Production Method 1

955978-77-5

955978-75-3

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Toluene ;  2 h, 60 °C; 60 °C → 0 °C
1.2 Solvents: Dimethylformamide ;  16 h, rt → reflux

Reference

Preparation of furanopyrimidines as inhibitors of phosphatidylinositol 3-kinase

, World Intellectual Property Organization, , ,

Production Method 2

955978-77-5

955978-75-3

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Toluene ;  rt → 60 °C; 2 h, 60 °C; < 5 °C
1.2 Solvents: Dimethylformamide ;  overnight, reflux

Reference

Preparation of indole and benzimidazole derivatives as dual 5-HT2a and 5-HT6 receptor antagonists

, World Intellectual Property Organization, , ,

Production Method 3

955978-77-5

955978-75-3

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Toluene ;  2 h, 60 °C; 60 °C → 0 °C
1.2 Solvents: Dimethylformamide ;  16 h, reflux

Reference

Preparation of thienopyrimidine derivatives as inhibitors of PI3 kinase

, World Intellectual Property Organization, , ,

Production Method 4

955978-77-5

955978-75-3

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Toluene ;  2 h, 60 °C; 60 °C → 0 °C

Reference

2-(Morpholin-4-yl)pyrimidine derivatives as PI3K inhibitors and their preparation, pharmaceutical compositions and use in the treatment of diseases

, World Intellectual Property Organization, , ,

Production Method 5

955978-77-5

955978-75-3

Reaction Conditions

1.1 Reagents: Triphenylphosphine Solvents: Toluene ;  2 h, 60 °C; 60 °C → 0 °C
1.2 Solvents: Dimethylformamide ;  16 h, rt → reflux

Reference

Preparation of thienopyrimidine derivatives as PI3 kinase inhibitors

, World Intellectual Property Organization, , ,

Production Method 6

55289-35-5

955978-75-3

Reaction Conditions

1.1 Reagents: Potassium ethoxide Solvents: Dimethylformamide ;  overnight, -50 °C; -50 °C → rt
1.2 Reagents: Zinc Solvents: Ethanol ,  Acetic acid ;  overnight, -50 °C; -50 °C → rt
1.3 Reagents: Ammonia Solvents: Methanol ,  Water ;  2 - 4 d, rt

Reference

Two-step, regioselective, multigram-scale synthesis of 2-(trifluoromethyl)indoles from 2-nitrotoluenes

Walewska-Krolikiewicz, Magdalena; Wilk, Bogdan; Kwast, Andrzej ; Wrobel, Zbigniew, Tetrahedron Letters, 2021, 86,

4-Bromo-2-(trifluoromethyl)-1H-indole Raw materials

• 1-Bromo-2-methyl-3-nitrobenzene
• Acetamide, N-[3-bromo-2-(bromomethyl)phenyl]-2,2,2-trifluoro-

4-Bromo-2-(trifluoromethyl)-1H-indole Preparation Products

• 4-Bromo-2-(trifluoromethyl)-1H-indole (955978-75-3)

• 1. An alumina stabilized graphene oxide wrapped SnO2 hollow sphere LIB anode with improved lithium storage?
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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Indoles and derivatives Indoles

4-Bromo-2-(trifluoromethyl)-1H-indole (CAS No. 955978-75-3): A Versatile Building Block in Modern Organic Synthesis

The 4-Bromo-2-(trifluoromethyl)-1H-indole (CAS 955978-75-3) represents a highly valuable heterocyclic compound in contemporary pharmaceutical and materials chemistry. As a brominated indole derivative featuring a trifluoromethyl group at the 2-position, this compound has gained significant attention from researchers working in medicinal chemistry, agrochemical development, and organic electronics. The unique combination of electron-withdrawing groups and the indole scaffold makes it particularly interesting for designing novel bioactive molecules.

Recent search trends on scientific databases reveal growing interest in "trifluoromethyl indole synthesis" and "brominated heterocycles applications", reflecting the compound's importance in modern research. The 4-Bromo-2-(trifluoromethyl)-1H-indole serves as a crucial intermediate for developing kinase inhibitors, with particular relevance to cancer research, as evidenced by numerous patent applications in this area. Its electron-deficient aromatic system also makes it valuable for creating organic semiconductors, aligning with current interests in flexible electronics and OLED materials.

The compound's physicochemical properties contribute to its widespread utility. With a molecular weight of 264.03 g/mol and the presence of both bromine and trifluoromethyl substituents, it offers excellent opportunities for cross-coupling reactions and further functionalization. Researchers frequently search for "palladium-catalyzed reactions of bromoindoles" and "trifluoromethyl group transformations", highlighting the synthetic versatility of this building block. The electron-withdrawing nature of the substituents also influences the indole nitrogen's basicity, making it valuable for designing pH-sensitive compounds.

In pharmaceutical applications, the 4-Bromo-2-(trifluoromethyl)-1H-indole scaffold appears in several drug discovery programs targeting inflammatory diseases and CNS disorders. The trifluoromethyl group's ability to enhance metabolic stability and lipophilicity makes this compound particularly attractive for medicinal chemists. Current search data shows increased interest in "CF3-substituted indoles in drug design" and "brominated heterocycles in CNS drugs", reflecting these applications.

The synthesis of 4-Bromo-2-(trifluoromethyl)-1H-indole typically involves electrophilic bromination of the corresponding indole precursor, followed by careful purification processes. Analytical techniques like HPLC, NMR, and mass spectrometry are essential for quality control, as purity significantly impacts its performance in subsequent reactions. Researchers often search for "analytical methods for bromoindoles" and "purification of trifluoromethyl compounds", indicating the technical challenges associated with working with this class of compounds.

From a commercial perspective, the demand for 4-Bromo-2-(trifluoromethyl)-1H-indole has been steadily increasing, particularly from contract research organizations and pharmaceutical companies. Market analysis reveals growing interest in "high-value indole derivatives" and "fluorinated building blocks market trends". The compound's price and availability fluctuate based on raw material costs and synthetic complexity, making it a subject of interest for procurement specialists searching for "bulk suppliers of bromoindoles".

Environmental and handling considerations for 4-Bromo-2-(trifluoromethyl)-1H-indole follow standard laboratory safety protocols. While not classified as hazardous under normal handling conditions, proper personal protective equipment should be used when working with this compound. Storage recommendations typically suggest keeping it in a cool, dry place under inert atmosphere to maintain stability, addressing common search queries about "storage conditions for halogenated indoles".

The future research directions for 4-Bromo-2-(trifluoromethyl)-1H-indole derivatives appear promising, particularly in the development of targeted therapies and advanced materials. Emerging search terms like "indole derivatives in personalized medicine" and "fluorinated compounds for organic electronics" suggest expanding applications. The compound's versatility ensures its continued relevance in both academic and industrial research settings, making it a valuable asset for synthetic chemists and material scientists alike.

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