Overview
Dibromopyrazine is a brominated derivative of pyrazine, a nitrogen-containing heterocycle. It exists as two common isomers (2,3- and 2,5-dibromopyrazine), differing in bromine atom positioning. The compound serves as a versatile building block in organic synthesis due to its reactive bromine sites, which enable nucleophilic substitutions or metal-catalyzed coupling reactions. Primarily traded in B2B markets, it is classified as a fine chemical with applications in pharmaceuticals, agrochemicals, and advanced materials. Industrial-scale production typically involves direct bromination of pyrazine under controlled conditions. Regulatory compliance (e.g., REACH) is mandatory for EU imports/exports.
Physical and Chemical Properties
Dibromopyrazine forms crystalline solids with moderate thermal stability. The 2,3-isomer melts at ~90-95°C, while the 2,5-isomer has a slightly higher melting point. Both isomers exhibit good solubility in polar aprotic solvents like dimethylformamide (DMF) but are poorly soluble in water (<0.1 g/L at 20°C). Key reactivity includes participation in Suzuki-Miyaura and Buchwald-Hartwig cross-coupling reactions, making it valuable for constructing complex molecules. Stability tests indicate decomposition above 200°C, releasing hydrogen bromide (HBr). Hygroscopicity is low, but moisture-sensitive applications may require inert atmosphere handling.
Main Applications
In pharmaceuticals, dibromopyrazine intermediates appear in antiviral and anticancer drug candidates, such as kinase inhibitors. Its bromine atoms allow precise structural modifications during multi-step syntheses. Agrochemical manufacturers use it to produce herbicides and fungicides with pyrazine backbones. Specialty applications include flame retardant additives for polymers, where bromine content enhances fire resistance. Emerging research explores its use in organic electronics as a precursor for conductive polymers.
Safety and Storage
Classified as an irritant (GHS07), dibromopyrazine requires handling with nitrile gloves, safety goggles, and fume hoods to prevent skin/eye contact or inhalation of dust. Spills should be contained with inert absorbents (e.g., vermiculite) and disposed as hazardous waste. Storage recommendations include amber glass or HDPE containers under nitrogen blanket to prevent degradation. Shelf life typically exceeds 2 years when kept at 2-8°C in sealed conditions. Incompatible with strong oxidizers and bases due to potential exothermic reactions.
B2B Procurement Guide
Industrial buyers should verify isomer specificity (2,3- vs. 2,5-), as reactivity differs. Technical (≥95%) and analytical (≥98%) grades are common, with HPLC certificates required for pharmaceutical use. Bulk orders (25kg drums) reduce costs by ~20% compared to lab-scale packaging. Lead times vary by supplier but average 4-6 weeks for custom synthesis. Preferred suppliers include fine chemical specialists with ISO 9001 certification. Request safety data sheets (SDS) and batch-specific COAs for regulatory documentation. Spot prices fluctuate with bromine market trends.
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