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256145

Sigma-Aldrich

2-Ethylacrolein

contains hydroquinone as stabilizer

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Synonym(s):
2-Ethylpropenal, 2-Methylenebutyraldehyde
Linear Formula:
CH2=C(CH2CH3)CHO
CAS Number:
Molecular Weight:
84.12
Beilstein:
1098378
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

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.)

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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This Item
T27855232548282510
2-Ethylacrolein contains hydroquinone as stabilizer

Sigma-Aldrich

256145

2-Ethylacrolein

2-Thiopheneethanol 98%

Sigma-Aldrich

T27855

2-Thiopheneethanol

3-Ethoxymethacrolein 96%

Sigma-Aldrich

232548

3-Ethoxymethacrolein

refractive index

n20/D 1.425 (lit.)

refractive index

n20/D 1.551 (lit.)

refractive index

n20/D 1.4792 (lit.)

refractive index

n20/D 1.539 (lit.)

bp

92-93 °C (lit.)

bp

108-109 °C/13 mmHg (lit.)

bp

78-81 °C/14 mmHg (lit.)

bp

187-188 °C (lit.)

density

0.859 g/mL at 25 °C (lit.)

density

1.153 g/mL at 25 °C (lit.)

density

0.96 g/mL at 25 °C (lit.)

density

0.901 g/mL at 25 °C (lit.)

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

2-8°C

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

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

Signal Word

Danger

Hazard Statements

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

Certificates of Analysis (COA)

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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)
Sergey A Kozmin et al.
Journal of the American Chemical Society, 124(17), 4628-4641 (2002-04-25)
Described is a concise, highly stereocontrolled strategy to the Aspidosperma family of indole alkaloids, one that is readily adapted to the asymmetric synthesis of these compounds. The strategy is demonstrated by the total synthesis of (+/-)-tabersonine (rac-1), proceeding through a
Synthesis of Diethyl 5-Ethyl-2, 3-Pyridinedicarboxylate
Cheng C, et al.
Asian Journal of Chemistry, 26(3), 918-918 (2014)
Ravindra A De Silva et al.
Journal of the American Chemical Society, 131(28), 9622-9623 (2009-06-26)
An entirely carbohydrate-based immunogen consisting of a zwitterionic polysaccharide (ZPS) PS A1 and the well-known tumor antigen Tn has been designed, synthesized, and studied for immunological effects. The PS A1 motif was included to act as an MHCII elicitor for
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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