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278033

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:
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 Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

176.0 °F - closed cup

Flash Point(C)

80 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water insoluble liquid

JAN Code

278033-VAR:
278033-5G:
278033-BULK:
278033-25G:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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