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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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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
Synthesis of (?)-and (−)-botryodiplodin using stereoselective radical cyclizations of acyclic esters and acetals.
Nouguier R et al.
Tetrahedron Asymmetry, 14(19), 3005-3018 (2003)
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
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)
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