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1125-21-9

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2,6,6-Trimethyl-2-cyclohexene-1,4-dione suppliers in China
Cas No: 1125-21-9
No Data 100 Gram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High quality Oxoisophorone supplier in China
Cas No: 1125-21-9
No Data 1 Kilogram 30 Metric Ton/Month Simagchem Corporation Contact Supplier
High purity Various Specifications 4-oxoisophorone CAS:1125-21-9
Cas No: 1125-21-9
USD $ 100.0-500.0 / Gram 1 Gram 99999 Gram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
2,6,6-Trimethyl-2-cyclohexene-1,4-dione
Cas No: 1125-21-9
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
Large Stock 99.0% 4-oxoisophorone 1125-21-9 Producer
Cas No: 1125-21-9
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
4-Ketoisophorone
Cas No: 1125-21-9
No Data 1 Kilogram 1 Metric Ton/Week Henan Allgreen Chemical Co.,Ltd Contact Supplier
High Quality Oxoisophorone
Cas No: 1125-21-9
No Data 1 1 Ality Chemical Corporation Contact Supplier
2.6.6-Trimethyl-2-Cyclohexene-1.4-Dione
Cas No: 1125-21-9
No Data 23 Metric Ton 3000 Kilogram/Month ORCHID CHEMICAL SUPPLIES LTD Contact Supplier
4-oxoisophorone
Cas No: 1125-21-9
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier
2,6,6-Trimethyl-2-Cyclohexene-1,4-Dione
Cas No: 1125-21-9
No Data 1 Metric Ton 1 million Metric Ton/Year COLORCOM LTD. Contact Supplier

1125-21-9 Usage

Occurrence

Reported found among the volatile components in saffron and in cigarette smoke. Also reported found in saffron, cognac, black tea, green tea, microbial fermented tea, lemon balm, cooked shrimp, roasted shrimp, corn oil and lamb’s lettuce.

Chemical Properties

clear yellow to orange liquid or low melting solid

Chemical Properties

2,6,6,-Trimethylcyclohex-2-ene-1,4-dione has a woody, musty sweet aroma.
InChI:InChI=1/C9H12O2/c1-6-4-7(10)5-9(2,3)8(6)11/h4H,5H2,1-3H3

1125-21-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2,6,6-Trimethyl-2-cyclohexene-1,4-dione

1.2 Other means of identification

Product number -
Other names 2,6,6-trimethylcyclohex-2-ene-1,4-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1125-21-9 SDS

1125-21-9Synthetic route

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With 2,5-Dimethyl-1,4-benzoquinone In toluene at 80℃; Reagent/catalyst; Solvent; Temperature;98.98%
With chromium(VI) oxide
With chromium(VI) oxide; sulfuric acid In acetone
With chromic acid
With sodium anthraquinone-2-sulfonate; oxygen In water at 30℃; Irradiation;
3,5,5-trimethylcyclohex-3-en-1-one
471-01-2

3,5,5-trimethylcyclohex-3-en-1-one

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With diisobutyl ketone; oxygen; 1,4-diaza-bicyclo[2.2.2]octane at 40℃; for 5h;93%
With (5,10,15,20-tetraphenylporphyrinato)manganese(III) chloride; oxygen; triethylamine In 1,2-dimethoxyethane; water for 9h; Ambient temperature;92%
62.8%
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With tert.-butylhydroperoxide; cobalt acetylacetonate In acetone at 28℃; for 15h; Solvent; Concentration; Temperature;79%
With tert.-butylhydroperoxide; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; water In neat (no solvent) at 20℃; for 24h; Catalytic behavior; Mechanism; Reagent/catalyst; Solvent; Temperature; Sealed tube; regioselective reaction;78%
With tert.-butylhydroperoxide; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In water at 20℃; for 24h; Catalytic behavior; Concentration; Temperature; Solvent; Time;78%
3,5,5-trimethylcyclohex-3-en-1-one
471-01-2

3,5,5-trimethylcyclohex-3-en-1-one

A

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

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

B

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

C

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions
ConditionsYield
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.
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

