What Is 6-Amino-1-benzyl-5-bromouracil?

6-Amino-1-benzyl-5-bromouracil is a chemically modified uracil in which three positions of the pyrimidine ring have been functionalized: a bromine atom at C-5, an amino group at C-6, and a benzyl group on the N-1 nitrogen. These modifications collectively alter the electronic distribution, hydrogen-bonding capacity, and lipophilicity of the parent uracil scaffold.

The compound is catalogued under Aladdin SKU A485025 and corresponds to reference number CDS005634 in the Sigma catalog. It is supplied as a research-grade reagent intended for use in synthetic chemistry, medicinal chemistry investigations, and related biochemical studies.

Physicochemical Properties and Handling

As a halogenated heterocyclic compound, 6-Amino-1-benzyl-5-bromouracil is expected to be a solid at room temperature. The presence of the bromine atom at C-5 increases molecular weight relative to unsubstituted uracil and may influence crystal packing and melting behavior. The amino and carbonyl groups provide hydrogen-bond donor and acceptor sites that affect solubility profiles.

Solubility: Polar aprotic solvents such as DMSO are typically suitable for dissolving halogenated uracil analogs. Aqueous solubility may be limited due to the hydrophobic benzyl group; always verify solubility empirically before use in biological assays.

Handling precautions: As with all organobromine research reagents, standard laboratory safety practices apply. Use appropriate personal protective equipment (PPE), work in a well-ventilated area or fume hood, and consult the Safety Data Sheet (SDS) before use.

Research Applications of Brominated Uracil Derivatives

Halogenated uracil derivatives occupy an important niche in medicinal chemistry as building blocks and bioactive scaffolds. The C-5 halogen in uracil analogs is known to influence interactions with nucleic acid-processing enzymes, and such compounds have historically served as starting points for antiviral and anticancer agent development.

The N-1 benzyl group in 6-Amino-1-benzyl-5-bromouracil provides a handle for further synthetic elaboration and may modulate membrane permeability, making this compound useful as an intermediate in the synthesis of more complex nucleobase-derived pharmaceuticals or chemical biology probes.

Note: Specific biological activity data for this exact compound are not available in the current source material. Researchers should conduct primary literature searches and experimental validation for any intended application.

Storage, Stability, and Quality

To maintain reagent integrity, store 6-Amino-1-benzyl-5-bromouracil according to the conditions specified on the product label and Certificate of Analysis (CoA). General best practices for halogenated heterocyclic compounds include storage in a cool, dry environment protected from light and moisture.

Aladdin Scientific supplies this compound under SKU A485025 with quality benchmarked against established reference standards, including the Sigma reference CDS005634. Customers are encouraged to request the CoA at time of purchase to verify purity specifications relevant to their application.

If long-term storage is required, aliquoting stock solutions in an appropriate solvent (e.g., DMSO) and storing at the recommended temperature can help minimize freeze-thaw degradation.