Ethyl 2-butynoate

Ethyl 2-butynoate Basic information
Product Name:Ethyl 2-butynoate
Synonyms:TETROLIC ACID ETHYL ESTER;2-BUTYNOIC ACID ETHYL ESTER;ETHYL 2-BUTYNOATE;ETHYL TETROLATE;Ethyl 1-propynecarboxylate;Ethyl 3-methylpropiolate;2-Butynoic acid ethyl ester~Ethyl tetrolate;Ethyltetrolate,Tetrolicacidethy
CAS:4341-76-8
MF:C6H8O2
MW:112.13
EINECS:224-395-6
Product Categories:Acetylenes;Acetylenic Carboxylic Acids & Their Derivatives
Mol File:4341-76-8.mol
Ethyl 2-butynoate Structure
Ethyl 2-butynoate Chemical Properties
Boiling point 160-161 °C/730 mmHg (lit.)
density 0.962 g/mL at 25 °C (lit.)
refractive index n20/D 1.436(lit.)
Fp 145 °F
storage temp. Inert atmosphere,2-8°C
solubility Chloroform, Ethyl Acetate
form Powder
Specific Gravity0.962
color Grey to red to brown
Water Solubility Miscible with water, chloroform and ethyl acetate.
Sensitive Air Sensitive
BRN 1744948
InChIKeyFCJJZKCJURDYNF-UHFFFAOYSA-N
CAS DataBase Reference4341-76-8(CAS DataBase Reference)
NIST Chemistry ReferenceEthyl 2-butynoate(4341-76-8)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-36
RIDADR 1993
WGK Germany 3
10-23
Hazard Note Irritant
HazardClass 3.2
PackingGroup III
HS Code 29161900
MSDS Information
ProviderLanguage
SigmaAldrich English
Ethyl 2-butynoate Usage And Synthesis
UsesEthyl 2-butynoate is used as a precursor for the synthesis of 3-ethyl, 1-methyl 1-(2-nitrophenyl)-cyclopent-3-ene-1,3-dicarboxylate, alkenylsilanols and tricyclic aziridine derivatives. It acts as a methanogenesis inhibitor. As an electron deficient alkyne derivative, it plays a vital role in the preparation of 1,3-dienes catalyzed by rhodium(I)/H8-BINAP complex.
UsesEthyl 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
Synthesis Reference(s)Organic Syntheses, Coll. Vol. 7, p. 226, 1990
The Journal of Organic Chemistry, 38, p. 3588, 1973 DOI: 10.1021/jo00960a032
General DescriptionEthyl 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.
DI-TERT-BUTYL ACETYLENEDICARBOXYLATE ETHYL 2-BUTYNOATE, (ETHYL TETROLATE, TETROLIC ACID ETHY Ethyl heptanoate LINOLENIC ACID ETHYL ESTER Ethyl pyruvate ETHYL PHENYLPROPIOLATE Ethyl glyoxalate Ethyl 2-butynoate Diethyl maleate ETHYL 2-PENTYNOATE 2-Butynoic acid Diethyl methylmalonate ETHYL 3-BUTYNOATE ISOXADIFEN-ETHYL 2-Butyne Ethyl propiolate 2-NONYNOIC ACID CIS-3-HEXEN-1-YL ESTER Ethyl cinnamate

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