4-[[2-methyl-1-oxo-1,2-dihydrophthalazin-4-yl]methoxy]benzaldehyde
A
2,4-thiazolidinedion
B
5-[4-[[2-Methyl-1-oxo-1,2-dihydro-phthalazin-4-yl]methoxy]phenyl methylene]thiazolidin-2,4-dione
Conditions | Yield |
---|---|
A 98% B n/a |
Conditions | Yield |
---|---|
Stage #1: thiourea; chloroacetyl chloride In water for 0.333333h; Stage #2: With hydrogenchloride In water for 7 - 8h; Reflux; | 94% |
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With hydrogenchloride; water for 12h; Reflux; | 89% |
With hydrogenchloride; ethanol Reflux; | 83% |
With hydrogenchloride; water for 10h; Reflux; | 77.2% |
Conditions | Yield |
---|---|
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
A
2,4-thiazolidinedion
B
5-[4-[2-[4-Phenyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione
Conditions | Yield |
---|---|
A 87% B n/a |
Conditions | Yield |
---|---|
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
A
2,4-thiazolidinedion
B
5-[4-[2-[4-ethyl-1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione
Conditions | Yield |
---|---|
A 83% B n/a |
Conditions | Yield |
---|---|
With water; potassium carbonate In PEG 400 at 80℃; for 2h; | 82% |
(2,4-dimethylphenyl)thiourea
chloroacetyl chloride
2,4-thiazolidinedion
Conditions | Yield |
---|---|
With water; potassium carbonate In PEG 400 at 80℃; for 2h; | 82% |
2-allylamino-Δ2-thiazolin-4-one
2,4-thiazolidinedion
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 81% |
4-[2-[1-oxo-1,2-dihydrophthalazin-2-yl]ethoxy]benzaldehyde
A
2,4-thiazolidinedion
B
5-[4-[2-[1-oxo-1,2-dihydro-phthalazin-2-yl]ethoxy]phenyl methylene]thiazolidin-2,4-dione
Conditions | Yield |
---|---|
A 80% B n/a |
Conditions | Yield |
---|---|
With water; potassium carbonate In PEG 400 at 80℃; for 2h; | 80% |
Conditions | Yield |
---|---|
With water; potassium carbonate In PEG 400 at 80℃; for 2h; | 80% |
Conditions | Yield |
---|---|
With water; potassium carbonate In PEG 400 at 80℃; for 2h; | 79% |
Conditions | Yield |
---|---|
With water; potassium carbonate In PEG 400 at 80℃; for 2h; | 78% |
Conditions | Yield |
---|---|
In water at 100℃; for 24h; | 78% |
2-(phenylimino)thiazolidin-4-one
A
2,4-thiazolidinedion
B
3-phenyl-2,4-thiazolidinedione
Conditions | Yield |
---|---|
With hydrogenchloride for 1h; Heating; | A 21% B 65% |
Conditions | Yield |
---|---|
With water; potassium carbonate In PEG 400 at 80℃; for 2h; | 65% |
Conditions | Yield |
---|---|
With chloroacetic acid for 3h; Heating; | 62% |
With chloroacetic acid In water for 5h; Heating; | 60% |
2-acetylallylamino-4-acetoxythiazole
2,4-thiazolidinedion
Conditions | Yield |
---|---|
With hydrogenchloride for 2h; Heating; | 56% |
2,4-thiazolidinedion
Conditions | Yield |
---|---|
In ethanol; water for 2h; Reflux; | 44% |
Conditions | Yield |
---|---|
With water |
Conditions | Yield |
---|---|
With hydrogenchloride at 130℃; |
2-phenylaminothiazol-4-one
A
2,4-thiazolidinedion
B
3-phenyl-2,4-thiazolidinedione
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With hydrogenchloride beim Eindampfen; |
Conditions | Yield |
---|---|
beim Schmelzen; | |
With hydrogenchloride |
diethyl 2-thiocyanatomalonate
2,4-thiazolidinedion
Conditions | Yield |
---|---|
With hydrogenchloride beim Eindampfen; |
2,4-thiazolidinedion
(2S)-benzyl-6-(formyl)-2,3-dihydro-4H-benzopyran
5-[1-((S)-2-Benzyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione
Conditions | Yield |
---|---|
With sodium acetate at 140℃; for 0.416667h; | 100% |
2,4-thiazolidinedion
(2R)-benzyl-6-(formyl)-2,3-dihydro-4H-benzopyran
5-[1-((R)-2-Benzyl-chroman-6-yl)-meth-(E)-ylidene]-thiazolidine-2,4-dione
Conditions | Yield |
---|---|
With sodium acetate at 140℃; for 0.416667h; | 100% |
2,4-thiazolidinedion
4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde
5-{4-[2-(5-ethyl-pyridin-2-yl)ethoxy]benzylidene}-2,4-thiazolidinedione
Conditions | Yield |
---|---|
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 ethanol | 21.6 g (57.6%) |
2,4-thiazolidinedion
(S)-4-<<(quinolin-2-yl)pyrrolidin-2-yl>methoxy>benzaldehyde