B

2,3,6,7-tetrahydro-2,2,6,6-tetramethylanthracene-1,4,5,8-tetrone
96493-78-6

2,3,6,7-tetrahydro-2,2,6,6-tetramethylanthracene-1,4,5,8-tetrone

Conditions
ConditionsYield
With potassium dichromate; air; phosphomolybdic acid; copper(II) sulfate at 90 - 95℃; for 100h;A 56%
B n/a
With potassium dichromate; air; phosphpmolybdic acid; copper(II) sulfate at 90 - 95℃; for 100h; basic treatment during workup;
With potassium dichromate; phosphomolybdic acid; oxygen; copper(II) sulfate 1. 100 deg C, 100 hours; Multistep reaction;
(S)-4-Hydroxy-3,5,5-trimethyl-4-(toluene-4-sulfonylmethyl)-cyclohex-2-enone
518316-69-3

(S)-4-Hydroxy-3,5,5-trimethyl-4-(toluene-4-sulfonylmethyl)-cyclohex-2-enone

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With caesium carbonate In acetonitrile at 20℃; for 0.3h;54%
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

isophorone oxide
10276-21-8

isophorone oxide

B

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

C

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions
ConditionsYield
With [2,2]bipyridinyl; silver(I) acetate; lithium perchlorate In water; acetonitrile electrochemical oxidation;
With N-hydroxyphthalimide; oxygen at 60℃; for 10h;
9-hydroxymegastigma-4,7-dien-3-one
896107-70-3

9-hydroxymegastigma-4,7-dien-3-one

A

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

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

B

2,6,6-trimethyl-1,4-cyclohexanedione
20547-99-3

2,6,6-trimethyl-1,4-cyclohexanedione

C

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

D

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone
13215-88-8

4-(But-2-enylidene)-3,5,5-trimethylcyclohex-2-enone

E

megastigmatrienone

megastigmatrienone

Conditions
ConditionsYield
In water Heating; pH=1;
alpha-ionone
127-41-3

alpha-ionone

A

dehydrovomifoliol
15764-81-5

dehydrovomifoliol

B

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

C

3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one
79734-43-3

3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one

Conditions
ConditionsYield
With t-butyl chromate In tert-butyl alcohol; benzene at 60℃;A 700 mg
B 105 mg
C 750 mg
6,9-dihydroxymegastigma-4,7-dien-3-one
23526-45-6, 24427-77-8, 50763-72-9, 50763-73-0

6,9-dihydroxymegastigma-4,7-dien-3-one

A

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

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

B

2,3,5-trimethylphenol
697-82-5

2,3,5-trimethylphenol

C

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
Heating; pH=1;
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

2,6,6-trimethyl-1,4-cyclohexanedione
20547-99-3

2,6,6-trimethyl-1,4-cyclohexanedione

B

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

C

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

D

3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
In water at 28℃; for 96h; Aspergillus niger, culture broth;
In water at 28℃; for 96h; Aspergillus niger, culture broth; Yield given. Yields of byproduct given;
In water at 28℃; for 96h; Aspergillus niger, culture broth; Yield given;
(-)-3-Hydroxy-2,5-dioxo-1,1,3-trimethyl-cyclohexan

(-)-3-Hydroxy-2,5-dioxo-1,1,3-trimethyl-cyclohexan

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With sulfuric acid
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

3-formyl-5,5-dimethyl-2-cycolohexen-1-one
56621-35-3

3-formyl-5,5-dimethyl-2-cycolohexen-1-one

B

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With methanesulfonic acid; oxygen; molybdovanadophosphate on active carbon In toluene at 80℃; under 760 Torr; for 20h; Product distribution; regioselectivity of the aerobic oxidation, effect of the pore size of supports, or without support at various temperatures;
With phosphomolybdic acid; potassium tert-butylate; oxygen In dimethyl sulfoxide at 115℃; for 8h; Product distribution; Further Variations:; Reagents; reaction time;A 1.9 % Chromat.
B 88.4 % Chromat.
With N-hydroxyphthalimide; oxygen; copper dichloride In acetonitrile at 100℃; under 9000.9 Torr; for 3h; Autoclave;
3,5,5-trimethylcyclohex-3-en-1-one
471-01-2

