17623-96-0

Basic information

• Product Name: 2-BROMOINDAN
• Synonyms: 2-BROMOINDAN;2-BROMO-2,3-DIHYDRO-1H-INDENE;2-BroMo-2,3-dihydroindene;β-BroMoindane;1H-Indene, 2-broMo-2,3-dihydro-
• CAS NO: 17623-96-0
• Molecular Formula: C₉H₉Br
• Molecular Weight: 197.07
• Product Categories: Aromatics;Intermediates;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 17623-96-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 249.2±29.0 °C(Predicted)
• Appearance: /
• Density: 1.483±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-BROMOINDAN(CAS DataBase Reference)
• NIST Chemistry Reference: 2-BROMOINDAN(17623-96-0)
• EPA Substance Registry System: 2-BROMOINDAN(17623-96-0)

Safety Data

• Hazardous Substances Data: 17623-96-0(Hazardous Substances Data)

Usage

Description

2-BROMOINDAN, also known as 2-Bromoindan or 2-Bromo-1H-indene, is an organic compound with the molecular formula C9H9Br. It is a colorless to pale yellow liquid at room temperature and is commonly used as an intermediate in the synthesis of various pharmaceuticals and chemicals. Its chemical structure allows for further functionalization and modification, making it a versatile building block in organic synthesis.

Uses

Used in Pharmaceutical Synthesis:
2-BROMOINDAN is used as a key intermediate in the synthesis of αtipamezole, a potential PET (Positron Emission Tomography) ligand for the α2-adrenergic receptor in the brain. This application is significant for the development of diagnostic tools and treatments related to the central nervous system, as α2-adrenergic receptors play a crucial role in various physiological processes and are implicated in several neurological disorders.
In the synthesis of αtipamezole, 2-BROMOINDAN serves as a starting material, which undergoes a series of chemical reactions to form the final product. The use of 2-BROMOINDAN in this process highlights its importance in the development of novel pharmaceuticals and its potential impact on the field of medical research and drug discovery.

Upstream product

• 1775-27-5 2-bromoindanone 
• 83-33-0 inden-1-one 
• 4254-29-9 indan-2-ol 
• 7789-60-8 phosphorus tribromide 
• 4254-31-3 2-acetoxyindane 
• 95-13-6 1-indene 
• 496-11-7 INDANE 
• 615-13-4 2-indanone 

Downstream Products

• 95717-93-4 t-butyl Nε-(4-chloro-3-sulfamoylbenzoyl)-Nα-(2,3-dihydro-1H-inden-2-yl)-L-lysinate 
• 2975-41-9 2,3-dihydro-1H-inden-2-amine 
• 101168-70-1 2-(4-methoxyphenyl)-2,3-dihydro-1H-indene 
• 496-11-7 INDANE 
• 33982-86-4 (2,3-dihydro-1H-inden-2-yl)(phenyl)methanone 
• 1380434-28-5 (2,3-dihydro-1H-inden-2-yl)(4-methoxyphenyl)methanone 
• 1383435-88-8 di-methyl 4-(2,3-dihydro-1H-inden-2-yl)phthalate 
• 1383435-87-7 phenyl 4-(2,3-dihydro-1H-inden-2-yl)benzoate 
• 5323-50-2 N-propylphthalimide 
• 1282036-74-1 2-(3-(2,3-dihydro-1H-inden-2-yl)propyl)isoindoline-1,3-dione 

Relevant articles and documents

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N-alkylpiperidine carbamates as potential anti-Alzheimer's agents

Compounds capable of interacting with single or multiple targets involved in Alzheimer's disease (AD) pathogenesis are potential anti-Alzheimer's agents. In our aim to develop new anti-Alzheimer's agents, a series of 36 new N-alkylpiperidine carbamates was designed, synthesized and evaluated for the inhibition of cholinesterases [acetylcholinesterase (AChE) and butyrylcholinesterase (BChE)] and monoamine oxidases [monoamine oxidase A (MAO-A and monoamine oxidase B (MAO-B)]. Four compounds are very promising: multiple AChE (IC50 = 7.31 μM), BChE (IC50 = 0.56 μM) and MAO-B (IC50 = 26.1 μM) inhibitor 10, dual AChE (IC50 = 2.25 μM) and BChE (IC50 = 0.81 μM) inhibitor 22, selective BChE (IC50 = 0.06 μM) inhibitor 13, and selective MAO-B (IC50 = 0.18 μM) inhibitor 16. Results of enzyme kinetics experiments showed that despite the carbamate group in the structure, compounds 10, 13, and 22 are reversible and non-time-dependent inhibitors of AChE and/or BChE. The resolved crystal structure of the complex of BChE with compound 13 confirmed the non-covalent mechanism of inhibition. Additionally, N-propargylpiperidine 16 is an irreversible and time-dependent inhibitor of MAO-B, while N-benzylpiperidine 10 is reversible. Additionally, compounds 10, 13, 16, and 22 should be able to cross the blood-brain barrier and are not cytotoxic to human neuronal-like SH-SY5Y and liver HepG2 cells. Finally, compounds 10 and 16 also prevent amyloid β1–42 (Aβ1–42)-induced neuronal cell death. The neuroprotective effects of compound 16 could be the result of its Aβ1–42 anti-aggregation effects.

Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.