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5-Bromo-2,1,3-Benzothiadiazole

    • Product Name 5-Bromo-2,1,3-Benzothiadiazole
    • Alias 4-Bromo-1,2,3-benzothiadiazole
    • Einecs 629-084-9
    • Mininmum Order 1 g
    • Factory Site Tengfei Creation Center,55 Jiangjun Avenue, Jiangning District,Nanjing
    • Price Inquiry admin@sinochem-nanjing.com
    • Manufacturer Sinochem Nanjing Corporation
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    Specifications

    HS Code

    677110

    Chemical Name 5-Bromo-2,1,3-benzothiadiazole
    Cas Number 59447-55-1
    Molecular Formula C6H3BrN2S
    Molecular Weight 215.08 g/mol
    Appearance Light yellow to orange powder
    Melting Point 141-143°C
    Solubility Soluble in organic solvents like dichloromethane, THF
    Purity Typically ≥98%
    Smiles Brc1cc2nsnc2cc1
    Inchi InChI=1S/C6H3BrN2S/c7-4-1-2-5-6(3-4)10-9-8-5/h1-3H
    Synonyms 5-Bromo-1,2,3-benzothiadiazole, 5-Bromo-benzothiadiazole
    Storage Conditions Store in a cool, dry place, protected from light

    As an accredited 5-Bromo-2,1,3-Benzothiadiazole factory, we enforce strict quality protocols—every batch undergoes rigorous testing to ensure consistent efficacy and safety standards.

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    Application of 5-Bromo-2,1,3-Benzothiadiazole

    Applications of 5-Bromo-2,1,3-Benzothiadiazole in Industrial Manufacturing

    As a direct manufacturer of 5-Bromo-2,1,3-Benzothiadiazole, we support multiple advanced material sectors where this heteroaromatic intermediate delivers key performance and structural attributes. Below we detail several precisely focused downstream application scenarios, based on actual industry adoption, with clear technical and regulatory context for each.

    1. High-Efficiency Organic Photovoltaic Active Materials

    Downstream photovoltaic manufacturers utilize 5-Bromo-2,1,3-Benzothiadiazole as a core electron-deficient building block in the synthesis of donor–acceptor–donor (D–A–D) small molecules and conjugated polymers. Its role is crucial in tuning bandgap, morphology, and absorption edge to maximize power conversion efficiency in printed solar cell architectures. This material enters at the precision coupling stage during organic semiconductor polymer backbone development, where end-use product quality critically depends on high purity and batch consistency of intermediates.

    Industry compliance standards

    • IEC 61215: Crystalline silicon terrestrial photovoltaic modules
    • IEC 61646: Thin-film terrestrial photovoltaic modules
    • ISO 9001:2015 Quality management for material traceability
    • RoHS for heavy metal content limits

    Typical usage ratio

    • 5–20 mol% in copolymer feed, adjusted based on bandgap target and solubility requirements of final organic photoactive material

    Downstream process integration

    • Enter Suzuki or Stille coupling polymerization for incorporating electron-accepting moieties into functional polymer chains
    • Used in pilot-scale and commercial-scale semiconductor ink formulation prior to roll-to-roll film coating

    Final product types

    • Bulk heterojunction solar cell active layers
    • Organic photodetector thin films
    • Semi-transparent photovoltaic modules

    2. Blue-Green Light-Emitting Diode (LED) Polymer Systems

    Specialty optoelectronics firms employ 5-Bromo-2,1,3-Benzothiadiazole as a unique chromophoric unit in OLED and PLED emissive layer design, where it acts to modulate emission wavelength and facilitate charge transport. Its introduction during the conjugated polymer synthesis phase enables tailored emission in the blue-green spectrum, matching specific luminous efficacy requirements for display or lighting system end use. Consistent high-purity grade is required to minimize defects and ensure stable photophysical properties throughout device operation.

