4-ethoxy-1,1,1-trifluoro-3-buten-2-one

Structural formula
General
Surname	4-ethoxy-1,1,1-trifluoro-3-buten-2-one
other names	ETFBO
Molecular formula	C 6 H 7 F 3 O 2
Brief description	yellow liquid
External identifiers / databases
EC number	629-004-6
ECHA InfoCard	100.157.225
PubChem	5709222
ChemSpider	2060604
Wikidata	Q22668720
properties
Molar mass	168.11 g mol −1
Physical state	liquid
density	1.18 g cm −3
boiling point	51-53 ° C (12 mmHg )
Refractive index	1.406 (20 ° C)
safety instructions
H and P phrases	H: 226-351
	P: 281
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

4-Ethoxy-1,1,1-trifluoro-3-buten-2-one ( ETFBO ) is a chemical compound from the group of organic fluorine compounds. ETFBO is used as a synthesis module for the production of fluorine-containing pharmaceuticals and pesticides.

Extraction and presentation

ETFBO can be obtained by adding trifluoroacetyl chloride to ethyl vinyl ether . The connection is established in Germany by Solvay in Bad Wimpfen , among others .

Reactions

ETFBO is z. B. used for the synthesis of 4-trifluoromethylnicotinic acid .

Wittig olefination of ETFBO leads to 1-ethoxy-3-trifluoromethyl-1,3-butadiene, which acts as a diene in Diels-Alder reactions . Reaction with various dienophiles gives aromatics with a trifluoromethyl group .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Data sheet 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one, contains 0.5% BHT as stabilizer, technical grade from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
↑ Patent US8981115 : Process for the synthesis of halogenated cyclic compounds. Registered on April 29, 2013 , published on March 17, 2015 , applicant: Solvay SA, inventor: Max Braun. ‌
↑ EP 1 803 703 A1: “Halogenated alkenone ethers, for example 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (“ ETFBO ”), are building blocks in chemical synthesis. They can be prepared by reacting an acid chloride with a vinyl ether in the presence of a base; the base can also be used as a solvent in excess. "
↑ Solvay inaugurates new facility in Bad Wimpfen: ETFBO synthesis module for crop protection products , November 10, 2014.
↑ Patent EP0744400 : Process for the production of 4-trifluoromethylnicotinic acid. Applied on May 13, 1996 , published on September 11, 2002 , applicant: Ishihara Sangyo Kaisha , inventor: Japanese. ‌
^ Richard T. Taylor: Encyclopedia of Reagents for Organic Synthesis . John Wiley & Sons, Ltd, 2001, ISBN 978-0-470-84289-8 , 1-ethoxy-3-trifluoromethyl-1,3-butadiene, doi : 10.1002 / 047084289X.rn00599 .

[sa-1] ↑ ^a ^b ^c ^d ^e ^f Data sheet 4-Ethoxy-1,1,1-trifluoro-3-buten-2-one, contains 0.5% BHT as stabilizer, technical grade from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).

[2] Patent US8981115 : Process for the synthesis of halogenated cyclic compounds. Registered on April 29, 2013 , published on March 17, 2015 , applicant: Solvay SA, inventor: Max Braun. ‌

[3] EP 1 803 703 A1: “Halogenated alkenone ethers, for example 4-ethoxy-1,1,1-trifluoro-3-buten-2-one (“ ETFBO ”), are building blocks in chemical synthesis. They can be prepared by reacting an acid chloride with a vinyl ether in the presence of a base; the base can also be used as a solvent in excess. "

[4] Solvay inaugurates new facility in Bad Wimpfen: ETFBO synthesis module for crop protection products , November 10, 2014.

[5] Patent EP0744400 : Process for the production of 4-trifluoromethylnicotinic acid. Applied on May 13, 1996 , published on September 11, 2002 , applicant: Ishihara Sangyo Kaisha , inventor: Japanese. ‌

[6] Richard T. Taylor: Encyclopedia of Reagents for Organic Synthesis . John Wiley & Sons, Ltd, 2001, ISBN 978-0-470-84289-8 , 1-ethoxy-3-trifluoromethyl-1,3-butadiene, doi : 10.1002 / 047084289X.rn00599 .