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5,5-Dimethyl-1,3-cyclohexanedione

Base Information Edit
  • Chemical Name:5,5-Dimethyl-1,3-cyclohexanedione
  • CAS No.:126-81-8
  • Molecular Formula:C8H12O2
  • Molecular Weight:140.182
  • Hs Code.:29142900
  • European Community (EC) Number:204-804-4
  • NSC Number:242994,43759,17544,14984
  • UNII:B2B5DSX2FC
  • DSSTox Substance ID:DTXSID8021987
  • Nikkaji Number:J2.014A
  • Wikipedia:Dimedone
  • Wikidata:Q418261
  • Mol file:126-81-8.mol
5,5-Dimethyl-1,3-cyclohexanedione

Synonyms:5,5-dimethylcyclohexane-1,3-dione

Suppliers and Price of 5,5-Dimethyl-1,3-cyclohexanedione
Supply Marketing:Edit
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Dimedone
  • 100g
  • $ 70.00
  • TRC
  • Dimedone
  • 250g
  • $ 110.00
  • TRC
  • Dimedone
  • 25g
  • $ 50.00
  • TCI Chemical
  • Dimedone >99.0%(T)
  • 25g
  • $ 19.00
  • TCI Chemical
  • Dimedone >99.0%(T)
  • 100g
  • $ 43.00
  • TCI Chemical
  • Dimedone >99.0%(T)
  • 500g
  • $ 172.00
  • Sigma-Aldrich
  • 5,5-Dimethyl-1,3-cyclohexanedione 95%
  • 100g
  • $ 75.10
  • Sigma-Aldrich
  • 5,5-Dimethyl-1,3-cyclohexanedione for HPLC derivatization, for the determination of aldehyde formaldehyde, ≥99.0%
  • 250g
  • $ 188.00
  • Sigma-Aldrich
  • 5,5-Dimethyl-1,3-cyclohexanedione 95%
  • 25g
  • $ 28.20
  • Sigma-Aldrich
  • 5,5-Dimethyl-1,3-cyclohexanedione for HPLC derivatization, for the determination of aldehyde formaldehyde, ≥99.0%
  • 50g
  • $ 52.00
Total 146 raw suppliers
Chemical Property of 5,5-Dimethyl-1,3-cyclohexanedione Edit
Chemical Property:
  • Appearance/Colour:yellow crystals 
  • Vapor Pressure:0.0042mmHg at 25°C 
  • Melting Point:146-148 °C(lit.) 
  • Refractive Index:1.49 
  • Boiling Point:233.7 °C at 760 mmHg 
  • PKA:4.8(at 25℃) 
  • Flash Point:85.1 °C 
  • PSA:34.14000 
  • Density:1.016 g/cm3 
  • LogP:1.33470 
  • Storage Temp.:2-8°C 
  • Solubility.:4.01g/l 
  • Water Solubility.:0.416 g/100 mL (25 ºC) 
  • XLogP3:0.8
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:0
  • Exact Mass:140.083729621
  • Heavy Atom Count:10
  • Complexity:162
Purity/Quality:

99% *data from raw suppliers

Dimedone *data from reagent suppliers

Safty Information:
  • Pictogram(s): IrritantXi 
  • Hazard Codes:Xi 
  • Statements: 36/37/38 
  • Safety Statements: 24/25-36-26 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Other Classes -> Aliphatic Ketones, Other
  • Canonical SMILES:CC1(CC(=O)CC(=O)C1)C
  • Uses Part of furannulation strategy for the synthesis of naturally occurring fused 3-methylfurans.1 A mentha compound showing antimicrobial properties against common bacteria in the food industry such as E.coli and P.aeruginosa as well as strains of yeast. Used in the synthesis of fused 3-methylfurans via furannulation. Reagent used in synthesis of fused 3-methylfuransDimedone is used in organic chemistry to identify the presence of aldehyde group. It is also used as a catalyst in the formation of transition-metal complexes. Further, it is also employed in colorimetry, crystallography, luminescence and spectrophotometric analysis. In addition to this, it is used in the synthesis of naturally occurring fused 3-methylfurans.
Technology Process of 5,5-Dimethyl-1,3-cyclohexanedione

