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280208

Sigma-Aldrich

Dimethyl acetylsuccinate

Synonym(s):

2-Acetylbutanedioic acid-1,4-dimethyl ester

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About This Item

Linear Formula:
CH3O2CCH2CH(COCH3)CO2CH3
CAS Number:
10420-33-4
Molecular Weight:
188.18
EC Number:
233-897-4
MDL number:
MFCD00008448
UNSPSC Code:
12352100
PubChem Substance ID:
24856938

form

solid

bp

129-134 °C/12 mmHg (lit.)

mp

33 °C (lit.)

solubility

water: soluble 56.2 g/L at 20 °C

density

1.16 g/mL at 25 °C (lit.)

SMILES string

COC(=O)CC(C(C)=O)C(=O)OC

InChI

1S/C8H12O5/c1-5(9)6(8(11)13-3)4-7(10)12-2/h6H,4H2,1-3H3

InChI key

XREKLQOUFWBSFH-UHFFFAOYSA-N

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General description

Dimethyl acetylsuccinate undergoes sulfuric acid catalyzed Pechmann condensation with the corresponding resorcinol derivative to give 7-hydroxycoumarins.

Application

Dimethyl acetylsuccinate has been used in the synthesis of 2-oxofuro[2,3-b]pyrroles and 19-methyl-15-oxa-20-azatricyclo[12.3.3.0(1,14)]icos-18-en-18-carboxylates.
Reactant involved in:
  • Cyclization for the synthesis of β-carbolines
  • Synthesis of photochromic molecules with improved fatigue resistances and dark form stabilities
  • Asymmetric hydrogenation of acylsuccinate followed by lactonization for synthesis of oxotetrahydrofurancarboxylates
  • Amidation for synthesis of amino-acid derivatives of dihydropyranocoumarins

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 1

flash_point_f

280.4 °F - closed cup

flash_point_c

138 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Raphael M Franzini et al.
Chembiochem : a European journal of chemical biology, 9(18), 2981-2988 (2008-11-28)
Templated nucleic acid detection is an emerging bioanalytical method that makes use of the target DNA or RNA strand to initiate a fluorogenic reaction. The Staudinger reduction holds particular promise for templated sensing of nucleic acids because the involved functional
Orazio A Attanasi et al.
The Journal of organic chemistry, 69(8), 2686-2692 (2004-04-13)
New and interesting 2-oxofuro[2,3-b]pyrroles and 19-methyl-15-oxa-20-azatricyclo[12.3.3.0(1,14)]icos-18-en-18-carboxylates have been obtained in good yields by the one-pot reaction, in basic medium, of 1,2-diaza-1,3-butadienes with diethyl or dimethyl acetylsuccinate or methyl 2-(1,3-dioxo-2-cyclotetradecyl)acetate, respectively, under mild conditions. Treatment of the same starting materials with

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