Product Name

  • Name

    2,2-Dimethyl-1,3-dioxane-4,6-dione

  • EINECS 217-992-8
  • CAS No. 2033-24-1
  • Article Data56
  • CAS DataBase
  • Density 1.201 g/cm3
  • Solubility 2.5 g/100 mL (20 °C) in water
  • Melting Point 92-96 °C(lit.)
  • Formula C6H8O4
  • Boiling Point 356.7 °C at 760 mmHg
  • Molecular Weight 144.127
  • Flash Point 195.1 °C
  • Transport Information
  • Appearance white to beige crystals
  • Safety 37/39-24/25-53-45-36-26
  • Risk Codes 36/37/38-45
  • Molecular Structure Molecular Structure of 2033-24-1 (2,2-Dimethyl-1,3-dioxane-4,6-dione)
  • Hazard Symbols IrritantXi, ToxicT
  • Synonyms 2,2-Dimethyl-1,3-dioxan-4,6-dione;2,2-Dimethyl-4,6-dioxo-1,3-dioxane;2,2-Dimethyl-m-dioxane-4,6-dione;2,2-Propanediol cyclic malonate;Cyclic isopropylidene malonate;Isopropylidenemalonate;Meldrumic acid;
  • PSA 52.60000
  • LogP 0.21260

Synthetic route

2,2-dimethyl-5-(phenyl-λ3-iodaneylidene)-1,3-dioxane-4,6-dione
34107-52-3

2,2-dimethyl-5-(phenyl-λ3-iodaneylidene)-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

iodobenzene
591-50-4

iodobenzene

C

acetone
67-64-1

acetone

Conditions
ConditionsYield
With dirhodium tetraacetate In dichloromethane at 20℃; Product distribution;A 33%
B 100%
C 5%
5-(bis(4-tert-phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-(bis(4-tert-phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1,1-bis(4-t-butylphenyl)methane
19099-48-0

1,1-bis(4-t-butylphenyl)methane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 99%
5-((2-methoxyphenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-((2-methoxyphenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

o-benzyl anisole
883-90-9

o-benzyl anisole

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 98%
5-(bis(4-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
1190929-81-7

5-(bis(4-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

4,4'-dianisylmethane
726-18-1

4,4'-dianisylmethane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 96%
5-((4-(tert-butyl)phenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-((4-(tert-butyl)phenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-benzyl-4-tert-butylbenzene
16251-99-3

1-benzyl-4-tert-butylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 96%
5-((3-methoxyphenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-((3-methoxyphenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

m-benzylanisole
23450-27-3

m-benzylanisole

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 95%
6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene
68695-08-9

6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

Conditions
ConditionsYield
With benzophenone In methanol Irradiation;93%
5-(bis(3-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-(bis(3-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

bis(3-methoxyphenyl)methane
51095-48-8

bis(3-methoxyphenyl)methane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 93%
5-(2-(4-isopropylphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-(2-(4-isopropylphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1,4-bis(1-methylethyl)benzene
100-18-5

1,4-bis(1-methylethyl)benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 65℃; under 760.051 Torr; for 96h; Sealed tube;A n/a
B 91%
2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)hexan-2-yl)-1,3-dioxane-4,6-dione
1190929-78-2

2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)hexan-2-yl)-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-(hexan-2-yl)-4-(octyloxy)benzene
1190929-84-0

1-(hexan-2-yl)-4-(octyloxy)benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 90%
2,2-dimethyl-5-(2-(2-(octyloxy)phenyl)propan-2-yl)-1,3-dioxane-4,6-dione
1190929-75-9

2,2-dimethyl-5-(2-(2-(octyloxy)phenyl)propan-2-yl)-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-isopropyl-2-(octyloxy)benzene
1190929-83-9

1-isopropyl-2-(octyloxy)benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 48h;A n/a
B 90%
5-(2-(4-butylphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-(2-(4-butylphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-butyl-4-(1-methylethyl)benzene
55169-03-4

1-butyl-4-(1-methylethyl)benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 90%
2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)butan-2-yl)-1,3-dioxane-4,6-dione
1190929-77-1

2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)butan-2-yl)-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-(sec-butyl)-4-octyloxybenzene
148924-08-7

1-(sec-butyl)-4-octyloxybenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 86%
5-[1-(2-ethylphenyl)-1-methylethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione
1098072-98-0

5-[1-(2-ethylphenyl)-1-methylethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-ethyl-2-isopropylbenzene
18970-44-0

1-ethyl-2-isopropylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 83%
2,2-dimethyl-5(1-(4-(octyloxy)phenyl)cyclohexyl)-1,3-dioxane-4,6-dione
1190929-76-0

