34598-49-7

Basic information

• Product Name: 5-Bromoindanone
• Synonyms: 5-BROMOINDAN-1-ONE;5-BROMOINDANONE;5-BROMO-2,3-DIHYDRO-1H-INDEN-1-ONE;5-BROMO-1-INDANONE;BUTTPARK 145\15-97;1-Indanone, 5-bromo-;5-Bromo-1-indanone,98%;5-Bromo-1-indanone 98%
• CAS NO: 34598-49-7
• Molecular Formula: C₉H₇BrO
• Molecular Weight: 211.06
• EINECS: -0
• Product Categories: Carbonyl Compounds;Indane/Indanone and Derivatives;Heterocycles series;Indanone & Indene;Ketone;Fused Ring Systems;Halides;C9;Carbonyl Compounds;Ketones;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 34598-49-7.mol

Chemical Properties

• Melting Point: 126-129 °C(lit.)
• Boiling Point: 303.7 °C at 760 mmHg
• Flash Point: 120.2 °C
• Appearance: Beige to brown/Powder
• Density: 1.18 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000915mmHg at 25°C
• Refractive Index: 1.5720 (estimate)
• Storage Temp.: -20°C
• BRN: 2357199
• CAS DataBase Reference: 5-Bromoindanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromoindanone(34598-49-7)
• EPA Substance Registry System: 5-Bromoindanone(34598-49-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36-36/37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 34598-49-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromoindanone is used as a starter for indanone-based pharmaceuticals. Its unique chemical structure and properties make it a valuable component in the development of new drugs and therapeutic agents. 5-Bromoindanone's ability to participate in the synthesis of complex molecules contributes to its importance in this application.
Used in Chemical Synthesis:
In the field of chemical synthesis, 5-Bromoindanone is utilized as a key intermediate for the production of imidazolyl and triazolyl substituted biphenyl compounds. These compounds have a wide range of applications, including potential uses in various industries such as pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C9H7BrO/c10-7-2-3-8-6(5-7)1-4-9(8)11/h2-3,5H,1,4H2

Upstream product

• 335159-82-5 3-(m-bromophenyl)propionyl chloride 
• 3132-99-8 m-bromobenzoic aldehyde 
• 141-82-2 malonic acid 
• 83-33-0 inden-1-one 
• 42287-90-1 3-(3-bromophenyl)propanoic acid 
• 15852-73-0 (3-Bromophenyl)methanol 
• 107558-73-6 diethyl 2-(3-bromobenzyl)-malonate 
• 932-77-4 3-bromobenzyl chloride 
• 31736-73-9 4-bromophenyl 2-chloroethyl ketone 
• 3650-77-9 methyl 3-(3'-bromophenyl)-acrylate 
• 151583-29-8 methyl 3-(3'-bromophenyl)-propionate 
• 2039-86-3 3-bromostyrene 
• 108-86-1 bromobenzene 
• 34598-50-0 5-bromo-1-indanol 

Downstream Products

• 6134-54-9 5-bromoindane 
• 34598-50-0 5-bromo-1-indanol 
• 25724-79-2 5-cyano-1-indanone 
• 218608-69-6 2,2,5-tribromoindan-1-one 
• 289056-04-8 5-(4-fluorophenyl)-2,3-dihydroinden-1-one 
• 20854-58-4 5-(4-methoxyphenyl)-2,3-dihydro-1H-inden-1-one 
• 185945-75-9 5-phenyl-2,3-dihydroindene-1-one 
• 723760-74-5 5-bromo-6-nitro-2,3-dihydro-1H-inden-1-one 
• 848760-74-7 5-(4'-hydroxymethyl-phenyl)-indan-1-one 
• 33065-61-1 6-bromo-1H-indene 
• 75476-78-7 5-bromo-1H-indene 
• 863479-23-6 5-(3-methoxyphenyl)-2,3-dihydro-1H-inden-1-one 
• 721949-01-5 5-(4-hydroxyphenyl)-2,3-dihydro-1H-inden-1-one 

Relevant articles and documents

Kinetic resolution of racemic benzofused alcohols catalysed by HMFO variants in presence of natural deep eutectic solvents

5-Hydroxymethylfurfural oxidase (HMFO) has demonstrated to be a useful biocatalyst for the selective oxidation of alcohols employing oxygen as mild oxidant with no requirement of expensive organic cofactors. This wild-type HMFO biocatalyst and an engineered thermostable variant have been tested in the kinetic resolution of different benzofused alcohols. The use of natural deep eutectic solvents was also explored in HMFO-catalysed oxidation of alcohols. The oxidation of racemic 1-indanol showed a higher conversion and selectivity in presence of 60% v/v of different NADES, especially for those containing carbohydrates. By choosing properly the biocatalyst and the NADES, good enantioselectivity values can be obtained, demonstrating the advantages of employing these neoteric solvents in biocatalysed processes.

NEW COMPOUNDS SUITABLE AS CATALYSTS FOR POLYMERIZATION REACTIONS

The invention relates to a compound of formula (I) and a process for synthesizing said compound. The invention further relates to the use of said compound as a catalyst, preferably for polymerization, such as, olefin polymerization. The invention also relates to the polymers produced using said catalyst and articles comprising said polymers.

