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Merck

11709

Barbituric acid

for spectrophotometric det. of cyanide, ≥99.5%

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
UNSPSC Code:
41115710
NACRES:
NA.21
PubChem Substance ID:
329749535
EC Number:
200-658-0
Beilstein/REAXYS Number:
120502
MDL number:
MFCD00006666

Product Name

Barbituric acid, for spectrophotometric det. of cyanide, ≥99.5%

InChI key

HNYOPLTXPVRDBG-UHFFFAOYSA-N

InChI

1S/C4H4N2O3/c7-2-1-3(8)6-4(9)5-2/h1H2,(H2,5,6,7,8,9)

SMILES string

O=C1CC(=O)NC(=O)N1

assay

≥99.5% (HPLC)
≥99.5%

form

solid

quality

for spectrophotometric det. of cyanide

technique(s)

UV/Vis spectroscopy: suitable

ign. residue

≤0.05%

mp

248-252 °C (dec.) (lit.)

anion traces

chloride (Cl-): ≤50 mg/kg
sulfate (SO42-): ≤500 mg/kg

cation traces

Ca: ≤10 mg/kg
Cd: ≤5 mg/kg
Co: ≤5 mg/kg
Cr: ≤5 mg/kg
Cu: ≤5 mg/kg
Fe: ≤5 mg/kg
Mg: ≤10 mg/kg
Mn: ≤5 mg/kg
Ni: ≤5 mg/kg
Pb: ≤5 mg/kg
Zn: ≤5 mg/kg

Quality Level

100

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Application

Barbituric acid with aromatic aldehydes was used in an experimental study, meant to demonstrate the increased efficiency of Knoevenagel condensation reaction for barbituric acid and various aromatic aldehydes on basic alumina, in the absence of organic solvents under microwave irradiation. It may also be used in electrochemical oxidation of iodine, using cyclic voltammetry and controlled-potential coulometry.

General description

Barbituric acid is also known as malonurea or 6-hydroxyuracil, it is an odourless powder and is soluble in water. It has a very high pharmacological activity and can be used to synthesize addition derivatives of it, to be used in novel drug discovery. It basically acts on the central nervous system (CNS) depressants, thereby possessing a wide range from mild sedation to total anaesthesia.

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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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3627
BCCM4952
BCCJ0363
BCCJ0578
BCCJ0230

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Electrochemical study of iodide in the presence of barbituric acid. Application to coulometric titration of barbituric acid.
Nematollahi D and Hesari M
Microchemical Journal, Devoted to the Application of Microtechniques in All Branches of Science, 70 (1), 7-11 (2001)
Bioactive Heterocyclic Compound Classes.
Clemens L and Dinges J.
Pharmaceutics, 24-27 (2012)
Microwave enhanced knoevenagel condensation of barbituric acid with aromatic aldehydes on basic alumina.
Khalafi NA and Hashemi A.
Iranian Journal of Chemistry and Chemical Engineering, 20 (1), 9-11 (2001)
David C Chiara et al.
The Journal of biological chemistry, 288(27), 19343-19357 (2013-05-17)
GABA type A receptors (GABAAR), the brain's major inhibitory neurotransmitter receptors, are the targets for many general anesthetics, including volatile anesthetics, etomidate, propofol, and barbiturates. How such structurally diverse agents can act similarly as positive allosteric modulators of GABAARs remains
Thomas Gelbrich et al.
Acta crystallographica. Section C, Crystal structure communications, 66(Pt 1), o55-o58 (2010-01-06)
Both title structures exhibit essentially planar barbiturate rings. The crystal structure of enallylpropymal (5-allyl-5-isopropyl-1-methylbarbituric acid), C(11)H(16)N(2)O(3), is composed of centrosymmetric N-H...O hydrogen-bonded dimers, while 1,5-di(but-2-enyl)-5-ethylbarbituric acid, C(14)H(20)N(2)O(3), forms N-H...O hydrogen-bonded helical chains. Each of the ten known crystal structures of
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