57696-89-6

Basic information

• Product Name: 3,5,5-Trimethylcyclohexane-1,2-dione
• Synonyms: 2-Cyclohexanedione,3,5,5-trimethyl-1;3,5,5-trimethyl-2-cyclohexanedione;3,5,5-TRIMETHYL-1,2-CYCLOHEXANEDIONE;FEMA 3459;Tobacco Ketone;1,2-Cyclohexanedione, 3,5,5-trimethyl-;1,2-Cyclohexandion, 3,5,5-trimethyl-;3,5,5-Trimethylcyclohexane-1,2-dione
• CAS NO: 57696-89-6
• Molecular Formula: C₉H₁₄O₂
• Molecular Weight: 154.21
• EINECS: 1312995-182-4
• Mol File: 57696-89-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: 89-92℃
• Boiling Point: 214.6 °C at 760 mmHg
• Flash Point: >100°(212°F)
• Appearance: white crystallien powder
• Density: 0.976 g/cm³
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: 1.444
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 3,5,5-Trimethylcyclohexane-1,2-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5,5-Trimethylcyclohexane-1,2-dione(57696-89-6)
• EPA Substance Registry System: 3,5,5-Trimethylcyclohexane-1,2-dione(57696-89-6)

Safety Data

• Statements: 36/38
• Safety Statements: 36-26
• TSCA: Yes
• Hazardous Substances Data: 57696-89-6(Hazardous Substances Data)

Usage

Description

3,5,5-Trimethylcyclohexane-1,2-dione is an organic compound with the molecular formula C10H16O3. It is a dione derivative of cyclohexane, featuring three methyl groups attached to the cyclohexane ring. 3,5,5-Trimethylcyclohexane-1,2-dione is known for its potential applications in the pharmaceutical and chemical industries due to its unique structural properties.

Uses

Used in Pharmaceutical Industry:
3,5,5-Trimethylcyclohexane-1,2-dione is used as a key intermediate compound for the synthesis of Tetrahydro-carbazolone analogs, which are known to exhibit inhibitory effects against hepatitis C virus. The application reason for using this compound in the pharmaceutical industry is to develop novel therapeutic agents that can help in the treatment of hepatitis C, a viral infection that affects the liver and can lead to severe health complications if left untreated.

InChI:InChI=1/C9H14O2/c1-6-4-9(2,3)5-7(10)8(6)11/h6H,4-5H2,1-3H3/t6-/m0/s1

Synthetic route

isophorone oxide (10276-21-8) + trifluoroborane diethyl ether (109-63-7) + benzene (71-43-2) → 2,4,4-trimethylcyclopentan-1-one (4694-12-6) + 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + (+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde (10275-88-4)

isophorone oxide (10276-21-8) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With hydrogenchloride

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With permanganate(VII) ion at 0℃; Destillation des angesaeuerten Reaktionsprodukts;
Multi-step reaction with 2 steps 1: methanol; aqueous hydrogen peroxide; aq. NaOH solution 2: aqueous HCl View Scheme

3-(1,1-dimethyl-3-oxo-butyl)-furan-2,4-dione → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With hydrogenchloride at 120℃;

6-bromo-2,4,4-trimethyl-cyclohex-2-enone (684214-94-6) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With sulfuric acid

2,2-dibromo-3,5,5-trimethyl-cyclohexanone → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With potassium hydroxide

2,2-dibromo-3,5,5-trimethyl-cyclohexanone → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + 1-hydroxy-2,4,4-trimethyl-cyclopentanecarboxylic acid (861573-63-9)

Conditions	Yield
With potassium hydroxide

(+/-)-2r,6t-dibromo-2,4,4-trimethyl-cyclohexanone (108127-54-4) + sodium acetate (127-09-3) + acetic acid (64-19-7) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + 6-bromo-2,4,4-trimethyl-cyclohex-2-enone (684214-94-6)

2,6-Diacetoxy-3,3,5-trimethyl-cyclohexanon-(1) (100533-42-4) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With hydrogenchloride In ethanol

dihydroisophorone (873-94-9) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
(i) Br2, (ii) aq. KOH; Multistep reaction;
Multi-step reaction with 2 steps 1: glacial acetic acid; bromine 2: diluted KOH-solution View Scheme
Multi-step reaction with 2 steps 1: glacial acetic acid; bromine 2: KOH-solution View Scheme

hydrogenchloride (7647-01-0) + isophorone oxide (10276-21-8) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

hydrogenchloride (7647-01-0) + 3-(1,1-dimethyl-3-oxo-butyl)-furan-2,4-dione → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

isophorone oxide (10276-21-8) + methanol. KOH-solution → 2-methoxy-3,5,5-trimethylcyclohex-2-enone (5682-76-8) + 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + permanganate → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
at 0℃; Destillation des angesaeuerten Reaktionsprodukts;

methanol (67-56-1) + 3,4-epoxy-1,1,3-trimethyl-cyclohexanone-(5) → 2-methoxy-3,5,5-trimethylcyclohex-2-enone (5682-76-8) + 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With potassium hydroxide

4-methoxy-1.1.3-trimethyl-cyclohexen-(3)-one-(5) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With hydrogenchloride; acetic acid

2,2-dibromo-3,5,5-trimethyl-cyclohexanone + diluted KOH-solution → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + 1-hydroxy-2,4,4-trimethyl-cyclopentanecarboxylic acid (861573-63-9)

isophorone oxide → 2,4,4-trimethylcyclopentan-1-one (4694-12-6) + 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene at 20℃; for 0.166667h; Rearrangement;	A 76 % Spectr. B 2 % Spectr.

isophorone oxide → 2,4,4-trimethylcyclopentan-1-one (4694-12-6) + 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + (+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde (10275-88-4)

Conditions	Yield
With 1,3,5-Tri-tert-butylbenzene; zeolite beta according Wadlinger In benzene at 80℃; for 2h; Product distribution; Further Variations:; Reagents; Solvents; Temperatures; Rearrangement;	A 25 % Spectr. B 15 % Spectr. C 56 % Spectr.
With zeolite NaHY In chlorobenzene at 132℃; for 2h; Rearrangement;	A 7 % Spectr. B 29 % Spectr. C 58 % Spectr.

isophorone oxide → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + (+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde (10275-88-4)

Conditions	Yield
With boron trifluoride diethyl etherate In benzene at 20℃; for 0.166667h; Rearrangement;	A 2 % Spectr. B 76 % Spectr.

