Product Name

  • Name

    2,4-Thiazolidinedione

  • EINECS 218-941-2
  • CAS No. 2295-31-0
  • Article Data140
  • CAS DataBase
  • Density 1.516 g/cm3
  • Solubility Soluble in water (30 mg/ml at 3°C), methanol, DMSO, ethanol, and ethyl ether.
  • Melting Point 125-127 °C(lit.)
  • Formula C3H3NO2S
  • Boiling Point 305.7 °C at 760 mmHg
  • Molecular Weight 117.128
  • Flash Point 138.7 °C
  • Transport Information
  • Appearance White to off-white powder
  • Safety 24/25-36-26
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 2295-31-0 (2,4-Thiazolidinedione)
  • Hazard Symbols IrritantXi
  • Synonyms 1,3-Thiazolidine-2,4-dione;2, 4-Thiazolidinedione;2,4-Dioxothiazolidine;TZD;Usaf ek-5496;thiazolidine-2,4-dione;2,4(3H,5H)-Thiazoledione;Thiazolidinedione;Thiazolidinedione-2,4;
  • PSA 71.47000
  • LogP 0.29820

Synthetic route

4-[[2-methyl-1-oxo-1,2-dihydrophthalazin-4-yl]methoxy]benzaldehyde
214282-10-7

4-[[2-methyl-1-oxo-1,2-dihydrophthalazin-4-yl]methoxy]benzaldehyde

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

5-[4-[[2-Methyl-1-oxo-1,2-dihydro-phthalazin-4-yl]methoxy]phenyl methylene]thiazolidin-2,4-dione
214281-86-4

5-[4-[[2-Methyl-1-oxo-1,2-dihydro-phthalazin-4-yl]methoxy]phenyl methylene]thiazolidin-2,4-dione

Conditions
ConditionsYield
A 98%
B n/a
thiourea
17356-08-0

thiourea

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
Stage #1: thiourea; chloroacetyl chloride In water for 0.333333h;
Stage #2: With hydrogenchloride In water for 7 - 8h; Reflux;
94%
thiourea
17356-08-0

thiourea

chloroacetic acid
79-11-8

chloroacetic acid

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With hydrogenchloride; water at 0℃; Reflux;91%
In water for 10h; Solvent; Reflux;90%
Stage #1: thiourea; chloroacetic acid In water for 0.25h;
Stage #2: With hydrogenchloride; water at 100℃; Cooling;
90%
pseudothiohydantoin
556-90-1

pseudothiohydantoin

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With hydrogenchloride; water for 12h; Reflux;89%
With hydrogenchloride; ethanol Reflux;83%
With hydrogenchloride; water for 10h; Reflux;77.2%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

monophenylthiourea
103-85-5

monophenylthiourea

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;88%
4-[2-[4-phenyl-1-oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde
214282-18-5

4-[2-[4-phenyl-1-oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

5-[4-[2-[4-Phenyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione
214281-81-9

5-[4-[2-[4-Phenyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione

Conditions
ConditionsYield
A 87%
B n/a
p-methylphenylthiourea
622-52-6

p-methylphenylthiourea

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;84%
4-[2-[4-ethyl-1-oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde
214282-16-3

4-[2-[4-ethyl-1-oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

5-[4-[2-[4-ethyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione
214281-78-4

5-[4-[2-[4-ethyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione

Conditions
ConditionsYield
A 83%
B n/a
1-(4-bromophenyl)thiourea
2646-30-2

1-(4-bromophenyl)thiourea

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;82%
(2,4-dimethylphenyl)thiourea
16738-20-8

(2,4-dimethylphenyl)thiourea

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;82%
2-allylamino-Δ2-thiazolin-4-one
39130-99-9

2-allylamino-Δ2-thiazolin-4-one

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;81%
4-[2-[1-oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde
214282-14-1

4-[2-[1-oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

5-[4-[2-[1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione
214281-74-0

5-[4-[2-[1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione

Conditions
ConditionsYield
A 80%
B n/a
1-(4-methoxy-2-methylphenyl)thiourea

1-(4-methoxy-2-methylphenyl)thiourea

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;80%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

