Quinoline-8-sulfonic acid

Structural formula
General
Surname	Quinoline-8-sulfonic acid
Molecular formula	C 9 H 7 NO 3 S
External identifiers / databases
EC number	201-611-7
ECHA InfoCard	100.001.465
PubChem	66561
Wikidata	Q1074408
properties
Molar mass	209.23 g mol −1
Physical state	firmly
Melting point	> 300 ° C
solubility	soluble in water
safety instructions
GHS labeling of hazardous substances danger
H and P phrases	H: 314
	P: 260-301 + 330 + 331-303 + 361 + 353-305 + 351 + 338-405-501
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Quinoline-8-sulfonic acid is a heterocyclic chemical compound which consists of a quinoline structure that has a sulfonic acid group in the 8-position .

presentation

The compound can be obtained by sulfonating quinoline with oleum at 90 ° C. The isomer substituted in the 5-position is essentially formed as a by-product .

use

Quinoline-8-sulfonic acid can be used to make 8-hydroxyquinoline , a complexing agent that is used as a disinfectant and antifungal agent . This is achieved by ipso - hydroxylation of the compound with hot sodium hydroxide solution .

The isomeric quinoline-6-sulfonic acid , which is only accessible in low yield by direct sulfonation of quinoline, can also be produced by thermal isomerization of quinoline-8-sulfonic acid. This works because the isomer substituted in the 6-position is thermodynamically more stable.

Individual evidence

↑ ^a ^b ^c ^d data sheet quinoline-8-sulfonic acid from AlfaAesar, accessed on April 30, 2017 ( PDF )(JavaScript required) .
↑ MV Dorogov, SI Filimonov, DB Kobylinsky, SA Ivanovsky, PV Korikov, MY Soloviev, MY Khahina, EE Shalygina, DV Kravchenko, AV Ivachtchenko: A Convenient Synthesis of Novel 3- (Heterocyclylsulfonyl) propanoic Acids and their Amide Derivatives. In: Synthesis . 18, 2004, pp. 2999-3004; doi: 10.1055 / s-2004-834888 .
↑ JA Joules, K. Mills: Heterocyclic Chemistry. 5th edition, Blackwell Publishing, Chichester, 2010, ISBN 978-1-4051-9365-8 , pp. 177-199.
↑ NN Woroshtzow, JM Kogan: About the effect of sulphurous acid and its salts on quinoline derivatives. In: Ber. German Chem. Ges. 1930, pp. 2354-2362; doi: 10.1002 / cber.19300630878 .
^ GE McCasland: The Preparation of 8-Quinolinesulfonic Acid. In: J. Org. Chem. 11, 1946, pp. 277-280; doi: 10.1021 / jo01173a010 .

[alfa-1] ta sheet quinoline-8-sulfonic acid from AlfaAesar, accessed on April 30, 2017 ( PDF )(JavaScript required) .

[2] MV Dorogov, SI Filimonov, DB Kobylinsky, SA Ivanovsky, PV Korikov, MY Soloviev, MY Khahina, EE Shalygina, DV Kravchenko, AV Ivachtchenko: A Convenient Synthesis of Novel 3- (Heterocyclylsulfonyl) propanoic Acids and their Amide Derivatives. In: Synthesis . 18, 2004, pp. 2999-3004; doi: 10.1055 / s-2004-834888 .

[joules-3] JA Joules, K. Mills: Heterocyclic Chemistry. 5th edition, Blackwell Publishing, Chichester, 2010, ISBN 978-1-4051-9365-8 , pp. 177-199.

[4] NN Woroshtzow, JM Kogan: About the effect of sulphurous acid and its salts on quinoline derivatives. In: Ber. German Chem. Ges. 1930, pp. 2354-2362; doi: 10.1002 / cber.19300630878 .

[5] GE McCasland: The Preparation of 8-Quinolinesulfonic Acid. In: J. Org. Chem. 11, 1946, pp. 277-280; doi: 10.1021 / jo01173a010 .