    Industry compliance standards

    • ANSI/IES LM-80 for luminous efficacy and longevity testing
    • IEC 62471 for photobiological safety of lamps and lamp systems
    • REACH, SVHC restrictions for raw materials
    • ISO 14001 for environmental management in LED device manufacturing

    Typical usage ratio

    • 2–15 mol% in emitter-layer polymerization, optimized according to desired emission color and processing viscosity

    Downstream process integration

    • Introduced at the heteroaromatic coupling step during advanced monomer synthesis
    • Used as a functionalized intermediate in final polymerization before purification and casting into thin-film emissive layers

    Final product types

    • Polymer-based OLED display panels
    • Flexible PLED lighting modules
    • Blue-green emission specialty signage

    3. N-type Semiconducting Polymer Manufacturing for Flexible Electronics

    Producers of flexible and wearable electronics materials incorporate 5-Bromo-2,1,3-Benzothiadiazole in the synthesis of n-type semiconducting polymers. It supports molecular orbital alignment and increases electron mobility, a necessary property in next-generation thin-film transistor (TFT) backplanes and printed logic circuits. The compound is integrated at the key cross-coupling stage during oligomer assembly, allowing control over uniformity, solubility, and device reliability for subsequent solution processing methods such as inkjet or gravure printing.

    Industry compliance standards

    • IPC-2221: Generic standards on printed board design
    • ISO/TS 80004-9: Nano-enabled electronics safety guidance
    • RoHS for exclusion of hazardous substances in electronic substrates
    • UL 94 flammability standards for polymeric materials

    Typical usage ratio

    • 10–25 mol% in precursor monomer feed, altered per mobility and film morphology specification

    Downstream process integration

    • Incorporated via Pd-catalyzed cross-coupling during the donor-acceptor backbone construction
    • Processed for polymer solubilization, followed by spin coating or slot die coating onto substrate

    Final product types

    • Printed transistor arrays for flexible displays
    • Wearable electronic sensor interfaces
    • Transparent logic circuit modules

    4. Intermediate for Specialty Dye and Pigment Synthesis

    Advanced dye and pigment producers use 5-Bromo-2,1,3-Benzothiadiazole as a crucial halogenated building block in the creation of complex fused ring systems found in high-performance dyes. Its chemical structure supports specific absorption and stability characteristics desired for applications such as high-resolution inkjet printing, security marking, or photostable outdoor coatings. The material is introduced at the heteroaromatic substitution stage for efficient construction of chromophoric cores, where trace impurities or inconsistent reactivity directly impact color fidelity and fastness.

    Industry compliance standards

    • EN 71-3: Safety of toys – migration of certain elements
    • ISO 28340: Pigments and extenders — General methods of test
    • OEKO-TEX® Standard 100 for textile dye applications
    • EU REACH Annex XVII for restricted azo colorants

    Typical usage ratio

    • 5–12% w/w in typical dye precursor formulation, modified depending on target absorption maxima and solubility for intended application medium

    Downstream process integration

    • Chemical intermediate in heterocyclic ring closure and azo coupling reactions
    • Used before purification, blending, and milling of finished pigment powders

    Final product types

    • High-definition inkjet printing inks
    • Photostable textile colorants
    • Anti-counterfeiting and fluorescent dyes
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    More Introduction

    5-Bromo-2,1,3-Benzothiadiazole: A Vital Building Block in Modern Chemistry

    Not every specialty chemical stands out in a world filled with compounds that promise to solve problems in labs and industries. 5-Bromo-2,1,3-benzothiadiazole stands apart. With hands-on laboratory experience, I’ve learned that the name might sound complicated, but inside the flask, this compound opens ambitious doors for researchers and developers alike. Folks in the field use this molecule again and again as a trusted starter for synthesizing more elaborate materials. Its structure—anchored by a benzothiadiazole skeleton with a bromine tagging the fifth position—does not just make it a chemical curiosity; its features speak directly to the needs of those pushing progress in electronics, pharmaceuticals, and advanced materials.

    Anatomy and Strengths of 5-Bromo-2,1,3-Benzothiadiazole

    On paper, 5-Bromo-2,1,3-benzothiadiazole shows up with the formula C6H3BrN2S. Its molecular weight clocks in at 215.08 g/mol—not too heavy to limit flexibility in reactions, not so light that it loses substance for downstream transformations. What jumps out to chemists is its crystalline appearance when purified, often forming solid, off-white to pale yellow needles or powders that rarely clump or degrade under typical storage. This quality isn’t just an aesthetic plus. High-purity samples matter when reproducibility and minimal contamination are crucial—the way it should be, whether the material runs through an organic synthesis at scale or in the hands of a grad student aiming for a clean NMR spectrum.

    The chemical holds up under typical laboratory conditions. Stability makes it easy to store without specialized atmospheres or expensive containers. That’s a practical relief for someone like me who’s seen more sensitive reagents double in price due to handling issues. With a boiling point exceeding 300°C under ideal conditions, and decomposition happening above 150°C in air, this compound doesn’t throw unexpected curveballs in the middle of crucial syntheses. Water solubility falls on the low end, but that's a deliberate feature for many organic intermediates—soluble just enough in most non-polar and slightly polar solvents to allow careful tuning of reactions.

