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Sigma-Aldrich

2,2-Dimethyl-1,3-dioxane-4,6-dione

2,2-Dimethyl-1,3-dioxane-4,6-dione

98%

Sinônimo(s):

Malonic acid cyclic isopropylidene ester, Meldrum’s acid, cycl-Isopropylidene malonate

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10 G
R$ 354,00
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R$ 633,00
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About This Item

Fórmula empírica (Notação de Hill):
C6H8O4
Número CAS:
2033-24-1
Peso molecular:
144.13
Beilstein:
117310
Número CE:
217-992-8
Número MDL:
MFCD00006638
Código UNSPSC:
12352100
ID de substância PubChem:
24852618
NACRES:
NA.22

R$ 354,00

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Nível de qualidade

200

Ensaio

98%

Formulário

solid

pf

92-96 °C (lit.)

solubilidade

dioxane: soluble 5%, clear to very slightly hazy, colorless to faintly yellow

grupo funcional

ester
ketal

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

CC1(C)OC(=O)CC(=O)O1

InChI

1S/C6H8O4/c1-6(2)9-4(7)3-5(8)10-6/h3H2,1-2H3

chave InChI

GXHFUVWIGNLZSC-UHFFFAOYSA-N

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Descrição geral

2,2-Dimethyl-1,3-dioxane-4,6-dione (Meldrum′s acid) is widely used in organic synthesis, especially for multiple C-C bond formations due to its adequate acidity (pKa 4.83) and steric rigidity[1]. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.[2]

Meldrum′s acid is used as a valuable starting material to synthesize heterocycles and as intermediates in organic synthesis reactions.[3][4]

Aplicação

2,2-Dimethyl-1,3-dioxane-4,6-dione was used in the synthesis of:
  • macrocyclic β-keto lactone[5]
  • 4-pyridyl-substituted heterocycles[6]
  • 2-substituted indoles[7]
  • isofraxidin.[8]

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

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Certificados de análise (COA)

Lot/Batch Number
BCCH9274
STBJ3104
STBF4868V
STBG8233
STBD6952V

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Mohammad Bagher Teimouri et al.
ACS combinatorial science, 13(6), 659-666 (2011-09-17)
An efficient and practical method has been developed for the diversity-oriented synthesis of chromone-containing tripeptides via pseudo-five-component reaction between 3-formylchromones, Meldrum's acid, isocyanides and primary aromatic amines for the generation of a wide range of structurally interesting and pharmacologically significant
Liam Payne et al.
Molecules (Basel, Switzerland), 25(21) (2020-10-30)
Donor-acceptor Stenhouse adducts (DASAs) are a novel class of solvatochromic photoswitches with increasing importance in photochemistry. Known for their reversibility between open triene and closed cyclized states, these push-pull molecules are applicable in a suite of light-controlled applications. Recent works
New route to 2-substituted indoles by pyrolysis of N-acylacetylphenylhydroxylamines.
Hirao K-I, et al.
Tetrahedron Letters, 33(11), 1459-1462 (1992)
Tetrahedron, 63, 389-389 (2007)
Sheng Cui et al.
Journal of the American Chemical Society, 132(2), 436-437 (2009-12-22)
The enantioselective conjugate addition of alkynyl nucleophiles has been a long-standing challenge in synthetic chemistry. This paper describes a highly practical asymmetric conjugate alkynylation of Meldrum's acid-derived acceptors using cinchonidine (<$100/kg) as the chiral mediator. The process provides practical access
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Artigos

Knoevenagel Condensation Reaction

Knoevenagel Condensation is an organic reaction named after Emil Knoevenagel. It is a classic C-C bond formation reaction and a modification of the Aldol Condensation.

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    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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    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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