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160407

Sigma-Aldrich

Dibenzyl malonate

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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.)

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

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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

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC2103V
BGBC0651V
BGBB0047
MKAA3549
18406LH

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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

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