278033
Diethyl isopropylidenemalonate
97%
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About This Item
Linear Formula:
(CH3)2C=C(COOC2H5)2
CAS Number:
Molecular Weight:
200.23
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
229-876-4
Beilstein/REAXYS Number:
1776122
MDL number:
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
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
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
Regulatory Information
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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