3,5,5-trimethylcyclohex-3-en-1-one

A

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

B

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

C

β-isophorone oxide

β-isophorone oxide

D

5-hydroxy-4,4,6-trimethyl-7-oxa-bicyclo[4.1.0]heptan-2-one

5-hydroxy-4,4,6-trimethyl-7-oxa-bicyclo[4.1.0]heptan-2-one

Conditions
ConditionsYield
With tert.-butylhydroperoxide; silica gel; titanium(IV) oxide In ethylbenzene at 79.85℃; for 0.208333h; Product distribution; Further Variations:; Catalysts; time; Isomerization; oxidation;
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

CuSO4 *5H2 O

CuSO4 *5H2 O

H3 [P(Mo3 O10)4 ]*H2 O

H3 [P(Mo3 O10)4 ]*H2 O

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
MoO3 In hexane; toluene
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

isophorone oxide
10276-21-8

isophorone oxide

B

3-formyl-5,5-dimethyl-2-cycolohexen-1-one
56621-35-3

3-formyl-5,5-dimethyl-2-cycolohexen-1-one

C

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; copper(II) sulfate In acetonitrile at 75℃; under 9000.9 Torr; for 5h; Autoclave;
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

isophorone oxide
10276-21-8

isophorone oxide

B

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With N-hydroxyphthalimide; oxygen; calcium chloride In acetonitrile at 75℃; under 9000.9 Torr; for 5h; Autoclave;
With N-hydroxyphthalimide; oxygen In acetonitrile at 110℃; under 9000.9 Torr; for 5h; Catalytic behavior; Temperature; Time; Concentration;
(S)-4-hydroxy-3,5,5-trimethyl-4-[(3E,5E,7E,9E,11E,13E,15E)-3,7,12,16-tetramethyl-2-oxo-18-((R)-2,6,6-trimethyl-4-(triethylsilyloxy)cyclohex-1-en-1-yl)octadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-yl]cyclohex-2-enone

(S)-4-hydroxy-3,5,5-trimethyl-4-[(3E,5E,7E,9E,11E,13E,15E)-3,7,12,16-tetramethyl-2-oxo-18-((R)-2,6,6-trimethyl-4-(triethylsilyloxy)cyclohex-1-en-1-yl)octadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-yl]cyclohex-2-enone

A

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

B

(all-E)-(3R)-Triophaxanthin

(all-E)-(3R)-Triophaxanthin

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride Inert atmosphere;
3,5,5-trimethylcyclohex-3-en-1-one
471-01-2

3,5,5-trimethylcyclohex-3-en-1-one

A

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

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

B

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen at 70℃; for 12h; Reagent/catalyst;
With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; oxygen at 70℃; for 12h;
3,5,5-trimethylcyclohex-3-en-1-one
471-01-2

3,5,5-trimethylcyclohex-3-en-1-one

A

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

2-hydroxy-4,4,6-trimethylcyclohexa-2,5-diene-1-one

B

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

C

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions
ConditionsYield
With water; oxygen; triethylamine; acetylacetone In acetone at 21℃; for 18h; Kinetics; Catalytic behavior; Reagent/catalyst; Temperature; Solvent; Overall yield = 65.4 %;
3,5,5-trimethylcyclohex-3-en-1-one
471-01-2

3,5,5-trimethylcyclohex-3-en-1-one

A

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

B

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions
ConditionsYield
With pyridine; iron(III)-acetylacetonate; oxygen at 59.99℃; under 760.201 Torr; Kinetics; Activation energy; Temperature; Pressure; Inert atmosphere;
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

isophorone oxide
10276-21-8

isophorone oxide

B

3-formyl-5,5-dimethyl-2-cycolohexen-1-one
56621-35-3

3-formyl-5,5-dimethyl-2-cycolohexen-1-one

C

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

D

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

Conditions
ConditionsYield
With tert.-butylhydroperoxide; cetyltrimethylammonim bromide; L-proline; copper dichloride In water at 80℃; for 24h; Reagent/catalyst;
With tert.-butylhydroperoxide; N-hydroxyphthalimide; Cu3Al(OH)2(7+)*3.5CO3(2-) In acetonitrile at 90℃; for 24h; Catalytic behavior; Reagent/catalyst; Temperature;
4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

