26976-59-0

Basic information

• Product Name: 3-hydroxy-2,3-dihydro-1H-inden-1-one
• Synonyms: 3-Hydroxy-1-indanone
• CAS NO: 26976-59-0
• Molecular Formula: C₉H₈O₂
• Molecular Weight: 148.1586
• Mol File: 26976-59-0.mol

Chemical Properties

• Boiling Point: 296°C at 760 mmHg
• Flash Point: 124.7°C
• Density: 1.322g/cm³
• Vapor Pressure: 0.000667mmHg at 25°C
• Refractive Index: 1.635
• CAS DataBase Reference: 3-hydroxy-2,3-dihydro-1H-inden-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-2,3-dihydro-1H-inden-1-one(26976-59-0)
• EPA Substance Registry System: 3-hydroxy-2,3-dihydro-1H-inden-1-one(26976-59-0)

Safety Data

• Hazardous Substances Data: 26976-59-0(Hazardous Substances Data)

Upstream product

• 606-23-5 1H-indene-1,3(2H)-dione 
• 13167-95-8 1H-indene-1,2,3-trione 2-oxime 
• 40774-41-2 3-Bromoindan-1-one 
• 30385-41-2 3-Acetoxyindan-1-on 
• 111-34-2 -butyl vinyl ether 
• 84761-77-3 2-formylphenyl triflate 
• 60414-82-6 2,3-dihydro-1H-indene-1,3-diol 
• 6351-10-6 1-Indanol 
• 26452-98-2 2,3-dihydro-1H-inden-1-yl-acetate 
• 83-33-0 inden-1-one 
• 64-17-5 ethanol 
• 496-11-7 INDANE 
• 89-98-5 2-chloro-benzaldehyde 
• 1238625-83-6 3-(2-formylphenyl)-N-methyl-N-phenylpropiolamide 

Downstream Products

• 60414-82-6 2,3-dihydro-1H-indene-1,3-diol 
• 130999-32-5 1-Phenylindan-1,3-diol 
• 41523-30-2 2-(p-diethylaminophenylmethylidene)-3-hydroxy-1-indanone 
• 102325-53-1 spiro[imidazolidine-4,1'-indene]-2,5-dione 
• 606-23-5 1H-indene-1,3(2H)-dione 

Relevant articles and documents

MIL-101 as reusable solid catalyst for autoxidation of benzylic hydrocarbons in the absence of additional oxidizing reagents

Materiaux de l'Institute Lavosier-101 (MIL-101) promotes benzylic oxidation of hydrocarbons exclusively by molecular oxygen in the absence of any other oxidizing reagent or initiator. Using indane as model compound, the selectivity toward the wanted ol/one mixture is higher for MIL-101(Cr) (87% selectivity at 30% conversion) than for MIL-101(Fe) (71% selectivity at 30% conversion), a fact that was associated with the preferential adsorption of indane within the pore system. Product distribution and quenching experiments with 2,2,6,6-tetramethyl-1-piperidinyloxy, benzoic acid, and dimethylformamide show that the reaction mechanism is a radical chain autoxidation of the benzylic positions by molecular oxygen, and the differences in selectivity have been attributed to the occurrence of the autoxidation process inside or outside the metal organic framework pores. MIL-101 is reusable, does not leach metals to the solution, and maintains the crystal structure during the reaction. The scope of the benzylic oxidation was expanded to other benzylic compounds including ethylbenzene, n-butylbenzene, iso-butylbenzene, 1-bromo-4-butylbenzene, sec-butylbenzene, and cumene.

Protected indanones by a Heck-Aldol annulation reaction

Monoprotected 3-hydroxyindan-1-ones have been prepared in moderate to good yields by a new tandem reaction involving salicylaldehyde triflates and commercially available 2-hydroxyethyl vinyl ether. This one-pot annulation reaction proceeds in the presence of a palladium bidentate catalyst and results in the formation of two new ring systems.

N-Hydroxyphthalimide Anchored on Diamond Nanoparticles as a Selective Heterogeneous Metal-free Oxidation Catalyst of Benzylic Hydrocarbons and Cyclic Alkenes by Molecular O2

N-hydroxyphthalimide (NHPI) derived from trimellitic anhydride has been covalently anchored (4 wt %) through ester bonds to the surface of commercial diamond nanoparticles previously functionalized by chemical and thermal treatments (DH). IR spectroscopy of the NHPI/DH solid shows the presence of a characteristic peak at 1735 cm?1 attributable to the ester bond, while solid-state MAS 13C NMR spectroscopy shows two broad bands corresponding to carbon atoms of carbonyl groups (167 ppm) and aromatic carbons (127 ppm). NHPI/DH promotes autoxidation of isobutylbenzene involving superoxide (O2 .?) and hydroperoxide (HOO?) radicals; NHPI/DH can be reused at least three times and reach a minimum turnover number as high as 20 600, which is probably due to the inertness of the diamond surface, allowing free diffusion of reactive oxygen species. Analogous materials in which NHPI was anchored on activated carbon and multiwall carbon nanotubes were inefficient as autoxidation catalysts. NHPI/DH is able to promote also selective aerobic oxidation of other benzylic hydrocarbons and cycloalkenes.