N-(4-chlorophenyl)thiourea
3696-23-9

N-(4-chlorophenyl)thiourea

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;80%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

o-chlorophenylthiourea
5344-82-1

o-chlorophenylthiourea

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;79%
1-(4-hydroxy-2-methylphenyl)thiourea

1-(4-hydroxy-2-methylphenyl)thiourea

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;78%
2-chloroethanal
107-20-0

2-chloroethanal

thiourea
17356-08-0

thiourea

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
In water at 100℃; for 24h;78%
2-(phenylimino)thiazolidin-4-one
17823-27-7

2-(phenylimino)thiazolidin-4-one

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

3-phenyl-2,4-thiazolidinedione
1010-53-3

3-phenyl-2,4-thiazolidinedione

Conditions
ConditionsYield
With hydrogenchloride for 1h; Heating;A 21%
B 65%
p-nitrophenylthiourea
3696-22-8

p-nitrophenylthiourea

chloroacetyl chloride
79-04-9

chloroacetyl chloride

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;65%
S-Thiocarbamoyl-β-mercaptopropionic acid
4240-92-0

S-Thiocarbamoyl-β-mercaptopropionic acid

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With chloroacetic acid for 3h; Heating;62%
With chloroacetic acid In water for 5h; Heating;60%
2-acetylallylamino-4-acetoxythiazole
113917-94-5

2-acetylallylamino-4-acetoxythiazole

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With hydrogenchloride for 2h; Heating;56%
2-imino-4-thiazolidinone acetate salt

2-imino-4-thiazolidinone acetate salt

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
In ethanol; water for 2h; Reflux;44%
2-thioxo-4-thiazolidinone
141-84-4

2-thioxo-4-thiazolidinone

chloroacetic acid
79-11-8

chloroacetic acid

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water
2-thioxo-4-thiazolidinone
141-84-4

2-thioxo-4-thiazolidinone

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

mercaptoacetic acid
68-11-1

mercaptoacetic acid

Conditions
ConditionsYield
With hydrogenchloride at 130℃;
2-phenylaminothiazol-4-one
17823-27-7

2-phenylaminothiazol-4-one

A

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

B

3-phenyl-2,4-thiazolidinedione
1010-53-3

3-phenyl-2,4-thiazolidinedione

Conditions
ConditionsYield
With hydrogenchloride
α-thiocyanato-acetic acid amide
5875-28-5

α-thiocyanato-acetic acid amide

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With hydrogenchloride beim Eindampfen;
S-carbamoylthio-acetic acid
4695-06-1

S-carbamoylthio-acetic acid

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
beim Schmelzen;
With hydrogenchloride
diethyl 2-thiocyanatomalonate
55602-07-8

diethyl 2-thiocyanatomalonate

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With hydrogenchloride beim Eindampfen;
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

(2S)-benzyl-6-(formyl)-2,3-dihydro-4H-benzopyran
109209-99-6

(2S)-benzyl-6-(formyl)-2,3-dihydro-4H-benzopyran

5-[1-((S)-2-Benzyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione
109208-74-4, 109208-75-5, 109229-59-6

5-[1-((S)-2-Benzyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione

Conditions
ConditionsYield
With sodium acetate at 140℃; for 0.416667h;100%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

(2R)-benzyl-6-(formyl)-2,3-dihydro-4H-benzopyran
109210-00-6

(2R)-benzyl-6-(formyl)-2,3-dihydro-4H-benzopyran

5-[1-((R)-2-Benzyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione
109208-74-4, 109208-75-5, 109229-59-6

5-[1-((R)-2-Benzyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione

Conditions
ConditionsYield
With sodium acetate at 140℃; for 0.416667h;100%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde
114393-97-4

4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde

5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione
136401-69-9

5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione

Conditions
ConditionsYield
With pyrrolidine In methanol at 10 - 50℃; for 8h;100%
With piperidine In ethanol for 15h; Heating / reflux;81%
With piperidine In ethanol Heating;64%
With ammonia In ethanol21.6 g (57.6%)
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

