1,3-diethyl 2-acetamidopropanedioate

• ChemBase ID: 53500
• Molecular Formular: C9H15NO5
• Molecular Mass: 217.2191
• Monoisotopic Mass: 217.09502259
• SMILES: C(C(=O)OCC)(C(=O)OCC)NC(=O)C
• Canonical SMILES: CCOC(=O)C(C(=O)OCC)NC(=O)C
• InChI: InChI=1S/C9H15NO5/c1-4-14-8(12)7(10-6(3)11)9(13)15-5-2/h7H,4-5H2,1-3H3,(H,10,11)
• InChIKey: ISOLMABRZPQKOV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl 2-acetamidopropanedioate
• IUPAC Traditional name: 1,3-diethyl 2-acetamidopropanedioate
• Synonyms: Diethyl (acetylamino)malonate; Acetamidomalonic acid diethyl ester; Diethyl acetamidomalonate; diethyl 2-acetamidomalonate; Acetamidomalonic acid diethylester; DIETHYL ACETAMINOMALONATE; 乙酰胺基丙二酸二乙酯; 乙酰氨基丙二酸二乙酯

Database IDs

• CAS Number: 1068-90-2
• EC Number: 213-952-9
• MDL Number: MFCD00009146
• Beilstein Number: 783883
• PubChem SID: 162058263; 24894215
• PubChem CID: 14041

CALCULATED PROPERTIES

• Acid pKa: 10.526375
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.13775574
• LogD (pH = 7.4): 0.13743992
• Log P: -0.3289069
• Molar Refractivity: 50.4627 cm^3
• Polarizability: 20.204498 Å^3
• Polar Surface Area: 81.7 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 95-98 °C; 95-98 °C(lit.); 96°C; 96-99°C
• Boiling Point: 185 °C/20 mmHg(lit.); 185°C; 185°C/20mm

Safety Information

• Storage Warning: IRRITANT
• RTECS: OO0360000
• German water hazard class: 3
• TSCA Listed: false; 是
• GHS Hazard statements: H303
• GHS Precautionary statements: P312
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0% (HPLC); 98%; 98+%
• Grade: purum
• Linear Formula: CH3CONHCH(CO2C2H5)2

DETAILS

MP Biomedicals - 05202940

MP Biomedicals Rare Chemical collection

Sigma Aldrich - D84601

Packaging
25, 100, 500 g in poly bottle

REFERENCES

• Intermediate for synthesis of racemic amino acids, by reaction with an electrophile, e.g alkyl halide, followed by hydrolysis and decarboxylation. The reactivity can be reversed by conversion to the dehydro-derivative, which then undergoes nucleophilic attack with alkyllithiums, Grignards, malonate anion, etc.: Angew. Chem. Int. Ed., 21, 203 (1982):
  
• Substituents can also be introduced by Michael addition to a wide variety of acceptors: Synth. Commun., 18, 367 (1988).
• For use in a novel pyrrole synthesis, see 1,4-Dichloro-2-butyne, A13300.
• Compare also Diethyl formamidomalonate, L01189.