185698
Barbituric acid
99%, powder, ReagentPlus®
Synonyme(s) :
2,4,6-Trihydroxypyrimidine, Malonylurea
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A propos de cet article
Formule empirique (notation de Hill) :
C4H4N2O3
Numéro CAS:
Poids moléculaire :
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
Service technique
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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
Classe de stockage
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)
A simple method for knoevenagel condensation of a, ?-conjugated and aromatic aldehydes with barbituric acid.
Jursic BS.
Journal of Heterocyclic Chemistry, 38(3), 655-657 (2001)
Photocatalytic reduction of CO2 by graphitic carbon nitride polymers derived from urea and barbituric acid.
Qin J, et al.
Applied Catalysis. B, Environmental, 179, 1-8 (2015)