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126-81-8 Usage

Chemical Description

Dimedone is a cyclic ketone used in organic synthesis.

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 126-81-8 differently. You can refer to the following data:
1. Part of furannulation strategy for the synthesis of naturally occurring fused 3-methylfurans.1
2. A mentha compound showing antimicrobial properties against common bacteria in the food industry such as E.coli and P.aeruginosa as well as strains of yeast.
3. Used in the synthesis of fused 3-methylfurans via furannulation.
4. Reagent used in synthesis of fused 3-methylfuransDimedone is used in organic chemistry to identify the presence of aldehyde group. It is also used as a catalyst in the formation of transition-metal complexes. Further, it is also employed in colorimetry, crystallography, luminescence and spectrophotometric analysis. In addition to this, it is used in the synthesis of naturally occurring fused 3-methylfurans.

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 6656, 1955 DOI: 10.1021/ja01629a086Organic Syntheses, Coll. Vol. 2, p. 200, 1943

General Description

5,5-dimethyl-1,3-cyclohexanedione (Dimedone) is basically a highly sensitive and very specific reagent used for the determination of aldehydes. It is highly advantageous as it is environment friendly, give high yields and is a simple workup procedure.

Purification Methods

Crystallise dimedone from acetone (ca 8mL/g), water or aqueous EtOH. Dry it in air. [Schneider & Todd Org Synth Coll Vol II 200 1943, Beilstein 7 H 559, 7 IV 1999.]

Check Digit Verification of cas no

The CAS Registry Mumber 126-81-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 6 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 126-81:
(5*1)+(4*2)+(3*6)+(2*8)+(1*1)=48
48 % 10 = 8
So 126-81-8 is a valid CAS Registry Number.
InChI:InChI=1/C8H16O2/c1-8(2)4-6(9)3-7(10)5-8/h6-7,9-10H,3-5H2,1-2H3

126-81-8 Well-known Company Product Price

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  • Alfa Aesar

  • (A10140)  Dimedone, 98%   

  • 126-81-8

  • 25g

  • 237.0CNY

  • Detail
  • Alfa Aesar

  • (A10140)  Dimedone, 98%   

  • 126-81-8

  • 100g

  • 783.0CNY

  • Detail
  • Alfa Aesar

  • (A10140)  Dimedone, 98%   

  • 126-81-8

  • 500g

  • 3272.0CNY

  • Detail
  • Sigma-Aldrich

  • (38490)  5,5-Dimethyl-1,3-cyclohexanedione  for HPLC derivatization, for the determination of aldehyde formaldehyde, ≥99.0%

  • 126-81-8

  • 38490-10G

  • 193.05CNY

  • Detail
  • Sigma-Aldrich

  • (38490)  5,5-Dimethyl-1,3-cyclohexanedione  for HPLC derivatization, for the determination of aldehyde formaldehyde, ≥99.0%

  • 126-81-8

  • 38490-50G

  • 511.29CNY

  • Detail
  • Sigma-Aldrich

  • (38490)  5,5-Dimethyl-1,3-cyclohexanedione  for HPLC derivatization, for the determination of aldehyde formaldehyde, ≥99.0%

  • 126-81-8

  • 38490-250G

  • 1,752.66CNY

  • Detail

126-81-8SDS

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 5,5-Dimethyl-1,3-cyclohexanedione

1.2 Other means of identification

Product number -
Other names 5,5-dimethylcyclohexane-1,3-dione

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:126-81-8 SDS

126-81-8Synthetic route

5,5-dimethyl-3-propoxycyclohex-2-en-1-one

5,5-dimethyl-3-propoxycyclohex-2-en-1-one

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With water In acetonitrile at 20℃; under 900.09 Torr; for 0.226667h; Flow reactor;97%
3-(benzyloxy)-5,5-dimethylcyclohex-2-enone
13120-57-5

3-(benzyloxy)-5,5-dimethylcyclohex-2-enone

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In tetrahydrofuran at 20℃; for 3h;95%
all-trans-retinylidene dimedone
70424-15-6

all-trans-retinylidene dimedone

A

all-trans-Retinal
116-31-4

all-trans-Retinal

B

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With methylamine In water; benzene for 0.25h; Product distribution; Mechanism; Ambient temperature; retro-Knoevenagel fragmentation; variation of reaction conditions;A 91%
B 75%
3-methoxy-5,5-dimethyl-cyclohex-2-enone
4683-45-8

