4-Bromo-6-chlorobenzoimidazol-2-one: Properties & Lab FAQ
4-Bromo-6-chlorobenzoimidazol-2-one: Properties & Lab FAQ
4-Bromo-6-chlorobenzoimidazol-2-one is a halogenated benzimidazolone heterocycle widely used as a versatile synthetic building block in medicinal chemistry and pharmaceutical research.
- Chemical Name
- 4-Bromo-6-chlorobenzoimidazol-2-one
- SKU / Catalog Number
- B178947
- Core Scaffold
- Benzimidazol-2-one (benzimidazolone)
- Halogen Substituents
- Bromine at position 4, Chlorine at position 6
- Compound Class
- Halogenated heterocyclic building block
- Primary Use
- Synthetic intermediate in medicinal chemistry and drug discovery
What Is 4-Bromo-6-chlorobenzoimidazol-2-one?
4-Bromo-6-chlorobenzoimidazol-2-one (Aladdin SKU B178947) is a halogenated derivative of the benzimidazol-2-one scaffold. The benzimidazolone core consists of a benzene ring fused to an imidazoline ring bearing a carbonyl group at the 2-position, conferring a planar, aromatic-like character and hydrogen-bond donor/acceptor capacity at the NH and C=O groups.
The introduction of bromine at position 4 and chlorine at position 6 of the benzene ring creates a compound with two distinct electrophilic handles. These halogen atoms can participate in cross-coupling reactions (e.g., Suzuki, Buchwald–Hartwig) and nucleophilic aromatic substitution, making this compound a highly flexible intermediate for the assembly of more complex molecular architectures.
Physicochemical Properties and Solubility
The benzimidazolone scaffold is known for moderate polarity arising from the lactam carbonyl and N–H moieties. The two halogen substituents (Br and Cl) increase the molecular weight and lipophilicity relative to the unsubstituted parent compound. Researchers should expect limited aqueous solubility typical of halogenated heterocycles of this type.
For stock solution preparation, polar aprotic solvents such as DMSO or DMF are generally recommended as primary dissolution media. If aqueous buffers are required downstream, diluting a concentrated DMSO stock into the aqueous phase is a common approach, keeping the organic co-solvent below concentrations that may interfere with biological assays (typically ≤0.1–1% v/v DMSO). Actual solubility values for this specific compound should be verified experimentally or consulted from the Certificate of Analysis supplied with the product.
Handling, Storage, and Safety
As with all halogenated organic intermediates, standard laboratory safe-handling practices should be followed. Work in a well-ventilated fume hood, wear appropriate personal protective equipment including nitrile gloves, laboratory coat, and safety glasses. Avoid inhalation of dust or vapors.
Storage conditions for benzimidazolone derivatives typically involve a cool, dry environment away from light and moisture to prevent hydrolysis or photodegradation. Specific recommended storage temperature and shelf-life information are detailed on the product label and Certificate of Analysis. Always consult the Safety Data Sheet (SDS) for hazard classifications, first-aid measures, and disposal requirements before working with this compound.
Applications in Synthesis and Drug Discovery
The benzimidazol-2-one motif is a privileged scaffold in medicinal chemistry, appearing in numerous pharmacologically active compounds with reported activity across multiple target classes. The dual halogenation of 4-Bromo-6-chlorobenzoimidazol-2-one at positions 4 and 6 provides orthogonal reactivity: the C–Br bond is generally more reactive than C–Cl in palladium-catalyzed cross-coupling reactions, enabling sequential, chemoselective functionalization of the two positions to introduce different substituents in a controlled manner.
Typical applications include: (1) Suzuki–Miyaura coupling to introduce aryl or heteroaryl groups; (2) Buchwald–Hartwig amination for N–C bond formation; (3) nucleophilic aromatic substitution under appropriate activating conditions; and (4) use as a core fragment in fragment-based drug discovery (FBDD) campaigns. N-alkylation of the benzimidazolone NH also offers a further dimension of structural diversification.
Ordering and Quality Assurance
4-Bromo-6-chlorobenzoimidazol-2-one is available from Aladdin Scientific under catalog number B178947. Each lot is accompanied by a Certificate of Analysis (CoA) detailing purity, analytical data (typically including NMR and/or HPLC confirmation), and batch-specific results. Researchers are encouraged to download the CoA from the Aladdin website using the lot number printed on the product label to verify that the material meets their experimental requirements prior to use.
For bulk quantities, custom packaging, or questions about availability and lead times, please contact Aladdin Scientific's technical support or your regional sales representative. Return, refund, and shipping policies are governed by Aladdin's standard terms; please consult the Help & Customer Service section of the Aladdin website for details.
Frequently asked questions
What solvents are recommended for dissolving 4-Bromo-6-chlorobenzoimidazol-2-one?
DMSO and DMF are generally recommended for preparing stock solutions of halogenated benzimidazolone derivatives due to their strong solvating power. For biological assays requiring aqueous conditions, dilute a concentrated DMSO stock into the aqueous buffer, keeping DMSO below assay-interfering levels (typically ≤1% v/v). Always verify solubility experimentally for your specific conditions.
Can both the bromine and chlorine substituents be selectively functionalized in cross-coupling reactions?
Yes. In palladium-catalyzed cross-coupling chemistry, the C–Br bond of 4-Bromo-6-chlorobenzoimidazol-2-one is generally more reactive than the C–Cl bond, enabling chemoselective reaction at the bromine position under mild conditions. The chlorine can subsequently be engaged under more forcing conditions or with appropriate catalyst systems, allowing sequential introduction of two different functional groups. Optimization of reaction conditions is advised for each specific transformation.
How should 4-Bromo-6-chlorobenzoimidazol-2-one be stored to maintain stability?
Benzimidazolone derivatives are generally stored in a cool, dry place protected from light and moisture. Refer to the specific storage temperature indicated on the product label and Certificate of Analysis for B178947. Ensure the container is tightly sealed after each use to prevent moisture uptake, and consult the SDS for full stability and handling information.
What is the significance of the benzimidazolone scaffold in drug discovery?
The benzimidazol-2-one scaffold is considered a privileged structure in medicinal chemistry because it combines a planar aromatic framework with hydrogen-bond donor (N–H) and acceptor (C=O) functionalities, facilitating binding interactions with diverse biological targets. It appears in marketed drugs and investigational compounds across multiple therapeutic areas. Halogenated derivatives such as B178947 extend this versatility by providing reactive handles for further structural elaboration.
Where can I find the Certificate of Analysis and Safety Data Sheet for B178947?
The Certificate of Analysis (CoA) and Safety Data Sheet (SDS) for 4-Bromo-6-chlorobenzoimidazol-2-one (B178947) are available on the Aladdin Scientific website. Navigate to the product page for B178947 and use your lot number to download the batch-specific CoA. The SDS can be downloaded from the same page or requested from Aladdin customer support.
References
- Aladdin Scientific product page for 4-Bromo-6-chlorobenzoimidazol-2-one, SKU B178947.
- Gomtsyan, A. Heterocycles in drugs and drug discovery. Chemistry of Heterocyclic Compounds, 2012. (General reference on benzimidazolone privileged scaffold — specific details to be verified.)
- Johansson Seechurn, C. C. C.; Kitching, M. O.; Colacot, T. J.; Snieckus, V. Palladium-catalyzed cross-coupling: a historical contextual perspective to the 2010 Nobel Prize. Angew. Chem. Int. Ed. 2012, 51, 5062–5085. (General reference on chemoselectivity of C–Br vs C–Cl in cross-coupling — to be verified for specific applicability.) doi:10.1002/anie.201107017
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