Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

280208

Sigma-Aldrich

Dimethyl acetylsuccinate

Synonym(s):

2-Acetylbutanedioic acid-1,4-dimethyl ester

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

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

Looking for similar products? Visit Product Comparison Guide

General description

Dimethyl acetylsuccinate undergoes sulfuric acid catalyzed Pechmann condensation with the corresponding resorcinol derivative to give 7-hydroxycoumarins[1].

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[2].
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 Code

13 - Non Combustible Solids

WGK

WGK 1

Flash Point(F)

280.4 °F - closed cup

Flash Point(C)

138 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
STBJ7429
STBG9654
STBF5636V
STBF1877V
STBF0649V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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

Questions

Reviews

No rating value

Active Filters

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service