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1,3-Cyclohexanedione

Base Information
  • Chemical Name:1,3-Cyclohexanedione
  • CAS No.:504-02-9
  • Molecular Formula:C6H8O2
  • Molecular Weight:112.128
  • Hs Code.:2914.29
  • European Community (EC) Number:207-980-0
  • NSC Number:57477
  • UNII:6UK3D2BXJT
  • DSSTox Substance ID:DTXSID1044433
  • Nikkaji Number:J6.214F
  • Wikipedia:1,3-Cyclohexanedione
  • Wikidata:Q15401966
  • Metabolomics Workbench ID:49846
  • ChEMBL ID:CHEMBL363919
  • Mol file:504-02-9.mol
1,3-Cyclohexanedione

Synonyms:1,3-cyclohexanedione

Suppliers and Price of 1,3-Cyclohexanedione
Supply Marketing:
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
  • 1,3-Cyclohexanedione
  • 250g
  • $ 135.00
  • TRC
  • 1,3-Cyclohexanedione
  • 100g
  • $ 65.00
  • TCI Chemical
  • 1,3-Cyclohexanedione [for HPLC Labeling] >98.0%(GC)(T)
  • 5g
  • $ 69.00
  • TCI Chemical
  • 1,3-Cyclohexanedione >98.0%(GC)(T)
  • 250g
  • $ 128.00
  • TCI Chemical
  • 1,3-Cyclohexanedione >98.0%(GC)(T)
  • 25g
  • $ 20.00
  • SynQuest Laboratories
  • Cyclohexane-1,3-dione 99%
  • 100 g
  • $ 32.00
  • SynQuest Laboratories
  • Cyclohexane-1,3-dione 99%
  • 500 g
  • $ 112.00
  • SynQuest Laboratories
  • Cyclohexane-1,3-dione 99%
  • 1 kg
  • $ 216.00
  • Sigma-Aldrich
  • 1,3-Cyclohexanedione 97%
  • 500g
  • $ 172.00
  • Sigma-Aldrich
  • 1,3-Cyclohexanedione for synthesis. CAS 504-02-9, chemical formula C H -1,3-(=O) ., for synthesis
  • 8203670100
  • $ 56.30
Total 229 raw suppliers
Chemical Property of 1,3-Cyclohexanedione
Chemical Property:
  • Appearance/Colour:beige crystalline powder 
  • Vapor Pressure:0.0204mmHg at 25°C 
  • Melting Point:101-105 °C(lit.) 
  • Refractive Index:1.548 
  • Boiling Point:235.1 °C at 760 mmHg 
  • PKA:5.26(at 25℃) 
  • Flash Point:85.7 °C 
  • PSA:34.14000 
  • Density:1.127 g/cm3 
  • LogP:0.69860 
  • Storage Temp.:2-8°C 
  • Solubility.:Chloroform (Slightly), Methanol (Slightly) 
  • Water Solubility.:soluble 
  • XLogP3:0
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:2
  • Rotatable Bond Count:0
  • Exact Mass:112.052429494
  • Heavy Atom Count:8
  • Complexity:113
Purity/Quality:

99% *data from raw suppliers

1,3-Cyclohexanedione *data from reagent suppliers

Safty Information:
  • Pictogram(s):  
  • Hazard Codes: 
  • Safety Statements: 24/25 
MSDS Files:

SDS file from LookChem

Useful:
  • Chemical Classes:Other Classes -> Aliphatic Ketones, Other
  • Canonical SMILES:C1CC(=O)CC(=O)C1
  • General Description 1,3-Cyclohexanedione is a versatile 1,3-dicarbonyl compound used in multicomponent reactions, such as the synthesis of dihydropyrimidinones, polyhydroquinolines, and 1,8-dioxodecahydroacridine derivatives. It participates in Knoevenagel condensations, Hantzsch reactions, and other cyclization processes, often under green conditions like solvent-free or aqueous media, with or without catalysts. Its reactivity with active methylene compounds and aldehydes makes it valuable for constructing heterocyclic frameworks with potential pharmaceutical applications, including calcium channel blockers and mitotic inhibitors. 1,3-Cyclohexanedione's utility is further highlighted by its compatibility with recyclable ionic liquid catalysts and microwave-assisted synthesis.
Technology Process of 1,3-Cyclohexanedione

There total 90 articles about 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 water; In acetonitrile; at 20 ℃; for 0.226667h; under 900.09 Torr; Flow reactor;
DOI:10.1021/acs.oprd.9b00067
Guidance literature:
With water; at 20 ℃; for 0.226667h; under 900.09 Torr; Flow reactor;
DOI:10.1021/acs.oprd.9b00067
Refernces

Facile synthesis of benzo-fused 2,8-dioxabicyclo[3.3.1]nonane derivatives via a domino Knoevenagel condensation/hetero-Diels-Alder reaction sequence

10.1016/j.tet.2007.11.036

The study presents a two-step synthesis method for benzo-fused 2,8-dioxabicyclo[3.3.1]nonane derivatives, utilizing a domino Knoevenagel condensation/intramolecular hetero-Diels-Alder reaction sequence. The process involves an initial intermolecular Knoevenagel condensation of a compound with active methylene compounds to form a heterodiene, which then undergoes intramolecular hetero-Diels-Alder cycloaddition. The research successfully optimized the reaction conditions, including the choice of catalyst and solvent, to achieve high yields of the desired products. The method demonstrates a novel route for constructing complex heterocycles with potential applications in medicinal chemistry.

