5,5-Dimethyl-1,3-cyclohexanedione

Base Information

• 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

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

Chemical Property of 5,5-Dimethyl-1,3-cyclohexanedione

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): Xi
• 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:

Reference yield: 97.0%

5,5-dimethyl-3-propoxycyclohex-2-en-1-one → dimedone (126-81-8)

Guidance literature:

With water; In acetonitrile; at 20 ℃; for 0.226667h; under 900.09 Torr; Flow reactor;

DOI:10.1021/acs.oprd.9b00067

Reference yield: 95.0%

3-(benzyloxy)-5,5-dimethylcyclohex-2-enone (13120-57-5) → dimedone (126-81-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ja055530f

Reference yield: 91.0%

all-trans-retinylidene dimedone (70424-15-6) → all-trans-Retinal (116-31-4) + dimedone (126-81-8)

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

upstream raw materials:

3-chloro-5,5-dimethylcyclohex-2-en-1-one

phorone

ethanol

sodium diethylmalonate

Downstream raw materials:

5,5-dimethyl-3-(1-pyrrolidinyl)-2-cyclohexen-1-one

3-methoxy-5,5-dimethyl-cyclohex-2-enone

2,2'-phenylmethylene-bis(5,5-dimethylcyclohexane-1,3-dione)

3,3-dimethyl-3,4-dihydroacridin-1(2H)-one

Refernces

• 1、 Henshall et al.. "". . p. 6656. Retrieved 1955.
• 2、 Mohanta, Nirmala,Chaudhari, Moreshwar B.,Digrawal, Naveen Kumar,Gnanaprakasam, Boopathy. "Rapid and Multigram Synthesis of Vinylogous Esters under Continuous Flow: An Access to Transetherification and Reverse Reaction of Vinylogous Esters". . p. 1034 - 1045. Retrieved 2019/05/24.
• 3、 Han, Guang-Fan,Cui, Bin,Chen, Li-Zhuang,Hu, Xiao-Lei. "Synthesis of 10-amino-9-aryl-2,3,4,5,6,7,9,10-octahydroacridine- 1,8-dione derivatives". scheme or table. p. 195 - 199. Retrieved 2012/04/17.