1,3-diethyl 2,2-bis(hydroxymethyl)propanedioate

• ChemBase ID: 59303
• Molecular Formular: C9H16O6
• Molecular Mass: 220.21974
• Monoisotopic Mass: 220.09468823
• SMILES: C(=O)(C(C(=O)OCC)(CO)CO)OCC
• Canonical SMILES: OCC(C(=O)OCC)(C(=O)OCC)CO
• InChI: InChI=1S/C9H16O6/c1-3-14-7(12)9(5-10,6-11)8(13)15-4-2/h10-11H,3-6H2,1-2H3
• InChIKey: WIOHBOKEUIHYIC-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,3-diethyl 2,2-bis(hydroxymethyl)propanedioate
• IUPAC Traditional name: 1,3-diethyl 2,2-bis(hydroxymethyl)propanedioate
• Synonyms: Diethyl bis(hydroxymethyl)malonate; Diethyl 2,2-bis(hydroxymethyl)malonate; Diethyl bis(hydroxymethyl)malonate; 1,3-diethyl 2,2-bis(hydroxymethyl)propanedioate; Bis(hydroxymethyl)malonic acid diethyl ester; 双羟甲基丙二酸二乙酯

Database IDs

• CAS Number: 20605-01-0
• EC Number: 243-916-8
• MDL Number: MFCD00009130
• Beilstein Number: 1788515
• PubChem SID: 162064066; 24851874
• PubChem CID: 311844

CALCULATED PROPERTIES

• Acid pKa: 14.264538
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.788255
• LogD (pH = 7.4): -0.78825504
• Log P: -0.788255
• Molar Refractivity: 50.6481 cm^3
• Polarizability: 20.264492 Å^3
• Polar Surface Area: 93.06 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 47-52°C; 49-51 °C(lit.)
• Flash Point: >110°C(230°F); 110 °C; 230 °F
• Hydrophobicity(logP): 0.474

Safety Information

• Storage Warning: IRRITANT; Irritant
• German water hazard class: 3
• TSCA Listed: false; 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 95+%; 97%
• Linear Formula: (HOCH2)2C(CO2CH2CH3)2

DETAILS

MP Biomedicals - 05221865

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 198358

Packaging
25, 100 g in glass bottle
Application
Reagent for preparing 1,3-dioxanes from acetals,1 aldehydes,1,2,3 and ketones.3,4

REFERENCES

• Intermediate for the preparation of substituted malonic, acrylic and isobutyric esters: J. Chem. Soc., 257 (1930); J. Org. Chem., 20, 780 (1955). For conversion to the useful dienophiles, ɑ-bromomethylacrylic acid and its ethyl ester, see: Org. Synth. Coll., 7, 210 (1990), and to bis(bromomethyl)acetic acid and its methyl ester, Org. Synth. Coll., 7, 319 (1990).