(S)-4-<<(quinolin-2-yl)pyrrolidin-2-yl>methoxy>benzaldehyde
199117-89-0

(S)-4-<<(quinolin-2-yl)pyrrolidin-2-yl>methoxy>benzaldehyde

5-[1-[4-((S)-1-Quinolin-2-yl-pyrrolidin-2-ylmethoxy)-phenyl]-meth-(Z)-ylidene]-thiazolidine-2,4-dione

5-[1-[4-((S)-1-Quinolin-2-yl-pyrrolidin-2-ylmethoxy)-phenyl]-meth-(Z)-ylidene]-thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperidine; benzoic acid In toluene for 4h; Heating;100%
4-[N-benzyl-N-[3-isopropyl-4-(methoxymethoxy)phenyl]amino]-3,5-dimethylbenzaldehyde
936133-26-5

4-[N-benzyl-N-[3-isopropyl-4-(methoxymethoxy)phenyl]amino]-3,5-dimethylbenzaldehyde

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

(Z)-5-[4-[N-benzyl-N-[3-isopropyl-4-(methoxymethoxy)phenyl]amino]-3,5-dimethylphenylmethylene]thiazolidine-2,4-dione
936133-31-2

(Z)-5-[4-[N-benzyl-N-[3-isopropyl-4-(methoxymethoxy)phenyl]amino]-3,5-dimethylphenylmethylene]thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperidine In ethanol for 20h; Knoevenagel condensation; Heating;100%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-[1-(benzyloxycarbonyl)piperidin-4-yloxy]benzaldehyde

4-[1-(benzyloxycarbonyl)piperidin-4-yloxy]benzaldehyde

5-[4-[1-(Benzyloxycarbonyl)piperidin-4-yloxy]phenyl methylene] thiazolidine-2,4-dione

5-[4-[1-(Benzyloxycarbonyl)piperidin-4-yloxy]phenyl methylene] thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperidine; benzoic acid In toluene for 1h; Heating / reflux;100%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

C16H13BrO2
1443442-70-3

C16H13BrO2

C19H14BrNO3S
1443442-68-9

C19H14BrNO3S

Conditions
ConditionsYield
With ammonium acetate; acetic acid In toluene Reflux;100%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4,7-dichloroisatin
18711-13-2

4,7-dichloroisatin

5-(4,7-dichloro-3-hydroxy-2-oxoindolin-3-yl)thiazolidine-2,4-dione

5-(4,7-dichloro-3-hydroxy-2-oxoindolin-3-yl)thiazolidine-2,4-dione

Conditions
ConditionsYield
With water at 20℃; for 12h;100%
piperidine
110-89-4

piperidine

2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde
114393-97-4

4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde

5-{4-[2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione
144809-28-9

5-{4-[2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione

Conditions
ConditionsYield
In ethanol99.5%
In ethanol2.14 g (64%)
In ethanol
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

5-[(4-hydroxyphenyl)methylene]-2,4-thiazolidinedione
103788-60-9

5-[(4-hydroxyphenyl)methylene]-2,4-thiazolidinedione

Conditions
ConditionsYield
piperidine; benzoic acid In toluene at 20℃; Reflux;99.37%
With piperidine; acetic acid In toluene at 80℃; Dean-Stark;98%
With piperidine; benzoic acid In toluene for 1.5h; Knoevenagel Condensation; Dean-Stark; Inert atmosphere; Reflux;98%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

piperonal
120-57-0

piperonal

5-([1,3]benzodioxol-5-ylmethylene)-1,3-thiazolidine-2,4-dione
6318-41-8

5-([1,3]benzodioxol-5-ylmethylene)-1,3-thiazolidine-2,4-dione

Conditions
ConditionsYield
With urea In neat (no solvent) for 2h; Knoevenagel Condensation;99%
With sodium acetate; acetic acid
With sodium acetate In acetic acid
With morpholine In benzene
With piperidine In toluene for 4h; Knoevenagel Condensation; Reflux; Dean-Stark;
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

