Methanesulfonyl fluoride

Structural formula
General
Surname	Methanesulfonyl fluoride
other names	MSF
Molecular formula	CH 3 FO 2 S
Brief description	colorless to yellowish liquid with an unpleasant odor
External identifiers / databases
CAS number 558-25-8 EC number 209-192-2 ECHA InfoCard 100.008.358 PubChem 11207 ChemSpider 10734 DrugBank DB13058 Wikidata Q6823571
properties
Molar mass	98.10 g mol −1
Physical state	liquid
density	1.427 g cm −3 (25 ° C)
boiling point	123-124 ° C
solubility	decomposes in water
Refractive index	1.360 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 300 + 330-314 P: 260-264-280-284-305 + 351 + 338-310
Toxicological data	> 24 mg kg −1 ( LD 50 ,  rabbit ,  transdermal ) 2 mg kg −1 ( LD 50 ,  rat ,  oral )
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

Methanesulfonyl fluoride is a chemical compound from the group of sulfonyl halides .

Extraction and presentation

Methanesulfonyl fluoride can be obtained by reacting methanesulfonyl chloride with fluorides such as ammonium fluoride or potassium fluoride .

${\displaystyle \mathrm {CH_{3}SO_{2}Cl+NH_{4}F\longrightarrow CH_{3}SO_{2}F+NH_{4}Cl} }$

This type of synthesis was already carried out in 1932 by W. Davies and JH Dick with zinc (II) fluoride .

properties

Methanesulfonyl fluoride is a moisture-sensitive, colorless to yellowish liquid with an unpleasant odor that decomposes in water.

use

Methanesulfonyl fluoride acts as an inhibitor of acetylcholinesterase (antiChEs) and is being studied as a treatment for Alzheimer's disease . It's a thrombin inhibitor . It was also used as an insecticidal fumigant .

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on methanesulphonyl fluoride in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
2. ↑ Data sheet Methanesulfonyl fluoride, 98% from AlfaAesar, accessed on August 10, 2016 ( PDF )(JavaScript required) .
3. ↑ Entry on methanesulfonyl fluoride in the Hazardous Substances Data Bank , accessed on August 10, 2016.
4. ↑ T. Gramstad, RN Haszeldine: 33. Perfluoroalkyl derivatives of sulfur. Part IV. Perfluoroalkanesulphonic acids. In: Journal of the Chemical Society . 1956, p. 173, doi : 10.1039 / JR9560000173 .
5. ^ NN Melnikov: Chemistry of Pesticides . Springer Science & Business Media, 2012, ISBN 978-1-4684-6251-7 ( books.google.com ).
6. ↑ Advances in Inorganic Chemistry and Radiochemistry . Academic Press, 1960, ISBN 978-0-08-057851-4 ( books.google.com ).
7. ^ William Davies, John Henry Dick: 57. Aliphatic sulphonyl fluorides. In: Journal of the Chemical Society (Resumed). 1932, p. 483, doi : 10.1039 / JR9320000483 .
8. ↑ Data sheet Methanesulfonyl fluoride, 98% from Sigma-Aldrich , accessed on August 10, 2016 ( PDF ).
9. ↑ DE Moss, P. Berlanga, MM Hagan, H. Sandoval, C. Ishida: Methanesulfonyl fluoride (MSF): a double-blind, placebo-controlled study of safety and efficacy in the treatment of senile dementia of the Alzheimer type. In: Alzheimer Disease & Associated Disorders . Volume 13, Number 1, January 1999, pp. 20-25, PMID 10192638 .
10. ^ DE Moss, RG Fariello, J. Sahlmann, I. Sumaya, F. Pericle, E. Braglia: A randomized phase I study of methanesulfonyl fluoride, an irreversible cholinesterase inhibitor, for the treatment of Alzheimer's disease. In: British Journal of Clinical Pharmacology . Volume 75, number 5, May 2013, pp. 1231-1239, doi : 10.1111 / bcp.12018 , PMID 23116458 , PMC 3635594 (free full text).
11. ^ NN Melnikov: Chemistry of Pesticides . Springer, 1971, ISBN 978-1-4684-6251-7 , pp. 276 ( Google Books ).