There total 65 articles about 5,5-Dimethyl-1,3-cyclohexanedione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:
Guidance literature:
With water; In acetonitrile; at 20 ℃; for 0.226667h; under 900.09 Torr; Flow reactor;
DOI:10.1021/acs.oprd.9b00067
Guidance literature:
With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1021/ja055530f
Guidance literature:
With methylamine; In water; benzene; for 0.25h; Product distribution; Mechanism; Ambient temperature; retro-Knoevenagel fragmentation; variation of reaction conditions;
DOI:10.1002/hlca.19800630607
Refernces Edit

Lewis Acid-Catalyzed Synthesis of Benzofurans and 4,5,6,7-Tetrahydrobenzofurans from Acrolein Dimer and 1,3-Dicarbonyl Compounds

10.1021/acs.joc.9b00270

The study presents a novel Lewis acid-catalyzed approach for the synthesis of benzofurans and 4,5,6,7-tetrahydrobenzofurans from acrolein dimer and 1,3-dicarbonyl compounds. The method employs N-bromosuccinimide (NBS) as an oxidizing agent and utilizes a combination of Lewis acid catalysts to achieve high yields of 2,3-disubstituted benzofurans. The researchers successfully synthesized two commercial drug molecules, benzbromarone and amiodarone, using this method. The study also explores the substrate scope and optimizes the reaction conditions. Additionally, the authors propose a mechanism involving NBS-assisted auto-tandem catalysis and provide evidence by isolating an intermediate that can be further converted to tetrahydrobenzofurans. This work offers an efficient and practical route to synthesize benzofuran derivatives with potential applications in pharmaceutical chemistry.

Three-component reaction of 5,5-dimethylcyclohexan-1,3-dione, aromatic aldehydes, and acetonitrile in the presence of chlorosulfonic acid forming N-[(2-Hydroxy-4,4-dimethyl-6-oxocyclohexene-1-yl)-aryl-methyl]-acetamides

10.1080/00397910902898643

The study investigates a three-component reaction involving 5,5-dimethylcyclohexan-1,3-dione (dimedone), aromatic aldehydes, and acetonitrile in the presence of chlorosulfonic acid, resulting in the formation of N-[(2-hydroxy-4,4-dimethyl-6-oxocyclohexene-1-yl)-aryl-methyl]-acetamides. Dimedone acts as a dienophile, aromatic aldehydes serve as the Michael acceptors, and acetonitrile functions as the nucleophile in this reaction. Chlorosulfonic acid is used as a catalyst to promote the reaction. This method provides a straightforward and efficient route for synthesizing these acetamides in good yields, highlighting the utility of multicomponent reactions in generating structurally diverse compounds with potential biological and pharmaceutical relevance.

Synthesis, characterization and application of nano-CoAl2O4 as an efficient catalyst in the preparation of hexahydroquinolines

10.1002/aoc.3815

This study focuses on the synthesis, characterization, and application of nano-CoAl2O4 as an efficient catalyst in the preparation of hexahydroquinolines. The researchers prepared nano-CoAl2O4 using a solution of metal sulfates, polyethylene glycol, and sodium hydroxide, and then calcined it at 800°C for 6 hours. The catalyst was characterized by various techniques including FT-IR, EDX, XRD, SEM, VSM, and TEM. In the synthesis of hexahydroquinolines, nano-CoAl2O4 was used to catalyze the condensation reaction between ethyl acetoacetate, dimedone, and various aldehydes under solvent-free conditions at 80°C. The study demonstrated that the use of nano-CoAl2O4 as a catalyst resulted in high yields, short reaction times, and the ability to reuse the catalyst multiple times without significant loss of efficiency.

Expedient synthesis of a novel class of pseudoaromatic amino acids: Tetrahydroindazol-3-yl- and tetrahydrobenzisoxazol-3-ylalanine derivatives

10.1016/j.tetlet.2003.11.133

The study presents a concise synthesis method for a novel class of homochiral aromatic amino acid surrogates, featuring tetrahydroindazole or benzisoxazole systems. These surrogates were synthesized through the acylation of cyclic 1,3-diketone by the side-chain carboxyl functionality of specific amino acid precursors, followed by a regioselective condensation with hydrazine, N-benzylhydrazine, and hydroxylamine. The synthetic strategy is versatile, allowing for the creation of structurally diverse derivatives. These novel amino acids can be efficiently incorporated into proteins and have potential applications in imparting unique properties to biological peptides. The study also includes the synthesis of Na-Fmoc-protected derivatives, which are useful for solid-phase peptide assembly, and the exploration of the stereochemistry integrity of the homochiral starting material through chemical transformations. The synthesized amino acids offer opportunities as structural surrogates of tryptophan and as building blocks for designing molecular probes.

