1,3-di-tert-butyl propanedioate

• ChemBase ID: 70769
• Molecular Formular: C11H20O4
• Molecular Mass: 216.2741
• Monoisotopic Mass: 216.13615912
• SMILES: C(=O)(CC(=O)OC(C)(C)C)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)CC(=O)OC(C)(C)C
• InChI: InChI=1S/C11H20O4/c1-10(2,3)14-8(12)7-9(13)15-11(4,5)6/h7H2,1-6H3
• InChIKey: CLPHAYNBNTVRDI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-di-tert-butyl propanedioate
• IUPAC Traditional name: 1,3-di-tert-butyl propanedioate
• Synonyms: Di-tert-butyl malonate; 1,3-di-tert-butyl propanedioate; Di-tert-butyl malonate; Malonic acid di-tert-butyl ester; 丙二酸二叔丁酯

Database IDs

• CAS Number: 541-16-2
• EC Number: 208-769-6
• MDL Number: MFCD00008810
• Beilstein Number: 1781766
• Merck Index: 143034
• PubChem SID: 24882558; 162036480; 24855386
• PubChem CID: 68324

CALCULATED PROPERTIES

• Acid pKa: 11.642157
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.06859
• LogD (pH = 7.4): 2.0685654
• Log P: 2.0685902
• Molar Refractivity: 56.1372 cm^3
• Polarizability: 22.553574 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -6°C; -7 - -6°C; -7--6 °C(lit.)
• Boiling Point: 110-111 °C/22 mmHg(lit.); 65-67°C/1mm
• Flash Point: 192.2 °F; 88°C(190°F); 89 °C
• Density: 0.965; 0.966 g/mL at 25 °C(lit.)
• Refractive Index: 1.4190; n20/D 1.418; n20/D 1.418(lit.)
• Hydrophobicity(logP): 2.983

Safety Information

• Storage Warning: IRRITANT
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 43
• Safety Statements: 23-24-37
• TSCA Listed: false; 是
• GHS Pictograms: GHS07
• GHS Hazard statements: H317-H227
• GHS Precautionary statements: P210-P261-P302+P352-P321-P403+P235-P501A
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)
• Storage Temperature: 2-8°C

Product Information

• Purity: >97% (GC); ≥98.0% (GC); 95%; 95+%; 98%; 98+%, stab. with potassium carbonate
• Grade: purum
• Linear Formula: (CH3)3COCOCH2COOC(CH3)3

DETAILS

MP Biomedicals - 05208111

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 254487

Packaging
10 g in glass bottle

Sigma Aldrich - 63350

Other Notes
Reagent for the synthesis of ketones1; Condensation reactions2,3

REFERENCES

• Alternative to Diethyl malonate, A15468, permitting removal of the t-butyl groups and decarboxylation by thermolysis in the presence of mild acid: J. Am. Chem. Soc., 74, 831 (1952). In the presence of Cu(OAc)₂, condenses with paraformaldehyde to form the useful electrophilic alkene, di-t-butyl methylenemalonate: J. Org. Chem., 48, 3603 (1983), which is more stable than the ethyl or methyl esters, and can be stored for some weeks at room temperature. For references to use of methylenemalonic esters in Michael addition and cycloaddition reactions, see: Org. Synth. Coll., 7, 142 (1990).