Conditions
ConditionsYield
With Cm-ADH10 at 40℃; for 6h; Enzymatic reaction;46 mg
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

B

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

C

3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

D

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

Conditions
ConditionsYield
With perfluorodecanoic acid; CYP102A1 from Bacillus megaterium; oxygen; NADPH; bovine liver catalase In dimethyl sulfoxide at 30℃; for 20h; pH=7.4; Kinetics; Reagent/catalyst; Enzymatic reaction; stereoselective reaction;
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

B

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

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

C

3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

3-(hydroxymethyl)-5,5-dimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
Stage #1: 3,5,5-Trimethylcyclohex-2-en-1-one With sodium hydroxide In water at 0 - 2℃; for 0.166667h;
Stage #2: With dihydrogen peroxide In water at 0 - 2℃; for 6h;
A n/a
B 12 mg
C n/a
3,5,5-Trimethylcyclohex-2-en-1-one
78-59-1

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

A

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

B

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

C

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

Conditions
ConditionsYield
With Peroxygenase from Chaetomium globosum; dihydrogen peroxide In aq. phosphate buffer at 30℃; for 0.5h; pH=7; Catalytic behavior; Kinetics; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
C n/a
4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone
14203-59-9

4-hydroxy-3,5,5-trimethyl-cyclohex-2-enone

A

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

B

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

4-hydroxy-3,5,5-trimethyl-2-cyclohexen-1-one

Conditions
ConditionsYield
With Peroxygenase from Chaetomium globosum; dihydrogen peroxide In aq. phosphate buffer at 30℃; for 1h; pH=7; Catalytic behavior; Reagent/catalyst; Resolution of racemate; Enzymatic reaction; enantioselective reaction;
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

acrylonitrile
107-13-1

acrylonitrile

(1R,2R,4S)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carbonitrile

(1R,2R,4S)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carbonitrile

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-methylaminopropylated silica gel In tetrahydrofuran; hexane at -70 - 20℃; Michael reaction;100%
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -50℃; for 0.333333h;
Stage #2: acrylonitrile In tetrahydrofuran; hexane at -50 - 20℃; for 3h;
99%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

2,6,6-trimethyl-1,4-cyclohexanedione
20547-99-3

2,6,6-trimethyl-1,4-cyclohexanedione

Conditions
ConditionsYield
With phenylsilane; isopropyl alcohol; Mn(dpm)3 at 23℃;99%
With triethanolamine; [RuII(2,2′-bipyrazyl)2(4,4′-dichloro-2,2′-bipyridyl)]Cl2; thermophilic Old Yellow Enzyme; paraquat dichloride In ethanol; water at 20℃; for 4h; pH=8; Reagent/catalyst; Solvent; Time; pH-value; UV-irradiation;88%
With acetic acid; zinc
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

trans (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone
20548-02-1

trans (4R,6R)-4-hydroxy-2,2,6-trimethylcyclohexanone

Conditions
ConditionsYield
With hydrogen; Ra-Ni In methanol at 25℃; under 825.07 Torr; for 8h;98.1%
With hydrogen; Raney/Ni In ethanol at 20℃; under 5171.62 Torr; for 72h;
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

ethylene glycol
107-21-1

ethylene glycol

7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one
14203-64-6

7,9,9-trimethyl-1,4-dioxa-spiro[4.5]dec-6-en-8-one

Conditions
ConditionsYield
With phenylphosphonate In benzene for 24h;96.7%
With toluene-4-sulfonic acid; trimethyl orthoformate In dichloromethane for 4h; Heating;87%
With toluene-4-sulfonic acid In benzene for 10h; Heating;73%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

