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283479

Sigma-Aldrich

Diethyl diallylmalonate

98%

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About This Item

Linear Formula:
(H2C=CHCH2)2C(CO2C2H5)2
CAS Number:
Molecular Weight:
240.30
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

98%

form

liquid

refractive index

n20/D 1.446 (lit.)

bp

128-130 °C/12 mmHg (lit.)

density

0.994 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C(CC=C)(CC=C)C(=O)OCC

InChI

1S/C13H20O4/c1-5-9-13(10-6-2,11(14)16-7-3)12(15)17-8-4/h5-6H,1-2,7-10H2,3-4H3

InChI key

LYUUVYQGUMRKOV-UHFFFAOYSA-N

General description

Low catalyst loading in ring-closing metathesis reaction of diethyl diallylmalonate has been reported. Cationic nickel (with monodentate phosphoramidites and Wilke′s azaphospholene as ligands) catalyzed cycloisomerisation of diethyl diallylmalonate has been reported.

pictograms

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signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

235.4 °F - closed cup

flash_point_c

113 °C - closed cup

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Renat Kadyrov
Chemistry (Weinheim an der Bergstrasse, Germany), 19(3), 1002-1012 (2012-11-28)
An efficient procedure is described for ring-closing metathesis reactions. A conversion of 95% for diethyl diallylmalonate in dilute solution could be achieved within a few minutes, reaching TOF = 4173 min(-1), with very low loading of commercially available Ru catalysts that
Christian Böing et al.
Chemical communications (Cambridge, England), (11)(11), 1456-1458 (2005-03-10)
Cationic nickel catalysts with monodentate phosphoramidites and Wilke's azaphospholene as ligands are highly regio- and enantioselective catalysts for the cycloisomerisation of diethyl diallylmalonate.

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