3-methoxy-5,5-dimethyl-cyclohex-2-enone

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile for 0.5h; Heating;90%
beim Aufbewahren;
3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one
6267-39-6

3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile for 0.5h; Heating;89%
3-allyloxy-5,5-dimethyl-cyclohex-2-enone
31928-99-1

3-allyloxy-5,5-dimethyl-cyclohex-2-enone

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile for 1.5h; Heating;87%
5,5-dimethyl-3-(prop-2-ynyloxy)cyclohex-2-enone
877823-42-2

5,5-dimethyl-3-(prop-2-ynyloxy)cyclohex-2-enone

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile for 2h; Heating;84%
2-Diazo-3-hydroxy-5,5-dimethyl-1-cyclohexanone
79671-63-9

2-Diazo-3-hydroxy-5,5-dimethyl-1-cyclohexanone

A

dimedone
126-81-8

dimedone

B

4,4-dimethylcyclopentanone-2-carboxaldehyde
81887-97-0

4,4-dimethylcyclopentanone-2-carboxaldehyde

C

2-Diazo-5,5-dimethyl-3-cyclohexen-1-one
81887-99-2

2-Diazo-5,5-dimethyl-3-cyclohexen-1-one

Conditions
ConditionsYield
With sulfuric acid In tetrahydrofuran; water at 18 - 20℃; for 5h; Product distribution; Mechanism;A 9%
B 80%
C 3%
5,5-dimethyl-3-(3-methyl-cyclohexyloxy)-cyclohex-2-enone
877823-43-3

5,5-dimethyl-3-(3-methyl-cyclohexyloxy)-cyclohex-2-enone

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile for 3h; Heating;75%
2-benzoyl-5,5-dimethyl-1,3-cyclohexanedione
16690-04-3

2-benzoyl-5,5-dimethyl-1,3-cyclohexanedione

ethylenediamine
107-15-3

ethylenediamine

A

2-phenyl-2-imidazoline
936-49-2

2-phenyl-2-imidazoline

B

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
for 1h; Heating;A 62%
B n/a
guanazole
1455-77-2

guanazole

9-(4-chlorophenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydroxanthene-1,8-dione
15782-02-2

9-(4-chlorophenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydroxanthene-1,8-dione

A

2-amino-9-(4-chloro-phenyl)-6,6-dimethyl-5,6,7,9-tetrahydro-4H-[1,2,4]triazolo[5,1-b]quinazolin-8-one

2-amino-9-(4-chloro-phenyl)-6,6-dimethyl-5,6,7,9-tetrahydro-4H-[1,2,4]triazolo[5,1-b]quinazolin-8-one

B

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 0.166667h; Heating;A 56%
B n/a
1H-benzimidazol-2-amine
934-32-7

1H-benzimidazol-2-amine

3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione
19744-83-3

3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione

A

dimedone
126-81-8

dimedone

B

3,3-dimethyl-12-phenyl-1,2,3,4,5,12-hexatrahydro-[4,5]imidazolo [2,1-b]quinazolin-1-one

3,3-dimethyl-12-phenyl-1,2,3,4,5,12-hexatrahydro-[4,5]imidazolo [2,1-b]quinazolin-1-one

Conditions
ConditionsYield
In N,N-dimethyl-formamide Heating;A 0.13 g
B 51%
3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione
19744-83-3

3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione

guanazole
1455-77-2

guanazole

A

2-amino-6,6-dimethyl-9-phenyl-5,6,7,9-tetrahydro[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one
872410-93-0

2-amino-6,6-dimethyl-9-phenyl-5,6,7,9-tetrahydro[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one

B

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 0.166667h; Heating;A 51%
B n/a
2,2'-((4-methoxyphenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)
7560-94-3

2,2'-((4-methoxyphenyl)methylene)bis(3-hydroxy-5,5-dimethylcyclohex-2-enone)

A

9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione
19419-25-1

9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione

B

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With zinc(II) chloride In water at 120℃; for 3h; Green chemistry;A 47%
B 37%
triphenylbismuthonio-4,4-dimethyl-2,6-dioxocyclohexane-1-ide
105071-90-7

triphenylbismuthonio-4,4-dimethyl-2,6-dioxocyclohexane-1-ide

phenylacetylene
536-74-3

phenylacetylene

A

6,6-dimethyl-4-oxo-2-phenyl-4,5,6,7-tetrahydrobenzofuran
18150-87-3

6,6-dimethyl-4-oxo-2-phenyl-4,5,6,7-tetrahydrobenzofuran

B

triphenylbismuthane
603-33-8

triphenylbismuthane

C

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With copper(l) chloride In benzene for 1h; Product distribution; Heating; different alkynes;A 31%
B n/a
C 13%
3-chloro-5,5-dimethylcyclohex-2-en-1-one
17530-69-7