acetic anhydride
108-24-7

acetic anhydride

2,3,5-trimethyl-1,4-hydroquinone diacetate
7479-28-9

2,3,5-trimethyl-1,4-hydroquinone diacetate

Conditions
ConditionsYield
at 60℃; for 9h; Temperature; Molecular sieve;96.5%
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione; acetic anhydride; methanetrisulfonic acid at 25 - 100℃; for 3.5 - 24h;
Stage #2: With sodium carbonate at 20℃; Product distribution / selectivity;
0%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

trimethyl orthoformate
149-73-5

trimethyl orthoformate

4-Methoxy-2,6,6-trimethyl-cyclohexa-2,4-dienone

4-Methoxy-2,6,6-trimethyl-cyclohexa-2,4-dienone

Conditions
ConditionsYield
With hydrogenchloride In methanol Heating;95%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

propynoic acid ethyl ester
623-47-2

propynoic acid ethyl ester

ethyl 3-(1′-hydroxy-3′,5′,5′-trimethyl-4′-oxocyclohex-2′-en-1′-yl)propiolate

ethyl 3-(1′-hydroxy-3′,5′,5′-trimethyl-4′-oxocyclohex-2′-en-1′-yl)propiolate

Conditions
ConditionsYield
Stage #1: propynoic acid ethyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;
95%
(R,R)-2,3-butandiol
24347-58-8

(R,R)-2,3-butandiol

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

(2R,3R)-2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one
917878-27-4

(2R,3R)-2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 24h; Heating;94%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

phenylacetylene
536-74-3

phenylacetylene

4-hydroxy-2,6,6-trimethyl-4-(phenylethynyl)cyclohex-2-enone

4-hydroxy-2,6,6-trimethyl-4-(phenylethynyl)cyclohex-2-enone

Conditions
ConditionsYield
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;
94%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

(+/-)-4-hydroxy-2,6,6-trimethyl-2-cyclohexenone
19620-37-2

(+/-)-4-hydroxy-2,6,6-trimethyl-2-cyclohexenone

Conditions
ConditionsYield
With aluminum isopropoxide In cyclohexane for 5h; Heating;93.2%
With C29H34BNOP2Ru In dichloromethane; isopropyl alcohol Schlenk technique; Inert atmosphere; Reflux;84%
With sodium tetrahydroborate; cerium(III) chloride66%
2,2-dimethyl-3-butyne
917-92-0

2,2-dimethyl-3-butyne

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

4-(3′,3′-dimethylbut-1′-yn-1′-yl)-4-hydroxy-2,6,6-trimethylcyclohex-2-enone

4-(3′,3′-dimethylbut-1′-yn-1′-yl)-4-hydroxy-2,6,6-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Stage #1: 3,3-Dimethylbut-1-yne With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;
93%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

acetic anhydride
108-24-7

acetic anhydride

4-acetoxy-2,6,6-trimethylcyclohexa-2,4-dienone
124743-97-1

4-acetoxy-2,6,6-trimethylcyclohexa-2,4-dienone

Conditions
ConditionsYield
With 2-(Dimethylamino)pyridine; triethylamine at 48℃; for 17h;92.6%
With TEA
With dmap; triethylamine
cyclohexyl acrylate
3066-71-5

cyclohexyl acrylate

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

(1S,2S,4R)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid cyclohexyl ester

(1S,2S,4R)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid cyclohexyl ester

Conditions
ConditionsYield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -50℃; for 0.333333h;
Stage #2: cyclohexyl acrylate In tetrahydrofuran; hexane at -50 - 20℃; for 7h;
92%
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-methylaminopropylated silica gel In tetrahydrofuran; hexane at -70 - 20℃; for 18h; Product distribution; Further Variations:; Reagents; Michael reaction;90%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

(-)-8-phenylmenthyl acrylate
72526-00-2

(-)-8-phenylmenthyl acrylate

A

(2S,1R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1S,2S)-1,5,5-trimethyl-6,8-dioxobicyclo[2.2.2]octane-2-carboxylate
946149-26-4

