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256145

Sigma-Aldrich

2-Ethylacrolein

contains hydroquinone as stabilizer

Sinónimos:

2-Ethylpropenal, 2-Methylenebutyraldehyde

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About This Item

Fórmula lineal:
CH2=C(CH2CH3)CHO
Número de CAS:
922-63-4
Peso molecular:
84.12
Beilstein/REAXYS Number:
1098378
EC Number:
213-079-3
MDL number:
MFCD00010129
UNSPSC Code:
12352100
PubChem Substance ID:
24855507
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.)

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

signalword

Danger

Hazard Classifications

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

Storage Class

3 - Flammable liquids

wgk_germany

WGK 3

flash_point_f

33.8 °F - closed cup

flash_point_c

1 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificados de análisis (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)
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
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
Synthesis of Diethyl 5-Ethyl-2, 3-Pyridinedicarboxylate
Cheng C, et al.
Asian Journal of Chemistry, 26(3), 918-918 (2014)
An efficient approach to Aspidosperma alkaloids via [4+ 2] cycloadditions of aminosiloxydienes: Stereocontrolled total synthesis of (?)-tabersonine. Gram-scale catalytic asymmetric syntheses of (+)-tabersonine and (+)-16-methoxytabersonine. Asymmetric syntheses of (+)-aspidospermidine and (-)-quebrachamine
Kozmin SA, et al.
Journal of the American Chemical Society, 124(17), 4628-4641 (2002)
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