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185698

Sigma-Aldrich

Barbituric acid

ReagentPlus®, 99%

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Synonym(s):
2,4,6-Trihydroxypyrimidine, Malonylurea
Empirical Formula (Hill Notation):
C4H4N2O3
CAS Number:
Molecular Weight:
128.09
Beilstein/REAXYS Number:
120502
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.21

Quality Level

product line

ReagentPlus®

assay

99%

form

powder

mp

248-252 °C (dec.) (lit.)

SMILES string

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)

InChI key

HNYOPLTXPVRDBG-UHFFFAOYSA-N

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1 of 4

This Item
8.001331.001321279019
vibrant-m

185698

Barbituric acid

vibrant-m

8.00133

Barbituric acid

vibrant-m

1.00132

Barbituric acid

vibrant-m

1279019

Fluorouracil Related Compound A

assay

99%

assay

≥99% (acidimetric)

assay

≥99% (acidimetric)

assay

-

mp

248-252 °C (dec.) (lit.)

mp

250-252 °C (decomposition)

mp

250-252 °C (decomposition)

mp

248-252 °C (dec.) (lit.)

form

powder

form

solid

form

solid

form

powder

product line

ReagentPlus®

product line

-

product line

EMSURE®

product line

-

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

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)


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Customers Also Viewed

Slide 1 of 4

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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)
Selective reduction of barbituric acids using SmI2/H2O: synthesis, reactivity, and structural analysis of tetrahedral adducts.
Michal Szostak et al.
Angewandte Chemie (International ed. in English), 52(48), 12559-12563 (2013-10-15)
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)
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)

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