2,2-dimethyl-5(1-(4-(octyloxy)phenyl)cyclohexyl)-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-cyclohexyl-4-(octyloxy)benzene
172752-17-9

1-cyclohexyl-4-(octyloxy)benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 82%
5-(2-(4-isopropoxyphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-(2-(4-isopropoxyphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-isopropoxy-4-isopropylbenzene
28530-36-1

1-isopropoxy-4-isopropylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 82%
5-((4-fluorophenyl)(4-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
1266101-51-2

5-((4-fluorophenyl)(4-methoxyphenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-(4-fluorobenzyl)-4-methoxybenzene
38695-26-0

1-(4-fluorobenzyl)-4-methoxybenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 81%
5-((4-fluorophenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
1266101-38-5

5-((4-fluorophenyl)(phenyl)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

4-fluorodiphenylmethane
587-79-1

4-fluorodiphenylmethane

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 81%
5-(2-(4-neopentylphenyl)propan-2-yl)-2,2-dimethy-1,3-dioxane-4,6-dione

5-(2-(4-neopentylphenyl)propan-2-yl)-2,2-dimethy-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-isopropyl-4-neopentylbenzene
37920-33-5

1-isopropyl-4-neopentylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 81%
2,2-dimethyl-5-(1-methyl-1-phenylethyl)-1,3-dioxane-4,6-dione
81710-07-8

2,2-dimethyl-5-(1-methyl-1-phenylethyl)-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

Isopropylbenzene
98-82-8

Isopropylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A 80%
B n/a
5-(2-([1,1'-biphenyl]-4-yl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione
1190929-69-1

5-(2-([1,1'-biphenyl]-4-yl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

4-isopropylbiphenyl
7116-95-2

4-isopropylbiphenyl

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 80%
5-(2-(3-(tert-butyl)phenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione
1381982-75-7

5-(2-(3-(tert-butyl)phenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-tert-butyl-3-isopropylbenzene
20033-12-9

1-tert-butyl-3-isopropylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 65℃; under 760.051 Torr; for 24h; Sealed tube;A n/a
B 80%
malonic acid
141-82-2

malonic acid

acetone
67-64-1

acetone

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

Conditions
ConditionsYield
With sulfuric acid; acetic anhydride at 60℃;78%
Stage #1: malonic acid With sulfuric acid; acetic anhydride at 0℃; for 1h;
Stage #2: acetone In acetic anhydride at 0℃; for 30h;
77%
With sulfuric acid; acetic anhydride at -5 - 0℃; for 3h;70.9%
2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)propan-2-yl)-1,3-dioxane-4,6-dione
1190929-65-7

2,2-dimethyl-5-(2-(4-(octyloxy)phenyl)propan-2-yl)-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-isopropyl-4-(octyloxy)benzene
1190929-82-8

1-isopropyl-4-(octyloxy)benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 78%
5-(2-(4-(tert-butyl)phenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione
1381982-70-2

5-(2-(4-(tert-butyl)phenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

p-tert.-Butyl-cumol
4132-49-4

p-tert.-Butyl-cumol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethyl acetate at 65℃; under 760.051 Torr; for 48h; Sealed tube;A n/a
B 76%
5-(2-(4-isobutylphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-(2-(4-isobutylphenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-isobutyl-4-isopropylbenzene
34349-70-7

1-isobutyl-4-isopropylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 72%
2,2-dimethyl-5-(3-methyl-2-(4-(octyloxy)phenyl)butan-2-yl)-1,3-dioxane-4,6-dione
1190929-79-3

2,2-dimethyl-5-(3-methyl-2-(4-(octyloxy)phenyl)butan-2-yl)-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-(3-methylbutan-2-yl)-4-(octyloxy)benzene
1190929-85-1

1-(3-methylbutan-2-yl)-4-(octyloxy)benzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 24h;A n/a
B 70%
5-(2-(4-(tert-butoxy)phenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

5-(2-(4-(tert-butoxy)phenyl)propan-2-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione

