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280208 Sigma-Aldrich

Dimethyl acetylsuccinate

Synonym: 2-Acetylbutanedioic acid-1,4-dimethyl ester

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Properties

Related Categories Building Blocks, C8 to C9, Carbonyl Compounds, Chemical Synthesis, Esters,
InChI Key   XREKLQOUFWBSFH-UHFFFAOYSA-N
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.)

Description

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

Packaging

100, 500 g in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
1
Flash Point(F) 
280.4 °F
Flash Point(C) 
138 °C

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Protocols & Articles
Peer-Reviewed Papers
15

References

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