Skip to Content
Merck
All Photos(2)

Key Documents

View All Documentation

160407

Sigma-Aldrich

Dibenzyl malonate

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

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

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.)

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

Looking for similar products? Visit Product Comparison Guide

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.

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
BGBC2103V
BGBC0651V
BGBB0047
MKAA3549
18406LH

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Babak Karimi et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 19(31), 10142-10145 (2013-06-22)
Go Mannich! A highly efficient and enantioselective method for the direct asymmetric reaction of dibenzyl malonate with N-tert-butoxycarbonyl aldimines in the presence of Yb(OTf)3 and iPr-pybox complexes is described (see scheme; pybox = pyridine bisoxazoline).
Synthesis of bone-targeted oestrogenic compounds for the inhibition of bone resorption.
Bulman Page PC, et al.
Tetrahedron, 57(9), 1837-1847 (2001)
J D Perry et al.
Journal of applied microbiology, 101(5), 977-985 (2006-10-17)
Enzyme substrates based on 4-methylumbelliferone are widely used for the detection of Escherichia coli and enterococci in water, by detection of beta-glucuronidase and beta-glucosidase activity respectively. This study aimed to synthesize and evaluate novel umbelliferone-based substrates with improved sensitivity for
Prerana D Tomke et al.
Ultrasonics sonochemistry, 38, 496-502 (2017-06-22)
Poly (ethylene glutarate), poly (ethylene malonate) and poly (ethylene phthalate), were enzymatically synthesized by immobilized Candida antarctica lipase B in solvent free conditions. The synthesis of these polyesters was based on the ester-ester exchange reaction between ethylene glycol diacetate and
Riin Rebane et al.
Journal of chromatography. A, 1390, 62-70 (2015-03-12)
Derivatization is one of the most common ways for improving chromatographic separation and sensitivity for LC-ESI-MS analysis. The aim of this work was to design new derivatization reagents for LC-ESI-MS analysis of amino acids which would (1) provide good reversed

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service