2-Thiobarbituric acid

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
2-Thiobarbituric acid Structure
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
pka3.96±0.20(Predicted)
color Clear colorless
PH1.7-1.9 (10g/l, H2O, 20℃)
Water Solubility <6 g/L (20 ºC)
BRN 120663
Stability:Stable. Incompatible with strong oxidizing agents.
InChIKeyRVBUGGBMJDPOST-UHFFFAOYSA-N
CAS DataBase Reference504-17-6(CAS DataBase Reference)
NIST Chemistry Reference4,6(1H,5h)-pyrimidinedione, dihydro-2-thioxo-(504-17-6)
EPA Substance Registry System4,6(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
13-23
TSCA Yes
HS Code 29335995
MSDS Information
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2-Thiobarbituric acid English
ACROS English
SigmaAldrich English
ALFA English
2-Thiobarbituric acid Usage And Synthesis
Chemical PropertiesOff-White to Yellow Powder. soluble in hot water, alcohol, ether, alkali and sodium carbonate solution, slightly soluble in water.
Uses4,6-Dihydroxy-2-mercaptopyrimidine can be used to quantitate lipopolysaccharides, carrageenan, and sialic acids, and to detect lipid hydroperoxides and lipid oxidation.
Uses2-Thiobarbituric acid has been used to measure malondialdehyde (MDA) in lipid peroxidation assay.
Preparation2-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.
DefinitionChEBI: 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 Description2-Thiobarbituric acid is a molecule made up of heteroatoms: nitrogen, sulphur and oxygen.
Biochem/physiol Actions2-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 MethodsCrystallise 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 materialsSodium Methoxide-->Thiourea
Preparation Products2-Methylthio-4,6-pyrimidinedione-->4,6-Dihydroxy-2-methythiopyrimidine-->5-FURFURYLIDENE-2-THIOBARBITURIC ACID
Barbituric acid Solvent Red 43 Calcium thioglycolate 3-Mercaptopropionic acid Sodium thioglycolate Ethyl 2-(Chlorosulfonyl)acetate Ascoric Acid 2-Ethylhexyl mercaptoacetate 5-(4-ISOPROPYLBENZYLIDENE)-2-THIOXODIHYDROPYRIMIDINE-4,6(1H,5H)-DIONE 4,6-Dihydroxypyrimidine Folic acid 2-Thiobarbituric acid Mercaptoacetic acid 2-ISOPROPYL-6-METHYL-4-PYRIMIDINOL POTASSIUM THIOGLYCOLATE 2-Mercaptoethanol Succimer 5-(aminomethylene)-1,3-diphenyl-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione

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