185698

Barbituric acid

ReagentPlus^®, 99%

• Synonym(s): 2,4,6-Trihydroxypyrimidine, Malonylurea
• Empirical Formula (Hill Notation): C₄H₄N₂O₃
• CAS Number: 67-52-7
• Molecular Weight: 128.09
• Beilstein/REAXYS Number: 120502
• EC Number: 200-658-0
• MDL number: MFCD00006666
• UNSPSC Code: 12352100
• PubChem Substance ID: 24851157
• NACRES: NA.21

Properties

• Quality Level: 200
• product line: ReagentPlus^®
• assay: 99%
• form: powder
• mp: 248-252 °C ((lit.)); 248-252 °C (dec.) (lit.)
• SMILES string: [O=C1CC(=O)NC(=O)N1]; O=C1CC(=O)NC(=O)N1
• InChI: [1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)]; 1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)
• InChI key: [HNYOPLTXPVRDBG-UHFFFAOYSA-N]; HNYOPLTXPVRDBG-UHFFFAOYSA-N

Description

General description

Barbituric acid is a useful acid for organic and drug syntheses. Its dihydrate form can be synthesized from barbituric acid via crystallization from aqueous solution. Crystal structure of barbituric acid (in tautomeric form) has been investigated by a three dimensional fourier transform method. Its enol crystal form has been reported to be thermodynamically stable.

Application

Barbituric acid (BA) may be used in the preparation of the corresponding hemiaminals, via chemoselective reduction in the presence of SmI₂/H₂O reagent. It may be used in the preparation of BA- modified conjugated carbon nitride nanosheets.

It may be used to synthesize:

• 5-ylidenebarbituric acid derivatives via Knoevenagel condensation with aromatic and α,β-conjugated aromatic aldehydes
• 5-diaminomethylenebarbiturates by reacting with substituted carbodiimides

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 1
• flash_point_f: 302.0 °F - closed cup
• flash_point_c: 150.00 °C - closed cup
• ppe: Eyeshields, Gloves, type N95 (US)