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:
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 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
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