106698-07-1

Basic information

• Product Name: 1-acetyl-5-bromoindolin-3-one
• Synonyms: 1-acetyl-5-bromoindolin-3-one;1-Acetyl-5-bromo-1,2-dihydro-3H-indol-3-one;3H-Indol-3-one, 1-acetyl-5-broMo-1,2-dihydro-
• CAS NO: 106698-07-1
• Molecular Formula: C₁₀H₈BrNO₂
• Molecular Weight: 254.082
• Mol File: 106698-07-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 487.7 °C at 760 mmHg
• Flash Point: 248.7 °C
• Appearance: /
• Density: 1.655
• Vapor Pressure: 1.16E-09mmHg at 25°C
• Refractive Index: 1.626
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 1-acetyl-5-bromoindolin-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-acetyl-5-bromoindolin-3-one(106698-07-1)
• EPA Substance Registry System: 1-acetyl-5-bromoindolin-3-one(106698-07-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 106698-07-1(Hazardous Substances Data)

Usage

Description

1-Acetyl-5-bromoindolin-3-one is an organic compound that serves as a valuable research intermediate in the field of pharmaceutical chemistry. It is characterized by its unique molecular structure, which includes an indole core with an acetyl group at the 1st position and a bromine atom at the 5th position. 1-Acetyl-5-bromoindolin-3-one is known for its potential applications in the development of indole derivatives and analogs, particularly those with 5-HT6 receptor antagonistic properties.

Uses

Used in Pharmaceutical Research:
1-Acetyl-5-bromoindolin-3-one is used as a research intermediate for the preparation of indole derivatives and analogs. Its application is primarily driven by its ability to contribute to the development of compounds with 5-HT6 receptor antagonistic activity, which can be crucial in the treatment of various neurological and psychiatric disorders.
Used in Drug Development:
In the pharmaceutical industry, 1-Acetyl-5-bromoindolin-3-one is utilized as a key component in the synthesis of novel drugs targeting the 5-HT6 receptor. This receptor is associated with cognitive functions, and its modulation has been linked to potential therapeutic benefits in conditions such as Alzheimer's disease, schizophrenia, and obesity. The compound's role in drug development is to facilitate the creation of new molecules with improved efficacy and selectivity for the 5-HT6 receptor.
Used in Chemical Synthesis:
1-Acetyl-5-bromoindolin-3-one is also employed in chemical synthesis as a versatile building block for the creation of various indole-based compounds. Its unique structure allows for further functionalization and modification, enabling the synthesis of a wide range of molecules with diverse biological activities and potential applications in different fields, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C10H8BrNO2/c1-6(13)12-5-10(14)8-4-7(11)2-3-9(8)12/h2-4H,5H2,1H3

Upstream product

• 106698-05-9 1-acetyl-5-bromo-3-hydroxy-2-methoxyindole 
• 33588-54-4 5-bromoindoxyl diacetate 
• 61995-52-6 1-(5-bromo-1H-indol-1-yl)ethan-1-one 
• 868694-19-3 5-bromo-3-iodo-1H-indole 
• 10075-50-0 5-bromo-1H-indole 
• 17357-14-1 5-bromo-3-indoxyl acetate 
• 32253-75-1 5-bromo-2-<(carboxymethyl)amino>-benzoic acid 
• 610-71-9 2,5-dibromobenzoic acid 

Downstream Products

• 1276688-15-3 (S)-1-acetyl-5-bromo-2-((S)-2-nitro-1-phenylethyl)indolin-3-one 

Relevant articles and documents

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Indoxyl-based umpolung strategy for the synthesis of unsymmetrical 3,3′-biindoles

3,3′-Bisindoles are known to be important structural motifs found in bioactive natural products, pharmaceuticals, and functional materials. Herein, a novel indoxyl-based approach was established for the synthesis of unsymmetrical 3,3′-biindoles from indoles and indoxyls. This approach generated moderate to excellent yields of the desired products (24 examples, up to 98% yield). The present method features broad substrate scope, operational simplicity, high atom economy, and utilization of non-toxic and inexpensive molecular iodine as catalyst. The applicability of this method has been demonstrated by the facile gram-scale synthesis.

Indole-3-piperazinyl derivatives: Novel chemical class of 5-HT6 receptor antagonists

N1-Arylsulfonyl-3-piperazinyl indole derivatives were designed and identified as a novel class of 5-HT6 receptors ligands. All the compounds have high affinity and antagonist activity towards 5-HT6 receptor. The compound 7a (Ki = 3.4 nM, functional assay IC 50 = 310 nM) shows enhanced cognitive effect when tested in NORT and Morris water maze models. Synthesis, SAR and PK profile of these novel compounds constitute the subject matter of this Letter.