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210153

Sigma-Aldrich

2,2,5-Trimethyl-1,3-dioxane-4,6-dione

97%

Synonym(s):

cycl-Isopropylidene methylmalonate, Methyl Meldrum’s acid, Methylmalonic acid cyclic isopropylidene ester

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About This Item

Empirical Formula (Hill Notation):
C7H10O4
CAS Number:
3709-18-0
Molecular Weight:
158.15
Beilstein:
124044
EC Number:
223-050-7
MDL number:
MFCD00006637
UNSPSC Code:
12352100
PubChem Substance ID:
24852619
NACRES:
NA.22

Assay

97%

form

solid

mp

111-114 °C (lit.)

SMILES string

CC1C(=O)OC(C)(C)OC1=O

InChI

1S/C7H10O4/c1-4-5(8)10-7(2,3)11-6(4)9/h4H,1-3H3

InChI key

KJMCAXYHYPDRAV-UHFFFAOYSA-N

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General description

X-ray irradiated single crystals of 2,2,5-trimethyl-1,3-dioxane-4,6-dione have been investigated by electron spin resonance (ESR), electron nuclear double resonance (ENDOR) and electron-electron double resonance (ELDOR) spectra.

Application

2,2,5-Trimethyl-1,3-dioxane-4,6-dione was used for trapping the adduct formed during the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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An ESR, ENDOR, and ELDOR study of tunneling rotation of a hindered methyl group in x-irradiated 2, 2, 5-trimethyl-1, 3-dioxane-4, 6-dione crystals.
Geoffroy M, et al.
J. Chem. Phys., 70(9), 4238-4242 (2008)
Issa Yavari et al.
Molecular diversity, 10(2), 247-250 (2006-06-14)
The adduct produced in the reaction between alkyl isocyanides and dialkyl acetylenedicarboxylates was trapped by 2,2,5-trimethyl-1,3-dioxane-4,6-dione (methyl Meldrum's acid), to afford highly functionalized ketenimines in good yields.

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