    What Makes This Compound Different?

    In research and industry, choices matter. Many compounds could serve as a benzothiadiazole building block, but not every analog presents the same handling convenience, reactivity profile, or compatibility with downstream chemistry. Substituting bromine at the fifth position isn’t just a minor tweak; it’s a deliberate switch that gives this molecule a unique fingerprint in cross-coupling reactions and heterocycle functionalizations.

    Conventional benzothiadiazole carries a reputation as a robust, electron-deficient building block used in electronics and photochemistry. The bromine variant takes the game a notch higher for those leaning on halogen-mediated chemistry. Thanks to the bromine’s position, the compound proves invaluable for Suzuki-Miyaura or Stille couplings, reactions that glue the benzothiadiazole core to aromatic rings, polymer backbones, or other functional fragments. The selectivity and predictability of reactions starting from the 5-bromo form save both time and resources compared to less-specific halogenated analogs, such as the 4-bromo or multi-bromo series.

    Other members of its chemical family, including simple benzothiadiazoles or those with fluorine or chlorine at different sites, do not show the same range of utility in modern materials synthesis. For example, the chloro derivative requires more unforgiving conditions or riskier reagents to reach the same product outcomes, while the unsubstituted molecule limits downstream expansion by cross-coupling chemistry. Those years I spent trying to optimize organic solar cell dyes taught me the headaches of working with non-brominated starting materials—poor yields, lower purity, higher costs. The brominated compound streamlines these steps in real-world settings, not just on paper.

    Applications in Modern Research and Industry

    The path from a simple reagent bottle to a world-changing material starts with the right molecular anchor. 5-Bromo-2,1,3-benzothiadiazole gives that advantage to researchers involved in cutting-edge electronic and optoelectronic materials. Take organic photovoltaics. Here, materials scientists seek to squeeze out new efficiencies from polymers that harvest sunlight and turn it into electricity. The benzothiadiazole core, particularly with a 5-bromo group, integrates seamlessly into polymer backbones, where it modifies light absorption, charge flow, and mechanical integrity.

    In organic light-emitting diodes (OLEDs), the need for materials that reliably emit intense, tunable colors is relentless. Chemists can use 5-bromo-2,1,3-benzothiadiazole to construct donor-acceptor structures, where the electron-deficient benzothiadiazole tweaks the electronic properties of the host material, and the bromo substituent allows quick coupling with complex fragments. The result: improved efficiency, longer device life, and brighter displays for the consumer electronics dominating our daily lives.

    The pharmaceutical field, while less reliant on benzothiadiazole blocks for blockbuster drug molecules, finds value in the scaffold for exploratory synthesis. It’s not just about cranking out another intermediate; it’s about the flexibility to test new chemical spaces efficiently and reliably. Researchers wanting to make library compounds for screening turn to well-positioned compounds like this, thanks to straightforward customization. That attention to practical details—purity, yield, ease of transformation—means research dollars stretch further and timelines shrink.

    Hands-On Insights: Real Laboratory Experience

    I remember my own frustrations early in my research career, fighting stubbornly with old, impure chemical stocks that seemed to sabotage syntheses at random intervals. Products like 5-bromo-2,1,3-benzothiadiazole changed that story. It doesn't require an arsenal of tricks or a team of postdocs to store and handle. A simple desiccator or dry flask works well enough, and it hardly absorbs moisture or decomposes unless you edge far out of normal practices.

    During a series of Suzuki reactions, using the 5-bromo derivative as a coupling partner gave clean conversions and allowed for simple monitoring by thin-layer chromatography. That meant less time spent troubleshooting, less waste, and more focus on getting to the next phase—characterizing new, exciting materials. Particularly in academic labs where every reagent counts and budgets have limits, these sorts of easy wins stack up over months and years. The day a reaction proceeds smoothly and gives the expected spectrum without major chromatography is one step closer to a publishable result or a patentable material.

    I’ve witnessed the switch to this compound by several colleagues working in materials chemistry. A postdoc who replaced her old 2-bromobenzothiadiazole source with this 5-bromo form saw improvements in reaction reproducibility and cuts in purification time. Instead of long, frustrating hours at the chromatography column, she moved more quickly to product analysis and prototype testing—a tangible difference in daily lab work.