A

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

B

1-tert-butoxy-4-isopropylbenzene
16215-76-2

1-tert-butoxy-4-isopropylbenzene

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 48h;A n/a
B 70%
methanol
67-56-1

methanol

5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion
7270-63-5

5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion

A

6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene
68695-08-9

6,6-dimethyl-4,8-dioxo-5,7-dioxa-1,2-diazaspiro<2.5>oct-1-ene

B

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

C

methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate
62609-79-4

methyl 2,2-dimethyl-5-oxo-1,3-dioxolane-4-carboxylate

D

2,2-dimethyl-4,6-dioxo-5-methoxy-1,3-dioxane
97801-91-7

2,2-dimethyl-4,6-dioxo-5-methoxy-1,3-dioxane

Conditions
ConditionsYield
for 1.16667h; Product distribution; Irradiation;A 4.5%
B 3%
C 64%
D 2.5%
In tetrahydrofuran at 18 - 20℃; for 9h; UV-irradiation;A 23%
B 8%
C 25%
D n/a
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

2-Methylbutyraldehyde
96-17-3, 57456-98-1

2-Methylbutyraldehyde

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

d,l-2-ethylhexanal
123-05-7

d,l-2-ethylhexanal

5-(2-Ethyl-1-pyrrolidin-1-yl-hexyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
93498-12-5

5-(2-Ethyl-1-pyrrolidin-1-yl-hexyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

benzaldehyde
100-52-7

benzaldehyde

2,2-Dimethyl-5-(phenyl-pyrrolidin-1-yl-methyl)-[1,3]dioxane-4,6-dione
93498-11-4

2,2-Dimethyl-5-(phenyl-pyrrolidin-1-yl-methyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

propionaldehyde
123-38-6

propionaldehyde

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione
93498-07-8

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

butyraldehyde
123-72-8

butyraldehyde

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione
93498-08-9

2,2-Dimethyl-5-(1-pyrrolidin-1-yl-butyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
pyrrolidine
123-75-1

pyrrolidine

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

isobutyraldehyde
78-84-2

isobutyraldehyde

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione
93498-09-0

2,2-Dimethyl-5-(2-methyl-1-pyrrolidin-1-yl-propyl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
In diethyl ether for 0.166667h;100%
4-methyleneoxetan-2-one
674-82-8

4-methyleneoxetan-2-one

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione
84257-12-5

2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h;100%
Stage #1: 4-methyleneoxetan-2-one; cycl-isopropylidene malonate With triethylamine In dichloromethane at 0 - 20℃; for 2h;
Stage #2: With hydrogenchloride In dichloromethane; water
100%
With triethylamine In dichloromethane at 20℃;100%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

1,1-bis(phenylsulfonyl)ethylene
39082-53-6

1,1-bis(phenylsulfonyl)ethylene

5-(2,2-Bis-benzenesulfonyl-ethyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
87625-91-0

5-(2,2-Bis-benzenesulfonyl-ethyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
N-benzyl-trimethylammonium hydroxide In 1,4-dioxane100%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

(+/-)-3-Methyl-4,4,4-trichlorobutanoyl Chloride
91238-98-1

(+/-)-3-Methyl-4,4,4-trichlorobutanoyl Chloride

2,2-Dimethyl-5-(4,4,4-trichloro-3-methyl-butyryl)-[1,3]dioxane-4,6-dione
91265-41-7

2,2-Dimethyl-5-(4,4,4-trichloro-3-methyl-butyryl)-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
With pyridine In dichloromethane 1. 1 h/-5 deg C 2. 30 min/room temperature;100%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

Rhodinoic acid chloride
88373-61-9

Rhodinoic acid chloride

5-(3,7-Dimethyl-oct-7-enoyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione
88373-62-0

5-(3,7-Dimethyl-oct-7-enoyl)-2,2-dimethyl-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
With pyridine In dichloromethane at 0℃;100%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

C18H14N4O2
107798-95-8

C18H14N4O2

2-<(4,4-dimethyl-2,6-dioxo-3,5-dioxanylidene)methyl>-3-methylindole
103865-88-9

2-<(4,4-dimethyl-2,6-dioxo-3,5-dioxanylidene)methyl>-3-methylindole

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 0.333333h; Ambient temperature;100%
With triethylamine In tetrahydrofuran for 0.5h; Ambient temperature; Yield given;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

Hexanoyl chloride
142-61-0

Hexanoyl chloride

2,2-dimethyl-5-(1-oxohexyl)-1,3-dioxane-4,6-dione
254907-27-2

2,2-dimethyl-5-(1-oxohexyl)-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
With dmap In dichloromethane at 20℃; for 16h; Inert atmosphere;100%
With pyridine In dichloromethane62%
With pyridine In dichloromethane Ambient temperature;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

orthoformic acid triethyl ester
122-51-0

orthoformic acid triethyl ester

5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
15568-86-2

5-(ethoxymethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
at 80℃; for 3h;100%
With zinc diacetate at 90℃; for 1h; Condensation;85%
at 105℃; for 2h;80%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

phenylacetyl chloride
103-80-0

phenylacetyl chloride

5-(1-hydroxy-2-phenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
66696-84-2

