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210145

Sigma-Aldrich

2,2-Dimethyl-1,3-dioxan-4,6-dion

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

98%

Synonym(e):

Malonsäure-cycl.-isopropylidenester, cycl.-Isopropyliden-malonat, ‘Meldrum’s Säure’

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10 G
CHF 26.30
25 G
CHF 47.40
100 G
CHF 112.00

About This Item

Empirische Formel (Hill-System):
C6H8O4
CAS-Nummer:
2033-24-1
Molekulargewicht:
144.13
Beilstein:
117310
EG-Nummer:
217-992-8
MDL-Nummer:
MFCD00006638
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24852618
NACRES:
NA.22

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Assay

98%

Form

solid

mp (Schmelzpunkt)

92-96 °C (lit.)

Löslichkeit

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

Funktionelle Gruppe

ester
ketal

Lagertemp.

2-8°C

SMILES String

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

InChI

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

InChIKey

GXHFUVWIGNLZSC-UHFFFAOYSA-N

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Allgemeine Beschreibung

Benzyl substituted Meldrum′s acids, available via aldol condensation and reduction with triethylammonium formate,[1] were used to form indanones upon hydrolysis, loss of CO2, and Friedel-Crafts cyclization with chlorosulfonic acid.[2] Knoevenagel condensations between aldehydes and Meldrum′s acid are accelerated in ionic liquids.[3]

Anwendung

Used in an efficient synthesis of isofraxidin.[4]

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 2

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCCH9274
STBJ3104
STBF4868V
STBG8233
STBD6952V

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1,3-Dimethylbarbitursäure ≥99.0% (T)

Sigma-Aldrich

39565

1,3-Dimethylbarbitursäure

Davood Nematollahi et al.
Chemical & pharmaceutical bulletin, 58(1), 23-26 (2010-01-05)
Electrochemical oxidation of catechols in the presence of phenyl-Meldrum's acid as a nucleophile in aqueous solution has been studied in detail by means of cyclic voltammetry and controlled potential coulometry. The results indicate that the o-benzoquinone derived from catechols participates
The synthesis of β-keto lactones via cyclization of β-keto ester dianions or the cyclization of Meldrum's acid derivatives.
Lermer L, et al.
Canadian Journal of Chemistry, 70(5), 1427-1445 (1992)
New multicomponent domino reactions (MDRs) in water: highly chemo-, regio-and stereoselective synthesis of spiro {[1, 3] dioxanopyridine}-4, 6-diones and pyrazolo [3, 4-b] pyridines.
Ma N, et al.
Green Chemistry, 12?(8), 1357-1361 (2010)
Songlei Zhu et al.
Molecules (Basel, Switzerland), 17(12), 13856-13863 (2012-11-24)
A series of 4-aryl-6-methyl-3,4-dihydro-2H-pyrano[3,2-c]quinolin-2,5(6H)-diones were synthesized via the three-component reactions of aromatic aldehydes, 4-hydroxy-1-methylquinolin-2(1H)-one, and Meldrum's acid catalyzed by L-proline. The structures of the products were identified by spectroscopic analysis. A mechanism for this three-component reaction catalyzed by L-proline was
Characterization of Meldrum?s acid derivative 5-(5-Ethyl-1, 3, 4-thiadiazol-2-ylamino) methylene-2, 2-dimethyl-1, 3-dioxane-4, 6-dione by Raman and FT-IR spectroscopy and DFT calculations
De Toledo TA, et al.
Journal of Molecular Structure, 37-42, 1091-1091 (2015)
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Artikel

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.
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      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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