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T33200

Sigma-Aldrich

Thiosalicylic acid

97%

Synonym(s):

2-Sulfanylbenzoic acid, 2-Mercaptobenzoic acid

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About This Item

Linear Formula:
HSC6H4CO2H
CAS Number:
147-93-3
Molecular Weight:
154.19
Beilstein:
508507
EC Number:
205-704-3
MDL number:
MFCD00004836
UNSPSC Code:
12352100
PubChem Substance ID:
24900130
NACRES:
NA.22

Assay

97%

mp

162-165 °C (lit.)

SMILES string

OC(=O)c1ccccc1S

InChI

1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9)

InChI key

NBOMNTLFRHMDEZ-UHFFFAOYSA-N

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Application

Thiosalicylic acid can be used as:
  • A nucleophilic trapping agent for the desulfenylation of 3-indolyl sulfides to obtain 3-unsubstituted indoles.
  • A starting material to prepare 2′-mercaptoacetophenone, which is used in the synthesis of thioflavanone by reacting with lithium diisopropylamide and benzaldehyde.
  • A stabilizing agent in the synthesis of metal nanoparticles.

It can also be used to prepare 2-thioxanthone-thioacetic acid bimolecular system, which is used as a photoinitiator for free radical polymerization.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The Journal of Organic Chemistry, 59, 6372-6372 (1994)
Synthesis and characterization of thiosalicylic acid stabilized gold nanoparticles
Pattabi RM and Pattabi M
Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy, 74(1), 195-199 (2009)
A new chemical method to desulfenylate indol-3-yl sulfides
Hamel P, et al.
Phosphorus, Sulfur, and Silicon and the Related Elements, 74(1-4), 391-391 (1993)
G Serrano et al.
Journal of the American Academy of Dermatology, 23(3 Pt 1), 479-483 (1990-09-01)
A photocontact dermatitis developed in three patients after the application of gel containing 0.5% piroxicam. Patch tests were positive to thiomersal and thiosalicylic acid. Photopatch tests with piroxicam at several concentrations were positive in the three patients but negative in
One-Component Bimolecular Photoinitiating Systems, 2
Aydin M, et al.
Macromolecular Rapid Communications, 24(12), 718-723 (2003)
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