3-chloro-5,5-dimethylcyclohex-2-en-1-one

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With potassium hydroxide
phorone
504-20-1

phorone

ethanol
64-17-5

ethanol

sodium diethylmalonate
996-82-7

sodium diethylmalonate

dimedone
126-81-8

dimedone

phorone
504-20-1

phorone

sodium diethylmalonate
996-82-7

sodium diethylmalonate

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With ethanol
1,3-dichloro-5,5-dimethyl-cyclohexa-1,3-diene
51238-67-6

1,3-dichloro-5,5-dimethyl-cyclohexa-1,3-diene

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With hydrogen bromide; acetic acid Eingiessen der Loesung in Eiswasser;
With sulfuric acid
acetone
67-64-1

acetone

diethyl malonate
105-53-3

diethyl malonate

A

Ethyl 5,5-dimethylcyclohexane-1,3-dione-4-carboxylate
4029-25-8

Ethyl 5,5-dimethylcyclohexane-1,3-dione-4-carboxylate

B

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With diethyl ether; sodium ethanolate
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

A

dimedone
126-81-8

dimedone

B

6-Methoxy-2,2-dimethyl-[1,3]dioxin-4-one
197520-90-4

6-Methoxy-2,2-dimethyl-[1,3]dioxin-4-one

Conditions
ConditionsYield
In diethyl ether
3-piperidino-5,5-dimethyl-2-cyclohexene-1-thione
70134-04-2

3-piperidino-5,5-dimethyl-2-cyclohexene-1-thione

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With hydrogenchloride In propan-1-ol for 2.5h; Heating;0.2 g
dimedone
3471-13-4

dimedone

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
In water Equilibrium constant; var. solvents and temp.;
benzyl methacrylate
2495-37-6

benzyl methacrylate

A

formaldehyd
50-00-0

formaldehyd

B

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With sodium periodate; osmium(VIII) oxide In tert-butyl alcohol chemical degradation;
5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one
18940-21-1

5,5-dimethyl-3-(phenylamino)cyclohex-2-en-1-one

A

dimedone
126-81-8

dimedone

B

aniline
62-53-3

aniline

Conditions
ConditionsYield
With water at 25℃; Rate constant; Mechanism; pH range: 1-9;
3-Amino-5,5-dimethyl-2-cyclohexene-1-thione
70133-97-0

3-Amino-5,5-dimethyl-2-cyclohexene-1-thione

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With hydrogenchloride In propan-1-ol for 2.5h; Heating;0.2 g
3-N,N-dimethylamino-5,5-dimethyl-2-cyclohexene-1-thione
57966-11-7

3-N,N-dimethylamino-5,5-dimethyl-2-cyclohexene-1-thione

dimedone
126-81-8

dimedone

Conditions
ConditionsYield
With hydrogenchloride In propan-1-ol for 2.5h; Heating;0.2 g
5,5-dimethyl-3-oxocyclohex-1-enyl ethenylcarbamate
138421-72-4

5,5-dimethyl-3-oxocyclohex-1-enyl ethenylcarbamate

A

3,3,6,6-tetramethyl-9-methyl-1,2,3,4,5,6,7,8-octahydroxanthene-1,8-dione
19225-63-9

3,3,6,6-tetramethyl-9-methyl-1,2,3,4,5,6,7,8-octahydroxanthene-1,8-dione

B

dimedone
126-81-8

dimedone

C

1,3,5-triethenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione
6504-96-7

