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255661

Sigma-Aldrich

Dimethyl ethylidenemalonate

98%

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About This Item

Linear Formula:
CH3CH=C(CO2CH3)2
CAS Number:
17041-60-0
Molecular Weight:
158.15
MDL number:
MFCD00008447
UNSPSC Code:
12352100
PubChem Substance ID:
24855472

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

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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

206.6 °F - closed cup

Flash Point(C)

97.00 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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)

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