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Sigma-Aldrich

Diethyl isopropylidenemalonate

97%

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About This Item

Linear Formula:
(CH3)2C=C(COOC2H5)2
CAS Number:
6802-75-1
Molecular Weight:
200.23
Beilstein/REAXYS Number:
1776122
EC Number:
229-876-4
MDL number:
MFCD00009147
UNSPSC Code:
12352100
PubChem Substance ID:
24856502
NACRES:
NA.22

assay

97%

refractive index

n20/D 1.451 (lit.)

bp

175-178 °C/120 mmHg (lit.)

density

1.021 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)\C(=C(/C)C)C(=O)OCC

InChI

1S/C10H16O4/c1-5-13-9(11)8(7(3)4)10(12)14-6-2/h5-6H2,1-4H3

InChI key

WEISAZNMMVPNTH-UHFFFAOYSA-N

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General description

Reduction of diethyl isopropylidenemalonate with sodium borohydride has been reported.

Application

Diethyl isopropylidenemalonate has been used in the synthesis of retinoids having functional groups at the side-chain terminus.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

176.0 °F - closed cup

flash_point_c

80 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Certificates of Analysis (COA)

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Reduction of alkylidenecyanoacetates with sodium borohydride.
Marshall JA and Carroll RD.
The Journal of Organic Chemistry, 30(8), 2748-2754 (1965)
Y F Shealy et al.
Journal of medicinal chemistry, 31(6), 1124-1130 (1988-06-01)
Retinoids that have two functional groups at the side-chain terminus have been synthesized. The two terminal functional groups are combinations of the carboxyl, carbethoxy, and N-(ethylamino)carbonyl groups. The synthesis route is based on the sodium amide catalyzed condensation of (E,E)-beta-ionylideneacetaldehyde

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