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + PhX → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 30percent H2O2; NaOH (6M) / methanol / 15 - 20 °C 1.2: 65 percent / Na2SO3; NaHCO3 / H2O; methanol 2.1: 2 percent Spectr. / BF3*Et2O / benzene / 0.17 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: 30percent H2O2; NaOH (6M) / methanol / 15 - 20 °C 1.2: 65 percent / Na2SO3; NaHCO3 / H2O; methanol 2.1: 2 percent Spectr. / BF3*Et2O / benzene / 0.17 h / 20 °C View Scheme

isophorone oxide (10276-21-8) → 3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + (+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde (10275-88-4)

Conditions	Yield
With ZSM-5 zeolite In toluene at 80℃; Autoclave;

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + 2-(phenylsulfinyl)thiophene (578017-25-1, 790714-98-6) → 2-hydroxy-4,4,6-trimethyl-6-(2-(phenylthio)thiophen-3-yl)cyclohex-2-en-1-one

Conditions	Yield
With trifluoroacetic anhydride In 1,2-dichloro-ethane at -10℃; for 4h; regioselective reaction;	60%

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) → 3,3-dimethyl-5-oxohexanoic acid (20624-63-9)

Conditions	Yield
With methanol; potassium hydroxide; dihydrogen peroxide

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) → 2,4,4-trimethyl-adipic acid (3937-59-5)

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; magnesium sulfate

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) → 1-hydroxy-2,4,4-trimethyl-cyclopentanecarboxylic acid (861573-63-9)

Conditions	Yield
With potassium hydroxide at 140℃;

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + N,N-Dimethylthiocarbamoyl chloride (16420-13-6) → 3,5,5-trimethyl-2-<(dimethylthiocarbamoyl)oxy>-2-cyclohexen-1-one (112621-58-6)

Conditions	Yield
With lithium hydroxide In chloroform for 2h; Ambient temperature;

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + dihydrogen peroxide (7722-84-1) + magnesium sulfate (7487-88-9) + aqueous NaOH → 2,4,4-trimethyl-adipic acid (3937-59-5)

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + dihydrogen peroxide (7722-84-1) + aqueous methanol. KOH → 3,3-dimethyl-5-oxohexanoic acid (20624-63-9) + 2,4,4-trimethyl-adipic acid (3937-59-5)

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) + KOH-solution → 1-hydroxy-2,4,4-trimethyl-cyclopentanecarboxylic acid (861573-63-9)

Conditions	Yield
at 140℃;

3,5,5-Trimethyl-1,2-cyclohexanedione (57696-89-6) → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1 M aq. LiOH / CHCl3 / 2 h / Ambient temperature 2: 83 percent / Li, LiOAc, AcOH / 0.25 h / Heating View Scheme

Upstream product

• 10276-21-8 isophorone oxide 
• 109-63-7 trifluoroborane diethyl ether 
• 71-43-2 benzene 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 684214-94-6 6-bromo-2,4,4-trimethyl-cyclohex-2-enone 
• 108127-54-4 (+/-)-2r,6t-dibromo-2,4,4-trimethyl-cyclohexanone 
• 127-09-3 sodium acetate 
• 64-19-7 acetic acid 
• 100533-42-4 2,6-Diacetoxy-3,3,5-trimethyl-cyclohexanon-⁽¹⁾ 
• 873-94-9 dihydroisophorone 
• 7647-01-0 hydrogenchloride 
• 67-56-1 methanol 

Downstream Products

• 112621-58-6 3,5,5-trimethyl-2-<(dimethylthiocarbamoyl)oxy>-2-cyclohexen-1-one 
• 78-59-1 3,5,5-Trimethylcyclohex-2-en-1-one 
• 4694-12-6 2,4,4-trimethylcyclopentan-1-one 

Relevant articles and documents

Nanocrystalline ZSM-5: A catalyst with high activity and selectivity for epoxide rearrangement reactions

Nanocrystalline ZSM-5 (～20-50 nm) has been tested as a catalyst in the liquid phase rearrangement of 1,2-epoxyoctane, 2-methyl-2,3-epoxybutane and isophorone oxide together with a microcrystalline ZSM-5 sample (～5 μm) employed as a reference. Whereas this last material shows a low activity for the three epoxide rearrangement reactions considered, nanocrystalline ZSM-5 leads in all cases to high epoxide conversion. This different catalytic performance is attributed to the differences in the accessibility of the reactant molecules to the catalyst active sites. The smallest crystal size of the nanocrystalline zeolite contributes favourably to both the formation of a high external surface area, with no steric constraints, and to a faster intracrystalline diffusion of the epoxide molecules towards the acid sites located within the zeolite micropores. When sterically hindered epoxides are tested, the catalytic rearrangement occurs mainly on the external surface of the nanocrystalline zeolite. Moreover, it is remarkable that for the three epoxides investigated the high catalytic activity observed over nanocrystalline ZSM-5 is accompanied by the attainment of high selectivities, typically around or over 80%, towards products with commercial applications.