5-(1-hydroxy-2-phenylethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; Acylation;100%
With dmap Inert atmosphere;75%
Stage #1: cycl-isopropylidene malonate With pyridine In dichloromethane at 0℃;
Stage #2: phenylacetyl chloride In dichloromethane at 0 - 20℃;
Stage #3: With hydrogenchloride In dichloromethane; water Cooling with ice;
71%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

tert-butyl alcohol
75-65-0

tert-butyl alcohol

mono-tert-butyl malonate
40052-13-9

mono-tert-butyl malonate

Conditions
ConditionsYield
for 6h; Reflux;100%
Reflux;97%
Stage #1: cycl-isopropylidene malonate; tert-butyl alcohol for 5h; Reflux;
Stage #2: With ammonia; water In ethanol at 5℃; for 0.0833333h;
Stage #3: With hydrogenchloride In water
62%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion
7270-63-5

5-diazo-2,2-dimethyl-1,3-dioxane-4,6-dion

Conditions
ConditionsYield
With N,N,N,N,N,N-hexamethylphosphoric triamide; 4-toluenesulfonyl azide; triethylamine for 3h; Ambient temperature;100%
With 2-azido-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran at 0℃; for 0.166667h;95%
With 2-azido-1,3-dimethylimidazolinium chloride; triethylamine In tetrahydrofuran at 0℃; for 0.166667h; Inert atmosphere;95%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester
109579-08-0

(S)-[1-benzyl-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h;100%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 12h; Inert atmosphere;95%
Stage #1: cycl-isopropylidene malonate; N-tert-butoxycarbonyl-L-phenylalanine With dmap In dichloromethane for 0.166667h; Cooling with ice;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane for 10h; Cooling with ice;
77%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

5-(cyclopropyl(hydroxy)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione
146380-13-4

5-(cyclopropyl(hydroxy)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; Acylation;100%
Stage #1: cycl-isopropylidene malonate With pyridine In dichloromethane at 0℃; for 0.25h;
Stage #2: cyclopropanecarboxylic acid chloride In dichloromethane at 0 - 20℃; for 3h;
60%
With pyridine In dichloromethane at 0 - 20℃; for 3h; Acylation;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

5-(4-hydroxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione
17474-27-0

5-(4-hydroxy-benzylidene)-2,2-dimethyl-[1,3]dioxane-4,6-dione

Conditions
ConditionsYield
at 50℃; for 1h; Knoevenagel condensation;100%
In water; toluene at 23 - 33℃; for 4.66667h; Knoevenagel condensation; Large scale reaction;99%
With cobalt(III) oxide In water for 0.0833333h; Knoevenagel Condensation; Reflux;99%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

4-dimethylamino-benzaldehyde
100-10-7

4-dimethylamino-benzaldehyde

5-(4-N,N-dimethylaminobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
15795-57-0

5-(4-N,N-dimethylaminobenzylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
at 50℃; for 1h; Knoevenagel condensation;100%
With ethylammonium nitrate at 20℃; for 0.5h; Knoevenagel condensation;97%
In various solvent(s) at 20℃; for 0.5h; Knoevenagel condensation;97%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

isopropyl alcohol
67-63-0

isopropyl alcohol

i-propyl malonic half ester
56766-77-9

i-propyl malonic half ester

Conditions
ConditionsYield
In acetonitrile for 22h; Heating;100%
Reflux;76%
In toluene for 5h; Heating;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

N-tert-butoxycarbonyl-L-phenylalanine
13734-34-4

N-tert-butoxycarbonyl-L-phenylalanine

(2'S)-5-<(1-hydroxy-3-phenyl-2-t-butoxycarbonylamino)-propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione
112700-36-4, 112700-37-5

(2'S)-5-<(1-hydroxy-3-phenyl-2-t-butoxycarbonylamino)-propylidene>-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃;
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 14h; Inert atmosphere;
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

Boc-D-Phe-OH
18942-49-9

Boc-D-Phe-OH

5-[(2R)-2-(tert-Butoxycarbonylamino)-1-hydroxy-3-phenylpropylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
112700-37-5

5-[(2R)-2-(tert-Butoxycarbonylamino)-1-hydroxy-3-phenylpropylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;100%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 2h;
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

2-oxo-2H-chromene-3-carboxylic acid
531-81-7

2-oxo-2H-chromene-3-carboxylic acid

Conditions
ConditionsYield
With piperdinium acetate In ethanol for 2h; Heating;100%
With piperidine; acetic acid In benzene Knoevenagel condensation; Heating;92%
With lithium perchlorate for 0.0138889h; Irradiation;89%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

3-methoxy-2-hydroxybenzaldehyde
148-53-8

3-methoxy-2-hydroxybenzaldehyde

8-methoxy-2-oxo-2H-chromene-3-carboxylic acid
2555-20-6

8-methoxy-2-oxo-2H-chromene-3-carboxylic acid

Conditions
ConditionsYield
With piperdinium acetate In ethanol for 2h; Heating;100%
In water for 1h; Reflux;99%
With β‐cyclodextrin In water at 70℃; for 0.25h; Green chemistry;97%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

Farnesol
106-28-5

Farnesol

3-oxo-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyloxy)propanoic acid

3-oxo-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyloxy)propanoic acid

Conditions
ConditionsYield
In toluene at 100℃; Inert atmosphere;100%
In toluene Heating;85%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

[3-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-5-hydroxymethyl-phenyl]-methanol
642442-36-2

[3-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-5-hydroxymethyl-phenyl]-methanol

Malonic acid mono-[3-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-5-(2-carboxy-acetoxymethyl)-benzyl] ester

Malonic acid mono-[3-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-5-(2-carboxy-acetoxymethyl)-benzyl] ester

Conditions
ConditionsYield
at 120℃; for 4h;100%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

{3-[3,5-bis-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-benzyloxy]-5-hydroxymethyl-phenyl}-methanol
642442-37-3

{3-[3,5-bis-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-benzyloxy]-5-hydroxymethyl-phenyl}-methanol

Malonic acid mono-[3-[3,5-bis-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-benzyloxy]-5-(2-carboxy-acetoxymethyl)-benzyl] ester

Malonic acid mono-[3-[3,5-bis-(3,5-bis-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-benzyloxy)-benzyloxy]-5-(2-carboxy-acetoxymethyl)-benzyl] ester

Conditions
ConditionsYield
at 120℃; for 4h;100%
cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

C113H164O41

C113H164O41

C119H168O47

C119H168O47

Conditions
ConditionsYield
at 120℃; for 4h;100%

Meldrum's acid Consensus Reports

Reported in EPA TSCA Inventory.

Meldrum's acid Standards and Recommendations

ASSAY: 98.0% min
LOSS ON DRYING: 0.5% max

Meldrum's acid Specification

Meldrum's acid , its cas register number is 2033-24-1. It also can be called 2,2-Dimethyl-1,3-dioxane-4,6-dione; 2,2-Dimethyl-4,6-dioxo-m-dioxane; 2,2-Dimethyl-m-dioxane-4,6-dione; Isopropylidene malonate; m-Dioxane-4,6-dione, 2,2-dimethyl-; 1,3-Dioxane-4,6-dione, 2,2-dimethyl- ; Malonic acid, cyclic isopropylidene ester (8CI). It is a brown white solid. Meldrum's acid  is an intermediate for different organic syntheses. It is an important intermediate in syntheses of vitamins B1 and B6, barbiturate, non-steroidal anti-inflammatory agent, other numerous pharmaceutical, agrochemical and flavor & fragrance compound. As an alternative to its original preparation, Meldrum's acid can be synthesized from malonic acid, isopropenyl acetate, and catalytic sulfuric acid.

Physical properties about Meldrum's acid are: (1)ACD/LogP: -1.579; (2)ACD/LogD (pH 5.5): -1.58; (3)ACD/LogD (pH 7.4): -1.58; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 3.30; (7)ACD/KOC (pH 7.4): 3.30; (8)#H bond acceptors: 4; (9)Index of Refraction: 1.434; (10)Molar Refractivity: 31.24 cm3; (11)Molar Volume: 119.95 cm3; (12)Polarizability: 12.384 10-24cm3; (13)Surface Tension: 33.2239990234375 dyne/cm; (14)Density: 1.202 g/cm3; (15)Flash Point: 195.118 °C; (16)Enthalpy of Vaporization: 60.204 kJ/mol; (17)Boiling Point: 356.749 °C at 760 mmHg

When you are using Meldrum's acid, please be cautious about it as the following:
1. Wear suitable gloves and eye/face protection;
2. Avoid contact with skin and eyes;
3. Avoid exposure - obtain special instruction before use;
4. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
5. Wear suitable protective clothing;
6. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3;
(2)InChIKey=GXHFUVWIGNLZSC-UHFFFAOYSA-N;
(3)SmilesC1(OC(CC(O1)=O)=O)(C)C;

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 180mg/kg (180mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#04102,

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