(2S,1R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl (1S,2S)-1,5,5-trimethyl-6,8-dioxobicyclo[2.2.2]octane-2-carboxylate

B

(2S,1R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 1,5,5-trimethyl-6,8-dioxobicyclo[2.2.2]octane-2-carboxylate

(2S,1R,5R)-5-methyl-2-(1-methyl-1-phenylethyl)cyclohexyl 1,5,5-trimethyl-6,8-dioxobicyclo[2.2.2]octane-2-carboxylate

Conditions
ConditionsYield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.25h;
Stage #2: (-)-8-phenylmenthyl acrylate With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran; hexane at -40℃; for 14h; Further stages.;
A 92%
B 4%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

propynoic acid methyl ester
922-67-8

propynoic acid methyl ester

methyl 3-(1′-hydroxy-3′,5′,5′-trimethyl-4′-oxocyclohex-2′-en-1′-yl)propiolate

methyl 3-(1′-hydroxy-3′,5′,5′-trimethyl-4′-oxocyclohex-2′-en-1′-yl)propiolate

Conditions
ConditionsYield
Stage #1: propynoic acid methyl ester With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;
92%
(2S,3S)-butane-2,3-diol
19132-06-0

(2S,3S)-butane-2,3-diol

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

(2S,3S)-2,3,7,9,9-pentamethyl-1,4-dioxaspiro<4.5>dec-6-en-8-one
141245-61-6

(2S,3S)-2,3,7,9,9-pentamethyl-1,4-dioxaspiro<4.5>dec-6-en-8-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 4h; Heating;91%
With toluene-4-sulfonic acid In toluene for 24h; Heating;91%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

trimethylsilylacetylene
1066-54-2

trimethylsilylacetylene

4-hydroxy-2,6,6-trimethyl-4-((trimethylsilyl)ethynyl)cyclohex-2-enone

4-hydroxy-2,6,6-trimethyl-4-((trimethylsilyl)ethynyl)cyclohex-2-enone

Conditions
ConditionsYield
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Inert atmosphere; regioselective reaction;
91%
N,N-phenylbistrifluoromethane-sulfonimide
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

3,3,5-trimethyl-4-oxocyclohexa-1,5-dien-1-yl trifluoromethanesulfonate
221635-90-1

3,3,5-trimethyl-4-oxocyclohexa-1,5-dien-1-yl trifluoromethanesulfonate

Conditions
ConditionsYield
With lithium hexamethyldisilazane In tetrahydrofuran at -83℃;90%
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at -78℃; for 2h;
90%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 9.33333h;88.8%
With lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; Inert atmosphere;88%
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With lithium diisopropyl amide In tetrahydrofuran for 2h;
Stage #2: N,N-phenylbistrifluoromethane-sulfonimide In tetrahydrofuran at 20℃; for 12h; Further stages.;
85%
trimethylsilyl trifluoromethanesulfonate
27607-77-8

trimethylsilyl trifluoromethanesulfonate

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

oxophorone trimethylsilylenol ether
83020-75-1

oxophorone trimethylsilylenol ether

Conditions
ConditionsYield
With 2,3,5-trimethyl-pyridine In toluene at -40℃;90%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

(1R,2R,4S)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

(1R,2R,4S)-1,5,5-Trimethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium dibenzylamide In tetrahydrofuran; hexane at -50℃;
Stage #2: acrylic acid methyl ester In tetrahydrofuran; hexane at -50 - 20℃;
90%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

