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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:
3195-24-2
Molecular Weight:
240.30
EC Number:
221-696-4
MDL number:
MFCD00009126
UNSPSC Code:
12352100
PubChem Substance ID:
24857107
NACRES:
NA.22

Quality Level

100

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

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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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