3,5,5-Trimethylcyclohexane-1,2-dione supplier

Name
3,5,5-Trimethylcyclohexane-1,2-dione
EINECS 640-099-3
CAS No. 57696-89-6
Article Data11
CAS DataBase
Density 0.976 g/cm³
Solubility
Melting Point 89-92℃
Formula C₉H₁₄O₂
Boiling Point 214.6 °C at 760 mmHg
Molecular Weight 154.209
Flash Point 77.1 °C
Transport Information
Appearance white crystallien powder
Safety 36-26
Risk Codes 36/38
Molecular Structure
Hazard Symbols
Synonyms 1,2-Cyclohexanedione, 3,5,5-trimethyl-;3,5,5-Trimethyl-1,2-cyclohexanedione;
PSA 34.14000
LogP 1.58070

Synthetic route

: 10276-21-8
isophorone oxide

: 109-63-7
trifluoroborane diethyl ether

: 71-43-2
benzene

A: 4694-12-6
2,4,4-trimethylcyclopentan-1-one

B: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

C: 10275-88-4
(+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde

...Expand

: 10276-21-8
isophorone oxide

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

Conditions	Yield
With hydrogenchloride

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

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

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

Conditions	Yield
With hydrogenchloride at 120℃;

: 684214-94-6
6-bromo-2,4,4-trimethyl-cyclohex-2-enone

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

Conditions	Yield
With sulfuric acid

: 2,2-dibromo-3,5,5-trimethyl-cyclohexanone

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

Conditions	Yield
With potassium hydroxide

: 2,2-dibromo-3,5,5-trimethyl-cyclohexanone

A: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

B: 861573-63-9
1-hydroxy-2,4,4-trimethyl-cyclopentanecarboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 108127-54-4
(+/-)-2r,6t-dibromo-2,4,4-trimethyl-cyclohexanone

: 127-09-3
sodium acetate

: 64-19-7
acetic acid

A: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

B: 684214-94-6
6-bromo-2,4,4-trimethyl-cyclohex-2-enone

...Expand

: 100533-42-4
2,6-Diacetoxy-3,3,5-trimethyl-cyclohexanon-(1)

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

Conditions	Yield
With hydrogenchloride In ethanol

: 873-94-9
dihydroisophorone

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

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

: 7647-01-0
hydrogenchloride

: 10276-21-8
isophorone oxide

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 7647-01-0
hydrogenchloride

: 3-(1,1-dimethyl-3-oxo-butyl)-furan-2,4-dione

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 10276-21-8
isophorone oxide

methanol. KOH-solution: methanol. KOH-solution

A: 5682-76-8
2-methoxy-3,5,5-trimethylcyclohex-2-enone

B: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

...Expand

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

permanganate: permanganate

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

Conditions	Yield
at 0℃; Destillation des angesaeuerten Reaktionsprodukts;

: 67-56-1
methanol

3,4-epoxy-1,1,3-trimethyl-cyclohexanone-(5): 3,4-epoxy-1,1,3-trimethyl-cyclohexanone-(5)

A: 5682-76-8
2-methoxy-3,5,5-trimethylcyclohex-2-enone

B: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

Conditions	Yield
With potassium hydroxide

...Expand

4-methoxy-1.1.3-trimethyl-cyclohexen-(3)-one-(5): 4-methoxy-1.1.3-trimethyl-cyclohexen-(3)-one-(5)

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid

: 2,2-dibromo-3,5,5-trimethyl-cyclohexanone

diluted KOH-solution: diluted KOH-solution

A: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

B: 861573-63-9
1-hydroxy-2,4,4-trimethyl-cyclopentanecarboxylic acid

...Expand

: isophorone oxide

A: 4694-12-6
2,4,4-trimethylcyclopentan-1-one

B: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

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

: isophorone oxide

A: 4694-12-6
2,4,4-trimethylcyclopentan-1-one

B: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

C: 10275-88-4
(+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde

Conditions

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.

