160407

Dibenzyl malonate

• Linear Formula: CH₂(CO₂CH₂C₆H₅)₂
• CAS Number: 15014-25-2
• Molecular Weight: 284.31
• Beilstein: 1998264
• EC Number: 239-099-2
• MDL number: MFCD00004779
• UNSPSC Code: 12352100
• PubChem Substance ID: 24849869
• NACRES: NA.22

Properties

• form: liquid
• Quality Level: 100
• refractive index: n20/D 1.546 (lit.)
• bp: 188 °C/0.2 mmHg (lit.)
• density: 1.137 g/mL at 25 °C (lit.)
• functional group: ester; phenyl
• SMILES string: O=C(CC(=O)OCc1ccccc1)OCc2ccccc2
• InChI: 1S/C17H16O4/c18-16(20-12-14-7-3-1-4-8-14)11-17(19)21-13-15-9-5-2-6-10-15/h1-10H,11-13H2
• InChI key: RYFCSKVXWRJEOB-UHFFFAOYSA-N

Description

General description

Direct asymmetric reaction of dibenzyl malonate with N-tert-butoxycarbonyl aldimines in the presence of Yb(OTf)₃ and iPr-pybox (pybox = pyridine bisoxazoline) complexes has been investigated.

Application

Dibenzyl malonate was used in the preparation of tetraethyl 3,3-bis(benzyloxycarbonyl)propylene bisphosphonate. It was also used in the preparation of benzyl umbelliferone-3-carboxylate via Knoevenagel condensation with 2,4-dihydroxybezaldehyde.

Safety Information

• Storage Class Code: 10 - Combustible liquids
• WGK: WGK 3
• Flash Point(F): 230.0 °F - closed cup
• Flash Point(C): 110 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves