3,3,5-Trimethylcyclohexanone

Base Information

• Chemical Name: 3,3,5-Trimethylcyclohexanone
• CAS No.: 873-94-9
• Deprecated CAS: 33496-91-2
• Molecular Formula: C9H16O
• Molecular Weight: 140.225
• Hs Code.: 29142200
• European Community (EC) Number: 212-855-9
• UNII: QXG9U7N202
• DSSTox Substance ID: DTXSID5044996
• Nikkaji Number: J68.885A
• Wikidata: Q27287551
• ChEMBL ID: CHEMBL3186483
• Mol file: 873-94-9.mol

Synonyms:dihydro-isophorone

Chemical Property of 3,3,5-Trimethylcyclohexanone

Chemical Property:

• Appearance/Colour: clear colourless to very slightly yellow liquid
• Vapor Pressure: 0.582mmHg at 25°C
• Melting Point: -10 °C
• Refractive Index: n20/D 1.445(lit.)
• Boiling Point: 188.8 °C at 760 mmHg
• Flash Point: 64 °C
• PSA: 17.07000
• Density: 0.888 g/cm³
• LogP: 2.40170
• Storage Temp.: Store below +30°C.
• Solubility.: 30g/l
• Water Solubility.: 13 g/L (20 ºC)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 140.120115130
• Heavy Atom Count: 10
• Complexity: 147

Purity/Quality:

99%, ^*data from raw suppliers

3,3,5-Trimethylcyclohexanone >98.0%(GC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38-36/37
• Safety Statements: 26-39-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Aliphatic Ketones, Other
• Canonical SMILES: CC1CC(=O)CC(C1)(C)C
• Uses: 3,3,5-Trimethylcyclohexanone is used as a raw material for chemical syntheses e,g. monomer for specialty polycarbonate (Apec?); peroxides used as polymerization initiator. It is also used in coatings and paints to provide improved leveling, gloss and surface finish. 3,3,5-Trimethylcyclohexanone is used as a reactant in the selective catalytic hydrogenation of organic compounds in supercritical fluids.

Technology Process of 3,3,5-Trimethylcyclohexanone

There total 49 articles about 3,3,5-Trimethylcyclohexanone 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: 100.0%

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → dihydroisophorone (873-94-9)

Guidance literature:

With limonene.; Pd-BaSO₄; for 0.5h; Heating;

DOI:10.1016/S0040-4020(01)80811-5

Reference yield: 95.0%

cis-3,3,5-trimethylcyclohexyl t-butyldimethylsilyl ether → dihydroisophorone (873-94-9)

Guidance literature:

With potassium fluoride; jones reagent; In acetone; at 0 ℃; for 1h;

Reference yield: 90.0%

3,3,5-trimethylcyclohexanol (116-02-9) → dihydroisophorone (873-94-9)

Guidance literature:

3,3,5-trimethylcyclohexanol; With ammonium tungstate; In water; at 20 ℃; for 0.25h; Green chemistry;

With dihydrogen peroxide; In water; at 70 ℃; for 11h; Green chemistry;

DOI:10.1055/s-0036-1590949

upstream raw materials:

3,5,5-Trimethylcyclohex-2-en-1-one

ethanol

1-hydroxy-3,3,5-trimethyl-cyclohexanecarbonitrile

3,3,5-trimethylcyclohexanol

Downstream raw materials:

di-(3,3,5-trimethylcyclohexyl)amine

3,3,5-trimethylcyclohexanamine

(1-hydroxy-3,3,5-trimethyl-cyclohexyl)-acetic acid ethyl ester

1,3,3,5-tetramethyl-cyclohexanol

Refernces

Improved addition of phenyllithium to hindered ketones by the use of non-polar media

10.1016/S0040-4039(02)00597-X

The research focuses on the improved addition of phenyllithium (PhLi) to hindered ketones using non-polar media at room temperature. The study was conducted on six hindered ketones: (?)-fenchone, (?)-menthone, (+)-camphor, 3,3,5-trimethylcyclohexanone, 3,3,5,5-tetramethylcyclohexanone, and 2,4-dimethylpentan-3-one. The researchers aimed to enhance the low reactivity of these ketones towards PhLi, which traditionally yields modest results when performed in ethers like diethyl ether or THF. The experiments involved dissolving the ketones in a non-polar solvent, such as toluene or a toluene-diethyl ether mixture, and then slowly adding commercial PhLi via syringe. The mixtures were stirred at room temperature for 2 to 4 hours. The results showed significant improvements in yield compared to traditional methods, with the addition occurring in a stereospecific manner, favoring the less-hindered side. The configuration of the adducts was established using 13C NMR according to literature methods. This approach was found to be more efficient, cost-effective, and easier, offering a significant advantage for the synthesis of chiral inducers.

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