piperonal
120-57-0

piperonal

5-(3',4'-methylenedioxybenzylidene)-2,4-dioxotetrahydro-1,3-thiazole
139336-28-0

5-(3',4'-methylenedioxybenzylidene)-2,4-dioxotetrahydro-1,3-thiazole

Conditions
ConditionsYield
With acetic acid; 3-amino propanoic acid at 100℃; for 3h; Knoevenagel Condensation;99%
With morpholine; acetic acid In benzene Heating;95.59%
With piperidine; acetic acid at 140℃; for 0.5h; Knoevenagel Condensation; Autoclave; Microwave irradiation;94%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

2-Cyclohexylmethyl-2,3-dihydro-benzofuran-5-carbaldehyde
131194-70-2

2-Cyclohexylmethyl-2,3-dihydro-benzofuran-5-carbaldehyde

5-[1-(2-Cyclohexylmethyl-2,3-dihydro-benzofuran-5-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione
109208-85-7

5-[1-(2-Cyclohexylmethyl-2,3-dihydro-benzofuran-5-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione

Conditions
ConditionsYield
With sodium acetate at 140℃; for 0.416667h;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

epichlorohydrin
106-89-8

epichlorohydrin

3-(2-hydroxy-3-chloropropyl)-thiazolidine-2,4-dione
141037-39-0

3-(2-hydroxy-3-chloropropyl)-thiazolidine-2,4-dione

Conditions
ConditionsYield
With tetraethylammonium chloride at 80℃; for 2h;99%
for 6h; Heating / reflux;
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde
122321-03-3

4-{2-[methyl(pyridin-2-yl)amino]ethoxy}benzaldehyde

(Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione
160596-25-8

(Z)-5-[4-[2-[N-methyl-N-(pyridin-2-yl)amino]ethoxy]benzylidene]thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperazinomethyl polystyrene In toluene at 88℃; for 24h;99%
With piperdinium acetate In toluene for 2h; Heating;95%
With piperidine; silica gel; acetic acid In toluene at 130℃; for 0.333333h; Knoevenagel condensation; Microwave irradiation; Sealed vessel;93%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-[2-[N-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl)-N-methylamino]ethoxy]benzaldehyde
187341-14-6

4-[2-[N-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl)-N-methylamino]ethoxy]benzaldehyde

5-[1-(4-{2-[(6-Benzyloxy-2,5,7,8-tetramethyl-chroman-2-ylmethyl)-methyl-amino]-ethoxy}-phenyl)-meth-(Z)-ylidene]-thiazolidine-2,4-dione

5-[1-(4-{2-[(6-Benzyloxy-2,5,7,8-tetramethyl-chroman-2-ylmethyl)-methyl-amino]-ethoxy}-phenyl)-meth-(Z)-ylidene]-thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperidine; benzoic acid at 120℃; for 2h; Condensation;99%
With piperidinium benzoate In toluene Heating;98%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzaldehyde
79421-40-2

4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzaldehyde

5-[1-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenyl]-meth-(Z)-ylidene]-thiazolidine-2,4-dione
391904-95-3

5-[1-[4-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-phenyl]-meth-(Z)-ylidene]-thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperidine In ethanol Knoevenagel condensation;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzaldehyde
79421-40-2

4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzaldehyde

5-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)benzylidene]thiazolidine-2,4-dione
349636-48-2

5-[4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)benzylidene]thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperidine In ethanol for 6h; Knoevenagel condensation; Heating;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]benzaldehyde
199114-24-4

4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]benzaldehyde

5-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]phenylmethylene]thiazolidine-2,4-dione
199113-77-4

5-[4-[2-[4-methyl-2-propyl-6-oxo-1,6-dihydropyrimidin-1-yl]ethoxy]phenylmethylene]thiazolidine-2,4-dione

Conditions
ConditionsYield
With piperidine; benzoic acid In toluene Heating;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

