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256145

Sigma-Aldrich

2-Ethylacrolein

contains hydroquinone as stabilizer

Synonym(s):

2-Ethylpropenal, 2-Methylenebutyraldehyde

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About This Item

Linear Formula:
CH2=C(CH2CH3)CHO
CAS Number:
922-63-4
Molecular Weight:
84.12
Beilstein:
1098378
EC Number:
213-079-3
MDL number:
MFCD00010129
UNSPSC Code:
12352100
PubChem Substance ID:
24855507
NACRES:
NA.22

form

liquid

Quality Level

100

contains

hydroquinone as stabilizer

refractive index

n20/D 1.425 (lit.)

bp

92-93 °C (lit.)

density

0.859 g/mL at 25 °C (lit.)

functional group

aldehyde

storage temp.

2-8°C

SMILES string

CCC(=C)C=O

InChI

1S/C5H8O/c1-3-5(2)4-6/h4H,2-3H2,1H3

InChI key

GMLDCZYTIPCVMO-UHFFFAOYSA-N

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Application

2-Ethylacrolein can be used as a promoter to synthesize 2-alkylchroman-4-ones via rhodium-catalyzed annulation reaction of 1,3-dienes with salicylaldehydes or 2-hydroxybenzyl alcohols.
It can also be used as a reactant:
  • In the total synthesis of (±)-tabersonine, an indole alkaloid of the Aspidosperma family.
  • To prepare 2-ethylbicyclo[2.2.1]hept-5-ene-2-carboxaldehyde via enantioselective Diels-Alder reaction with cyclopentadiene in the presence of chiral Lewis acid catalyst.
  • To synthesize diethyl 5-ethyl-2,3-pyridinedicarboxylate by reacting with 2-chloro-3-oxo-succinic acid diethyl ester using ammonium acetate as a catalyst.

Pictograms

FlameSkull and crossbones
GHS02,GHS06

Signal Word

Danger

Hazard Statements

H225,H302 + H312,H330

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Flam. Liq. 2

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

33.8 °F - closed cup

Flash Point(C)

1 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCR6189
SHBK3165
SHBH9377
SHBH8134
SHBH8136

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L M Appelman et al.
Toxicology, 22(1), 79-87 (1981-01-01)
The subacute inhalation toxicity of alpha-ethylacrolein was examined in rats by repeated exposure of 4 groups of 10 males and 10 females each to alpha-ethylacrolein vapour at concentrations of 0, 2.0, 9.8 or 48.4 ppm, respectively, (6 h/day, 5 days/week)
Rhodium-Catalyzed Annulations of 1, 3-Dienes and Salicylaldehydes/2-Hydroxybenzyl Alcohols Promoted by 2-Ethylacrolein
Li Hong-Shuang, et al.
Advanced Synthesis & Catalysis, 360(21), 4246-4251 (2018)
Design of Bronsted acid-assisted chiral Lewis acid (BLA) catalysts for highly enantioselective Diels- Alder reactions
Ishihara K, et al.
Journal of the American Chemical Society, 120(28), 6920-6930 (1998)
Synthesis of Diethyl 5-Ethyl-2, 3-Pyridinedicarboxylate
Cheng C, et al.
Asian Journal of Chemistry, 26(3), 918-918 (2014)
Rhodium-Catalyzed Annulations of 1, 3-Dienes and Salicylaldehydes/2-Hydroxybenzyl Alcohols Promoted by 2-Ethylacrolein
Li Hong-Shuang, et al.
advanced synthesis and catalysis, 360(21), 4246-4251 (2018)
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