Thiosalicylic acid
Structural formula | ||||||||||||||||||||||
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General | ||||||||||||||||||||||
Surname | Thiosalicylic acid | |||||||||||||||||||||
other names |
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Molecular formula | C 7 H 6 O 2 S | |||||||||||||||||||||
Brief description |
light yellow, malodorous solid |
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properties | ||||||||||||||||||||||
Molar mass | 154.19 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
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Sublimation point |
164-165 ° 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 . |
Thiosalicylic acid is a sulfur analogue of salicylic acid , the phenolic hydroxyl group being replaced by a thiol group (mercapto group).
Extraction and presentation
The synthesis takes place by the reaction of 2-chloro- or 2-bromobenzoic acid with sodium hydrogen sulfide or potassium hydrogen sulfide in the presence of copper . The reduction of dithiosalicylic acid also produces thiosalicylic acid.
properties
Air oxygen oxidizes thiosalycilic acid to dithiosalicylic acid (a disulfide ). Dithiosalicylic acid is also formed when iron (III) chloride is added to an alcoholic solution of thiosalicylic acid . The reaction is z. B. also catalyzed by copper (II) salts.
use
The pure red vat dye thioindigo was first synthesized from thiosalicylic acid.
Individual evidence
- ↑ Entry on THIOSALICYLIC ACID in the CosIng database of the EU Commission, accessed on May 11, 2020.
- ↑ a b c d Data sheet thiosalicylic acid (PDF) from Merck , accessed on April 24, 2011.
- ^ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 1608.
- ↑ Mohammad Soleiman-Beigi, Zahra Taherinia: Simple and efficient oxidative transformation of thiols to disulfides using Cu (NO 3 ) 2 · 3H 2 O in H 2 O / AcOEt in monthly journals for chemistry ; 145 , 2014 , 1151–1154 doi : 10.1007 / s00706-014-1178-9 .
- ^ Hans Beyer and Wolfgang Walter: Organische Chemie , S. Hirzel Verlag, Stuttgart 1984, ISBN 3-7776-0406-2 , p. 696.