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2-Thiobarbituric acid

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2-Thiobarbituric acid Basic information

Product Name:
2-Thiobarbituric acid
Synonyms:
  • 6(1H,5H)-Pyrimidinedione,dihydro-2-thioxo-4
  • austranal
  • bathyran
  • Dihydro-2-thioxo-4,6-(1H,5H)-pyrimidinedione
  • dihydro-2-thioxo-4,6(1h,5h)-pyrimidinedione
  • Mealonylthiourea
  • Thiobarbituicacid
  • Thiobarbituric
CAS:
504-17-6
MF:
C4H4N2O2S
MW:
144.15
EINECS:
207-985-8
Product Categories:
  • Heterocyclic Compounds
  • Aromatics
  • PYRIMIDINE
  • Bases & Related Reagents
  • Nucleotides
  • Sulfur & Selenium Compounds
  • Aromatics Compounds
  • Building Blocks
  • C4 to C5
  • Chemical Synthesis
  • Heterocyclic Building Blocks
  • Pyrimidines
  • Heterocycle-Pyrimidine series
  • 504-17-6
Mol File:
504-17-6.mol
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2-Thiobarbituric acid Chemical Properties

Melting point:
245 °C (dec.)(lit.)
Density 
1.451 (estimate)
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)
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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
13-23
TSCA 
Yes
HS Code 
29335995

MSDS

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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.

Purification Methods

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

2-Thiobarbituric acid Preparation Products And Raw materials

Raw materials

Preparation Products

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