916914-03-9

Basic information

• Product Name: 2-(Difluoromethyl)-1H-indole
• Synonyms: 2-DIFLUOROMETHYLINDOL;2-(Difluoromethyl)-1H-indole
• CAS NO: 916914-03-9
• Molecular Formula: C9H7F2N
• Molecular Weight: 167.16
• Mol File: 916914-03-9.mol

Chemical Properties

• Boiling Point: 283 °C
• Flash Point: 125 °C
• Appearance: /
• Density: 1.287
• Refractive Index: 1.589
• CAS DataBase Reference: 2-(Difluoromethyl)-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Difluoromethyl)-1H-indole(916914-03-9)
• EPA Substance Registry System: 2-(Difluoromethyl)-1H-indole(916914-03-9)

Safety Data

• Hazardous Substances Data: 916914-03-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Chemical Research:
2-(Difluoromethyl)-1H-indole serves as a building block in the synthesis of various biologically active molecules, contributing to the advancement of pharmaceutical and chemical research. Its distinct structural features facilitate the creation of new compounds with potential therapeutic applications.
Used in Medicinal Chemistry and Drug Discovery:
In the field of medicinal chemistry, 2-(Difluoromethyl)-1H-indole is utilized for the development of potential drug candidates. Its unique structure allows it to target specific biological pathways and receptors, which is crucial for the discovery of new therapeutic agents.
Used in the Synthesis of Targeted Therapies:
2-(Difluoromethyl)-1H-indole is employed in the synthesis of compounds that can potentially target and modulate specific biological pathways, offering a route to develop targeted therapies for various diseases. Its reactivity and structural attributes are instrumental in the design and synthesis of such molecules.

InChI:InChI=1/C9H7F2N/c10-9(11)8-5-6-3-1-2-4-7(6)12-8/h1-5,9,12H

Upstream product

• 120-72-9 indole 
• 221044-05-9 N-(2-pyrimidyl)indole 
• 275818-95-6 sodium difluoromethanesulfinate 
• 58310-28-4 (Difluoromethyl)triphenylphosphonium bromide 
• 5344-90-1 2-Aminobenzyl alcohol 
• 381-73-7 Difluoroacetic acid 
• 95-53-4 o-toluidine 
• 916910-97-9 N-(o-tolyl)-2,2-difluoroacetimidoyl chloride 
• 916911-80-3 N-[2-(bromomethyl)phenyl]-2,2-difluoroacetimidoyl chloride 

Relevant articles and documents

Direct access to 2-difluoromethyl indoles via photoredox catalysis

A visible-light mediated approach to radical difluoromethylation of 3- and 3,5-substituted indoles was investigated using a readily synthesized difluoromethyl source, CF2HPPh3Br. Direct difluoromethylation of indoles in the two position is a rare feat in the literature. The reactions were conducted at room temperature, using Ir(ppy)3 as photocatalyst in acetone, to afford the 2-difluoromethyl indoles in relatively low to moderate yields.

The copper(ii)-catalyzed and oxidant-promoted regioselective C-2 difluoromethylation of indoles and pyrroles

A novel and efficient approach for the highly selective C-2 difluoromethylation of indole derivatives was developed by using sodium difluoromethylsulfinate (HCF2SO2Na) as the source of difluoromethyl groups and a Cu(ii) complex as the catalyst. Various substrates were well tolerated in this transformation and the desired products were obtained in moderate to good yields. Moreover, the late-stage C-2 difluoromethylation of bioactive molecules containing an indole ring was achieved in good yields. Generally, this reaction features excellent functional group compatibility, broad substrate scope and excellent C-2 selectivity. This journal is

Direct C–H difluoromethylation of heterocycles via organic photoredox catalysis

The discovery of modern medicine relies on the sustainable development of synthetic methodologies to meet the needs associated with drug molecular design. Heterocycles containing difluoromethyl groups are an emerging but scarcely investigated class of organofluoro molecules with potential applications in pharmaceutical, agricultural and material science. Herein, we developed an organophotocatalytic direct difluoromethylation of heterocycles using O2 as a green oxidant. The C–H oxidative difluoromethylation obviates the need for pre-functionalization of the substrates, metals and additives. The operationally straightforward method enriches the efficient synthesis of many difluoromethylated heterocycles in moderate to excellent yields. The direct difluoromethylation of pharmaceutical moleculars demonstrates the practicability of this methodology to late-stage drug development. Moreover, 2′-deoxy-5-difluoromethyluridine (F2TDR) exhibits promising activity against some cancer cell lines, indicating that the difluoromethylation methodology might provide assistance for drug discovery.

A New and Efficient One-Pot Synthesis of 2-Fluoroalkyl Substituted Indoles

A new simple and efficient one-pot synthesis of 2-fluoroalkyl substituted indoles from 2-aminobenzyl alcohols with fluorine-containing carboxylic acids in the presence of Ph3P, CCl4, and NEt3 is described. Various kinds of 2-fluoroalkyl substituted indole derivatives can be conveniently prepared.

Bromotriphenylphosphonium salt promoted one-pot cyclization to 2-fluoroalkyl-substituted indoles

2-Fluoroalkyl-substituted indoles were prepared in moderate to excellent yields through bromotriphenylphosphonium salt promoted ring formation with fluorine-containing carboxylic acids in the presence of triethylamine in toluene at reflux temperature. A range of 2-fluoroalkyl-substituted indole derivatives can be conveniently prepared.

Grignard cyclization reaction of fluorinated N-arylimidoyl chlorides: A novel and facile access to 2-fluoroalkyl indoles

2-Fluoroalkyl-substituted indole derivatives were simply prepared via the Grignard cyclization reaction (GCR) of corresponding fluorinated N-aryl imidoyl chlorides in good yields. This approach provides a novel and facile access to the biologically import

Fluorinated N-[2-(haloalkyl)phenyl]imidoyl chloride, a key intermediate for the synthesis of 2-fluoroalkyl substituted indole derivatives via Grignard cyclization process

Fluorinated N-[2-(haloalkyl)phenyl]imidoyl chloride, which was readily available from the corresponding anilines by using Uneyama's one-pot synthesis of fluorinated imidoyl chloride, was found to be a key intermediate for the facile synthesis of 2-fluoroa