1-tert-butyl 3-ethyl propanedioate

• ChemBase ID: 145718
• Molecular Formular: C9H16O4
• Molecular Mass: 188.22094
• Monoisotopic Mass: 188.10485899
• SMILES: CCOC(=O)CC(=O)OC(C)(C)C
• Canonical SMILES: CCOC(=O)CC(=O)OC(C)(C)C
• InChI: InChI=1S/C9H16O4/c1-5-12-7(10)6-8(11)13-9(2,3)4/h5-6H2,1-4H3
• InChIKey: OCOBFMZGRJOSOU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-tert-butyl 3-ethyl propanedioate
• IUPAC Traditional name: 1-tert-butyl 3-ethyl propanedioate
• Synonyms: tert-Butyl ethyl malonate; tert-Butyl ethyl malonate; Malonic acid tert-butyl ethyl ester; 1-tert-butyl 3-ethyl propanedioate; 丙二酸叔丁基乙酯; 丙二酸叔丁基乙基酯

Database IDs

• CAS Number: 32864-38-3
• EC Number: 251-269-8
• MDL Number: MFCD00009193
• Beilstein Number: 1776681
• PubChem SID: 162239921; 24858493
• PubChem CID: 96345

CALCULATED PROPERTIES

• Acid pKa: 11.953764
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.3714383
• LogD (pH = 7.4): 1.3714263
• Log P: 1.3714385
• Molar Refractivity: 47.0802 cm^3
• Polarizability: 18.894217 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 83-85 °C/8 mmHg(lit.); 98-100°C/22mm
• Flash Point: 188.6 °F; 87 °C; 87°C(188°F)
• Density: 0.994; 0.994 g/mL at 25 °C(lit.)
• Refractive Index: 1.4160; n20/D 1.416(lit.)
• Hydrophobicity(logP): 2.055

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• GHS Hazard statements: H227
• GHS Precautionary statements: P210-P280-P370+P378A-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: 95%; 95+%; 97%
• Linear Formula: (CH3)3CO2CCH2CO2C2H5

DETAILS

Sigma Aldrich - 306649

Packaging
5, 25 g in glass bottle

REFERENCES

• Alternative to, e.g. Diethyl malonate, A15468, permitting selective cleavage of either ester group: t-butyl with mild acid, or ethyl with aqueous alkali. For an example in cephalosporin synthesis, see: J. Antibiot., 39, 1236 (1986). Has also been used in a peptide-type synthesis: Angew. Chem. Int. Ed., 31, 785 (1992); and the synthesis of amino acid derivatives: J. Chem. Soc., Perkin 1, 1053 (1992)