86626-38-2

Basic information

• Product Name: 4-BROMO-2,3-DIHYDRO-1H-INDOLE
• Synonyms: 4-BROMO-2,3-DIHYDRO-1H-INDOLE;4-BROMO-2,3-DIHYDRO-1H-INDOLE HYDROCHLORIDE;4-bromoindoline hydrochloride;4-bromoindoline;1H-Indole,4-broMo-2,3-dihydro-;4-BroMo-2,3-dihydro-1H-indole 1HCl salt
• CAS NO: 86626-38-2
• Molecular Formula: C₈H₈BrN
• Molecular Weight: 198.06
• Mol File: 86626-38-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 278.845 °C at 760 mmHg
• Flash Point: 122.442 °C
• Appearance: /
• Density: 1.515 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• PKA: 4.20±0.20(Predicted)
• CAS DataBase Reference: 4-BROMO-2,3-DIHYDRO-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-2,3-DIHYDRO-1H-INDOLE(86626-38-2)
• EPA Substance Registry System: 4-BROMO-2,3-DIHYDRO-1H-INDOLE(86626-38-2)

Safety Data

• Hazardous Substances Data: 86626-38-2(Hazardous Substances Data)

Usage

General Description

4-Bromo-2,3-dihydro-1H-indole is a chemical compound with the molecular formula C8H8BrN. It is a derivative of indole, a heterocyclic organic compound commonly found in many natural products and pharmaceuticals. The presence of a bromine atom at the 4-position of the indole ring makes this compound useful in the synthesis of various biologically active molecules, such as pharmaceutical drugs and agrochemicals. 4-Bromo-2,3-dihydro-1H-indole has been studied for its potential pharmacological properties, including its role as a serotonin receptor agonist, antihypertensive agent, and potential anti-cancer agent. Its structural features make it an important building block in organic synthesis and medicinal chemistry.

Upstream product

• 120-72-9 indole 
• 99365-48-7 4-bromoindolin-2-one 
• 52488-36-5 4-bromo-1H-indole 
• 496-15-1 1-indoline 

Downstream Products

• 1160359-95-4 4-bromo-1-(4-fluorobenzyl)indoline 
• 885272-46-8 tert-butyl 4-bromo-2,3-dihydro-1H-indole-1-carboxylate 
• 52488-36-5 4-bromo-1H-indole 
• 106-47-8 4-chloro-aniline 
• 62-53-3 aniline 
• 179473-53-1 4-phenyl-2,3-dihydro-1H-indole 

Relevant articles and documents

Concerning the preparation of 6-bromotryptamine

Most of the previous syntheses of the marine natural product 6-bromotryptamine have almost certainly led to partial debromination resulting in an impure product containing tryptamine. We show that loss of bromine occurs when lithium aluminum hydride is employed as a reducing agent in the final reaction step leading to 6-bromotryptamine. Reductive-debromination is also likely to intrude during some of the syntheses of 6-bromoindole, the typical precursor to 6-bromotryptamine. None of the seven described syntheses of 6-bromotryptamine that involve a reduction sequence from 6-bromoindole have reported elemental analyses as a measure of purity.

Regioselective Formation of Substituted Indoles: Formal Synthesis of Lysergic Acid

A Diels–Alder reaction-based strategy for the synthesis of indoles and related heterocycles is reported. An intramolecular cycloaddition of alkyne-tethered 3-aminopyrones gives 4-substituted indolines in good yield and with complete regioselectivity. Additional substitution is readily tolerated in the transformation, allowing synthesis of complex and non-canonical substitution patterns. Oxidative conditions give the corresponding indoles. The strategy also allows the synthesis of carbazoles. The method was showcased in a formal synthesis of lysergic acid.

Hydrogenation or Dehydrogenation of N-Containing Heterocycles Catalyzed by a Single Manganese Complex

A highly chemoselective base-metal catalyzed hydrogenation and acceptorless dehydrogenation of N-heterocycles is presented. A well-defined Mn complex operates at low catalyst loading (as low as 2 mol %) and under mild reaction conditions. The described catalytic system tolerates various functional groups, and the corresponding reduced heterocycles can be obtained in high yields. Experimental studies indicate a metal-ligand cooperative catalysis mechanism.