A chelation effect on the pathway between intramolecular hydrodimerization and pinacol coupling

10.1021/ol0502026

The study by Scott T. Handy and Duncan Omune investigates the reductive cyclization of tethered bis-enones with one-carbon tethers, focusing on the influence of reaction conditions and α-substitution on the cyclization pathway. They found that the cyclization products, either pinacol or hydrodimerization-type, are highly dependent on these factors. The researchers synthesized three cyclization substrates and explored their reductive cyclization under electrochemical conditions and using samarium diiodide. They observed that electrochemical conditions favored pinacol-type products, while samarium diiodide favored reductive cyclization products. The study suggests that chelation and steric effects play a crucial role in determining the cyclization pathway, with Lewis acidic metals promoting pinacol formation and non-chelatable metals favoring reductive cyclization. This mechanistic understanding was further supported by experiments using magnesium in methanol, which resulted in pinacol products. The findings highlight the importance of reaction conditions in controlling the cyclization outcome and provide insights into the mechanism of reductive cyclization reactions.

Organocatalytic application of ionic liquids: [bmim][MeSO4] as a recyclable organocatalyst in the multicomponent reaction for the preparation of dihydropyrimidinones and -thiones

10.1055/s-0030-1260067

The research investigates the use of 1-butyl-3-methylimidazolium-based room-temperature ionic liquids (RTILs) as organocatalysts for the synthesis of 1,4-dihydropyrimidinones and thiones through a one-pot multicomponent reaction. The study aims to develop a greener synthetic pathway for these compounds, which have a broad range of biological activities, including as mitotic kinesin Eg5 inhibitors. The researchers found that the ionic liquid [bmim][MeSO4] was effective as a catalyst, yielding high product yields in short reaction times, and could be recovered and reused for five consecutive reactions without significant loss of catalytic efficiency. The chemicals used in the process include various aryl, heteroaryl, and aliphatic aldehydes, 1,3-dicarbonyl compounds such as ethyl acetoacetate and cyclohexane-1,3-dione, and urea or thiourea. The study concludes that the methodology has potential for bulk synthesis due to its ecocompatibility and the recyclability of the catalyst.

Pyridazine derivatives and related compounds part 10. Reactions of 3-diazopyrazolo[3,4-c]pyridazine with reactive methylene compounds and other groups

10.3987/COM-03-9960

The study investigates the synthesis and transformations of 3-diazopyrazolo[3,4-c]pyridazine, a heterocyclic diazo compound. It reacts with various reactive methylene compounds, such as ethyl cyanoacetate, diethyl malonate, and cyclohexane-1,3-dione, to form corresponding hydrazones and condensed 1,2,4-triazines. The diazo compound also undergoes azo coupling with aromatic amines and naphthols to produce arylazo derivatives. Additionally, it participates in cycloaddition reactions with dipolarophiles like phenyl isothiocyanate and dimethyl acetylenedicarboxylate, yielding cycloaddition products. The study explores the synthetic potential of fused pyridazine systems and highlights the diverse reactivity of the diazo compound, with products characterized by spectroscopic methods.

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.

1, 3-Disulfonic acid imidazolium hydrogen sulphate as an efficient and reusable ionic liquid for the multicomponent synthesis of polyhydroquinoline derivatives under solvent-free conditions

10.1007/s11164-015-2134-y

The research focuses on the development of an efficient and eco-friendly method for the synthesis of polyhydroquinoline derivatives, which are compounds with significant biological and pharmacological properties. The study reports a one-pot Hantzsch condensation process that utilizes 1,3-disulfonic acid imidazolium hydrogen sulfate (DSIMHS) as a recyclable ionic liquid catalyst under solvent-free conditions. This method was found to be highly effective, offering advantages such as short reaction times, high yields, mild reaction conditions, and the reusability of the catalyst. The chemicals involved in the process include aldehydes, 1,3-dicarbonyl compounds (dimedone or 1,3-cyclohexanedione), ethyl acetoacetate, and ammonium acetate. The conclusions drawn from the study emphasize the success of the developed procedure, which not only simplifies the synthesis of these important compounds but also aligns with green chemistry principles by minimizing the use of hazardous materials and solvents.

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