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256145

Sigma-Aldrich

2-Ethylacrolein

contains hydroquinone as stabilizer

Sinonimo/i:

2-Ethylpropenal, 2-Methylenebutyraldehyde

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About This Item

Formula condensata:
CH2=C(CH2CH3)CHO
Numero CAS:
922-63-4
Peso molecolare:
84.12
Beilstein:
1098378
Numero CE:
213-079-3
Numero MDL:
MFCD00010129
Codice UNSPSC:
12352100
ID PubChem:
24855507
NACRES:
NA.22

Forma fisica

liquid

Livello qualitativo

100

contiene

hydroquinone as stabilizer

Indice di rifrazione

n20/D 1.425 (lit.)

P. eboll.

92-93 °C (lit.)

Densità

0.859 g/mL at 25 °C (lit.)

Gruppo funzionale

aldehyde

Temperatura di conservazione

2-8°C

Stringa SMILE

CCC(=C)C=O

InChI

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

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Applicazioni

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.

Pittogrammi

FlameSkull and crossbones
GHS02,GHS06

Avvertenze

Danger

Indicazioni di pericolo

H225,H302 + H312,H330

Classi di pericolo

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

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

33.8 °F - closed cup

Punto d’infiammabilità (°C)

1 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
SHBK3165
SHBH9377
SHBH8134
SHBH8136
SHBG9818V

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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)
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
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
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)
Synthesis of Diethyl 5-Ethyl-2, 3-Pyridinedicarboxylate
Cheng C, et al.
Asian Journal of Chemistry, 26(3), 918-918 (2014)
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