Isophorone supplier | CasNO.78-59-1

Name
Isophoron
EINECS 201-126-0
CAS No. 78-59-1
Article Data198
CAS DataBase
Density 0.905 g/cm³
Solubility
Melting Point -8 °C(lit.)
Formula C₉H₁₄O
Boiling Point 215.2 °C at 760 mmHg
Molecular Weight 138.21
Flash Point 84.4 °C
Transport Information
Appearance light yellow liquid
Safety 13-23-36/37/39-46
Risk Codes 21/22-36/37-40
Molecular Structure
Hazard Symbols Xn
Synonyms 3,5,5-Trimethyl-2-cyclohexen-1-one;3,5,5-Trimethyl-2-cyclohexene-1-one;3,5,5-Trimethyl-2-cyclohexenone;Isoacetophorone;Isoforon;Isophoron;NSC 403657;NSC 4881;a-Isophoron;a-Isophorone;iso-phorone;2-Cyclohexen-1-one,3,5,5-trimethyl-;1,1,3-Trimethyl-3-cyclohexene-5-one;1,5,5-Trimethyl-3-oxocyclohexene;1-Cyclohexen-3-one, 1,5,5-trimethyl-;
PSA 17.07000
LogP 2.32180

Synthetic route

: 470-99-5
isophorol

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

Conditions

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 2,4-dichlorotoluene at 25℃; for 2h; Inert atmosphere;	99%
With pyridine; oxygen; Pd(II)-hydrotalcite In toluene at 80℃; for 3h;	96%
With iodosylbenzene; N,N-ethylenebis(3,5-dichlorosalicylideneiminato)Cr(III)Cl In dichloromethane at 20℃; for 0.666667h;	95%

: 10276-21-8
isophorone oxide

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

Conditions

Conditions	Yield
With iodine; triphenylphosphine In acetonitrile at 20℃; for 0.25h;	98%
With sodium hydroxide; thiourea dioxide; tetrabutylammomium bromide In tetrahydrofuran at 50℃; for 0.5h;	95%
Stage #1: isophorone oxide With bis(cyclopentadienyl)titanium dichloride; zinc In tetrahydrofuran; acetonitrile for 0.5h; Inert atmosphere; Stage #2: With sodium dihydrogenphosphate; water In tetrahydrofuran; acetonitrile for 0.333333h; Inert atmosphere;	88%

: 136116-41-1
Trimethyl-(3,5,5-trimethyl-cyclohex-2-enyloxy)-silane

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

Conditions

Conditions	Yield
With chromium(VI) oxide; tert.-butylhydroperoxide; triphenylhydroxysilane In dichloromethane for 17h; Ambient temperature;	98%

: 107742-85-8
6-Benzenesulfinyl-3,5,5-trimethyl-cyclohex-2-enone

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

Conditions

Conditions	Yield
With ammonium chloride; zinc In tetrahydrofuran at 25℃; for 2h;	98%

: 107742-84-7
3,5,5-Trimethyl-6-phenylsulfanyl-cyclohex-2-enone

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

Conditions

Conditions	Yield
With ammonium chloride; zinc In tetrahydrofuran at 25℃; for 3h;	95%

: 13271-49-3
3-bromo-5,5-dimethlycyclohex-2-en-1-one

: 917-54-4
methyllithium

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

Conditions

Conditions	Yield
With copper(I) thiophenolate In tetrahydrofuran; diethyl ether at 0℃; for 2.5h;	94%

: 99649-02-2, 99649-03-3
C9H14OS

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

Conditions

Conditions	Yield
In chloroform for 25h; Ambient temperature; Irradiation;	90%
With oxygen; methylene blue In chloroform for 24h; Irradiation; Yield given;

: 175602-66-1
(3,5,5-trimethyl-2-cyclohexenyl) ethyl ether

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

Conditions

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 8h; Heating;	90%

: 207395-09-3
(3,5,5-trimethyl-cyclohex-2-enyloxymethyl)-benzene

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

B: 100-52-7
benzaldehyde

Conditions

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 8h; Heating;	A 87% B 60%

: 81036-85-3
7-Bromo-9,9-dimethyl-1,4-dioxa-spiro[4.5]dec-7-ene

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran	86%
With n-butyllithium 1.) THF, -78 deg C, 2 h, 2.) a) -78 deg C, 1 h, b) RT, 1 h; Yield given. Multistep reaction;

: 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

Conditions

Conditions	Yield
With lithium acetate; lithium; acetic acid for 0.25h; Heating;	83%

: 141-79-7
4-methyl-pent-3-en-2-one

: 541-50-4
2-acetoacetic acid

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

Conditions

Conditions	Yield
Stage #1: 4-methyl-pent-3-en-2-one; 2-acetoacetic acid With copper(II) bis(trifluoromethanesulfonate) at 20℃; for 12h; Inert atmosphere; Stage #2: With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; Reagent/catalyst; Inert atmosphere;	83%

: 3-allyloxy-1,5,5-trimethyl-cyclohexene

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

Conditions

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 12h; Heating;	82%

: 117910-76-6
2-bromoisophorone

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

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; sodium iodide In 1,2-dichloro-ethane at 85℃; for 2h;	80%

: 77797-05-8
1'p.methoxyphenyl 1'-cyano 1,3,5,5-tetramethyl 2-cyclohexen 1-ol

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

B: 77797-11-6
p-methoxyphenyl-3' cyano-3' tetramethyl-3,3,5,5 cyclohexanone

C: 104-47-2
p-methoxybenzylnitrile

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -70℃; for 0.0833333h; Yield given;	A n/a B 80% C n/a
With n-butyllithium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide at -70℃; for 0.0833333h; Yields of byproduct given;	A n/a B 80% C n/a

...Expand

: 50987-46-7
1-methoxy-3,5,5-trimethyl-2-cyclohexene

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

Conditions

Conditions	Yield
With pyridinium chlorochromate In dichloromethane for 4h; Heating;	80%

: Diazo-acetic acid 3,5,5-trimethyl-cyclohex-2-enyl ester

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

B: 2b,4,4-Trimethyl-hexahydro-1-oxa-cyclopropa[cd]inden-2-one

Conditions

Conditions	Yield
With dirhodium(II) tetrakis(caprolactam) In dichloromethane Heating; Yields of byproduct given;	A n/a B 77%

: 67-64-1
acetone

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

B: 67-63-0
isopropyl alcohol

Conditions

Conditions	Yield
With diphenylgermylenedipotassium In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide for 0.5h; Product distribution; Ambient temperature; KH as reagent;	A 76% B n/a

: 141-79-7
4-methyl-pent-3-en-2-one

: 141-97-9
ethyl acetoacetate

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

Conditions

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol for 20h; Heating;	75%

: 19019-49-9
(+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one

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

Conditions

Conditions	Yield
With 2 In dichloromethane for 0.17h; Ambient temperature;	74%

: 76793-94-7
7,9,9-trimethyl-1,4-dithiaspiro<4,5>dec-6-ene

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

Conditions

Conditions	Yield
With Oxone; potassium bromide In water; acetonitrile at 20℃; for 1h;	72%
With O-phenyl phosphorodichloridate; N,N-dimethyl-formamide; sodium iodide 1.) acetonitrile, few min, room temp., 2.) 5 h, room temp.; Yield given. Multistep reaction;

: 24829-47-8
1-amino-3,3,5-trimethyl-cyclohexyl hydroperoxide

: 502-42-1
cycloheptanone

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

Conditions

Conditions	Yield
With ammonium acetate In ethanol	70.9%
With ammonium acetate In ethanol	70.9%

: 30221-55-7
trimethyl-3,5,5 cyclohexene-2 thione

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

Conditions

Conditions	Yield
With oxygen; methylene blue In dichloromethane for 5h; Irradiation;	70%
With oxygen In chloroform Product distribution; Rate constant; Mechanism; Irradiation; investigation of different oxidation methods;

: 126-81-8
dimedone

Cp2TiCH2*AlMe2Cl: Cp2TiCH2*AlMe2Cl

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

Conditions

Conditions	Yield
In tetrahydrofuran -40 deg C -> R.T., 90 min;	70%

: 10416-78-1
5,5-dimethyl-3-((trimethylsilyl)oxy)cyclohex-2-en-1-one

: 917-54-4
methyllithium

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

Conditions

Conditions	Yield
In diethyl ether for 20h; Ambient temperature;	69%

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

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

Conditions

Conditions	Yield
With formic acid; dihydrogen peroxide	69%

: (2R,3R)-2,3-Bis-(4,5-dimethoxy-2-nitro-phenyl)-7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-ene