1,3,3-Trimethyl-7-oxabicyclo<4.1.0>heptan-2,5-dion
38284-11-6

1,3,3-Trimethyl-7-oxabicyclo<4.1.0>heptan-2,5-dion

Conditions
ConditionsYield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With sodium hydrogencarbonate; sodium carbonate In water at 0 - 25℃; for 1h;
Stage #2: With dihydrogen peroxide In water for 3h;
89%
With sodium hydroxide; dihydrogen peroxide In water at 20 - 25℃; for 6h; pH 9-9.5;
Weitz-Scheffer epoxidation; Inert atmosphere;
With quinone oxidoreductase from Fragaria x ananassa, strawberry; NADPH In aq. buffer at 30℃; for 24h; pH=7.5; Reagent/catalyst;
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With sodium hydroxide In water at 0 - 2℃; for 0.166667h;
Stage #2: With dihydrogen peroxide In water at 0 - 2℃; for 6h;
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

methacrylic acid methyl ester
80-62-6

methacrylic acid methyl ester

(1S,2S,4R)-1,2,5,5-Tetramethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

(1S,2S,4R)-1,2,5,5-Tetramethyl-6,8-dioxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide In tetrahydrofuran; hexane at -50℃; for 0.333333h;
Stage #2: methacrylic acid methyl ester In tetrahydrofuran; hexane at -50 - 20℃;
89%
With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-methylaminopropylated silica gel In tetrahydrofuran; hexane at -70 - 20℃; Michael reaction;83%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

2.3-butanediol
513-85-9

2.3-butanediol

2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one
1402904-89-5

2,3,7,9,9-pentamethyl-1,4-dioxaspiro[4.5]dec-6-en-8-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid; trimethyl orthoformate at 50℃; for 7h; Inert atmosphere;88%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

t-butyldimethylsiyl triflate
69739-34-0

t-butyldimethylsiyl triflate

4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohexa-2,4-dienone

4-(tert-Butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohexa-2,4-dienone

Conditions
ConditionsYield
With 2,3,5-trimethyl-pyridine In toluene at -40℃;87%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

2-hydroxy-2,6,6-trimethyl-cyclohexane-1,4-dione

2-hydroxy-2,6,6-trimethyl-cyclohexane-1,4-dione

Conditions
ConditionsYield
Stage #1: 2,6,6-trimethyl-2-cyclohexene-1,4-dione With phenylsilane; oxygen; isopropyl alcohol; Mn(dpm)3 In 1,2-dichloro-ethane at 0 - 25℃;
Stage #2: With triethyl phosphite In 1,2-dichloro-ethane
87%
(Z)-3-methylpent-2-en-4-ynol
6153-05-5

(Z)-3-methylpent-2-en-4-ynol

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

2,6,6-trimethyl-2-cyclohexene-1,4-dione

(Z)-4-hydroxy-4-(5′-hydroxy-3′-methylpent-3′-en-1′-yn-1′-yl)-2,6,6-trimethylcyclohex-2-enone

(Z)-4-hydroxy-4-(5′-hydroxy-3′-methylpent-3′-en-1′-yn-1′-yl)-2,6,6-trimethylcyclohex-2-enone

Conditions
ConditionsYield
Stage #1: (Z)-3-methylpent-2-en-4-ynol With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: 2,6,6-trimethyl-2-cyclohexene-1,4-dione In tetrahydrofuran at -78 - 20℃; for 2.5h; Time; Inert atmosphere; regioselective reaction;
87%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

acetyl chloride
75-36-5

acetyl chloride

2,3,5-trimethyl-1,4-hydroquinone diacetate
7479-28-9

2,3,5-trimethyl-1,4-hydroquinone diacetate

Conditions
ConditionsYield
With 1-methyl-3-(3-triethoxysilanepropyl)imidazolium chloride at 100℃; for 1h;85.1%
2,6,6-trimethyl-2-cyclohexene-1,4-dione
1125-21-9

2,6,6-trimethyl-2-cyclohexene-1,4-dione

A

(4S)-hydroxy-(6R)-2,2,6-trimethylcyclohexanone
55058-51-0

(4S)-hydroxy-(6R)-2,2,6-trimethylcyclohexanone

B

(6R)-levodione
60046-49-3

(6R)-levodione

Conditions
ConditionsYield
With D-glucose; Saccharomyces cerevisiae (baker's yeast, Fermix(R)); oxygen In ethanol for 48h; Product distribution; Kinetics; Further Variations:; conc. of educt and reagents;A n/a
B 85%
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