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185698

Sigma-Aldrich

Barbituric acid

ReagentPlus®, 99%

Sinónimos:

2,4,6-Trihydroxypyrimidine, Malonylurea

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About This Item

Fórmula empírica (notación de Hill):
C4H4N2O3
Número de CAS:
67-52-7
Peso molecular:
128.09
Beilstein:
120502
Número CE:
200-658-0
Número MDL:
MFCD00006666
Código UNSPSC:
12352100
ID de la sustancia en PubChem:
24851157
NACRES:
NA.21
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grado

reagent

Nivel de calidad

200

Línea del producto

ReagentPlus®

Ensayo

99%

Formulario

powder

mp

248-252 °C ((lit.))
248-252 °C (dec.) (lit.)

cadena SMILES

[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)

Clave InChI

[HNYOPLTXPVRDBG-UHFFFAOYSA-N]
HNYOPLTXPVRDBG-UHFFFAOYSA-N

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Descripción general

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.[1] Its enol crystal form has been reported to be thermodynamically stable.[2]

Aplicación

Barbituric acid (BA) may be used in the preparation of the corresponding hemiaminals, via chemoselective reduction in the presence of SmI2/H2O reagent.[3] It may be used in the preparation of BA- modified conjugated carbon nitride nanosheets.[4]
It may be used to synthesize:
  • 5-ylidenebarbituric acid derivatives via Knoevenagel condensation with aromatic and α,β-conjugated aromatic aldehydes[5]
  • 5-diaminomethylenebarbiturates by reacting with substituted carbodiimides[6]

Información legal

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 1

Punto de inflamabilidad (°F)

302.0 °F - closed cup

Punto de inflamabilidad (°C)

150.00 °C - closed cup

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
WXBF3271V
WXBF4250V
WXBF0320V
WXBD8847V
WXBD7684V

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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)
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)
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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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