2,4-dibromo-1,3-thiazole
4175-77-3

2,4-dibromo-1,3-thiazole

Conditions
ConditionsYield
With phosphorus(V) oxybromide for 1.5h; Heating;99%
With phosphorus pentoxide; tetrabutylammomium bromide In toluene for 20h; Reflux; Inert atmosphere;95%
With phosphorus pentoxide; tetrabutylammomium bromide In toluene Schlenk technique; Inert atmosphere; Reflux;84%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

4-(4-formyl-2-methoxyphenoxy)isophthalonitrile
1262328-71-1

4-(4-formyl-2-methoxyphenoxy)isophthalonitrile

4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-2-methoxyphenoxy]isophthalonitrile
1262328-49-3

4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-2-methoxyphenoxy]isophthalonitrile

Conditions
ConditionsYield
With ammonium acetate; acetic acid at 100℃; Knoevenagel condensation;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

isopropyl 2-bromoacetate
29921-57-1

isopropyl 2-bromoacetate

isopropyl 2-(2,4-dioxo-3-thiazolidine)acetate
50773-26-7

isopropyl 2-(2,4-dioxo-3-thiazolidine)acetate

Conditions
ConditionsYield
Stage #1: thiazoline-2,4-dione With sodium hydride In tetrahydrofuran; mineral oil at 20℃;
Stage #2: isopropyl 2-bromoacetate In tetrahydrofuran; mineral oil for 3h; Reflux; Cooling with ice;
99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

5-fluoro-1H-indole-2,3-dione
443-69-6

5-fluoro-1H-indole-2,3-dione

C11H7FN2O4S

C11H7FN2O4S

Conditions
ConditionsYield
With water at 20℃; for 12h;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

5-iodoisatin
20780-76-1

5-iodoisatin

C11H7IN2O4S

C11H7IN2O4S

Conditions
ConditionsYield
With water at 20℃; for 12h;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

5-nitroisatin
611-09-6

5-nitroisatin

C11H7N3O6S

C11H7N3O6S

Conditions
ConditionsYield
With water at 20℃; for 12h;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

1-phenyl-indole-2,3-dione
723-89-7

1-phenyl-indole-2,3-dione

5-(3-hydroxy-2-oxo-1-phenylindolin-3-yl)thiazolidine-2,4-dione

5-(3-hydroxy-2-oxo-1-phenylindolin-3-yl)thiazolidine-2,4-dione

Conditions
ConditionsYield
With water at 20℃; for 12h;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

5-bromo-1-(hydroxymethyl)indoline-2,3-dione
53003-19-3

5-bromo-1-(hydroxymethyl)indoline-2,3-dione

5-(5-bromo-3-hydroxy-1-(hydroxymethyl)-2-oxoindolin-3-yl)thiazolidine-2,4-dione

5-(5-bromo-3-hydroxy-1-(hydroxymethyl)-2-oxoindolin-3-yl)thiazolidine-2,4-dione

Conditions
ConditionsYield
With water at 20℃; for 12h;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

ortho-bromobenzaldehyde
6630-33-7

ortho-bromobenzaldehyde

9-(2-bromophenyl)-5,7-dimethyl-5,9-dihydrothiazolo[5',4':5,6]pyrido[2,3-d]pyrimidine-2,6,8(3H,4H,7H)-trione

9-(2-bromophenyl)-5,7-dimethyl-5,9-dihydrothiazolo[5',4':5,6]pyrido[2,3-d]pyrimidine-2,6,8(3H,4H,7H)-trione

Conditions
ConditionsYield
With layered double hydroxides functionalized with (3r,5r,7r)-1-(3-(triethoxysilyl)propyl)-1,3,5,7-tetraazaadamantan-1-ium chloride In water at 100℃; for 0.333333h; Green chemistry;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

6-Amino-1,3-dimethylbarbituric acid
6642-31-5

6-Amino-1,3-dimethylbarbituric acid

2-Fluorobenzaldehyde
446-52-6

2-Fluorobenzaldehyde

9-(2-fluorophenyl)-5,7-dimethyl-5,9-dihydrothiazolo[5',4':5,6]pyrido[2,3-d]pyrimidine-2,6,8(3H,4H,7H)-trione

