Acetyl fluoride

Structural formula
General
Surname	Acetyl fluoride
other names	Ethanoyl fluoride
Molecular formula	C 2 H 3 FO
External identifiers / databases
CAS number 557-99-3 ECHA InfoCard 100.008.354 PubChem 11204 ChemSpider 10731 Wikidata Q481798
properties
Molar mass	62.04 g mol −1
density	1.032 g cm −3
Melting point	−84 ° C
boiling point	20.8 ° C
solubility	miscible in ethanol and diethyl ether soluble in chloroform and benzene
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 302 + 312-314-331-335-373 P: 260-264-270-271-280-301 + 312-301 + 330 + 331-302 + 352-303 + 361 + 353-304 + 340
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acetyl fluoride is a chemical compound from the group of acyl halides .

Extraction and presentation

Acetyl fluoride can be obtained by reacting hydrogen fluoride and acetic anhydride .

${\displaystyle {\ce {HF + (CH3CO)2O -> CH3CO2H + CH3COF}}}$

It is also possible to display it by reacting acetyl chloride with zinc fluoride or potassium fluoride in glacial acetic acid or acetic anhydride.

${\displaystyle {\ce {KF + CH3COCl -> CH3COF + KCl}}}$

properties

Acetyl fluoride attacks glass.

literature

• CA Bunton, JH Fendler: The Hydrolysis of Acetyl Fluoride. In: The Journal of Organic Chemistry . 31, 1966, p. 2307, doi : 10.1021 / jo01345a053
• Louis Pierce, Lawrence C. Krisher: Microwave Spectrum, Internal Barrier, Structure, Conformation, and Dipole Moment of Acetyl Fluoride. In: The Journal of Chemical Physics . 31, 1959, p. 875, doi : 10.1063 / 1.1730542
• AV Kudich, VA Bataev, AV Abramenkov, IA Godunov: Quantum-chemical study of the structure of the acetyl fluoride molecule in the ground and lowest excited singlet and triplet electronic states. In: Spectrochim Acta A Mol Biomol Spectrosc. 60, 2004, pp. 1995-2003, PMID 15248978 .

Individual evidence

1. ↑ ^{a b c d e} David R. Lide: CRC Handbook of Chemistry and Physics A Ready-reference Book of Chemical and Physical Data . CRC Press, 1995, ISBN 978-0-8493-0595-5 , pp. 6 ( limited preview in Google Book search).
2. ↑ ^{a b} SynQuest Labs, Inc .: Acetyl fluoride | SynQuest Labs, Inc. , accessed March 26, 2019
3. ↑ Matsuo Tanaka, Masahiro Fujiwara, Hisanori Ando: Dual Reactivity of the Formyl Cation as an Electrophile and a Broensted Acid in Superacids. In: The Journal of Organic Chemistry . 60, 1995, p. 3846, doi : 10.1021 / jo00117a041 .
4. ^ Frank C. Whitmore: Organic Chemistry, Volume One Part I: Aliphatic Compounds Part II: Alicyclic Compounds . Courier Corporation, 2012, ISBN 978-0-486-60700-9 , pp. 291 ( limited preview in Google Book search).
5. ^ Houben-Weyl Methods of Organic Chemistry Vol. V / 3, 4th Edition Fluorine and Chlorine Compounds . Georg Thieme Verlag, 2014, ISBN 3-13-179994-3 , p. 148 ( limited preview in Google Book search).
6. ↑ WLF Armarego, Christina Chai: Purification of Laboratory Chemicals . Butterworth-Heinemann, 2013, ISBN 0-12-382161-4 , pp. 976 ( limited preview in Google Book Search).