triethyl methanetricarboxylate

• ChemBase ID: 148386
• Molecular Formular: C10H16O6
• Molecular Mass: 232.23044
• Monoisotopic Mass: 232.09468823
• SMILES: CCOC(=O)C(C(=O)OCC)C(=O)OCC
• Canonical SMILES: CCOC(=O)C(C(=O)OCC)C(=O)OCC
• InChI: InChI=1S/C10H16O6/c1-4-14-8(11)7(9(12)15-5-2)10(13)16-6-3/h7H,4-6H2,1-3H3
• InChIKey: AGZPNUZBDCYTBB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triethyl methanetricarboxylate
• IUPAC Traditional name: triethyl methanetricarboxylate
• Synonyms: Triethyl methanetricarboxylate; Methanetricarboxylic acid triethyl ester; Tris(carboethoxy)methane; N-triethylmethanetricarboxylate; Triethyl methanetricarboxylate; 甲烷三羧酸三乙酯

Database IDs

• CAS Number: 6279-86-3
• EC Number: 228-477-2
• MDL Number: MFCD00009150
• Beilstein Number: 1793645
• PubChem SID: 24883241; 162242562; 24900338
• PubChem CID: 80471

CALCULATED PROPERTIES

• Acid pKa: 6.862826
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.8939805
• LogD (pH = 7.4): 0.31972072
• Log P: 0.91166764
• Molar Refractivity: 53.8326 cm^3
• Polarizability: 21.612305 Å^3
• Polar Surface Area: 78.9 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 25-26 °C(lit.); 26-29°C; 28 - 29°C
• Boiling Point: 253 °C(lit.); 253°C
• Flash Point: >110°C(230°F); 113 °C; 235.4 °F
• Density: 1.095; 1.095 g/mL at 25 °C(lit.)
• Refractive Index: 1.4255; n20/D 1.424(lit.); n20/D 1.426
• Hydrophobicity(logP): 1.543

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves; Eyeshields, Gloves, half-mask respirator (US), multi-purpose combination respirator cartridge (US)

Product Information

• Purity: ≥98.0% (GC); 95%; 97%; 98%
• Grade: purum
• Linear Formula: CH(CO2C2H5)3

DETAILS

Sigma Aldrich - T60208

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 64300

Other Notes
Convenient malonic ester derivative precluding dialkylation and elimination side-reactions1,2,3; review4

REFERENCES

• Methanetricarboxylates have been used as "blocked" malonic esters, restricting reaction with alkyl halides to monoalkylation. The unwanted carboxyl group can be removed by treatment with Na alkoxide, LDA or BCl₃: J. Org. Chem., 44, 3492 (1979). Adds to Michael acceptors under phase-transfer conditions, providing a useful 2-carbon chain extension method: Synthesis, 1125 (1990):
  
• The tricarboxylate also undergoes free-radical addition to the terminal position of alkenes: Angew. Chem. Int. Ed., 5, 586 (1966). Arylation with electron-rich aromatics is promoted by Mn(III): Synthesis, 567 (1991).
• Under similar conditions, diethyl malonate gives only 36% yield.