A Method for Synthesis of 3-Hydroxy-1-indanones via Cu-Catalyzed Intramolecular Annulation Reactions

We report a facile and highly efficient method that copper-catalyzed intramolecular annulation to synthesize 3-hydroxy-1-indanones employing simple 2-ethynylbenzaldehyde as starting materials was achieved successfully. This protocol provided a simple synthetic approach to afford 3-hydroxy-1-indanones under mild conditions in good to excellent yields.

Enantioselective Synthesis of 6,6-Disubstituted Pentafulvenes Containing a Chiral Pendant Hydroxy Group

Simple enantioselective synthesis of 6,6-disubstituted pentafulvenes bearing chiral pendant hydroxy groups are attained by cascade reactivity using commercially available proline-based organocatalysts. Condensation of cyclopentadiene with the acetyl function of a 1,2-formylacetophenone, followed by cyclization of a resulting fulvene-stabilized carbanion with the formyl group, generates bicyclic chiral alcohols with initial er values up to 94:6. Exceptional enantio-enrichment of the resultant alcohols results upon crystallization—even near racemic samples spontaneously de-racemize. This enables new families of substituted cyclopentadienes that are both enantiomerically and diastereomerically pure to be rapidly attained.

SPIROCYCLIC HAT INHIBITORS AND METHODS FOR THEIR USE

Compounds having a structure of Formula (IX) or a stereoisomer, tautomer or pharmaceutically acceptable salt thereof, wherein R1, R2a, R2b, R3a, R3b, R4a, R4b, Q1----Q2, R6, R7, A, B, W, x, and y are as defined herein and are provided. Pharmaceutical compositions comprising such compounds and methods for treating various HAT-related conditions or diseases, including cancer, by administration of such compounds are also provided.

Synthesis of 3-hydroxyindanones via potassium salt of amino acid catalyzed regioselective intramolecular aldolization of ortho-diacylbenzenes

First organocatalytic intramolecular aldolization of ortho-diacylbenzenes to construct highly functionalized 3-hydroxyindanones is described. In this transformation a high trans-selectivity is achieved by the use of metal salt of amino acid. This method allows an easy access to the strained spirocyclic 3-hydroxyindanones related to a number of natural product frameworks. Synthesis of a new class of indole skeleton substituted by 3-hydroxyindanones added an extra essence to this new protocol.

An unexpected addition of acetic acid to ortho-electron-deficient alkynyl-substituted aryl aldehydes catalyzed by palladium(II) acetate

An unexpected addition of acetic acid to ortho-electron-deficient alkynyl-substituted aryl aldehydes catalyzed by palladium(II) acetate was achieved, which provided a convenient method for the synthesis of dihydroisobenzofurans in moderate to good yields. The electron-withdrawing groups attached to alkynes may play an important role for the cyclization.

Direct synthesis of 1-indanones via pd-catalyzed olefination and ethylene glycol-promoted aldol-type annulation cascade

A wide range of multisubstituted 1-indanones of potential pharmaceutical use were synthesized in a one-pot fashion in moderate to excellent yields via palladium catalysis in ethylene glycol. The Heck reaction first installs an enol functionality on the aromatic ring; this is followed by an ethylene glycol promoted aldol-type annulation with a neighboring carbonyl group, resulting in the formation of various 1-indanones.

Aqueous phase C-H bond oxidation reaction of arylalkanes catalyzed by a water-soluble cationic Ru(III) complex [(pymox-Me2) 2RuCl2]+BF4-

The cationic complex [(pymox-Me2)RuCl2] -BF4- was found to be a highly effective catalyst for the C-H bond oxidation reaction of arylalkanes in water. For example, the treatment of ethylbenzene (1.0 mmol) with t-BuOOH (3.0 mmol) and 1.0 mol % of the Ru catalyst in water (3 mL) cleanly produced PhCOCH3 at room temperature. Both a large kinetic isotope effect (kH/k D) 14) and a relatively large Hammett value (ρ) -1.1) suggest a solvent-caged oxygen rebounding mechanism via a Ru(IV)-oxo intermediate species.