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A24001

Sigma-Aldrich

Acrolein diethyl acetal

96%

Synonym(s):

3,3-Diethoxy-1-propene

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About This Item

Linear Formula:
CH2=CHCH(OCH2CH3)2
CAS Number:
3054-95-3
Molecular Weight:
130.18
Beilstein:
1701567
EC Number:
221-276-0
MDL number:
MFCD00009239
UNSPSC Code:
12352100
PubChem Substance ID:
24890652
NACRES:
NA.22

Quality Level

200

Assay

96%

form

liquid

refractive index

n20/D 1.398 (lit.)

bp

125 °C (lit.)

density

0.854 g/mL at 25 °C (lit.)

SMILES string

CCOC(OCC)C=C

InChI

1S/C7H14O2/c1-4-7(8-5-2)9-6-3/h4,7H,1,5-6H2,2-3H3

InChI key

MCIPQLOKVXSHTD-UHFFFAOYSA-N

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Application

Acrolein diethyl acetal is widely used to carry out chemoselective Heck arylation to synthesize either 3-arylpropanoate esters or cinnamaldehyde derivatives.

It can also be used as one of the precursors to synthesize natural products like (−)-(Z)-Deoxypukalide, (−)-Laulimalide, botryodiplodin, neolaulimalide and isolaulimalide.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Statements

H225,H319

Precautionary Statements

P210 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

59.0 °F - closed cup

Flash Point(C)

15 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Synthesis of (-)?(Z)?Deoxypukalide.
Donohoe TJ et al.
Angewandte Chemie (International Edition in English), 47(38), 7314-7316 (2008)
Acrolein Diethyl Acetal: A Three?Carbon Homologating Reagent for the Synthesis of β?Arylpropanoates and Cinnamaldehydes by Heck Reaction Catalyzed by a Kaiser Oxime Resin Derived Palladacycle.
Alacid E and Najera C
The Journal of Organic Chemistry, 2008(18), 3102-3106 (2008)
An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides.
Battistuzzi G, et al.
Organic Letters, 5(5), 777-780 (2003)
Mohammad Saidur Rhaman et al.
Plant & cell physiology, 61(5), 967-977 (2020-03-08)
Myrosinase (β-thioglucoside glucohydrolase, enzyme nomenclature, EC 3.2.1.147, TGG) is a highly abundant protein in Arabidopsis guard cells, of which TGG1 and TGG2 function redundantly in abscisic acid (ABA)- and methyl jasmonate-induced stomatal closure. Reactive carbonyl species (RCS) are α,β-unsaturated aldehydes
Stefano Parisotto et al.
Organic & biomolecular chemistry, 15(4), 884-893 (2017-01-04)
As part of our ongoing work on the synthesis of a new class of plant hormones named Strigolactones (SLs) and their analogues, we became interested in tracing bioactive molecules with red emitting BODIPY fluorophores in order to unravel signaling and
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