Production Method 1

5430-45-5

927801-25-0

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide ,  Sulfuric acid ;  0 °C; overnight, rt
1.2 Reagents: Ammonia Solvents: Water ;  pH 8 - 9, cooled

Reference

Regioexhaustive Functionalization of the Carbocyclic Core of Isoquinoline: Concise Synthesis of Oxoaporphine Core and Ellipticine

Horvath, Daniel Vajk; Domonyi, Frigyes; Palko, Roberta; Lomoschitz, Andrea; Soos, Tibor, Synthesis, 2018, 50(11), 2181-2190

8-Bromo-5-chloroisoquinoline Raw materials

• 5-Chloroisoquinoline

8-Bromo-5-chloroisoquinoline Preparation Products

• 8-Bromo-5-chloroisoquinoline (927801-25-0)

• 1. Excited-state proton-coupled electron transfer within ion pairs?
  Gerald J. Meyer,Leif Hammarstr?m Chem. Sci., 2020,11, 3460-3473
• 2. Fate of nitrogen-15 in the subsequent growing season of greenhouse tomato plants (Lycopersicon esculentum Mill) as influenced by alternate partial root-zone irrigation
  Maomao Hou,Fenglin Zhong,Qiu Jin,Enjiang Liu,Jie Feng,Tengyun Wang,Yue Gao RSC Adv., 2017,7, 34392-34400
• 3. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002
• 4. Examination of deposit in commercial diluted phosphoric acid
  Analyst, 1880,5, 146-147
• 5. Examination of the hydrogen-bonding networks in small water clusters (n = 2–5, 13, 17) using absolutely localized molecular orbital energy decomposition analysis?
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoquinolines and derivatives Isoquinolines and derivatives
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Isoquinolines and derivatives

Introduction to 8-Bromo-5-chloroisoquinoline (CAS No. 927801-25-0)

8-Bromo-5-chloroisoquinoline, identified by the Chemical Abstracts Service Number (CAS No.) 927801-25-0, is a heterocyclic organic compound that has garnered significant attention in the field of pharmaceutical and chemical research. This compound belongs to the isoquinoline family, a class of molecules known for their diverse biological activities and structural versatility. The presence of both bromine and chlorine substituents in its molecular structure enhances its reactivity, making it a valuable intermediate in synthetic chemistry and drug development.

The isoquinoline scaffold is a privileged structure in medicinal chemistry, frequently employed in the design of bioactive molecules due to its ability to interact with various biological targets. The introduction of halogen atoms, such as bromine and chlorine, into the isoquinoline core modulates its electronic properties and influences its binding affinity to biological receptors. This modification has been strategically utilized to develop novel pharmacophores with enhanced potency and selectivity.

In recent years, 8-Bromo-5-chloroisoquinoline has been extensively studied for its potential applications in the synthesis of small-molecule inhibitors targeting cancer-related pathways. Isoquinoline derivatives have shown promise in disrupting key signaling cascades involved in tumor growth and progression. Specifically, research has highlighted the compound's role in modulating enzymes such as tyrosine kinases and transcription factors, which are critical in cancer cell proliferation and survival.

One of the most compelling aspects of 8-Bromo-5-chloroisoquinoline is its utility as a building block for more complex scaffolds. The halogenated isoquinoline core provides a versatile platform for further functionalization through cross-coupling reactions, such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the construction of structurally diverse libraries of compounds. These libraries are then subjected to high-throughput screening (HTS) to identify lead candidates with desirable pharmacological properties.

Recent advancements in computational chemistry have further accelerated the discovery process involving 8-Bromo-5-chloroisoquinoline. Molecular modeling techniques, including docking studies and quantum mechanical calculations, have been employed to predict the binding modes of this compound with target proteins. Such computational approaches not only save time but also provide insights into the structural optimization of analogs with improved pharmacokinetic profiles.

The synthesis of 8-Bromo-5-chloroisoquinoline typically involves multi-step organic transformations starting from readily available precursors. Key steps often include cyclization reactions to form the isoquinoline ring system followed by halogenation at specific positions using appropriate electrophilic or nucleophilic halogenating agents. The regioselectivity of these reactions is crucial, as it determines the final configuration of the molecule and its subsequent biological activity.

In addition to its pharmaceutical applications, 8-Bromo-5-chloroisoquinoline has found utility in materials science and agrochemical research. Its aromatic structure and halogen substituents make it a suitable candidate for developing organic semiconductors and ligands for metal-catalyzed reactions. Furthermore, derivatives of this compound have been explored as potential intermediates in the synthesis of pesticides and herbicides due to their ability to interfere with enzymatic pathways in pests.

The growing interest in 8-Bromo-5-chloroisoquinoline has led to several patents being filed by pharmaceutical companies aiming to commercialize derivatives with therapeutic potential. These patents often highlight novel synthetic routes and applications that expand the compound's utility beyond traditional drug development. The increasing investment in research underscores the perceived value of this molecule as a key intermediate in modern medicinal chemistry.

Future directions in the study of 8-Bromo-5-chloroisoquinoline may involve exploring its role in addressing emerging therapeutic challenges, such as antibiotic resistance or neurodegenerative diseases. The versatility of its molecular framework allows for modifications that could tailor its activity towards specific disease targets. Additionally, green chemistry principles are being increasingly applied to optimize synthetic methodologies, reducing environmental impact while maintaining high yields and purity standards.

In conclusion, 8-Bromo-5-chloroisoquinoline (CAS No. 927801-25-0) represents a significant advancement in chemical synthesis and drug discovery. Its unique structural features and reactivity make it an indispensable tool for researchers seeking to develop innovative therapeutics. As scientific understanding progresses, it is likely that new applications for this compound will continue to emerge, further solidifying its importance in both academic and industrial settings.

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