...Expand

: isophorone oxide

A: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

B: 10275-88-4
(+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde

Conditions

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

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

PhX: PhX

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

Conditions

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

: 10276-21-8
isophorone oxide

A: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

B: 10275-88-4
(+/-)-1,4,4-trimethyl-2-oxo-cyclopentanecarbaldehyde

Conditions

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

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 578017-25-1, 790714-98-6
2-(phenylsulfinyl)thiophene

: 2-hydroxy-4,4,6-trimethyl-6-(2-(phenylthio)thiophen-3-yl)cyclohex-2-en-1-one

Conditions

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

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 20624-63-9
3,3-dimethyl-5-oxohexanoic acid

Conditions

Conditions	Yield
With methanol; potassium hydroxide; dihydrogen peroxide

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 3937-59-5
2,4,4-trimethyl-adipic acid

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide; magnesium sulfate

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 861573-63-9
1-hydroxy-2,4,4-trimethyl-cyclopentanecarboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide at 140℃;

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 16420-13-6
N,N-Dimethylthiocarbamoyl chloride

: 112621-58-6
3,5,5-trimethyl-2-<(dimethylthiocarbamoyl)oxy>-2-cyclohexen-1-one

Conditions

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

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 7722-84-1
dihydrogen peroxide

: 7487-88-9
magnesium sulfate

aqueous NaOH: aqueous NaOH

: 3937-59-5
2,4,4-trimethyl-adipic acid

...Expand

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 7722-84-1
dihydrogen peroxide

aqueous methanol. KOH: aqueous methanol. KOH

A: 20624-63-9
3,3-dimethyl-5-oxohexanoic acid

B: 3937-59-5
2,4,4-trimethyl-adipic acid

...Expand

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

KOH-solution: KOH-solution

: 861573-63-9
1-hydroxy-2,4,4-trimethyl-cyclopentanecarboxylic acid

Conditions

Conditions	Yield
at 140℃;

: 57696-89-6
3,5,5-Trimethyl-1,2-cyclohexanedione

: 78-59-1
3,5,5-Trimethylcyclohex-2-en-1-one

Conditions

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

3,5,5-Trimethylcyclohexane-1,2-dione Chemical Properties

Molecule structure of 3,5,5-Trimethylcyclohexane-1,2-dione (CAS NO.57696-89-6):

IUPAC Name: 3,5,5-Trimethylcyclohexane-1,2-dione
Molecular Weight: 154.20626 g/mol
Molecular Formula: C₉H₁₄O₂
Density: 0.976 g/cm³
Boiling Point: 214.6 °C at 760 mmHg
Flash Point: 77.1 °C
Index of Refraction: 1.444
Molar Refractivity: 41.96 cm³
Molar Volume: 157.8 cm³
Surface Tension: 28.7 dyne/cm
Enthalpy of Vaporization: 45.09 kJ/mol
Vapour Pressure: 0.155 mmHg at 25 °C
XLogP3-AA: 1.4
H-Bond Acceptor: 2
Tautomer Count: 12
Exact Mass: 154.09938
MonoIsotopic Mass: 154.09938
Topological Polar Surface Area: 34.1
Heavy Atom Count: 11
Canonical SMILES: CC1CC(CC(=O)C1=O)(C)C
InChI: InChI=1S/C9H14O2/c1-6-4-9(2,3)5-7(10)8(6)11/h6H,4-5H2,1-3H3
InChIKey: WEUZZYGESXCTCU-UHFFFAOYSA-N

3,5,5-Trimethylcyclohexane-1,2-dione Uses

3,5,5-Trimethylcyclohexane-1,2-dione (CAS NO.57696-89-6) is used for flue-cured tobacco type, blended cigarette flavoring or feeding.

3,5,5-Trimethylcyclohexane-1,2-dione Specification

3,5,5-Trimethylcyclohexane-1,2-dione (CAS NO.57696-89-6) is also named as 1,2-cyclohexanedione, 3,5,5-trimethyl- ; 3,5,5-Trimethyl-1,2-cyclohexanedione ; 3,5,5-Trimethyl-cyclohexane-1,2-dione ; 3,5,5-Trimethylcyclohexane-1,2-dione, 98% .

Product Name

3,5,5-Trimethylcyclohexane-1,2-dione

Synthetic route

3,5,5-Trimethylcyclohexane-1,2-dione Chemical Properties

3,5,5-Trimethylcyclohexane-1,2-dione Uses

3,5,5-Trimethylcyclohexane-1,2-dione Specification

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