1,3,5-triethenyl-1,3,5-triazine-2,4,6(1H,3H,5H)-trione

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 240h; Product distribution; var. temp. and time, other N-vinyl carboxamides;
sodium enolate of dimedone
17372-26-8

sodium enolate of dimedone

dibenzoyl peroxide
94-36-0

dibenzoyl peroxide

A

sodium benzoate
532-32-1

sodium benzoate

B

2,2-Bis(benzoyloxy)-5,5-dimethyl-1,3-cyclohexandion
70990-31-7

2,2-Bis(benzoyloxy)-5,5-dimethyl-1,3-cyclohexandion

C

dimedone
126-81-8

dimedone

D

2-Benzoyloxy-6-hydroxy-4,4-dimethyl-2,5-cyclohexadien-1-on
78102-75-7

2-Benzoyloxy-6-hydroxy-4,4-dimethyl-2,5-cyclohexadien-1-on

E

Monobenzoyloxydimedon
70990-53-3

Monobenzoyloxydimedon

F

benzoic acid
65-85-0

benzoic acid

Conditions
ConditionsYield
In acetonitrile at 20 - 25℃; Kinetics; Mechanism;
3-nitro-benzaldehyde
99-61-6

3-nitro-benzaldehyde

dimedone
126-81-8

dimedone

3,3,6,6-tetramethyl-9-(3-nitrophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione
40588-50-9

3,3,6,6-tetramethyl-9-(3-nitrophenyl)-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

Conditions
ConditionsYield
With poly[(2-acrylamido-2-methylpropane sulfonic acid)-co-(acrylic acid)-co-(vinyl functionalized halloysite clay)] In water at 20℃; for 3h;100%
With N-sulfonic acid poly(4-vinylpyridinium) chloride at 100℃; for 0.133333h;98%
With cobalt (II) nanoparticles(att)SBA-15 In water at 60℃; for 0.5h; Green chemistry;98%
benzaldehyde
100-52-7

benzaldehyde

dimedone
126-81-8

dimedone

3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione
19744-83-3

3,3,6,6-tetramethyl-9-phenyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8-(2H)-dione

Conditions
ConditionsYield
With poly[(2-acrylamido-2-methylpropane sulfonic acid)-co-(acrylic acid)-co-(vinyl functionalized halloysite clay)] In water at 20℃; for 3h;100%
With sulfated polyborate catalyst In neat (no solvent) at 100℃; for 0.05h; Catalytic behavior; Temperature; Green chemistry;99%
With acetic acid at 110℃; for 0.25h; Microwave irradiation;98%
p-toluidine
106-49-0

p-toluidine

dimedone
126-81-8

dimedone

3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone
36646-78-3

3-(p-tolylamino)-5,5-dimethylcyclohex-2-enone

Conditions
ConditionsYield
at 20℃; for 0.5h; Solid phase reaction; condensation;100%
With fibrous nano silica sulfuric acid In neat (no solvent) at 80℃; for 0.0333333h; Green chemistry;97%
With silica sulfuric acid In acetonitrile for 0.0194444h; Microwave irradiation;96%
4-methoxy-benzaldehyde
123-11-5

4-methoxy-benzaldehyde

dimedone
126-81-8

dimedone

9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione
19419-25-1

9-(4-methoxyphenyl)-3,3,6,6-tetramethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione

Conditions
ConditionsYield
With poly[(2-acrylamido-2-methylpropane sulfonic acid)-co-(acrylic acid)-co-(vinyl functionalized halloysite clay)] In water at 20℃; for 3h;100%
With N-sulfonic acid poly(4-vinylpyridinium) chloride at 100℃; for 0.166667h;98%
With phospho sulphonic acid In neat (no solvent) at 110℃; for 0.5h; Green chemistry;98%
Ketene
463-51-4

Ketene

dimedone
126-81-8

dimedone

3-acetyloxy-5,5-dimethyl-2-cyclohexenone
18369-65-8

3-acetyloxy-5,5-dimethyl-2-cyclohexenone

Conditions
ConditionsYield
With acetic anhydride for 0.25h; Ambient temperature;100%
With benzene
With acetic acid
ethanol
64-17-5

ethanol

dimedone
126-81-8

dimedone

3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one
6267-39-6

3-ethoxy-5,5-dimethyl-2-cyclohexen-1-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 15.5h; Reflux; regioselective reaction;100%
With Amberlyst-15 at 80℃; under 2475.25 Torr; for 0.0766667h; Flow reactor;99%
With toluene-4-sulfonic acid In benzene for 6h; Reflux;98%
indan-1,2,3-trione hydrate
485-47-2

indan-1,2,3-trione hydrate

dimedone
126-81-8

dimedone

2-hydroxy-2-(4,4-dimethyl-2,6-dioxocyclohexane-1-yl)-1H-indene-1,3(2H)-dione
30511-21-8

