Thiosalicylic acid

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Structural formula
Structure of thiosalicylic acid
General
Surname Thiosalicylic acid
other names
  • 2-mercaptobenzoic acid
  • 2-sulfanylbenzoic acid
  • THIOSALICYLIC ACID ( INCI )
Molecular formula C 7 H 6 O 2 S
Brief description

light yellow, malodorous solid

External identifiers / databases
CAS number 147-93-3
EC number 205-704-3
ECHA InfoCard 100.005.187
PubChem 5443
ChemSpider 5248
DrugBank DB14026
Wikidata Q1312775
properties
Molar mass 154.19 g mol −1
Physical state

firmly

Sublimation point

164-165 ° C

safety instructions
GHS labeling of hazardous substances
07 - Warning

Caution

H and P phrases H: 315-319-335
P: 302 + 352-304 + 340-305 + 351 + 338
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.

Air oxidation of thiosalicylic acid, catalyzed by iron (III) or cupfer (II) salts

use

The pure red vat dye thioindigo was first synthesized from thiosalicylic acid.

Individual evidence

  1. ↑ Entry on THIOSALICYLIC ACID in the CosIng database of the EU Commission, accessed on May 11, 2020.
  2. ↑ a b c d Data sheet thiosalicylic acid (PDF) from Merck , accessed on April 24, 2011.
  3. ^ The Merck Index. An Encyclopaedia of Chemicals, Drugs and Biologicals. 14th edition, 2006, ISBN 978-0-911910-00-1 , p. 1608.
  4. ↑ 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 .
  5. ^ Hans Beyer and Wolfgang Walter: Organische Chemie , S. Hirzel Verlag, Stuttgart 1984, ISBN 3-7776-0406-2 , p. 696.