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160407

Dibenzyl malonate

Name: Dibenzyl malonate
Brand: ALDRICH

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About This Item

Linear Formula:

CH₂(CO₂CH₂C₆H₅)₂

CAS Number:

15014-25-2

Molecular Weight:

284.31

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24849869

EC Number:

239-099-2

Beilstein/REAXYS Number:

1998264

MDL number:

MFCD00004779

Form:

liquid

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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.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Evaluation of novel fluorogenic substrates for the detection of glycosidases in Escherichia coli and enterococci.

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

Synthesis of bone-targeted oestrogenic compounds for the inhibition of bone resorption.

Bulman Page PC, et al.

Tetrahedron, 57(9), 1837-1847 (2001)

Highly efficient catalytic enantioselective Mannich reaction of malonates with N-tert-butoxycarbonyl imines by using Yb(OTf)3/pybox catalysts at room temperature.

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).

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Global Trade Item Number

SKU	GTIN
160407-50G	04061836682606
160407-10G	04061838745514