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:
Molecular Weight:
188.18
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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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
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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)
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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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