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

Conditions

Conditions	Yield
In acetonitrile Photolysis;	68%

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

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

B: 1125-21-9
2,6,6-trimethyl-2-cyclohexene-1,4-dione

C: 14203-59-9
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions

Conditions	Yield
With Tri-n-octylamine; sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 70℃; for 2h; pH=1.5 - 2; Temperature; Reagent/catalyst;	A 8% B 24% C 67%
With Tri-n-octylamine; sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 90℃; for 2h; pH=1.5 - 2; Catalytic behavior; Reagent/catalyst; Temperature;	A 15% B 46% C 16%
With sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In water at 80℃; for 2h; pH=1.5 - 2; Temperature;	A 22% B 5% C 13%
With oxygen; triethylamine; iron tetrasulfophthalocyanine-TiO2 In dimethyl sulfoxide at 60℃; under 1500.12 Torr; for 24h;	A 10 % Chromat. B 57 % Chromat. C 21 % Chromat.

...Expand

: 544-97-8
dimethyl zinc(II)

: (5,5-dimethyl-3-oxo-cyclohex-1-enylsulfanyl)-acetic acid

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

Conditions

Conditions	Yield
With bis(methyldiphenylphosphine)nickel(II) chloride In tetrahydrofuran at 20℃; for 43h; cross-coupling;	64%

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

: 873-94-9
dihydroisophorone

Conditions

Conditions	Yield
With limonene.; Pd-BaSO4 for 0.5h; Heating;	100%
With limonene.; Pd-BaSO4 for 0.5h; Product distribution; Heating; further carrier of catalyst;	100%
With hydrogen; β-cyclodextrin/Pd In water at 25℃; under 15001.2 Torr; for 2h;	100%

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

: 13257-83-5
ethyl 3-trimethylsiloxy-2-butenoate

: 82084-31-9
1,3,3,8-Tetramethyl-5-oxo-8-trimethylsilanyloxy-bicyclo[4.2.0]octane-7-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In benzene for 24h; Ambient temperature; Irradiation;	100%

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

: 17304-82-4
2-chloroisophorone

Conditions

Conditions	Yield
With Oxone; sodium chloride In tetrachloromethane; water at 0 - 25℃;	100%
With pyridine; sulfuryl dichloride
With fluorosulfonylchloride
With calcium hypochlorite; Methamphetamin In dichloromethane; water for 3h;
With chlorine 1.) CH2Cl2, -3 - 8 deg C; 2.) CCl4, DMF, 75-80 deg C, 30 min; Yield given. Multistep reaction;

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

: 64-19-7
acetic acid

: 19019-49-9
(+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one

Conditions

Conditions	Yield
Stage #1: acetic acid With potassium permanganate; acetic anhydride In benzene at 85℃; for 0.5h; Stage #2: 3,5,5-Trimethylcyclohex-2-en-1-one In benzene at 85℃; Temperature;	100%
With potassium permanganate In benzene Heating;	86%

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

: 33496-82-1
(R)-3,3,5-trimethylcyclohexanone

Conditions

Conditions	Yield
With dodecacarbonyltetrarhodium(0); (S)-bis(4-(tert-butyl)phenyl)methyl-3-(1-acetyl-1H-indol-3-yl)-2-aminopropanoate; hydrogen; triphenylphosphine In toluene at 90℃; under 60006 Torr; for 10h; Autoclave;	99.8%
Stage #1: 3,5,5-Trimethylcyclohex-2-en-1-one With polymethylhydrosiloxane; copper(l) chloride; sodium t-butanolate; (R)-(2,3-methylenedioxy-6-(4-MeO-3,5-tBu2-C6H2)2P-C6H2)2 In tetrahydrofuran at -35℃; for 1h; Stage #2: In tetrahydrofuran Alkaline hydrolysis;	95%
With (R)-(-)-DTBM-SEGPHOS; sodium phenoxide; poly(methylhydrosiloxane); copper carbide In toluene; tert-butyl alcohol at 20℃; for 3h; ultrasonication;	86%

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

: 3,5,5-trimethyl-2-cyclohexen-1-ol

Conditions

Conditions	Yield
With (acetylacetonato)dicarbonylrhodium (l); L-valine; hydrogen; Oxalsaeurebis<(3R,4R)-3,4-bis(diphenylphosphino)pyrrolidid> at 25℃; under 45004.5 Torr; for 36h; Autoclave;	99.1%