2-hydroxy-2-(4,4-dimethyl-2,6-dioxocyclohexane-1-yl)-1H-indene-1,3(2H)-dione

Conditions
ConditionsYield
at 20℃; for 1h;100%
In water for 0.0166667h; Heating;90%
With acetic acid at 20℃; for 0.5h;62%
dimedone
126-81-8

dimedone

methyl vinyl ketone
78-94-4

methyl vinyl ketone

5,5-dimethyl-2-(3-oxobutyl)-1,3-cyclohexanedione
19757-98-3

5,5-dimethyl-2-(3-oxobutyl)-1,3-cyclohexanedione

Conditions
ConditionsYield
aluminum oxide; potassium fluoride In tetrahydrofuran for 72h; Ambient temperature;100%
With indium(III) chloride at 20℃; for 7h; Michael addition reaction;78%
With potassium hydroxide
dimedone
126-81-8

dimedone

2-bromodimedone
1195-91-1

2-bromodimedone

Conditions
ConditionsYield
With bromine; acetic acid at 20℃; for 2h;100%
With bromine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;99%
With bromine; acetic acid at 20℃;98%
dimedone
126-81-8

dimedone

1-amino-5,5-dimethylcyclohexen-3-one
873-95-0

1-amino-5,5-dimethylcyclohexen-3-one

Conditions
ConditionsYield
With ammonium acetate In acetic acid; benzene Heating;100%
With ammonium acetate In ethanol at 70℃; for 7h;95%
With ammonium acetate; tetraethoxy orthosilicate In ethanol Heating;94%
dimedone
126-81-8

dimedone

4-methoxy-aniline
104-94-9

4-methoxy-aniline

3-[(4-methoxyphenyl)amino]-5,5-dimethylcyclohex-2-en-1-one
24706-48-7

3-[(4-methoxyphenyl)amino]-5,5-dimethylcyclohex-2-en-1-one

Conditions
ConditionsYield
at 20℃; for 0.5h; Solid phase reaction; condensation;100%
With silica-supported phosphorous pentoxide at 80℃; for 0.05h; Neat (no solvent); chemoselective reaction;97%
With silica sulfuric acid In acetonitrile for 0.0166667h; Microwave irradiation;97%
isoquinoline N-oxide
1532-72-5

isoquinoline N-oxide

dimedone
126-81-8

dimedone

4-(1-isoquinolyl)dimedone

4-(1-isoquinolyl)dimedone

Conditions
ConditionsYield
With acetic anhydride at 90℃; for 8h;100%
With acetic anhydride In N,N-dimethyl-formamide at 90℃; for 8h; Product distribution; without DMF, reagent is the solvent;69%
4-chlorobenzaldehyde
104-88-1

4-chlorobenzaldehyde

dimedone
126-81-8

dimedone

2-((4-chlorophenyl)(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)methyl)-3-hydroxy-5,5-dimethylcyclohex-2-enone
139484-10-9

2-((4-chlorophenyl)(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-enyl)methyl)-3-hydroxy-5,5-dimethylcyclohex-2-enone

Conditions
ConditionsYield
at 50℃; for 1h; Knoevenagel condensation;100%
With ZnO nanorod-decorated graphene oxide In water at 100℃; for 0.166667h; Catalytic behavior; Solvent; Temperature; Time;99%
With nano Fe/NaY zeolite In ethanol for 1.16667h; Reflux;98%
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

dimedone
126-81-8

dimedone

2,2'-(4-nitrophenylmethylene)bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one)
7560-71-6

2,2'-(4-nitrophenylmethylene)bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one)

Conditions
ConditionsYield
at 50℃; for 1h; Knoevenagel condensation;100%
With NP (natural phosphate collected from an extracted ore in Yazd, Iran) In water at 20℃; for 2h; Green chemistry;100%
With 4 A molecular sieves In ethanol for 5h; Reflux;99%
benzaldehyde
100-52-7

benzaldehyde

dimedone
126-81-8

dimedone

bis(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexenyl)phenylmethane
7600-00-2

bis(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexenyl)phenylmethane

Conditions
ConditionsYield
at 100℃; for 1h; Knoevenagel condensation;100%
With ethyl 2-cyanoacetate; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃;100%
In neat (no solvent) at 60℃; for 2h; Michael Addition;100%
benzaldehyde
100-52-7