Fe3O4 magnetic nanoparticles in the layers of montmorillonite as a valuable heterogeneous nanocatalyst for the one-pot synthesis of indeno[1,2-b]indolone derivatives in aqueous media

10.1007/s11164-018-3659-7

This study presents the synthesis of montmorillonite (MMT) supported Fe3O4 magnetic nanoparticles, which were used as heterogeneous nanocatalysts for the one-pot synthesis of indeno[1,2-b]indolone derivatives in aqueous media. The MMT@Fe3O4 nanocomposites were characterized using various techniques including X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX), vibrating sample magnetometer (VSM), thermogravimetric analysis (TGA), and Fourier transform infrared spectroscopy (FT-IR). The catalyst exhibited high efficiency in promoting the cyclocondensation of ninhydrin, 1,3-diketone compounds, and amine derivatives to generate the desired indeno[1,2-b]indolone derivatives in excellent yields under mild conditions. This study highlights the advantages of using MMT@Fe3O4 as an environmentally friendly, cost-effective, and recyclable catalyst, providing a green and efficient approach for the synthesis of these heterocyclic compounds of biological and pharmacological importance.

Silica-bonded N-propylpiperazine sodium n-propionate as recyclable catalyst for synthesis of 4H-pyran derivatives

10.1016/S1872-2067(12)60693-7

The study focuses on the synthesis of 4H-pyran derivatives using a silica-bonded N-propylpiperazine sodium n-propionate (SBPPSP) as a recyclable catalyst. The catalyst was prepared from commercially available and inexpensive starting materials and was used to catalyze the synthesis of various 4H-pyran derivatives, including 3,4-dihydropyrano[c]chromenes, 2-amino-4H-pyrans, 1,4-dihydropyrano[2,3-c]pyrazoles, and 2-amino-4H-benzo[e]chromenes. The chemicals used in the study included aromatic aldehydes, malononitrile, dimedone, ethyl acetoacetate, 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, and α-naphthol, which served as reactants in the multi-component reactions to form the desired 4H-pyran derivatives. The purpose of these chemicals was to participate in condensation reactions under refluxing aqueous ethanol conditions, with SBPPSP facilitating the process and being easily recoverable and reusable, highlighting the environmental and economic benefits of the method.

A green procedure for the synthesis of 1,8-dioxodecahydroacridine derivatives under microwave irradiation in aqueous media without catalyst

10.1002/jhet.322

The study presents a green chemical procedure for the synthesis of 1,8-dioxodecahydroacridine derivatives under microwave irradiation in aqueous media without the use of a catalyst. The method offers advantages such as high yields (86-96%), a simple workup procedure, and environmental friendliness. The chemicals used in the study include various aromatic aldehydes, dimedone or 1,3-cyclohexanedione, and primary arylamines, which react under the specified conditions to form the target 1,8-dioxo-decahydroacridine derivatives. These compounds are significant due to their potential applications in pharmaceuticals, particularly as treatments for cardiovascular disorders and as calcium channel blockers, and also as photoinitiators. The study demonstrates that the electronic properties of the substituents on the aromatic rings do not significantly affect the reaction, and the method is applicable to a wide range of arylamines, including those with electron-withdrawing and electron-donating groups.

10.1021/jo01353a009

The study explores the synthesis of various substituted naphthyridines and biphenyls through different chemical reactions. Key chemicals involved include N-(3-amino-4-picolylidene)-p-toluidine, which serves as a precursor for multiple reactions to produce compounds like 1,7-naphthyridine-2-aldoxime, 2,9-diaza-6,8-dihydro-7,7-dimethyl-5-oxoanthracene, and 7,9-diazabenz[f]indane. These compounds are formed by reacting the precursor with different reagents such as isonitrosoacetone, dimethyldihydroresorcinol, and cyclopentanone under specific conditions like heating and refluxing. The products are characterized by their melting points, yields, and elemental analysis. In another part of the study, the reaction of various p-aroylpropionic acids with benzoyl chloride is investigated, yielding substituted phthalides in the biphenyl series. The study also delves into the infrared and ultraviolet spectral analysis of these products to understand their structural properties.

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