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185698

Sigma-Aldrich

Barbituric acid

ReagentPlus®, 99%

Synonym(s):

2,4,6-Trihydroxypyrimidine, Malonylurea

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About This Item

Empirical Formula (Hill Notation):
C4H4N2O3
CAS Number:
67-52-7
Molecular Weight:
128.09
Beilstein:
120502
EC Number:
200-658-0
MDL number:
MFCD00006666
UNSPSC Code:
12352100
PubChem Substance ID:
24851157
NACRES:
NA.21

Quality Level

200

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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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 Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

302.0 °F - closed cup

Flash Point(C)

150.00 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

185698-25G:
185698-500G:
185698-100G:
185698-VAR:
185698-BULK:

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Certificates of Analysis (COA)

Lot/Batch Number
WXBD4902V
WXBD3691V
WXBD1487V
WXBC8508V
WXBC6794V

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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)
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)
The crystal structure of anhydrous barbituric acid.
Bolton W.
Acta Crystallographica, 16(3), 166-173 (1963)
Preparation of 5-diaminomethylenebarbiturates by barbituric acid addition to carbodiimides.
Jursic BS et al.
Tetrahedron, 59(19), 3427-3432 (2003)
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