    Why Purity and Sourcing Matter

    With specialty chemicals, purity isn’t just a number on a certificate. Impurities in 5-bromo-2,1,3-benzothiadiazole can lead to chain reactions of problems—lower yields, side products, and even toxic byproducts. Reproducibility across suppliers can vary, and so personal experience matters. Trusted suppliers provide 97–99% purity grades, ideal for demanding applications, where surfacing an unexpected impurity late in product development can mean lost weeks of work.

    As research moves toward larger scales, whether for pilot plant polymer synthesis or custom pharmaceutical intermediates, consistent sourcing becomes as important as the magic of the molecule itself. Labs and start-ups should stick with established suppliers, verify batch consistency, and keep records of lot numbers. That might sound tedious, but in the world of analytical chemistry, a mismatch between batches can quickly turn a promising experiment into an expensive dead end.

    Challenges: Sustainability, Safety, and Waste

    The progress in electronics and pharmaceuticals comes with responsibility. 5-Bromo-2,1,3-benzothiadiazole, while not especially hazardous, calls for respectful handling. Like most bromoaromatics, it should be kept away from direct inhalation or skin exposure, since certain exposure routes could cause irritation or allergic reactions after long use. Few lab accidents have happened with skilled use, but safety goggles and gloves form the basics here.

    Waste disposal remains an issue many overlook. Brominated organic waste requires careful burning or reclamation through appropriate chemical waste streams. Over the years, labs that ignore this either pay with fines or environmental damage. Conversations with environmental chemists reinforce the ongoing need for labs to handle even small-scale waste with care, not cutting corners because of assumed minimal impact. Simple steps—labeling waste correctly, neutralizing before disposal, and using professional waste collection—matter.

    On sustainability, the core benzothiadiazole backbone in chemicals like this gets synthesized from petrochemical sources. Modern green chemistry stresses the need to minimize waste, avoid persistent pollutants, and find alternative feedstocks where practical. Some groups now test renewable routes to make the building blocks for these specialty chemicals, using biotechnological starting materials or more benign solvents. Labs moving toward green certifications get ahead of shifting regulations and public expectations.

    Potential Solutions and Improvements Ahead

    Solving issues linked to specialty chemicals requires more than just ticking regulatory boxes. Sourcing greener alternatives, investing in purification technologies, and minimizing waste are all areas where manufacturers and users can make a difference. Some suppliers now offer bio-based or solvent-minimized processes, although these options remain in development and often carry higher costs. Industry-wide, collaboration between chemists, engineers, and industrial designers could speed up wider adoption of more responsible production and use.

    At the lab bench, clear protocols for solvent recycling and halogen waste management should be standard. In group meetings, researchers can push for green chemistry checklists—steps as simple as switching to more sustainable reaction solvents and minimizing excess reagents. These little changes add up, especially as more labs and companies embrace them together.

    Professional societies and journals have begun to raise standards, too. Publishing environmentally conscious procedures now receives more attention and praise. Graduate students and new researchers entering the field bring strong motivation for cleaner chemistry—an encouraging sign for the future of compounds like 5-Bromo-2,1,3-benzothiadiazole.

    Staying Ahead in a Competitive Field

    Sticking to products with a proven track record allows research and development to proceed smoothly, especially when time and results govern progress. 5-Bromo-2,1,3-benzothiadiazole has earned its spot in a growing number of fields because it works for real researchers with real projects. Its unique characteristics cut down on frustrating repeats and promote a smoother, more confident development cycle.

    For anyone in organic synthesis looking to move from basic research to product prototyping, this compound has the transparency, flexibility, and robustness that accelerate those steps. That gives labs and companies the breathing room and confidence they need, whether building new electronics or rushing toward proof-of-concept drug candidates.

    Keeping pace with evolving standards matters. As research trends evolve toward more sustainable, economically sound syntheses, products that balance reliability, availability, and greener alternatives claim a larger share of the future. Paying attention to feedback from the trenches—chemist to chemist, not just from glossy product brochures—guides smarter, more responsible choices.

    Conclusion: A Foundation for Future Possibilities

    5-Bromo-2,1,3-benzothiadiazole draws strength from clear, useful differences compared to other chemical analogs. Its role in research and industry keeps growing because it delivers on its promises, helps push science forward, and supports responsible stewardship of every experiment and synthesis. Whether in the hands of a student learning his first coupling reaction or a team scaling up materials for the next generation of electronics, this building block continues to prove its worth, crafting both progress and trust one experiment at a time.