol, forming a stable thioether linkage, while the dioxane ring remains intact under mild basic conditions. This allows for the covalent modification of biomolecules with an acetal-protected aldehyde handle, which can later be deprotected and used for conjugation to other molecules (e.g., fluorescent tags). This property makes it useful in chemical biology and drug delivery research.
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| ln Vivo |
2-(2-Bromoethyl)-1,3-dioxane has no direct in vivo activity as it is a chemical intermediate. However, it can be used to synthesize prodrugs or active pharmaceutical ingredients that do have in vivo activity. For example, the compound is used in the synthesis of ketone adducts such as 2-[3-oxo-4(S)-(triphenylmethyl)amino-6-methylheptyl]-1,3-dioxane, which are intermediates in the synthesis of biologically active compounds (e.g., protease inhibitors). The in vivo fate (e.g., metabolism, pharmacokinetics, efficacy) is determined by the final drug molecule synthesized using this building block, not by the building block itself. Thus, in vivo studies for 2-(2-Bromoethyl)-1,3-dioxane are not applicable.
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| Enzyme Assay |
As a synthetic intermediate, 2-(2-Bromoethyl)-1,3-dioxane is not subjected to standard receptor binding assays. However, it can be used to synthesize alkylating agents that are then evaluated in biochemical assays. A standard method to test the reactivity of this compound as an alkylating agent is to monitor its reaction with a model nucleophile (e.g., 4-nitrobenzenethiol or sodium azide) in a cell-free system. In a quartz cuvette, a solution of 100 uM 2-(2-Bromoethyl)-1,3-dioxane is prepared in acetonitrile/water (1:1) containing 1 mM of the nucleophile and 1 mM potassium carbonate (pH 9-10). The reaction is monitored by UV-vis spectrophotometry at the absorption wavelength of the chromophore (e.g., 400 nm for 4-nitrobenzenethiol, where the thiolate form has a different absorbance from the thioether product). The pseudo-first-order rate constant (kobs) is calculated from the change in absorbance over time. This cell-free assay quantifies the alkylating ability of the compound, which is relevant for its use in chemical biology.
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| Cell Assay |
Since 2-(2-Bromoethyl)-1,3-dioxane is a chemical intermediate and not a direct biological agent, cellular assays are typically performed on the final conjugated or derivatized products synthesized from it. However, the compound's cytotoxicity can be evaluated in a standard MTT assay using human cell lines (e.g., HeLa or HEK293) to ensure that residual starting material is not toxic in downstream applications. Cells are seeded in 96-well plates (5,000-10,000 cells/well) in DMEM media with 10% FBS and 1% penicillin/streptomycin. After 24 hours, serial dilutions of 2-(2-Bromoethyl)-1,3-dioxane (1-1000 uM, final DMSO ≤0.5%) are added to the cells and incubated for 48 hours. MTT reagent is then added, and after 4 hours, the formazan crystals are dissolved in DMSO and absorbance measured at 570 nm. The IC50 is typically in the high micromolar range (>100 uM) for simple alkylating agents, but exact values depend on cell type. The compound is not intended for use as a therapeutic agent; cellular assays are primarily for toxicity profiling.
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| Animal Protocol |
There are no standard in vivo animal protocols for 2-(2-Bromoethyl)-1,3-dioxane as it is not a drug candidate. If the compound were used as a chemical probe for in vivo alkylation or as a linker for targeted drug delivery, a general protocol might involve its administration to mice (e.g., C57BL/6) via intraperitoneal injection (50-100 mg/kg) in a vehicle such as corn oil or 10% DMSO/90% saline. However, such studies are not typically reported for this compound. Due to the alkylating nature of the bromoethyl group (potential for genotoxicity), this compound would likely be considered too reactive for direct in vivo administration in therapeutic contexts. Thus, in vivo studies are not applicable; its role remains exclusively in the synthetic chemistry phase of drug development.
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| ADME/Pharmacokinetics |
2-(2-Bromoethyl)-1,3-dioxane has the molecular formula C6H11BrO2 and a molecular weight of 195.05 g/mol. As a small lipophilic molecule (LogP estimated ~1.5-2.0), it is soluble in organic solvents such as DMSO, dichloromethane, ethanol, and diethyl ether, but has low aqueous solubility. The compound is a colorless to light yellow liquid at room temperature. The dioxane ring is stable under basic and neutral conditions but is acid-labile (deprotection to the aldehyde). The bromoethyl group is susceptible to nucleophilic substitution. If administered in vivo (non-standard), the compound would likely be rapidly metabolized via glutathione conjugation (depletion of cellular glutathione) and undergo hydrolysis of the dioxane ring in the acidic environment of the stomach or lysosomes (pH 4-5). Clearance would be rapid, likely with a half-life of <1 hour.
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| Toxicity/Toxicokinetics |
2-(2-Bromoethyl)-1,3-dioxane is a biochemical reagent and is considered an alkylating agent. As such, it has the potential for genotoxicity (DNA alkylation) and should be handled with extreme caution. It may be a skin, eye, and respiratory tract irritant (H315, H319, H335). The bromoethyl group is reactive and may cause skin sensitization (allergic reaction) upon repeated exposure. Acute oral toxicity is estimated to be moderate (LD50 likely 500-1000 mg/kg in rats). Due to the risk of DNA damage, it should be considered a potential mutagen (presumed positive in Ames test based on structural alert for alkyl halides). Always handle in a chemical fume hood with appropriate personal protective equipment: nitrile gloves, safety goggles, and a lab coat. Avoid generating dust or aerosols. The compound should be stored in a tightly sealed container at 2-8degC (refrigerated), protected from light and moisture. It is strictly for research use only and is not for human or veterinary use.
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| References | |
| Additional Infomation |
2-(2-Bromoethyl)-1,3-dioxane has the CAS number 33884-43-4 and the molecular formula C6H11BrO2 with a molecular weight of 195.05 g/mol. It is also known as 1-Bromo-2-(1,3-dioxan-2-yl)ethane. The compound is a colorless to light yellow liquid. It serves as a biochemical reagent and an organic compound used as a biomaterial in life science research. In organic synthesis, it is used as a building block (linker) for the synthesis of complex molecules, polymer intermediates, and in cross-coupling reactions after conversion to the corresponding organometallic reagent (Grignard reagent). The reaction of the Grignard reagent prepared from 2-(2-bromoethyl)-1,3-dioxane with N-tert-butanesulfinyl aldimines is a known application. This compound is also used in the synthesis of ketone adducts, which are valuable intermediates for pharmaceutical chemistry. It is not a drug and has no direct biological activity. Purity is typically 95-98%.
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| Molecular Formula |
C6H11BRO2
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| Molecular Weight |
195.05
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| Exact Mass |
193.994
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| CAS # |
33884-43-4
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| PubChem CID |
520656
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| Appearance |
Colorless to light yellow liquid
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
9
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| Complexity |
71.5
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1COC(OC1)CCBr
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| InChi Key |
WMDHQEHPOVOEOG-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H11BrO2/c7-3-2-6-8-4-1-5-9-6/h6H,1-5H2
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| Chemical Name |
2-(2-bromoethyl)-1,3-dioxane
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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 | 5.1269 mL | 25.6345 mL | 51.2689 mL | |
| 5 mM | 1.0254 mL | 5.1269 mL | 10.2538 mL | |
| 10 mM | 0.5127 mL | 2.5634 mL | 5.1269 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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