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

: 7393-43-3
tetraallyl tin

: 21436-26-0
1-allyl-3,5,5-trimethyl-2-cyclohexen-1-ol

Conditions

Conditions	Yield
With n-butyllithium; neodymium(III) chloride In tetrahydrofuran; hexane for 1h; Ambient temperature;	99%
With n-butyllithium; neodymium(III) chloride 1.) hexane, THF, RT, 1 h, 2.) hexane, THF, 0 deg C, 1 h; Yield given. Multistep reaction;

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

: 638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3
manganese triacetate

: 19019-49-9
(+/-)-6-acetoxy-3,3,5-trimethylcyclohex-2-en-1-one

Conditions

Conditions	Yield
With acetic acid In benzene for 7h; Heating;	99%

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

: 766-84-7
3-chloro-benzonitrile

: 3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

Conditions

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

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

: 16537-17-0
3-chlorobenzoic acid tert-butyl ester

: tert-butyl 3-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzoate

Conditions

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

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

: 17228-64-7
6-chloro-2-methoxypyridine

: 3-((6-methoxypyridin-2-yl)methyl)-5,5-dimethylcyclohex-2-enone

Conditions

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

: 14345-97-2
2-chloro-3-methylthiophene

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

: 5,5-dimethyl-3-((3-methylthiophen-2-yl)methyl)cyclohex-2-enone

Conditions

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

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

: 2845-89-8
1-chloro-3-methoxy-benzene

: 3-(3-methoxybenzyl)-5,5-dimethylcyclohex-2-enone

Conditions

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	99%

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

: 471-01-2
3,5,5-trimethylcyclohex-3-en-1-one

Conditions

Conditions	Yield
at 206℃; under 750.075 Torr; for 48h; Catalytic behavior; Pressure; Temperature; Inert atmosphere;	98.3%
at 210 - 240℃; under 375.038 Torr; Pressure; Molecular sieve;	91.72%
With methylmagnesium bromide; acetic acid Isomerization;	82%

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

: 10276-21-8
isophorone oxide

Conditions

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In ethanol at 30 - 35℃; for 1h;	98%
With 3,3-dimethyldioxirane In dichloromethane; acetone at 20℃; for 24h;	90%
With Oxone; 1,1,1-trifluoro-2-propanone; edetate disodium; sodium hydrogencarbonate In acetonitrile at 0 - 1℃; for 1.5h;	90%

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

: 470-99-5
isophorol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In diethyl ether at 20℃; for 6h;	98%
With lithium aluminium tetrahydride In diethyl ether at -20℃;	95%
With Co-doped ammonia borane In methanol at 20℃; for 2h; Reagent/catalyst; chemoselective reaction;	95%

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

: 28750-52-9
2-hydroxy-4,4,6-trimethylcyclohexa-2,5-diene-1-one

Conditions

Conditions	Yield
With 18-crown-6 ether In benzene for 2h; Ambient temperature;	98%
With KO2; 18-crown-6 ether In benzene for 2h; Ambient temperature;
With potassium superoxide In benzene

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

: 27749-07-1
3,5,5-trimethyl-3-vinylcyclohexanone

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate; vinyl(2-thienyl)Cu(CN)Li2 In tetrahydrofuran; diethyl ether at -78℃; for 1h; Product distribution; Mechanism; effect of BF3*Et2O and other Lewis Acids;	98%
With (CH2=C)2Cu(CN)Li2 In diethyl ether at -50℃; for 2.5h; Product distribution; other solvents;	98%
With 2-ThNaCuCNC2H3Li Product distribution; with and without BF3*Et2O additive;
Multi-step reaction with 2 steps 1: 1) CuCN, TMEDA / 1) THF, -78 deg C, 20 min, 2) THF, 30 min 2: 1 M HCl View Scheme

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

2-ThLi*CuCN*C2H3Li: 2-ThLi*CuCN*C2H3Li

: 27749-07-1
3,5,5-trimethyl-3-vinylcyclohexanone

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate at -78℃; for 3h;	98%

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

vinyl-(2-thienyl)Cu(CN)Li2: vinyl-(2-thienyl)Cu(CN)Li2

: 27749-07-1
3,5,5-trimethyl-3-vinylcyclohexanone

Conditions

Conditions	Yield
With boron trifluoride diethyl etherate In tetrahydrofuran; diethyl ether at -78℃; for 1h;	98%

