Cas no 1393576-39-0 (6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline)

6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline is a brominated tetrahydroisoquinoline derivative with a quaternary carbon center at the 1-position. This compound serves as a versatile intermediate in organic synthesis, particularly in the preparation of pharmaceuticals and bioactive molecules. The bromine substituent at the 6-position enhances its reactivity for further functionalization, such as cross-coupling reactions, while the dimethyl group at the 1-position provides steric and electronic modulation. Its rigid tetrahydroisoquinoline scaffold is valuable for constructing heterocyclic frameworks. The compound is typically handled under inert conditions due to its sensitivity. It finds applications in medicinal chemistry research, including the development of CNS-targeting agents and enzyme inhibitors.
6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline structure
1393576-39-0 structure
Product Name:6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline
CAS No:1393576-39-0
MF:C11H14BrN
MW:240.139562129974
CID:4673435
Update Time:2025-06-08

6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline Chemical and Physical Properties

Names and Identifiers

    • 6-BROMO-1,1-DIMETHYL-1,2,3,4-TETRAHYDROISOQUINOLINE
    • ZINC95764320
    • AB77379
    • FCH2290785
    • AX8250940
    • 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline
    • Inchi: 1S/C11H14BrN/c1-11(2)10-4-3-9(12)7-8(10)5-6-13-11/h3-4,7,13H,5-6H2,1-2H3
    • InChI Key: WFFAZFOOYCMKDP-UHFFFAOYSA-N
    • SMILES: BrC1C=CC2=C(C=1)CCNC2(C)C

Computed Properties

  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 1
  • Heavy Atom Count: 13
  • Rotatable Bond Count: 0
  • Complexity: 191
  • XLogP3: 0
  • Topological Polar Surface Area: 12

6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline Pricemore >>

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Additional information on 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline

Introduction to 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline (CAS No. 1393576-39-0) in Modern Chemical Research

6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline, identified by the chemical identifier CAS No. 1393576-39-0, is a significant compound in the realm of pharmaceutical chemistry and medicinal biology. This heterocyclic amine derivative has garnered considerable attention due to its structural uniqueness and its potential applications in drug discovery and development. The compound’s molecular framework, featuring a brominated tetrahydroisoquinoline core, makes it a versatile scaffold for synthesizing bioactive molecules with therapeutic implications.

The tetrahydroisoquinoline backbone is a well-documented motif in natural products and pharmacologically active agents. Its structural features contribute to favorable pharmacokinetic properties, including good solubility and metabolic stability. The introduction of a bromo substituent at the 6-position enhances the electrophilicity of the molecule, making it a valuable intermediate for further functionalization via cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings. These transformations are pivotal in constructing more complex molecular architectures essential for designing novel therapeutic agents.

In recent years, there has been growing interest in tetrahydroisoquinoline derivatives as potential candidates for treating neurological disorders, cardiovascular diseases, and cancer. The brominated derivatives, in particular, have been extensively studied for their ability to modulate neurotransmitter receptors and signal transduction pathways. For instance, research has highlighted the role of 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline in modulating dopamine receptor activity, which is relevant to conditions such as Parkinson’s disease and depression. Preclinical studies have demonstrated its potential as a lead compound for further optimization into drugs targeting dopaminergic pathways.

The synthesis of 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline involves multi-step organic transformations that highlight the ingenuity of modern synthetic chemistry. Typically, the synthesis starts from readily available precursors like phenethylamines or benzylamines through cyclization reactions followed by bromination and subsequent alkylation steps. Advances in catalytic methods have enabled more efficient and scalable production processes for this compound. For example, palladium-catalyzed cross-coupling reactions have been employed to introduce various substituents at different positions of the tetrahydroisoquinoline ring system with high regioselectivity.

The pharmacological profile of 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline has been thoroughly investigated in vitro and in vivo. Studies have revealed its binding affinity to various protein targets including enzymes and receptors involved in critical biological processes. Notably, its interaction with monoamine oxidase (MAO) enzymes has been explored as a potential mechanism for its therapeutic effects. MAO inhibitors are known to play a role in managing neurodegenerative diseases by preventing the oxidative degradation of neurotransmitters such as dopamine.

Recent breakthroughs in computational chemistry have further accelerated the discovery process for compounds like 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline. Molecular modeling techniques allow researchers to predict binding affinities and pharmacokinetic properties with remarkable accuracy before conducting expensive wet-lab experiments. This integration of computational methods with traditional synthetic chemistry has led to faster identification of lead compounds with optimized pharmacological profiles.

The versatility of 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline as a building block extends beyond neurological applications. Its structural framework can be modified to target other disease pathways such as cancer proliferation and inflammation. For example, modifications at the 7-position or 3-position can introduce additional functional groups that enhance binding interactions with specific cancer-related proteins or kinases. Such modifications are crucial for developing targeted therapies that exhibit high selectivity and low toxicity.

The industrial production of 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline adheres to stringent quality control measures to ensure consistency and purity。 High-performance liquid chromatography (HPLC) and nuclear magnetic resonance (NMR) spectroscopy are commonly employed analytical techniques for characterizing the compound during synthesis and purification stages。 These methods provide detailed insights into the molecular structure and purity, which are critical for pharmaceutical applications。

The future prospects of 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline in drug development are promising。 Ongoing research aims to explore novel synthetic routes that improve yield and reduce environmental impact。 Additionally, collaborations between academic institutions and pharmaceutical companies are fostering innovation by combining expertise in organic synthesis, medicinal chemistry, and drug discovery。 Such partnerships are essential for translating laboratory findings into clinical candidates that can address unmet medical needs。

In conclusion, 6-Bromo-1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline (CAS No. 1393576-39-0) represents a fascinating compound with significant potential in modern chemical research。 Its unique structural features make it a valuable intermediate for synthesizing bioactive molecules with therapeutic applications across multiple disease areas。 As research continues to uncover new aspects of its pharmacology and synthetic utility, this compound is poised to play an increasingly important role in the development of next-generation pharmaceuticals。

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