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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)

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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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