benzaldehyde

dimedone
126-81-8

dimedone

3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione
2769-21-3

3,3,6,6-tetramethyl-9-phenyl-3,4,6,7,9,10-hexahydro-2H,5H-acridine-1,8-dione

Conditions
ConditionsYield
With C3H6N2O6S2(1+)*C2F3O2(1-); ammonium chloride at 80℃; for 0.166667h; Reagent/catalyst; Temperature;100%
With 1,3-disulfonic acid imidazolium trifluoroacetate; ammonium chloride In neat (no solvent) at 80℃; for 0.166667h; Reagent/catalyst;100%
With ammonium cerium (IV) nitrate; ammonium acetate In polyethylene glycol 400 at 25℃; for 0.25h;98%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

dimedone
126-81-8

dimedone

2,2′‐[(4‐hydroxyphenyl)methylene]bis(3‐hydroxy‐5,5‐dimethylcyclohex‐2‐enone)
71827-75-3

2,2′‐[(4‐hydroxyphenyl)methylene]bis(3‐hydroxy‐5,5‐dimethylcyclohex‐2‐enone)

Conditions
ConditionsYield
at 50℃; for 1h; Knoevenagel condensation;100%
With ZnAl2O4 In ethanol at 80℃; for 0.25h;96%
With 3-(N,N-dimethyldodecylammonium)propanesulfonic acid hydrogen sulphate at 100℃; for 1h; neat (no solvent);95%
telluroxanthen-Te,Te-dichlorid
69219-20-1

telluroxanthen-Te,Te-dichlorid

dimedone
126-81-8

dimedone

telluroniaxanthenyldimedone ylide
77151-13-4

telluroniaxanthenyldimedone ylide

Conditions
ConditionsYield
With triethylamine In benzene at 60 - 70℃; for 0.333333h;100%
[bis(acetoxy)iodo]benzene
3240-34-4

[bis(acetoxy)iodo]benzene

dimedone
126-81-8

dimedone

(4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine
35024-12-5

(4,4-dimethyl-2,6-dioxo-cyclohexyl)-phenyl-iodonium betaine

Conditions
ConditionsYield
With potassium hydroxide In methanol at 20℃; for 2h;100%
In dichloromethane at 20℃; for 1.5h;95%
In dichloromethane at 20℃; for 2h;92%
Benzylidenemalononitrile
2700-22-3

Benzylidenemalononitrile

dimedone
126-81-8

dimedone

2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
107752-97-6

2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Conditions
ConditionsYield
at 100℃; for 1h; Michael reaction;100%
With 2‑hydroxyethyl‑1‑ammonium 3‑hydroxypropane‑1‑sulfonate for 0.75h; Reagent/catalyst;99%
With urea/choline chloride eutectic salt In water at 20℃; Michael Addition; Green chemistry;96%
4-chlorobenzylidenemalonodinitrile
1867-38-5

4-chlorobenzylidenemalonodinitrile

dimedone
126-81-8

dimedone

2-amino-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
107753-00-4

2-amino-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Conditions
ConditionsYield
at 130℃; for 1h; Michael reaction;100%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 40℃; for 3h; Michael addition;95%
With N-benzyl-N,N,N-triethylammonium chloride at 20℃; for 0.0833333h;95%
bis(4-methylphenyl) selenoxide
25862-12-8

bis(4-methylphenyl) selenoxide

dimedone
126-81-8

dimedone

2-(Di-p-tolyl-λ4-selanylidene)-5,5-dimethyl-cyclohexane-1,3-dione

2-(Di-p-tolyl-λ4-selanylidene)-5,5-dimethyl-cyclohexane-1,3-dione

Conditions
ConditionsYield
In chloroform for 15h; Heating;100%
N,N'-dibenzoylsulfur diimide
25408-75-7

N,N'-dibenzoylsulfur diimide

dimedone
126-81-8

dimedone

A

benzamide
55-21-0

benzamide

B

8,8-Dimethyl-3-phenyl-4-oxa-1-thia-2-aza-spiro[4.5]dec-2-ene-6,10-dione
85078-62-2

8,8-Dimethyl-3-phenyl-4-oxa-1-thia-2-aza-spiro[4.5]dec-2-ene-6,10-dione

Conditions
ConditionsYield
In benzene at 20℃; for 2.5h;A n/a
B 100%
N,N'-bis-(4-chloro-benzoyl)-sulfur diimide
40014-48-0

N,N'-bis-(4-chloro-benzoyl)-sulfur diimide

dimedone
126-81-8

dimedone

A

3-(4-Chloro-phenyl)-8,8-dimethyl-4-oxa-1-thia-2-aza-spiro[4.5]dec-2-ene-6,10-dione
85078-63-3

