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Safety Information

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 1 petroleums
Hazardous rank II
Water insoluble liquid

JAN Code

A24001-25G:
A24001-BULK:
A24001-VAR:
A24001-100G:
A24001-10KG:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK1207
STBJ7606
STBH8286
STBH3551
STBG9081

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Synthesis of (?)-and (−)-botryodiplodin using stereoselective radical cyclizations of acyclic esters and acetals.
Nouguier R et al.
Tetrahedron Asymmetry, 14(19), 3005-3018 (2003)
Total synthesis of neolaulimalide and isolaulimalide.
Gollner A and Mulzer J.
Organic Letters, 10(20), 4701-4704 (2008)
Chemoselective Heck arylation of acrolein diethyl acetal catalyzed by an oxime-derived palladacycle.
Najera C and Botella L
Tetrahedron, 61(41), 9688-9695 (2005)
Total Synthesis of Microtubule-Stabilizing Agent (-)-Laulimalide1.
Ghosh AK et al.
The Journal of Organic Chemistry, 66(26), 8973-8982 (2001)
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)
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