9-(2-fluorophenyl)-5,7-dimethyl-5,9-dihydrothiazolo[5',4':5,6]pyrido[2,3-d]pyrimidine-2,6,8(3H,4H,7H)-trione

Conditions
ConditionsYield
With layered double hydroxides functionalized with (3r,5r,7r)-1-(3-(triethoxysilyl)propyl)-1,3,5,7-tetraazaadamantan-1-ium chloride In water at 100℃; for 0.0833333h; Green chemistry;99%
2,4-thiazolidinedion
2295-31-0

2,4-thiazolidinedion

benzaldehyde
100-52-7

benzaldehyde

5-benzylidene-2,4-thiazolidinedione
3774-99-0

5-benzylidene-2,4-thiazolidinedione

Conditions
ConditionsYield
With thiourea; urea at 110℃; for 0.0833333h; Knoevenagel condensation; Neat (no solvent);98%
With urea/choline chloride eutectic salt at 80℃; for 0.583333h; Catalytic behavior; Temperature; Aldol Condensation;97%
With Ce1Mg0.6Zr0.4O2 In ethanol; water at 75℃; for 1.5h; Knoevenagel Condensation;96%

2,4-Thiazolidinedione Consensus Reports

Reported in EPA TSCA Inventory.

2,4-Thiazolidinedione Specification

The 2,4-Thiazolidinedione, with the CAS registry number 2295-31-0,is also known as Diisobutyl ketone; Isovalerone. It belongs to the product categories of Thiazolidine-2,4-dione. This chemical's molecular formula is C3H3NO2S and molecular weight is 117.12.Its EINECS number is 218-941-2. What's more,Its systematic name is 2,4-Thiazolidinedione. It is a White to Off-White Powder which is used as inhibitor of enzyme.It is irritating to eyes, respiratory system and skin .When you use it,you should avoid contact with skin and eyes,and wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .In addition, 2,4-Thiazolidinedione could be stable under normal temperatures and pressures. It is not compatible with strong oxidizing agents, and you must not take it with incompatible materials, strong oxidants. And also prevent it to broken down into hazardous decomposition products: nitrogen oxides, carbon monoxide, oxides of sulfur, irritating and toxic fumes and gases, carbon dioxide, nitrogen.

Physical properties about 2,4-Thiazolidinedione are:
(1)ACD/LogP:  -0.07; (2)# of Rule of 5 Violations:  0; (3)ACD/LogD (pH 5.5):  -0.11; (4)ACD/LogD (pH 7.4):  -0.99; (5)ACD/BCF (pH 5.5):  1.00; (6)ACD/BCF (pH 7.4):  1.00; (7)ACD/KOC (pH 5.5):  19.86; (8)ACD/KOC (pH 7.4):  2.64; (9)#H bond acceptors:  3; (10)#H bond donors:  1; (11)#Freely Rotating Bonds:  0; (12)Index of Refraction:  1.577; (13)Molar Refractivity:  25.606 cm3; (14)Molar Volume:  77.222 cm3; (15)Surface Tension:  56.2439994812012 dyne/cm; (16)Density:  1.517 g/cm3; (17)Flash Point:  138.669 °C; (18)Enthalpy of Vaporization:  54.614 kJ/mol; (19)Boiling Point:  305.678 °C at 760 mmHg; (20)Vapour Pressure:  0.00100000004749745 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES:O=C1NC(=O)SC1;
(2)Std. InChI:InChI=1S/C3H3NO2S/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6);
(3)Std. InChIKey:ZOBPZXTWZATXDG-UHFFFAOYSA-N.

The toxicity data of 2,4-Thiazolidinedione are as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   National Technical Information Service. Vol. AD277-689,
mouse LD50 subcutaneous 335mg/kg (335mg/kg)   Farmaco, Edizione Scientifica. Vol. 9, Pg. 274, 1954.

 

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