3-(4-Chloro-phenyl)-8,8-dimethyl-4-oxa-1-thia-2-aza-spiro[4.5]dec-2-ene-6,10-dione

B

4-chlorobenzamide
619-56-7

4-chlorobenzamide

Conditions
ConditionsYield
In benzene at 20℃; for 2.5h;A 100%
B n/a
diphenyltellurium(IV) oxide
51786-98-2

diphenyltellurium(IV) oxide

dimedone
126-81-8

dimedone

diphenyltelluroniodimedonide
57857-71-3

diphenyltelluroniodimedonide

Conditions
ConditionsYield
In chloroform for 15h; Heating;100%
(Z)-1-nitro-1-(phenylthio)propene
67808-91-7

(Z)-1-nitro-1-(phenylthio)propene

dimedone
126-81-8

dimedone

3-Hydroxy-5,5-dimethyl-2-(1-methyl-2-nitro-2-phenylsulfanyl-ethyl)-cyclohex-2-enone
69477-90-3

3-Hydroxy-5,5-dimethyl-2-(1-methyl-2-nitro-2-phenylsulfanyl-ethyl)-cyclohex-2-enone

Conditions
ConditionsYield
With potassium fluoride In 1,2-dimethoxyethane 1) 30 min. RT, 2) 3h, 50-60 deg C;100%
(-)-menthyl 4-(methylseleninyl)benzoate
133706-55-5

(-)-menthyl 4-(methylseleninyl)benzoate

dimedone
126-81-8

dimedone

<4'-<(-)-menthyloxycarbonyl>phenyl>(methyl)selenonium 4,4-dimethyl-2,6-dioxocyclohexylide

<4'-<(-)-menthyloxycarbonyl>phenyl>(methyl)selenonium 4,4-dimethyl-2,6-dioxocyclohexylide

Conditions
ConditionsYield
With magnesium sulfate In chloroform for 12h; Ambient temperature;100%
dimedone
126-81-8

dimedone

N,N'-bis-(2,4-dichloro-benzoyl)-sulfur diimide
73339-77-2

N,N'-bis-(2,4-dichloro-benzoyl)-sulfur diimide

A

2,4-dichlorobenzamide
2447-79-2

2,4-dichlorobenzamide

B

3-(2,4-Dichloro-phenyl)-8,8-dimethyl-4-oxa-1-thia-2-aza-spiro[4.5]dec-2-ene-6,10-dione
85078-64-4

3-(2,4-Dichloro-phenyl)-8,8-dimethyl-4-oxa-1-thia-2-aza-spiro[4.5]dec-2-ene-6,10-dione

Conditions
ConditionsYield
In benzene at 20℃; for 2.5h;A n/a
B 100%
dimedone
126-81-8

dimedone

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione
75039-59-7

2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione

Conditions
ConditionsYield
for 1h; Heating;100%
In 5,5-dimethyl-1,3-cyclohexadiene for 3h; Reflux;100%
at 100℃; for 1h;100%
dimedone
126-81-8

dimedone

N,N'-bis(phenylsulfonyl)sulfoxylic diamide
81955-02-4

N,N'-bis(phenylsulfonyl)sulfoxylic diamide

A

benzenesulfonamide
98-10-2

benzenesulfonamide

B

4',4',6,6-tetramethyl-6,7-dihydro-2'H,6'H-spiro[1,3-benzoxathiol-2,1'-cyclohexan]-2',4,6'(5H)-trion
56995-07-4

4',4',6,6-tetramethyl-6,7-dihydro-2'H,6'H-spiro[1,3-benzoxathiol-2,1'-cyclohexan]-2',4,6'(5H)-trion

C

bis(4,4-dimethyl-2,6-dioxo-1-cyclohexyl) sulfide
3359-52-2

bis(4,4-dimethyl-2,6-dioxo-1-cyclohexyl) sulfide

Conditions
ConditionsYield
In benzene at 20℃; for 6h;A 100%
B 35%
C 12%

126-81-8Related news

Non-catalytic solvent-free synthesis of 5,6,7,8-tetrahydro-4H-chromenes from aldehydes, Dimedone (cas 126-81-8) and malononitrlie at ambient temperature09/30/2019