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

: 696-02-6
4-chloro-1,2-difluorobenzene

: 3-(3,4-difluorobenzyl)-5,5-dimethylcyclohex-2-enone

Conditions

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	98%

: 623-03-0
4-Cyanochlorobenzene

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

: 4-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)benzonitrile

Conditions

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	98%

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

: 95-49-8
2-methylchlorobenzene

: 5,5-dimethyl-3-(2-methylbenzyl)cyclohex-2-enone

Conditions

Conditions	Yield
With 2-(2,6-dimethoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; palladium diacetate; lithium tert-butoxide In 1,4-dioxane at 100℃; for 1h; Schlenk technique; Inert atmosphere;	98%

: 75-77-4
chloro-trimethyl-silane

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

: 1826-67-1
vinyl magnesium bromide

: 108612-90-4
trimethyl-(3,5,5-trimethyl-3-vinylcyclohex-1-enyloxy)silane

Conditions

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; magnesium; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -70℃; for 1.5h;	97%
With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(I) bromide dimethylsulfide complex In tetrahydrofuran at -78℃;	97%
Stage #1: vinyl magnesium bromide With copper(l) iodide In tetrahydrofuran at -10℃; for 0.0333333h; Metallation; Stage #2: 3,5,5-Trimethylcyclohex-2-en-1-one In tetrahydrofuran at -78℃; for 0.5h; Addition; Stage #3: chloro-trimethyl-silane With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; triethylamine In tetrahydrofuran at -78 - 20℃; silylation;	93%
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78℃;	80%
With N,N,N,N,-tetramethylethylenediamine 1) THF, -78 deg C, 20 min, 2) THF, 30 min; Multistep reaction;

...Expand

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

: 1160424-45-2
C23H35NO3

: C32H47NO3

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 120℃; for 0.5h; Knoevenagel Condensation; Microwave irradiation;	97%
With ethanol; sodium at 85℃; for 1h; pH=13; Temperature; Microwave irradiation;	97%
With sodium ethanolate In ethanol at 80℃; for 8h; pH=13;	65%

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

: 2446-83-5
di-isopropyl azodicarboxylate

: diisopropyl 1-((5,5-dimethyl-3-oxocyclohex-1-en-1-yl)methyl)hydrazine-1,2-dicarboxylate

Conditions

Conditions	Yield
Stage #1: 3,5,5-Trimethylcyclohex-2-en-1-one With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 0℃; for 1.66667h; Sealed tube; Inert atmosphere; Stage #2: di-isopropyl azodicarboxylate In tetrahydrofuran at -78℃; for 0.0833333h; Inert atmosphere; Sealed tube; regioselective reaction;	97%

Isophorone Chemical Properties

Molecular Structure of Isophorone (CAS NO.78-59-1):

IUPAC Name: 3,5,5-Trimethylcyclohex-2-en-1-one
Molecular Weight: 138.20686 [g/mol]
Molecular Formula: C₉H₁₄O
XLogP3-AA: 1.6
H-Bond Donor: 0
H-Bond Acceptor: 1
Index of Refraction: 1.455
Molar Refractivity: 41.43 cm³
Molar Volume: 152.6 cm³
Surface Tension: 26.4 dyne/cm
Density: 0.905 g/cm³
Flash Point: 84.4 °C
Enthalpy of Vaporization: 45.15 kJ/mol
Boiling Point: 215.2 °C at 760 mmHg
Vapour Pressure: 0.15 mmHg at 25 °C
Appearance: light yellow liquid
Melting Point: −8 °C(lit.)
storage temp.: 2-8 °C
Stability: Stable. Substances to be avoided include strong bases, strong acids and strong oxidizing agents.
Classification Code: Human Data; Mutation data; Skin / Eye Irritant; TSCA Flag T [Subject to the Section 4 test rule under TSCA]; Tumor data

Isophorone History

The use of Isophorone as a solvent resulted from the search for ways to dispose of or recycle acetone, which is a waste product of phenol synthesis by the Hock method.

Isophorone Uses

Isophorone (CAS NO.78-59-1) is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings and pesticides.[2] It is also used as a chemical intermediate and as an ingredient in wood preservatives and floor sealants.

