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167940

Sigma-Aldrich

Ethyl crotonate

99%

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About This Item

Linear Formula:
CH3CH=CHCOOC2H5
Molecular Weight:
114.14
Beilstein/REAXYS Number:
635834
EC Number:
210-808-7
MDL number:
MFCD00009289
UNSPSC Code:
12352100
PubChem Substance ID:
24850227
NACRES:
NA.22

vapor density

3.9 (vs air)

assay

99%

form

liquid

refractive index

n20/D 1.424 (lit.)

bp

142-143 °C (lit.)

density

0.918 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)\C=C\C

InChI

1S/C6H10O2/c1-3-5-6(7)8-4-2/h3,5H,4H2,1-2H3/b5-3+

InChI key

ZFDIRQKJPRINOQ-HWKANZROSA-N

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General description

Ethyl crotonate on hydroboration yields 2-tritiated 3-hydroxybutyric acid.

Application

Ethyl crotonate was used in the total synthesis of (+/-)-daurichromenic acid. It was also used in the synthesis of ethyl 3-methyl-4-oxooctanoate.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Danger

hcodes

H225,H319

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 2

Storage Class

3 - Flammable liquids

wgk_germany

WGK 2

flash_point_f

35.6 °F - closed cup

flash_point_c

2 °C - closed cup

ppe

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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P Willadsen et al.
European journal of biochemistry, 54(1), 247-252 (1975-05-01)
1. A specimen of stereospecifically 2-tritiated 3-hydroxybutyric acid was prepared by hydroboration of ethyl crotonate. It was assumed that the hydroboration reaction took a syn course and hence that (2R,3S) plus (2S,3R)-3-hydroxy[2 minus 3H1]butyric acid was formed after oxidation and
Synthesis of all stereoisomers of cognac lactones via microbial reduction and enzymatic resolution strategies.
Benedetti F, et al.
Tetrahedron Asymmetry, 12(3), 505-511 (2001)
Hongjuan Hu et al.
The Journal of organic chemistry, 69(11), 3782-3786 (2004-05-22)
A modular and concise total synthesis of (+/-)-daurichromenic acid has been accomplished in four steps from ethyl acetoacetate, ethyl crotonate, and trans,trans-farnesal. A series of analogues of this natural product, which has potent anti-HIV activity, were also prepared from ethyl
Amélie Slegers et al.
Molecules (Basel, Switzerland), 20(6), 10980-11016 (2015-06-18)
Developed from crosses between Vitis vinifera and North American Vitis species, interspecific hybrid grape varieties are becoming economically significant in northern areas, where they are now extensively grown for wine production. However, the varietal differences between interspecific hybrids are not

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