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255661

Dimethyl ethylidenemalonate

Name: Dimethyl ethylidenemalonate
Brand: ALDRICH

98%

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About This Item

Linear Formula:

CH₃CH=C(CO₂CH₃)₂

CAS Number:

17041-60-0

Molecular Weight:

158.15

UNSPSC Code:

12352100

PubChem Substance ID:

24855472

MDL number:

MFCD00008447

Assay:

98%

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Properties

assay

98%

refractive index

n20/D 1.447 (lit.)

density

1.111 g/mL at 25 °C (lit.)

SMILES string

COC(=O)\C(=C\C)C(=O)OC

InChI

1S/C7H10O4/c1-4-5(6(8)10-2)7(9)11-3/h4H,1-3H3

InChI key

FRCFZWCJSXQAMQ-UHFFFAOYSA-N

Description

General description

Palladium (0)-catalyzed deconjugative allylation of dimethyl ethylidenemalonate has been reported.

Application

Dimethyl ethylidenemalonate has been employed:

as electrophile in catalytic asymmetric Michael reactions of enamides and enecarbamates
in preparation of N-bound α-cyanocarbanion complexes

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

206.6 °F - closed cup

flash_point_c

97.00 °C - closed cup

ppe

Eyeshields, Gloves

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Novel synthesis of conjugated dienes attached to a quaternary carbon center via Pd(0)-catalyzed deconjugative allylation of alkenylidenemalonates.

Yoshihiro Sato et al.

The Journal of organic chemistry, 68(25), 9858-9860 (2003-12-06)

Palladium(0)-catalyzed deconjugative allylation of alkenylidenemalonates and alkylidenemalonates was achieved for the first time. Reactions of dimethyl 2-((E)-but-2-enylidene)malonate with various allylic acetates using LHMDS as a base in DMF in the presence of Pd(2)dba(3) (2.5 mol %) and PPh(3) (10 mol

Catalytic asymmetric Michael reactions with enamides as nucleophiles.

Florian Berthiol et al.

Angewandte Chemie (International ed. in English), 46(41), 7803-7805 (2007-09-05)

Carbon-carbon bond forming reactions of N-bound transition metal a-cyanocarbanions: a mechanistic probe for catalytic Michael reactions of nitriles

Naota T, et al.

Chemical Communications (Cambridge, England), 1, 63-64 (2001)

Global Trade Item Number

SKU	GTIN
255661-5G	04061837498343