185698
Barbituric acid
99%, powder, ReagentPlus®
Synonym(s):
2,4,6-Trihydroxypyrimidine, Malonylurea
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About This Item
Empirical Formula (Hill Notation):
C4H4N2O3
CAS Number:
Molecular Weight:
128.09
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.21
EC Number:
200-658-0
MDL number:
Beilstein/REAXYS Number:
120502
Assay:
99%
Form:
powder
Product Name
Barbituric acid, ReagentPlus®, 99%
Quality Level
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
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
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Storage Class
11 - Combustible Solids
wgk
WGK 1
flash_point_f
302.0 °F - closed cup
flash_point_c
150.00 °C - closed cup
ppe
Eyeshields, Gloves, type N95 (US)
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Preparation of 5-diaminomethylenebarbiturates by barbituric acid addition to carbodiimides.
Jursic BS et al.
Tetrahedron, 59(19), 3427-3432 (2003)
Madalynn G Marshall et al.
Angewandte Chemie (International ed. in English), 55(4), 1309-1312 (2015-12-15)
The thermodynamically stable enol crystal form of barbituric acid, previously prepared as powder by grinding or slurry methods, has been obtained as single crystals by slow cooling from methanol solution. The selection of the enol crystal was facilitated by a
The crystal structure of anhydrous barbituric acid.
Bolton W.
Acta Crystallographica, 16(3), 166-173 (1963)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 185698-25G | 04061835252848 |
| 185698-100G | 04061835252831 |
| 185698-500G | 04061835252855 |