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425117

Sigma-Aldrich

Ethyl 2-butynoate

98%

Synonym(s):

Ethyl tetrolate

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About This Item

Linear Formula:
CH3C≡CC(O)OCH2CH3
CAS Number:
4341-76-8
Molecular Weight:
112.13
Beilstein:
1744948
EC Number:
224-395-6
MDL number:
MFCD00015182
UNSPSC Code:
12352100
PubChem Substance ID:
24866611
NACRES:
NA.22

Assay

98%

form

liquid

refractive index

n20/D 1.436 (lit.)

bp

160-161 °C/730 mmHg (lit.)

density

0.962 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)C#CC

InChI

1S/C6H8O2/c1-3-5-6(7)8-4-2/h4H2,1-2H3

InChI key

FCJJZKCJURDYNF-UHFFFAOYSA-N

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General description

Ethyl 2-butynoate, a 2-alkynoate is a methanogenesis inhibitor. It is an electron deficient internal alkyne that has been reported to undergo codimerization with alkenes to form 1,3-dienes catalyzed by rhodium(I)/H8-BINAP complex. The annulation of thioamides with ethyl 2-butynoate catalyzed by tri-n-butylphosphine to form thiazolines has been investigated.

Application

Ethyl 2-butynoate was used in the study of its effect on in vitro degradation and microbial biomass production.
It may be used in the synthesis of the following:
  • 3-ethyl, 1-methyl 1-(2-nitrophenyl)-cyclopent-3-ene-1,3-dicarboxylate
  • tricyclic aziridine derivatives
  • alkenylsilanols

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

143.6 °F - closed cup

Flash Point(C)

62 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Bing Liu et al.
The Journal of organic chemistry, 67(13), 4595-4598 (2002-06-22)
The annulation of thioamides with 2-alkynoates and 2,3-dienoates under the catalysis of tri-n-butylphosphine was described. The annulation reaction provided a new entry to thiazolines, particularly those with 2-aryl substituents.
Synthesis of 2-azaspiro [4.4] nonan-1-ones via phosphine-catalysed [3+ 2]-cycloadditions.
Yong SR, et al.
Tetrahedron, 61(34), 8120-8129 (2005)
Yu Shibata et al.
Organic letters, 10(13), 2829-2831 (2008-06-12)
A cationic rhodium(I)/H(8)-BINAP complex catalyzes codimerization of alkenes bearing no alpha-hydrogen and electron-deficient internal alkynes, leading to 1,3-dienes in good yields with moderate to excellent regio- and stereoselectivity. The same complex also catalyzes codimerization of an acrylate and phenyl-substituted electron-rich
Dichloro [TADDOLato (2-)-O,O'] titanium/Dichlorobis [1-methylethoxy] titanium-Mediated, Highly Diastereo-and Enantioselective Additions of Silyl Enol Ethers to Nitro Olefins and [3+ 2] Cycloadditions of Primary Adducts to Acetylenes.
Seebach D, et al.
Helvetica Chimica Acta, 82(11), 1829-1842 (1999)
Efficient and stereoselective cross-coupling with highly substituted alkenylsilanols.
Denmark SE and Pan W.
Journal of Organometallic Chemistry, 653(1), 98-104 (2002)
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