Non-catalytic solvent-free assembling of aldehydes, dimedone and malononitrile at ambient temperature affords substituted 5,6,7,8-tetrahydro-4H-chromenes in 88–98% yields.detailed

Highly enantioselective Michael/cyclization tandem reaction between Dimedone (cas 126-81-8) and isatylidene malononitriles09/25/2019

A highly enantioselective Michael/cyclization tandem reaction between dimedone and isatylidene malononitriles has been developed. With 5 mol% of bifunctional organocatalyst C15, chiral spiro[2-amino-4H-pyran-oxindole] derivatives were obtained in excellent yields (97–99%) with excellent enantio...detailed

126-81-8Relevant articles and documents

Cyclocondensation of 2-aminobenzimidazole with dimedone and its arylidene derivatives

Lipson,Desenko,Shishkina,Shirobokova,Shishkin,Orlov

, p. 1041 - 1047 (2003)

The reactions of 2-aminobenzimidazole with substituted benzaldehydes and dimedone, 2-arylidene derivatives of dimedone, 9-arylhexahydro-1H-xanthene-1,8(2H)-diones and also with dimedone and DMF have been studied. The direction of formation of the pyrimidine ring has been established and discussed. An X-ray structural investigation of 2,2-dimethyl-2,3-dihydrobenzimidazo[1,2-a]quinazolin-4(1H)-one has has been carried out.

Two phases of C9H12O4: Why is the structure at 295 K so complicated?

Duncan, Laura L.,Patrick, Brian O.,Brock, Carolyn Pratt

, p. 502 - 511 (2002)

Molecules of 4,4′-dimethyl-2-hydroxy-6-oxocyclohexene-1-carboxylic acid, C9H12O4, crystallize at 295 K in a modulated superstructure with five half-molecules in the asymmetric unit; each molecule is located on one of the mirror planes of the space group Cmc21. Reflections with k ≠ 5n are systematically weak; a satisfactory refinement can be obtained in a Cmcm pseudocell having b′ = b/5. The important modulation involves small rotations of the molecules around axes perpendicular to the mirror plane; there is also an up/down disorder of the CMe2 fragment in four of the five molecules (two molecules with occupancy factors ca 4:1; two with occupancy factors ca 3:2). The modulation is a response to packing problems that can be traced to the differences between the thin, electron-and oxygen-rich 'head' of the molecule and the thicker, methyl-rich 'tail'. At 130 K the length of b is reduced by 2/5 and the Pmnb structure is ordered. Both structures can be described as modulated variants of the Cmcm substructure; the wavevectors are 2b′*/5 for the room-temperature structure and b′*/2 for the low-temperature structure, where b′* is the reciprocal axis of the subcell. The structure at room temperature can also be understood as a hybrid of the fully disordered pseudocell structure and the ordered structure that is found at low temperature.

Zinc chloride catalyzed collective synthesis of arylmethylene bis(3-hydroxy-2-cyclohexene-1-ones) and 1,8-dioxo-octahydroxanthene/acridine derivatives

Ganesan, Subramaniapillai Selva,Kothandapani, Jagatheeswaran,Ganesan, Asaithampi

, p. 682 - 687 (2015/04/14)

Catalytic amount of ZnCl2 efficiently promoted rapid synthesis of arylmethylene bis(3-hydroxy-2-cyclohexene-1-one) in water at room temperature in excellent yield. At elevated temperature, ZnCl2 also catalyzed one-pot synthesis of 1,8-dioxo-octahydroxanthene and 1,8-dioxo-decahydroacridine derivatives in good yield. In specific instances, unusual dissociation of dimedone from the arylmethylene bis(3-hydroxy-2-cyclohexene-1-one) was identified in the reaction medium. It was minimized/avoided by the addition of known excess dimedone to the reaction mixture in the one-pot synthesis of 1,8-dioxo-octahydroxanthene.

Synthesis of enaminones in aqueous media using catalytic dilute HCl

Cui, Bin,Wang, Rui-Hua,Chen, Li-Zhuang,Jin, Yan,Han, Guang-Fan

scheme or table, p. 1064 - 1070 (2011/04/26)

(Chemical Equation Presented) A green and convenient approach to the synthesis of β-enaminones from aromatic amines and 5-substituted-1,3- cyclohexanedione in the presence of dilute hydrochloric acid (30 mmol=L) as a catalyst in solvent-free media is described. This method provides several advantages such as environmental friendliness, low cost, good yields, and simple workup procedure. Copyright Taylor & Francis Group, LLC.

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