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190543

Sigma-Aldrich

Acrolein dimethyl acetal

98%

Synonym(s):

3,3-Dimethoxy-1-propene

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About This Item

Linear Formula:
H2C=CHCH(OCH3)2
CAS Number:
6044-68-4
Molecular Weight:
102.13
Beilstein:
1700037
EC Number:
227-936-4
MDL number:
MFCD00008632
UNSPSC Code:
12352100
PubChem Substance ID:
24851444
NACRES:
NA.22

Quality Level

100

Assay

98%

form

liquid

refractive index

n20/D 1.395 (lit.)

bp

89-90 °C (lit.)

density

0.862 g/mL at 25 °C (lit.)

functional group

acetal

SMILES string

COC(OC)C=C

InChI

1S/C5H10O2/c1-4-5(6-2)7-3/h4-5H,1H2,2-3H3

InChI key

OBWGMYALGNDUNM-UHFFFAOYSA-N

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General description

Acrolein dimethyl acetal undergoes cationic α-diimine palladium chelate catalyzed copolymerization with ethene to yield branched copolymers.

Application

Acrolein dimethyl acetal was used in the facile one step synthesis of 4-hydroxy-2E-nonenal and its dimethyl acetal via a cross-metathesis reaction with octen-3-ol.

Pictograms

Flame
GHS02

Signal Word

Danger

Hazard Statements

H225

Precautionary Statements

P210

Hazard Classifications

Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

26.6 °F - closed cup

Flash Point(C)

-3 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Weidong Li et al.
Journal of the American Chemical Society, 126(39), 12246-12247 (2004-09-30)
Acrolein dimethyl acetal (ADMA) can be copolymerized with ethene using a cationic alpha-diimine palladium chelate catalyst to yield branched copolymers. Catalyst deactivation occurs via methanol elimination to give an inert eta3-1-methoxyallyl palladium species. This process can be retarded by the
Laurent Soulère et al.
Chemistry and physics of lipids, 150(2), 239-243 (2007-10-05)
The facile one step synthesis of 4-hydroxy-2E-nonenal and its dimethyl acetal via a cross-metathesis reaction between commercially available octen-3-ol and acrolein or its dimethyl acetal is reported. The method was extended to the synthesis of C6 and C12 4-hydroxy-2E-enals, their

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