4-ethoxy-1,1,1-trifluoro-3-buten-2-one
Structural formula | |||||||||||||||||||
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General | |||||||||||||||||||
Surname | 4-ethoxy-1,1,1-trifluoro-3-buten-2-one | ||||||||||||||||||
other names |
ETFBO |
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Molecular formula | C 6 H 7 F 3 O 2 | ||||||||||||||||||
Brief description |
yellow liquid |
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properties | |||||||||||||||||||
Molar mass | 168.11 g mol −1 | ||||||||||||||||||
Physical state |
liquid |
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density |
1.18 g cm −3 |
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boiling point |
51-53 ° C (12 mmHg ) |
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Refractive index |
1.406 (20 ° C) |
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safety instructions | |||||||||||||||||||
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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 .