1,4-dimethyl 2-acetylbutanedioate

• ChemBase ID: 122924
• Molecular Formular: C8H12O5
• Molecular Mass: 188.17788
• Monoisotopic Mass: 188.06847348
• SMILES: C(C(=O)OC)(C(=O)C)CC(=O)OC
• Canonical SMILES: COC(=O)CC(C(=O)OC)C(=O)C
• InChI: InChI=1S/C8H12O5/c1-5(9)6(8(11)13-3)4-7(10)12-2/h6H,4H2,1-3H3
• InChIKey: XREKLQOUFWBSFH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,4-dimethyl 2-acetylbutanedioate
• IUPAC Traditional name: 1,4-dimethyl 2-acetylbutanedioate
• Synonyms: Acetylsuccinic acid dimethyl ester; 3-Carboxy-4-oxopentanoic acid dimethyl ester; 2-Acetylbutanedioic acid-1,4-dimethyl ester; Dimethyl acetylsuccinate; dimethyl 2-acetylsuccinate; 乙酰琥珀酸二甲酯; 乙酰丁二酸二甲酯

Database IDs

• CAS Number: 10420-33-4
• EC Number: 233-897-4
• MDL Number: MFCD00008448
• PubChem SID: 162217277; 24856938
• PubChem CID: 112039

CALCULATED PROPERTIES

• Acid pKa: 12.468588
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.19094284
• LogD (pH = 7.4): 0.1909392
• Log P: -0.042390455
• Molar Refractivity: 42.918 cm^3
• Polarizability: 17.2225 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 30-33°C; 33 - 35°C; 33 °C(lit.)
• Boiling Point: 129-134 °C/12 mmHg(lit.); 129-134°C/12mm
• Flash Point: >110°C(230°F); >113 °C; >235.4 °F
• Density: 1.16 g/mL at 25 °C(lit.); 1.160
• Hydrophobicity(logP): 0.096

Safety Information

• German water hazard class: 1
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 96%
• Linear Formula: CH3O2CCH2CH(COCH3)CO2CH3

DETAILS

Sigma Aldrich - 280208

Packaging
100, 500 g in glass bottle
Application
Reactant involved in:
• Cyclization for the synthesis of β-carbolines1
• Synthesis of photochromic molecules with improved fatigue resistances and dark form stabilities2
• Asymmetric hydrogenation of acylsuccinate followed by lactonization for synthesis of oxotetrahydrofurancarboxylates3
• Amidation for synthesis of amino-acid derivatives of dihydropyranocoumarins4