Skip to Content
Merck
All Photos(1)

Documents

425117

Sigma-Aldrich

Ethyl 2-butynoate

98%

Synonym(s):

Ethyl tetrolate

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

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)

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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.
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
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)
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service