6-Bromo-1-chloroisoquinoline
[CAS# 205055-63-6]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Isoquinoline compound
• Name: 6-Bromo-1-chloroisoquinoline
• Synonyms: 1-Chloro-6-bromoisoquinoline
• Molecular Formula: C₉H₅BrClN
• Molecular Weight: 242.50
• CAS Registry Number: 205055-63-6
• EC Number: 809-114-2
• SMILES: C1=CC2=C(C=CN=C2Cl)C=C1Br

Properties

• Density: 1.673

Safety Data

• Hazard Symbols: GHS05;GHS06;GHS07 Danger
• Hazard Statements: H301-H315-H318
• Precautionary Statements: P264-P264+P265-P270-P280-P301+P316-P302+P352-P305+P354+P338-P317-P321-P330-P332+P317-P362+P364-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Acute toxicity	Acute Tox.	3	H301
Serious eye damage	Eye Dam.	1	H318
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	3	H331

Discovory and Applicatios

6-Bromo-1-chloroisoquinoline is a chemical compound that has garnered attention for its utility in organic synthesis and medicinal chemistry. This compound features a halogenated isoquinoline structure, which imparts unique reactivity and interaction properties that are leveraged in various applications.

The discovery of 6-Bromo-1-chloroisoquinoline stems from the broader interest in halogenated heterocycles, which are known for their diverse reactivity patterns and roles as intermediates in chemical synthesis. The synthesis of this compound typically involves halogenation of the isoquinoline ring, with bromine and chlorine being introduced at specific positions to modify the molecule's electronic and steric properties. This strategic substitution pattern enables the compound to serve as a versatile building block in chemical transformations.

One of the primary applications of 6-Bromo-1-chloroisoquinoline is in the synthesis of complex organic molecules. The halogen atoms in this compound are particularly useful for cross-coupling reactions, such as Suzuki and Heck reactions, which are widely employed to construct complex molecular frameworks. These reactions facilitate the creation of new carbon-carbon bonds, making 6-Bromo-1-chloroisoquinoline a valuable reagent in the development of pharmaceuticals, agrochemicals, and materials.

In medicinal chemistry, 6-Bromo-1-chloroisoquinoline is explored for its potential as a scaffold for the development of bioactive compounds. The presence of halogen atoms in the isoquinoline ring can influence the compound's interaction with biological targets, such as enzymes and receptors. This property makes it a candidate for further modification to yield compounds with specific biological activities, including anticancer and antimicrobial properties. By modifying the isoquinoline core and introducing different functional groups, researchers can develop derivatives with enhanced efficacy and selectivity for therapeutic applications.

Additionally, the compound is used in the development of chemical probes and markers for biological research. The distinct chemical structure of 6-Bromo-1-chloroisoquinoline allows it to be employed in studying biochemical pathways and cellular processes. Its role as a functional group in the design of fluorescent or radioactive tracers enhances the ability to monitor biological systems and evaluate the effects of various interventions.

The synthesis of 6-Bromo-1-chloroisoquinoline involves standard procedures for halogenation of isoquinoline, including electrophilic aromatic substitution. The compound is typically prepared through the reaction of isoquinoline with bromine and chlorine under controlled conditions, followed by purification to obtain the desired product.

In summary, 6-Bromo-1-chloroisoquinoline is a valuable compound in organic synthesis and medicinal chemistry. Its halogenated structure provides reactivity and functionality that are harnessed in the creation of complex molecules and bioactive compounds. Its applications in both chemical synthesis and biological research highlight its importance as a versatile reagent and a scaffold for developing new therapeutics.

References

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DOI: 10.1007/s11274-018-2477-9

2015. Bringing nitrilase sequences from databases to life: the search for novel substrate specificities with a focus on dinitriles. Applied Microbiology and Biotechnology, 99(24), 10541-10553.
DOI: 10.1007/s00253-015-7023-1

2010. Reaction of unsaturated nitriles with hydrosilanes. Russian Journal of General Chemistry, 80(5), 926-930.
DOI: 10.1134/s1070363210050105