Conditions | Yield |
---|---|
With piperidine; benzoic acid In toluene for 4h; Heating; | 100% |
4-[N-benzyl-N-[3-isopropyl-4-(methoxymethoxy)phenyl]amino]-3,5-dimethylbenzaldehyde
2,4-thiazolidinedion
(Z)-5-[4-[N-benzyl-N-[3-isopropyl-4-(methoxymethoxy)phenyl]amino]-3,5-dimethylphenylmethylene]thiazolidine-2,4-dione
Conditions | Yield |
---|---|
With piperidine In ethanol for 20h; Knoevenagel condensation; Heating; | 100% |
2,4-thiazolidinedion
Conditions | Yield |
---|---|
With piperidine; benzoic acid In toluene for 1h; Heating / reflux; | 100% |
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid In toluene Reflux; | 100% |
2,4-thiazolidinedion
4,7-dichloroisatin
Conditions | Yield |
---|---|
With water at 20℃; for 12h; | 100% |
piperidine
2,4-thiazolidinedion
4-[2-(5-ethylpyridyl)ethoxy]benzaldehyde
5-{4-[2-(5-ethylpyridn-2-yl)ethoxy]benzylidene}-2,4-thiazolidene dione
Conditions | Yield |
---|---|
In ethanol | 99.5% |
In ethanol | 2.14 g (64%) |
In ethanol |
2,4-thiazolidinedion
4-hydroxy-benzaldehyde
5-[(4-hydroxyphenyl)methylene]-2,4-thiazolidinedione
Conditions | Yield |
---|---|
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
piperonal
5-([1,3]benzodioxol-5-ylmethylene)-1,3-thiazolidine-2,4-dione
Conditions | Yield |
---|---|
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
piperonal
5-(3',4'-methylenedioxybenzylidene)-2,4-dioxotetrahydro-1,3-thiazole
Conditions | Yield |
---|---|
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
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
Conditions | Yield |
---|---|
With sodium acetate at 140℃; for 0.416667h; | 99% |
2,4-thiazolidinedion
epichlorohydrin
3-(2-hydroxy-3-chloropropyl)-thiazolidine-2,4-dione
Conditions | Yield |
---|---|
With tetraethylammonium chloride at 80℃; for 2h; | 99% |
for 6h; Heating / reflux; |
2,4-thiazolidinedion
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
Conditions | Yield |
---|---|
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
4-[2-[N-(6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl)-N-methylamino]ethoxy]benzaldehyde
Conditions | Yield |
---|---|
With piperidine; benzoic acid at 120℃; for 2h; Condensation; | 99% |
With piperidinium benzoate In toluene Heating; | 98% |
2,4-thiazolidinedion
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
Conditions | Yield |
---|---|
With piperidine In ethanol Knoevenagel condensation; | 99% |
2,4-thiazolidinedion
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
Conditions | Yield |
---|---|
With piperidine In ethanol for 6h; Knoevenagel condensation; Heating; | 99% |
2,4-thiazolidinedion
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
Conditions | Yield |
---|---|
With piperidine; benzoic acid In toluene Heating; | 99% |
Conditions | Yield |
---|---|
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
4-(4-formyl-2-methoxyphenoxy)isophthalonitrile
4-[4-(2,4-dioxothiazolidin-5-ylidenemethyl)-2-methoxyphenoxy]isophthalonitrile
Conditions | Yield |
---|---|
With ammonium acetate; acetic acid at 100℃; Knoevenagel condensation; | 99% |
2,4-thiazolidinedion
isopropyl 2-bromoacetate
isopropyl 2-(2,4-dioxo-3-thiazolidine)acetate
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
With water at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 12h; | 99% |
Conditions | Yield |
---|---|
With water at 20℃; for 12h; | 99% |
2,4-thiazolidinedion
5-bromo-1-(hydroxymethyl)indoline-2,3-dione
Conditions | Yield |
---|---|
With water at 20℃; for 12h; | 99% |
2,4-thiazolidinedion
6-Amino-1,3-dimethylbarbituric acid
ortho-bromobenzaldehyde
Conditions | Yield |
---|---|
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
6-Amino-1,3-dimethylbarbituric acid
2-Fluorobenzaldehyde
Conditions | Yield |
---|---|
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% |
Conditions | Yield |
---|---|
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% |
Reported in EPA TSCA Inventory.
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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