2-Thiobarbituric acid

Base Information

• Chemical Name: 2-Thiobarbituric acid
• CAS No.: 504-17-6
• Deprecated CAS: 118738-55-9,121477-82-5,122508-78-5,124558-04-9,148021-12-9,5525-79-1,5658-01-5,91759-32-9,126660-87-5,127726-79-8,136771-68-1,145783-11-5,157796-99-1,709611-98-3,773866-14-1,863970-61-0,878388-18-2,886365-65-7,924832-30-4,1049677-34-0,1076199-44-4,1116339-76-4,1228272-12-5,1236029-05-2,1256721-97-7,1262632-60-9,1287678-13-0,1313510-54-1,1356834-57-5,1369625-13-7,1393847-12-5,956086-95-6,1423769-56-5,1583284-74-5,1612185-40-6,1622940-33-3,1683524-47-1,1696408-94-2,1773529-72-8,1802859-83-1,1825368-06-6,1850381-77-9,2171459-69-9,1049677-34-0,1076199-44-4,1116339-76-4,121477-82-5,122508-78-5,1228272-12-5,1236029-05-2,1256721-97-7,1262632-60-9,126660-87-5,127726-79-8,1287678-13-0,1313510-54-1,1356834-57-5,136771-68-1,1369625-13-7,1393847-12-5,1423769-56-5,145783-11-5,148021-12-9,157796-99-1,1583284-74-5,1612185-40-6,1622940-33-3,1683524-47-1,1696408-94-2,1773529-72-8,1802859-83-1,1825368-06-6,1850381-77-9,5525-79-1,5658-01-5,709611-98-3,773866-14-1,863970-61-0,878388-18-2,886365-65-7,91759-32-9,924832-30-4,956086-95-6
• Molecular Formula: C4H4N2O2S
• Molecular Weight: 144.154
• Hs Code.: 29335995
• European Community (EC) Number: 207-985-8
• NSC Number: 4733
• UNII: M1YZW5SS7C
• DSSTox Substance ID: DTXSID7060124
• Nikkaji Number: J12.869D
• Wikipedia: Thiobarbituric_acid
• Wikidata: Q418230
• Metabolomics Workbench ID: 54866
• ChEMBL ID: CHEMBL584805
• Mol file: 504-17-6.mol

Synonyms:2-mercaptobarbituric acid;2-thiobarbituric acid;thiobarbiturate;thiobarbituric acid;thiobarbituric acid, monosodium salt

Chemical Property of 2-Thiobarbituric acid

Chemical Property:

• Appearance/Colour: off-white to yellow powder
• Melting Point: 245 °C (dec.)(lit.)
• Refractive Index: 1.645
• Boiling Point: 463.4 °C at 760 mmHg
• PKA: 3.96±0.20(Predicted)
• Flash Point: 234 °C
• PSA: 90.29000
• Density: 1.69 g/cm³
• LogP: -0.43500
• Storage Temp.: Controlled Substance, -20°C Freezer
• Solubility.: 50g/l slightly soluble
• Water Solubility.: <6 g/L (20℃)
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 143.99934855
• Heavy Atom Count: 9
• Complexity: 171

Purity/Quality:

99% ^*data from raw suppliers

2-Thiobarbituric acid ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyrimidines
• Canonical SMILES: C1C(=O)NC(=S)NC1=O
• Uses: 4,6-Dihydroxy-2-mercaptopyrimidine can be used to quantitate lipopolysaccharides, carrageenan, and sialic acids, and to detect lipid hydroperoxides and lipid oxidation. 2-Thiobarbituric acid has been used to measure malondialdehyde (MDA) in lipid peroxidation assay.

Technology Process of 2-Thiobarbituric acid

There total 11 articles about 2-Thiobarbituric acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

thiourea (17356-08-0) + diethyl malonate (105-53-3) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6,157796-99-1,924832-30-4)

Guidance literature:

With sodium; In ethanol; for 6h; Reflux;

DOI:10.13005/ojc/330136

Reference yield: 67.0%

thiourea (17356-08-0) + diethyl malonate (105-53-3) → 6-hydroxy-2-mercapto-3H-pyrimidin-4-one (504-17-6)

Guidance literature:

thiourea; diethyl malonate; With sodium ethanolate; In ethanol; for 3h; Reflux;

With water; pH=7 - 8;

DOI:10.1016/j.bmc.2009.04.061

Reference yield: 25.0%

Propargylic aldehyde (624-67-9) + 5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 4,6-dihydroxy-2-mercaptopyrimidine (504-17-6,157796-99-1,924832-30-4) + 3-(5'-Iodo-2'-deoxyuridin-3'-yl)prop-2-enal

Guidance literature:

With triethylamine; In N-methyl-acetamide; ethyl acetate;

upstream raw materials:

sodium diethylmalonate

thiourea

malonic acid dimethyl ester

6-Amino-2-thiouracil

Downstream raw materials:

5-(2-β-D-glucopyranosyloxy-benzylidene)-2-thio-barbituric acid

5-(furan-2'-ylmethylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione

7,11-Bis-(4-methoxy-phenyl)-3-thioxo-2,4-diaza-spiro[5.5]undecane-1,5,9-trione

7,11-Bis-(3-methoxy-phenyl)-3-thioxo-2,4-diaza-spiro[5.5]undecane-1,5,9-trione

Refernces

• 1、 Eldin A. Osman, Essam,Hanafy, Noura S.,George, Riham F.,El-Moghazy, Samir M.. "Design and synthesis of some barbituric and 1,3-dimethylbarbituric acid derivatives: A non-classical scaffold for potential PARP1 inhibitors". . . Retrieved 2020/09/16.
• 2、 Sahoo, Jyotirmaya,Kumar, Paidesetty Sudhir. "Study of solvatochromic behavior and antimicrobial activities of some newly synthesized bis-azo-dapsone congeners". . p. 724 - 733. Retrieved 2017/01/18.