1186663-46-6

Basic information

• Product Name: 3-Bromo-5-fluoroindole
• Synonyms: 3-Bromo-5-fluoroindole;3-Bromo-5-fluoro-1H-indole;3-Bromo-5-fluoroindole Boc Protected
• CAS NO: 1186663-46-6
• Molecular Formula: C8H5BrFN
• Molecular Weight: 214
• Mol File: 1186663-46-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 320.5±22.0 °C(Predicted)
• Appearance: /
• Density: 1.750±0.06 g/cm3(Predicted)
• PKA: 14.49±0.30(Predicted)
• CAS DataBase Reference: 3-Bromo-5-fluoroindole(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-5-fluoroindole(1186663-46-6)
• EPA Substance Registry System: 3-Bromo-5-fluoroindole(1186663-46-6)

Safety Data

• Hazardous Substances Data: 1186663-46-6(Hazardous Substances Data)

Usage

General Description

3-Bromo-5-fluoroindole is a chemical compound with the molecular formula C8H5BrFN. It is a heterocyclic aromatic compound and belongs to the class of indole derivatives. 3-Bromo-5-fluoroindole is used in the pharmaceutical industry as a building block in the synthesis of various biologically active molecules. It possesses potential medicinal properties and is currently being investigated for its use in the development of new drugs. 3-Bromo-5-fluoroindole is known for its ability to act as a substrate in the production of pharmaceutical intermediates and has shown potential in the treatment of various diseases. Additionally, this compound has been studied for its potential application in the synthesis of novel materials and catalysts.

Upstream product

• 399-52-0 5-fluoro-1H-indole 

Downstream Products

• 1026089-07-5 3-bromo-5-fluoro-1-(phenylsulfonyl)-1H-indole 

Relevant articles and documents

Predicting the Substrate Scope of the Flavin-Dependent Halogenase BrvH

The recently described flavin-dependent halogenase BrvH is able to catalyse both the bromination and chlorination of indole, but shows significantly higher bromination activity. BrvH was annotated as a tryptophan halogenase, but does not accept tryptophan as a substrate. Its native substrate remains unknown. A predictive model with the data available for BrvH was analysed. A training set of compounds tested in vitro was docked into the active site of a complete protein model based on the X-ray structure of BrvH. The atoms not resolved experimentally were modelled by using molecular mechanics force fields to obtain this protein model. Furthermore, docking poses for the substrates and known non-substrates have been calculated. Parameters like distance, partial charge and hybridization state were analysed to derive rules for predicting activity. With this model for activity of the BrvH, a virtual screening suggested several structures for potential substrates. Some of the compounds preselected in this way were tested in vitro, and several could be verified as convertible substrates. Based on information on halogenated natural products, a new dataset was created to specifically search for natural products as substrates/products, and virtual screening in this database yielded further hits.

PhI(OAc)2/NaX-mediated halogenation providing access to valuable synthons 3-haloindole derivatives

This paper describes a mild phenyliodine diacetate mediated method for selective chlorination, bromination, and iodination of indole C-H bonds using sodium halide as a source for analogous halogenations. The combination of NaX and phenyliodine diacetate provides an invincible system for halogenation of indoles. This protocol was compatible with a wide array of indole substrates and provides straight forward access to potential halogenated arenes.

Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5,5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin

Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions.