873-94-9

Basic information

• Product Name: 3,3,5-Trimethylcyclohexanone
• Synonyms: 3,3,5-trimethyl-cyclohexanon;3,5,5-Triethylcyclohexanone;3,3,5-TRIMETHYLCYCLOHEXANONE;3,5,5-TRIMETHYL CYCLOHEXANONE;DIHYDROISOPHORONE;3,3,5-trimethylcyclohexan-1-one;Cyclohexanone, 3,3,5-trimethyl-;3,3,5-Trimethylcyclohexan-1-on
• CAS NO: 873-94-9
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22
• EINECS: 212-855-9
• Product Categories: C9;Carbonyl Compounds;Ketones;Building Blocks;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 873-94-9.mol
• Article Data: 97

Chemical Properties

• Melting Point: −10 °C(lit.)
• Boiling Point: 188-192 °C(lit.)
• Flash Point: 150 °F
• Appearance: clear colourless to very slightly yellow liquid
• Density: 0.887 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.582mmHg at 25°C
• Refractive Index: n20/D 1.445(lit.)
• Storage Temp.: Store below +30°C.
• Solubility: 30g/l
• Explosive Limit: 1.1%(V)
• Water Solubility: 13 g/L (20 ºC)
• BRN: 507452
• CAS DataBase Reference: 3,3,5-Trimethylcyclohexanone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,3,5-Trimethylcyclohexanone(873-94-9)
• EPA Substance Registry System: 3,3,5-Trimethylcyclohexanone(873-94-9)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38-36/37
• Safety Statements: 26-39-28A
• WGK Germany: 1
• RTECS: GW2185000
• Hazardous Substances Data: 873-94-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 873-94-9 differently. You can refer to the following data:
1. 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.
2. 3,3,5-Trimethylcyclohexanone is used as a reactant in the selective catalytic hydrogenation of organic compounds in supercritical fluids.

Synthesis Reference(s)

The Journal of Organic Chemistry, 43, p. 4647, 1978 DOI: 10.1021/jo00418a024Synthetic Communications, 15, p. 759, 1985 DOI: 10.1080/00397918508063869Tetrahedron Letters, 29, p. 5471, 1988 DOI: 10.1016/S0040-4039(00)80789-3

Flammability and Explosibility

Notclassified

InChI:InChI=1/C9H16O/c1-7-4-8(10)6-9(2,3)5-7/h7H,4-6H2,1-3H3/t7-/m1/s1

Upstream product

• 67-63-0 isopropyl alcohol 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 1140969-63-6 1,1-bis(hydroperoxy)-3,3,5-trimethylcyclohexane 
• 116-02-9 3,3,5-trimethylcyclohexanol 
• 40643-64-9 1-hydroxy-3,3,5-trimethyl-cyclohexanecarbonitrile 
• 344-25-2 D-Prolin 
• 147-85-3 L-proline 
• 67-56-1 methanol 
• 67217-68-9 1,1-dimethoxy-3,3,5-trimethyl-cyclohexane 
• 119-42-6 2-cyclohexylphenol 
• 1131-60-8 p-cyclohexylphenol 
• 109-05-7 2-Methylpiperidin 

Downstream Products

• 36101-73-2 di-(3,3,5-trimethylcyclohexyl)amine 
• 15901-42-5 3,3,5-trimethylcyclohexanamine 
• 16303-67-6 3,5,5-trimethyl-2-morpholin-4-ylmethyl-cyclohexanone 
• 93257-30-8 2-Acetylmercapto-3,5,5-trimethyl-cyclohexanon 
• 767-54-4 trans-3,3,5-trimethylcyclohexanol 
• 933-48-2 cis-3,3,5-trimethylcyclohexanol 
• 121642-49-7 trans-2-(1-hydroxy-3,3,5-trimethylcyclohexyl)-3-methylbut-3-enoic acid 
• 56040-98-3 (1S,5R)-1-(1-Isopropoxy-1-methyl-ethyl)-3,3,5-trimethyl-cyclohexanol 
• 56040-98-3 (1S,5S)-1-(1-Isopropoxy-1-methyl-ethyl)-3,3,5-trimethyl-cyclohexanol 

Relevant articles and documents

Could the energy cost of using supercritical fluids be mitigated by using CO2 from carbon capture and storage (CCS)?

This article explores the possibility of utilising supercritical CO 2 obtained from carbon capture and storage (CCS) as a solvent and examines the hydrogenation of isophorone to 3,3,5-trimethylcyclohexanone using supercritical CO2 with added N2, CO or H2O to emulate the contaminants expected in CO2 from CCS. None of the impurities appear to cause insuperable problems in the hydrogenation of isophorone when present at concentrations likely to be found in CO2 from CCS. N2 introduces modest changes in phase behaviour at some pressures, while CO and H2O reduce the activity of the catalyst. However, the activity can be largely regained by increasing the reaction temperature.

Study on the selective hydrogenation of isophorone

3,3,5-Trimethylcyclohexanone (TMCH) is an important pharmaceutical intermediate and organic solvent, which has important industrial significance. The selective hydrogenation of isophorone was studied over noble metal (Pd/C, Pt/C, Ir/C, Ru/C, Pd/SiO2, Pt/SiO2, Ir/SiO2, Ru/SiO2), and non-noble metal (RANEY Ni, RANEY Co, RANEY Cu, RANEY Fe, Ni/SiO2, Co/SiO2, Cu/SiO2, Fe/SiO2) catalysts and using solvent-free and solvent based synthesis. The results show that the solvent has an important effect on the selectivity of TMCH. The selective hydrogenation of isophorone to TMCH can be influenced by the tetrahydrofuran solvent. The conversion of isophorone is 100%, and the yield of 3,3,5-trimethylcyclohexanone is 98.1% under RANEY Ni and THF. The method was applied to the selective hydrogenation of isopropylidene acetone, benzylidene acetone and 6-methyl-5-ene-2-heptanone. The structures of the hydrogenation product target (4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one) were characterized using 1H-NMR and 13C-NMR. The yields of 4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one were 97.2%, 98.5% and 98.2%, respectively. The production cost can be reduced by using RANEY metal instead of noble metal palladium. This method has good application prospects. This journal is

Cucurbit[5]uril-mediated electrochemical hydrogenation of α,β-unsaturated ketones

The potential of cucurbit[5]uril to be used as inverse phase transfer catalyst in electrocatalytic hydrogenation of α,β-unsaturated ketones is illustrated. The interaction behavior among isophorone and cucurbit[5]uril was also investigated using cyclic voltammetry and UV/vis absorption spectroscopy. The results concerning to both techniques revealed an enhancement in the intensity of the absorption peak and also in the current cathodic peak of isophorone in presence of cucurbit[5]uril. This achievement is related to the increase of the isophorone solubility in the medium being an indicative of a host-guest complex formation. The electrochemical hydrogenation of isophorone using cucurbit[5]uril was more efficient than others well-stablish methodologies. Regarding to (R)-(+)-pulegone and (S)-(+)-carvone, the use of cucurbit[5]uril leads to an increase of 17% and 9%, on average, respectively, in the yields when compared to the control reaction. The efficiency of selective C=O bond hydrogenation of 1-acetyl-1-cyclohexene was evaluated. The presence of cucurbit[5]uril increased by 12% the hydrogenations yields of 1-acetyl-1-cyclohexene when compared to the control reaction. In this sense, these results open up an opportunity to carry out electrocatalytic reactions within the cucurbit[5]uril environment.

Iron-Catalyzed Chemoselective Reduction of α,β-Unsaturated Ketones

An iron-catalyzed chemo- and diastereoselective reduction of α,β-unsaturated ketones into the corresponding saturated ketones in mild reaction conditions is reported herein. DFT calculations and experimental work underline that transfer hydride reduction is a more facile process than hydrogenation, unveiling the fundamental role of the base.