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280208

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
UNSPSC Code:
12352100
PubChem Substance ID:
24856938
EC Number:
233-897-4
MDL number:
MFCD00008448
Form:
solid
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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.)

functional group

ester, ketone

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

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

WGK 1

flash_point_f

280.4 °F - closed cup

flash_point_c

138 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

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