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Merck
CN

256145

Sigma-Aldrich

2-乙基丙烯醛

contains hydroquinone as stabilizer

别名:

2-Ethylpropenal, 2-甲基烯丁醛

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关于此项目

线性分子式:
CH2=C(CH2CH3)CHO
CAS Number:
分子量:
84.12
Beilstein:
1098378
EC 号:
MDL编号:
UNSPSC代码:
12352100
PubChem化学物质编号:
NACRES:
NA.22
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表单

liquid

质量水平

包含

hydroquinone as stabilizer

折射率

n20/D 1.425 (lit.)

沸点

92-93 °C (lit.)

密度

0.859 g/mL at 25 °C (lit.)

官能团

aldehyde

储存温度

2-8°C

SMILES字符串

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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应用

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.

象形图

FlameSkull and crossbones

警示用语:

Danger

危险分类

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

储存分类代码

3 - Flammable liquids

WGK

WGK 3

闪点(°F)

33.8 °F - closed cup

闪点(°C)

1 °C - closed cup

个人防护装备

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

法规信息

新产品

历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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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)
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)
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)
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)

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