2-Thiobarbituric acid Chemical Properties

Melting point:

245 °C (dec.)(lit.)

Density 

1.451 (estimate)

bulk density

210kg/m3

refractive index 

1.7690 (estimate)

storage temp. 

Inert atmosphere,2-8°C

solubility 

50g/l slightly soluble

form 

Liquid

pka

3.96±0.20(Predicted)

color 

Clear colorless

PH

1.7-1.9 (10g/l, H2O, 20℃)

Water Solubility 

<6 g/L (20 ºC)

BRN 

120663

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

RVBUGGBMJDPOST-UHFFFAOYSA-N

CAS DataBase Reference

504-17-6(CAS DataBase Reference)

NIST Chemistry Reference

4,6(1H,5h)-pyrimidinedione, dihydro-2-thioxo-(504-17-6)

EPA Substance Registry System

4,6(1H,5H)-Pyrimidinedione, dihydro-2-thioxo- (504-17-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-37/39-26

RIDADR 

UN 3335

WGK Germany 

2

RTECS 

CQ7700000

F 

13-23

TSCA 

Yes

HS Code 

29335995

MSDS

• Language:English Provider:2-Thiobarbituric acid
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2-Thiobarbituric acid Usage And Synthesis

Chemical Properties

Off-White to Yellow Powder. soluble in hot water, alcohol, ether, alkali and sodium carbonate solution, slightly soluble in water.

Uses

2-Thiobarbituric acid has been used to measure malondialdehyde (MDA) in lipid peroxidation assay.

Uses

4,6-Dihydroxy-2-mercaptopyrimidine can be used to quantitate lipopolysaccharides, carrageenan, and sialic acids, and to detect lipid hydroperoxides and lipid oxidation.

Preparation

2-thiobarbituric acid was synthesized by the reaction of diethyl malonate with thiourea. Dissolve thiourea in methanol, add sodium methoxide and diethyl malonate, heat under reflux for 4-5h, then distill under reduced pressure to recover methanol to the end, and add hydrochloric acid to acidify to pH 1-2 after cooling. After standing overnight, thiobarbituric acid crystals were precipitated, filtered, and recrystallized with water to obtain the pure product.

Definition

ChEBI: 2-thiobarbituric acid is a barbiturate, the structure of which is that of barbituric acid in which the oxygen at C-2 is replaced by sulfur. It has a role as a reagent and an allergen.

General Description

2-Thiobarbituric acid is a molecule made up of heteroatoms: nitrogen, sulphur and oxygen.

Biochem/physiol Actions

2-Thiobarbituric acid (TBA) is useful to quantitate lipopolysaccharides, carrageenan, and sialic acids. It is also used to detect lipid hydroperoxides and lipid oxidation. It has applications in the field of medicine and biochemistry. TBA may possess the ability to prevent metal corrosion.

Synthesis

The general procedure for the synthesis of 4,6-dihydroxy-2-mercaptopyrimidine from the compound (CAS: 17356-08-0) and diethyl malonate was as follows: 6 g (0.25 mol) of sodium metal was dissolved in 200 mL of anhydrous ethanol. Subsequently, 15 g (0.25 mol) of thiourea and 40 mL of diethyl malonate were sequentially added to this solution. The reaction mixture was placed in an oil bath and refluxed for 6 hours. Upon completion of the reaction, ethanol was recovered by vacuum distillation. The clarified solution obtained was washed with water and then cooled in an ice bath overnight. After cooling, the solution was acidified with hydrochloric acid (HCl). The crude product precipitated after acidification was collected, washed with 50 mL of water and dried in an oven at 105°C-110°C for about 4 hours. Finally, thiobarbituric acid (TBA) was purified by ethanol recrystallization to give a melting point of about 243°C and a yield of about 80%.

Purification Methods

Crystallise it from water. [Beilstein 24 H 476, 24 I 414, 24 II 275, 24 III/IV 1884.]

References

[1] Oriental Journal of Chemistry, 2017, vol. 33, # 1, p. 304 - 317
[2] Medicinal Chemistry Research, 2013, vol. 22, # 9, p. 4075 - 4086
[3] Chemistry of Natural Compounds, 2001, vol. 37, # 6, p. 543 - 550
[4] Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1778 - 1786
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 14, p. 3953 - 3956

2-Thiobarbituric acid(504-17-6)Related Product Information

• Solvent Red 43
• Calcium thioglycolate
• Sodium thioglycolate
• 3-Mercaptopropionic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Folic acid
• POTASSIUM THIOGLYCOLATE
• 2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL
• Barbituric acid
• 4,6-Dihydroxypyrimidine
• 2-Ethylhexyl mercaptoacetate
• Mercaptoacetic acid
• Succimer
• Ascoric Acid
• 2-Mercaptoethanol
• 1,3-DIETHYL-2-THIOBARBITURIC ACID
• 4,6-DIHYDROXY-2-MERCAPTOPYRIMIDINE SODIUM SALT
• Pyrimidine