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Merck

210145

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

98%

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C6H8O4
CAS Number:
2033-24-1
Molecular Weight:
144.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24852618
EC Number:
217-992-8
Beilstein/REAXYS Number:
117310
MDL number:
MFCD00006638

Key Documents

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Product Name

2,2-Dimethyl-1,3-dioxane-4,6-dione, 98%

InChI key

GXHFUVWIGNLZSC-UHFFFAOYSA-N

InChI

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

SMILES string

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

assay

98%

form

solid

mp

92-96 °C (lit.)

solubility

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

functional group

ester
ketal

storage temp.

2-8°C

Quality Level

200

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General description

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. Knoevenagel condensation reaction between aldehydes and Meldrum′s acid are accelerated in ionic liquids.

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

Application

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

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCH9274
STBJ3104
STBF4868V
STBG8233
STBD6952V

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New route to 2-substituted indoles by pyrolysis of N-acylacetylphenylhydroxylamines.
Hirao K-I, et al.
Tetrahedron Letters, 33(11), 1459-1462 (1992)
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
Synthetic Communications, 36, 3043-3043 (2006)
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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