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2295-31-0

Basic Information
CAS No.: 2295-31-0
Name: 2,4-Thiazolidinedione
Article Data: 140
Cas Database
Molecular Structure:
Molecular Structure of 2295-31-0 (2,4-Thiazolidinedione)
Formula: C3H3NO2S
Molecular Weight: 117.128
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;
EINECS: 218-941-2
Density: 1.516 g/cm3
Melting Point: 125-127 °C(lit.)
Boiling Point: 305.7 °C at 760 mmHg
Flash Point: 138.7 °C
Solubility: Soluble in water (30 mg/ml at 3°C), methanol, DMSO, ethanol, and ethyl ether.
Appearance: White to off-white powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 24/25-36-26
Transport Information: N/A
PSA: 71.47000
LogP: 0.29820
Synthetic route
214282-10-7

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

A

2295-31-0

2,4-thiazolidinedion

B

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
17356-08-0

thiourea

79-04-9

chloroacetyl chloride

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%
17356-08-0

thiourea

79-11-8

chloroacetic acid

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%
556-90-1

pseudothiohydantoin

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%
79-04-9

chloroacetyl chloride

103-85-5

monophenylthiourea

2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;88%
214282-18-5

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

A

2295-31-0

2,4-thiazolidinedion

B

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
622-52-6

p-methylphenylthiourea

79-04-9

chloroacetyl chloride

2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;84%
214282-16-3

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

A

2295-31-0

2,4-thiazolidinedion

B

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
2646-30-2

1-(4-bromophenyl)thiourea

79-04-9

chloroacetyl chloride

2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;82%
16738-20-8

(2,4-dimethylphenyl)thiourea

79-04-9

chloroacetyl chloride

2295-31-0

2,4-thiazolidinedion

Conditions
ConditionsYield
With water; potassium carbonate In PEG 400 at 80℃; for 2h;82%
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Reported in EPA TSCA Inventory.

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.