40774-41-2

Basic information

• Product Name: 3-Bromo-1-indanone
• Synonyms: 3-Bromo-1-indanone;3-Bromoindan-1-one;1H-Inden-1-one, 3-broMo-2,3-dihydro-;3-Bromo-2,3-dihydro-1H-inden-1-one, 3-Bromo-2,3-dihydro-1-oxo-1H-indene
• CAS NO: 40774-41-2
• Molecular Formula: C₉H₇BrO
• Molecular Weight: 211.06
• Product Categories: Halides;Fused Ring Systems
• Mol File: 40774-41-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 271.3°Cat760mmHg
• Flash Point: 97.2°C
• Appearance: /
• Density: 1.631g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 3-Bromo-1-indanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-1-indanone(40774-41-2)
• EPA Substance Registry System: 3-Bromo-1-indanone(40774-41-2)

Safety Data

• Hazardous Substances Data: 40774-41-2(Hazardous Substances Data)

Usage

General Description

3-Bromo-1-indanone is a complex chemical compound that is often utilized in various scientific and industrial applications. 3-Bromo-1-indanone belongs to the family of Indanones, which are cyclic compounds containing a ketone group that is conjugated to an indene. Essentially, these compounds are defined by the presence of a two-ring structure with one of the rings containing a ketone group. The '3-Bromo' part of this chemical's name entails that a Bromine atom is attached at the third carbon in the compound's structure. It is generally used as an intermediate in organic synthesis or in the production of other chemicals. However, like many other chemicals, 3-Bromo-1-indanone needs to be handled with care due to its potential hazards.

InChI:InChI=1/C9H7BrO/c10-8-5-9(11)7-4-2-1-3-6(7)8/h1-4,8H,5H2

Upstream product

• 83-33-0 inden-1-one 
• 1775-27-5 2-bromoindanone 

Downstream Products

• 861856-86-2 3-phenethylaminoindan-1-one 
• 1010730-50-3 3-(7-fluoro-1H-indol-3-yl)-indan-1-one 
• 85721-00-2 C₁₆H₁₅Cl₂N*ClH 
• 85662-98-2 3-(3',4'-dichlorophenyl)-indan-1-one 
• 83-33-0 inden-1-one 
• 1312077-05-6 3-(prop-2-yn-1-ylamino)-2,3-dihydro-1H-inden-1-one 
• 64356-33-8 5-bromo-7H-benzo[c]fluoren-7-one 
• 90271-93-5 3-bromo-1H-inden-1-one 
• 1443227-12-0 (2aR,2a¹S,5R,5aR,9bR)-9b-hydroxy-5-methyl-3-phenyl-2,2a,2a1,5,5a,9b-hexahydro-1H-cyclopenta[jk]fluoren-1-one 
• 1443226-97-8 (2aR,2a¹R,5aR,9bR)-9b-hydroxy-3-phenyl-2,2a,2a1,5,5a,9b-hexahydro-1H-cyclopenta[jk]fluoren-1-one 
• 1443227-13-1 (3aS,6aS)-4-phenyl-3,3a,6,6a-tetrahydro-2H-indeno[1,2,3-ij]isochromen-2-one 
• 1443285-49-1 (3aS,6aR)-4-phenyl-3,3a,6,6a-tetrahydro-2H-indeno[1,2,3-ij]isochromen-2-one 
• 86939-10-8 indatraline 
• 80272-59-9 cis-3-(3,4-dichlorophenyl)-2,3-dihydro-1H-inden-1-ol 

Relevant articles and documents

Solvent free, light induced 1,2-bromine shift reaction of α-bromo ketones

Photolysis of α-bromopropiophenones in acetonitrile results in formation of β-bromopropiophenones with good product selectivity, which can be coined as 1,2-Br shift reaction. The product selectivity increases when the reaction is done in neat or solid state, where only the 1,2-Br shift product is formed in some cases. The reaction is suggested to proceed by C–Br bond homolysis to give a radical pair, followed by disproportionation and conjugate addition of HBr to the α,β-unsaturated ketone intermediate. When the unsaturated intermediate is stabilized by an extra conjugation, the reaction stops at the stage, in which the unsaturated ketone becomes a major product. The synthetic method described in this research fits in a category of eco-friendly organic synthesis nicely since the reaction does not use volatile organic solvents and any other additives such as acid, base or metal catalysts, etc. Besides, the method fits into perfect atom economy, which does not give any side products. The synthetic method should find much advantage over other alternative methods to obtain β-bromo carbonyl compounds.

Environmentally benign electrophilic and radical bromination 'on water': H2O2-HBr system versus N-bromosuccinimide

A H2O2-HBr system and N-bromosuccinimide in an aqueous medium were used as a 'green' approach to electrophilic and radical bromination. Several activated and less activated aromatic molecules, phenylsubstituted ketones and styrene were efficiently brominated 'on water' using both systems at ambient temperature and without an added metal or acid catalyst, whereas various non-activated toluenes were functionalized at the benzyl position in the presence of visible light as a radical activator. A comparison of reactivity and selectivity of both brominating systems reveals the H2O2-HBr system to be more reactive than NBS for benzyl bromination and for the bromination of ketones, while for electrophilic aromatic substitution of methoxy-substituted tetralone it was higher for NBS. Also, higher yields of brominated aromatics were observed when using H2O2-HBr 'on water'. Bromination of styrene reveals that not just the structure of the brominating reagent but the reaction conditions: amount of water, organic solvent, stirring rate and interface structure, play a key role in defining the outcome of bromination (dibromination vs bromohydroxylation). In addition, mild reaction conditions, a straightforward isolation procedure, inexpensive reagents and a lower environment impact make aqueous brominating methods a possible alternative to other reported brominating protocols.

PHOTOCHEMISTRY OF α-HALOCYCLOALKANONES AND α,α-DIHALOCYCLOALKANONES. IONIC AND RADICAL PHOTOCHEMICAL CARBON-HALOGEN BOND CLEAVAGE

The nature of the photochemical carbon-halogen bond cleavage in α-halo cycloalkanones depends on the halogen atom bonded and on the ring size of the cycloalkanone.In the 2-halo-1-indanone series the amount of radical products increased from iodine to chlorine, while in the case of 2-halo-3,4-dihydro-1(2H)-naphthalenone 43percent for iodo, 32percent for bromo, and 53percent for the chloro derivative were found.On the other hand, photochemical carbon-chlorine bond cleavage in 2,2-dichloro-1-indanone led to only radical products, while the formation of both radical and ionic products inthe ratio 1:1 was observed in the case of 2,2-dibromo-1-indanone.In the 2,2-dihalo-3,4-dihydro-1(2H)-naphthalenone series, the ratio of the radical to ionic products formed strongly depended on the halogen atom bonded: preferential formation of the radical product in the case of the chloro derivative (92percent) in contrast to 94percent of the ionic products in the case of the bromoderivative, was observed.