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39565

1,3-Dimethylbarbituric acid

≥99.0% (T)

Synonym(s):

1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione

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50 g
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$99.60
250 g

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About This Item

Empirical Formula (Hill Notation):
C6H8N2O3
CAS Number:
769-42-6
Molecular Weight:
156.14
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57649861
EC Number:
212-211-7
Beilstein/REAXYS Number:
139810
MDL number:
MFCD00006675
Assay:
≥99.0% (T)
Form:
solid

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Quality Segment

200

assay

≥99.0% (T)

form

solid

ign. residue

≤0.1%

mp

123-126 °C

solubility

hot water: soluble 0.5 g/10 mL, clear, colorless to faintly yellow

SMILES string

CN1C(=O)CC(=O)N(C)C1=O

InChI

1S/C6H8N2O3/c1-7-4(9)3-5(10)8(2)6(7)11/h3H2,1-2H3

InChI key

VVSASNKOFCZVES-UHFFFAOYSA-N

General description

1,3-Dimethylbarbituric acid (1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione) is an active methylene compound. It undergoes hollow Pd6 water-soluble cage, [{(tmen)Pd}6(timb)4](NO3)12 (tmen= N,N,N′,N′-tetramethylethylenediamine, timb=1,3,5-tris(1-imidazolyl)benzene)-catalyzed Knoevenagel condensation reaction with pyrene-1-carboxaldehyde.[1] It undergoes self-sorted Pd7 molecular boat having an internal nanocavity (catalyst)-assisted Knoevenagel condensation reaction with various aromatic aldehydes.[1] It has been synthesized by reacting 1,3-dimethylurea, malonic acid and acetic anhydride in acetic acid. It is widely used for the synthesis of various synthetic intermediates and heterocyclic compounds.

Application

1,3-Dimethylbarbituric acid may be used in the following studies:
  • Enantioselective synthesis of isochromene pyrimidinedione derivatives having five stereocenters, via one-pot Michael-Knoevenagel condensation-inverse-electron-demand hetero-Diels-Alder reaction.[2]
  • Synthesis of 5-aryl-6-(alkyl- or aryl-amino)-1,3-dimethylfuro [2,3-d]pyrimidine derivatives.[3]
  • Microwave promoted indirect functionalization of alcohols, via spirocyclisation employing a sequential one-pot Ir(III)/Pd(0) catalyzed process.[4]

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pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H302,H318

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Questions

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  1. 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/418/501/product-dating-information-06-25-mk.pdf

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  2. 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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