Efficient acceptorless photo-dehydrogenation of alcohols and: N -heterocycles with binuclear platinum(ii) diphosphite complexes

Although photoredox catalysis employing Ru(ii) and Ir(iii) complexes as photocatalysts has emerged as a versatile tool for oxidative C-H functionalization under mild conditions, the need for additional reagents acting as electron donor/scavenger for completing the catalytic cycle undermines the practicability of this approach. Herein we demonstrate that photo-induced oxidative C-H functionalization can be catalysed with high product yields under oxygen-free and acceptorless conditions via inner-sphere atom abstraction by binuclear platinum(ii) diphosphite complexes. Both alcohols (51 examples), particularly the aliphatic ones, and saturated N-heterocycles (24 examples) can be efficiently dehydrogenated under light irradiation at room temperature. Regeneration of the photocatalyst by means of reductive elimination of dihydrogen from the in situ formed platinum(iii)-hydride species represents an alternative paradigm to the current approach in photoredox catalysis.

Highly enantioselective [3+2] coupling of cyclic enamides with quinone monoimines promoted by a chiral phosphoric acid

Enantioselective [3+2] coupling of cyclic enamides with quinone monoimines was realised using a chiral phosphoric acid as a catalyst. This transformation allowed for the synthesis of highly enantioenriched polycyclic 2,3-dihydrobenzofurans (up to 99.9% ee). The absolute configuration of one product was determined by an X-ray crystal structural analysis. We also found a possible mechanism for this reaction.

Metal-free oxidation of secondary benzylic alcohols using aqueous TBHP

We report a simple, yet efficient metal-free oxidation of secondary benzylic alcohols in the presence of t-butyl hydroperoxide (70% TBHP) with high yields of up to 98%. This type of reaction can be carried out using a wide variety of substrates, requires no other organic solvent, and proves to be tolerant toward a variety of different functional groups.

Functionalization of styrenes by copper-catalyzed borylation/ ortho-cyanation and silver-catalyzed annulation processes

An efficient two-step method for the assembly of indanone derivatives starting from a simple vinyl arene has been developed. The sequence first involves addition of bis(pinacolato)diboron (B2pin2) and N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) to a broad range of styrenes by utilizing IMesCuCl as catalyst. This step simultaneously accomplishes hydroboration of the alkene and ortho cyanation of the benzene unit. The products thus obtained are further functionalized by a AgNO3/Selectfluor-mediated coupling of the BPin and cyano functionalities to annulate a new five-membered ring. This combined two-step sequence provides a versatile method for the site-selective derivatization of a broad range of vinyl arene substrates. A Cu and Ag sequence: The bis-functionalization of styrenes is accomplished through a copper-catalyzed process that enables hydroboration of the alkene and regioselective ortho cyanation of the arene. The resulting adducts are converted, by a radical cyclization process, into a cyclopentanone unit fused to the original aromatic ring. Together, these methods allow efficient cyclopentannulation of a broad range of styrene derivatives.

Rh-catalyzed reagent-free ring expansion of cyclobutenones and benzocyclobutenones

Here we report a reagent-free rhodium-catalyzed ring-expansion reaction via C-C cleavage of cyclobutenones. A variety of poly-substituted cyclopentenones and 1-indanones can be synthesized from simple cyclobutenones and benzocyclobutenones. The reaction condition is near pH neutral without additional oxidants or reductants. The potential for developing a dynamic kinetic asymmetric transformation of this reaction has also been demonstrated. Further study supports the proposed pathway involving Rh-insertion into the cyclobutenone C-C bond, followed by β-hydrogen elimination, olefin insertion and reductive elimination.

Catalytic asymmetric cross-dehydrogenative coupling: Activation of C-H bonds by a cooperative bimetallic catalyst system

A cooperative bimetallic catalyst system was applied in the catalytic asymmetric cross-dehydrogenative coupling of β-ketoesters and xanthene. Various optically active xanthene derivatives bearing a quaternary stereogenic carbon center were obtained in moderate to good yields (up to 90%) with excellent enantioselectivities (up to 99% ee). Meanwhile, a transition-state model was proposed to explain the origin of the asymmetric induction.

Preparation, physical properties and n-type FET characteristics of substituted diindenopyrazinediones and bis(dicyanomethylene) derivatives

A series of halogen and alkyl substituted diindenopyrazinediones and bis(dicyanomethylene) derivatives have been synthesized as new n-type organic semiconductors based on nitrogen-containing heterocycles. Halogen groups were introduced to improve the electron injection. Their crystal structures and solid physical properties are discussed. Alkyl groups were introduced to increase the solubility in organic solvents. Furthermore, hexanoyl groups were introduced by oxidation of alkyl groups to increase the solubility and electron affinity. Dicyanomethylene groups were also introduced to further enhance the electron-accepting properties. Drop-cast as well as vapour deposited thin films showed n-type FET properties.

Efficient synthesis of halo indanones via chlorosulfonic acid mediated Friedel-Crafts cyclization of aryl propionic acids and their use in alkylation reactions

Several halo indanones were synthesized from benzyl Meldrum's acid derivatives in two steps. Although several Lewis acids are effective for the Friedel-Crafts ring-closing reaction on more electron-rich arenes, in the case of the electron-deficient arenes this chemistry is not efficient. Here it is reported that chlorosulfonic acid (used as solvent) is an efficient reagent for cyclization of electron-withdrawing arenes. These molecules are potentially useful for subsequent alkylation reactions. The selective alkylation of 5,7-dibromo indanone is demonstrated using Pd-catalyzed Grignard coupling to provide monoalkylated indanone in good yield.