Isophorone Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD	intravenous	> 10mg/kg (10mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: PULSE RATE LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION	National Technical Information Service. Vol. OTS0535380,
guinea pig	LC50	inhalation	4600ppm/8H (4600ppm)		"Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 290, 1986.
guinea pig	LD50	oral	700mg/kg (700mg/kg)		National Technical Information Service. Vol. OTS0535380,
human	TCLo	inhalation	25ppm (25ppm)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Journal of Industrial Hygiene and Toxicology. Vol. 28, Pg. 262, 1946.
mouse	LC	inhalation	> 3500mg/kg/6H (3500mg/kg)	LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	National Technical Information Service. Vol. OTS0535380,
mouse	LD50	oral	2690mg/kg (2690mg/kg)		Toxicology and Applied Pharmacology. Vol. 17, Pg. 498, 1970.
rabbit	LD50	oral	1420mg/kg (1420mg/kg)		National Technical Information Service. Vol. OTS0535380,
rabbit	LD50	skin	1500uL/kg (1.5mL/kg)		Union Carbide Data Sheet. Vol. 11/15/1971,
rat	LC50	inhalation	7gm/m3 (7000mg/m3)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER LUNGS, THORAX, OR RESPIRATION: DYSPNEA	National Technical Information Service. Vol. OTS0572861,
rat	LD50	oral	1870mg/kg (1870mg/kg)		Union Carbide Data Sheet. Vol. 11/15/1971,
rat	LD50	skin	1390mg/kg (1390mg/kg)		National Technical Information Service. Vol. OTS0526403,

Isophorone Safety Profile

Moderately toxic by ingestion. Mildly toxic by inhalation. Human systemic effects by inhalation: olfactory changes, conjunctiva irritation, and respiratory changes. Human systemic irritant by inhalation. A skin and severe eye irritant. Questionable carcinogen with experimental carcinogenic data. Mutation data reported. Considered to be more toxic than mesityl oxide. However, due to its low volatility, it is not a dangerous industrial hazard. The response of guinea pigs and rats to repeated inhalation of the vapors indicates that it is one of the most toxic of the ketones. It is chiefly a kidney poison. It can cause irritation, lachrymation, possible opacity of the cornea, and necrosis of the cornea (experimental). It is irritating at the level of 25 ppm to humans. In animal experiments death during exposure was usually due to narcosis, but occasionally due to irritation of the lungs. Flammable and explosive when exposed to heat or flame; can react with oxidizing materials. To fight fire, use foam, CO₂, dry chemical.
Safety Information of Isophorone (CAS NO.78-59-1):
Hazard Codes: Harmful Xn
Risk Statements: 21/22-36/37-40
R21/22:Harmful in contact with skin and if swallowed.
R36/37:Irritating to eyes and respiratory system.
R40:Limited evidence of a carcinogenic effect.
Safety Statements: 13-23-36/37/39-46
S13:Keep away from food, drink and animal foodstuffs.
S23:Do not breathe vapour.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
S46:If swallowed, seek medical advice immediately and show this container or label.
WGK Germany: 1
RTECS: GW7700000

Isophorone Standards and Recommendations

OSHA PEL: TWA 4 ppm
ACGIH TLV: CL 5 ppm
DFG MAK: 2 ppm (11 mg/m³)
NIOSH REL: TWA (Ketones) 23 mg/m³

Isophorone Analytical Methods

For occupational chemical analysis use NIOSH: Isophorone, 2508.

Isophorone Specification

Isophorone (CAS NO.78-59-1), its Synonyms are 3,5,5-Trimethyl-2-cyclohexen-1-one ; 3,5,5-Trimethyl-2-cyclohexenone ; 3,5,5-Trimetil-2-cicloesen-1-one ; 1,1,3-Trimethyl-3-cyclohexene-5-one ; 2-Cyclohexen-1-one, 3,5,5-trimethyl- ; 3,5,5-Trimethyl-2-cyclohexen-1-on ; Isoacetophorone ; Isoforon ; Isoforone .

Product Name

Isophoron

Synthetic route

Isophorone Chemical Properties

Isophorone History

Isophorone Uses

Isophorone Toxicity Data With Reference

Isophorone Safety Profile

Isophorone Standards and Recommendations

Isophorone Analytical Methods

Isophorone Specification

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