256145
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:
Molecular Weight:
84.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
213-079-3
Beilstein/REAXYS Number:
1098378
MDL number:
Form:
liquid
InChI key
GMLDCZYTIPCVMO-UHFFFAOYSA-N
InChI
1S/C5H8O/c1-3-5(2)4-6/h4H,2-3H2,1H3
SMILES string
CCC(=C)C=O
form
liquid
contains
hydroquinone as stabilizer
Quality Level
bp
92-93 °C (lit.)
density
0.859 g/mL at 25 °C (lit.)
functional group
aldehyde
storage temp.
2-8°C
Related Categories
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:
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.
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 2 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Flam. Liq. 2
Storage Class
3 - Flammable liquids
wgk
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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Synthesis of Diethyl 5-Ethyl-2, 3-Pyridinedicarboxylate
Cheng C, et al.
Asian Journal of Chemistry, 26(3), 918-918 (2014)
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
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)
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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