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Merck
CN

190543

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:
Molecular Weight:
102.13
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
227-936-4
Beilstein/REAXYS Number:
1700037
MDL number:
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Product Name

Acrolein dimethyl acetal, 98%

InChI key

OBWGMYALGNDUNM-UHFFFAOYSA-N

InChI

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

SMILES string

COC(OC)C=C

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
ether

Quality Level

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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.

General description

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

pictograms

Flame

signalword

Danger

hcodes

pcodes

Hazard Classifications

Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

26.6 °F - closed cup

flash_point_c

-3 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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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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