Acrolein diethyl acetal, 96%

Name: Acrolein diethyl acetal, 96%
SKU: B24821.09
Price: 32.30 EUR

CAS: 3054-95-3 | C7H14O2 | 130.187 g/mol

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Catalog number B24821.09

also known as B24821-09

Price (EUR)

32,30

Each

Quantity:

10 g

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Price (EUR)

32,30

Each

Chemical Identifiers

CAS3054-95-3

IUPAC Name3,3-diethoxyprop-1-ene

Molecular FormulaC7H14O2

InChI KeyMCIPQLOKVXSHTD-UHFFFAOYSA-N

SMILESCCOC(OCC)C=C

Specifications

Specification Sheet

Appearance (Color)Clear colorless

Refractive Index1.3990-1.4050 @ 20?C

FormLiquid

Assay (GC)≥95.0%

Acrolein diethyl acetal is a reagent used for the synthesis of a variety of compounds, including cinnamaldehydes.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
Acrolein diethyl acetal is a reagent used for the synthesis of a variety of compounds, including cinnamaldehydes.

Solubility
Slightly soluble in water.

Notes
Store in a cool, dry place in tightly closed container. Incompatible with oxidizing agents.

RUO – Research Use Only

General References:

Gianfranco Battistuzzi; Sandro Cacchi and Giancarlo Fabrizi. An Efficient Palladium-Catalyzed Synthesis of Cinnamaldehydes from Acrolein Diethyl Acetal and Aryl Iodides and Bromides. Org. Lett. 2003, 5 (5), 777-780.
Carmen Nájera; Luis Botella. Chemoselective Heck arylation of acrolein diethyl acetal catalyzed by an oxime-derived palladacycle. Tetrahedron. 2005, 61 (41), 9688-9695.
Protected acrolein equivalent. Reacts with Grignard reagents (CuBr catalysis) to give predominantly (Z)-enol ethers which can be hydrolyzed to 3-substituted propionaldehydes: Tetrahedron Lett., 3833 (1975). The (E)-enol ether is formed selectively with a Ni(II)-phosphine catalyst: Chem. Lett., 351 (1985).
Heck coupling (see Palladium(II) acetate, 10516) occurs with aryl or vinyl bromides in the presence of morpholine or piperidine: J. Org. Chem., 46, 1061 (1981); J. Chem. Soc., Perkin 1, 2597 (1987):
In the presence of acid, generates the ethoxyallyl cation which is a powerful dienophile, undergoing Diels-Alder reactions at low temperatures: J. Am. Chem. Soc., 109, 2182 (1987).