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3054-95-3 - Acrolein diethyl acetal, 96% - 3,3-Diethoxy-1-propene - B24821 - Alfa Aesar

B24821 Acrolein diethyl acetal, 96%

CAS Number
3054-95-3
Synonyms
3,3-Diethoxy-1-propene

Size Price ($) Quantity Availability
10g 43.90
50g 111.00
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Acrolein diethyl acetal, 96%

MDL
MFCD00009239
EINECS
221-276-0

Chemical Properties

Formula
CH2=CHCH(OCH2CH3)2
Formula Weight
130.19
Boiling Point
124-125°
Flash Point
13°(55°F)
Density
0.852
Refractive Index
1.4010
Solubility
Slightly soluble in water.

Applications

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

Notes

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

Literature 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).

GHS Hazard and Precautionary Statements

Hazard Statements: H225-H319

Highly flammable liquid and vapour. Causes serious eye irritation.

Precautionary Statements: P210-P280-P240-P241-P233-P242-P303+P361+P353-P305+P351+P338-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
1701567
Hazard Class
3
Packing Group
II
Harmonized Tariff Code
2911.00
TSCA
No
RTECS
AS1370000

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