Basic information
- Standard SMILES
O=C(O)c1ccccc1S- InChIKey
NBOMNTLFRHMDEZ-UHFFFAOYSA-N- Molecular formula
- C7H6O2S
- Average molar mass
- 154.19 g/mol
- Monoisotopic mass
- 154.00885043
Overview
Thiosalicylic acid is a sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid. It has a role as a non-narcotic analgesic and an antipyretic. It is a conjugate acid of a thiosalicylate(1-).
Names & identifiers
- Preferred name
- 2-Mercaptobenzoic Acid
- IUPAC
- 2-sulfanylbenzoic acid
- English name
- Thiosalicylic acid
- Molecular formula
- C7H6O2S
- Molecular weight
- 154.19
Names & synonyms
Thiosalicylic acid2-Mercaptobenzoic acid147-93-32-Sulfanylbenzoic acido-Mercaptobenzoic acid2-Thiosalicylic acido-Thiosalicylic acid2-Carboxythiophenolo-Sulfhydrylbenzoic acido-Benzoic acid thiolo-CarboxythiophenolBenzoic acid, 2-mercapto-
Show more names
Thiosalicylic2-Thiobenzoic acidTHIOSALYCYLIC ACIDicyiLusafkf-2NSC 2184NSC 6664
o-MercaptobenzoesaeureSalicylic acid, 2-thio-BENZOIC ACID, O-MERCAPTO-Thiophenol-2-carboxylic acidCIP6LXN5XWDTXSID4049032NSC-2184NSC-660640
Database identifiers
- CAS
147-93-3- PubChem CID
- 5443
- DTXSID
DTXSID4049032- ChEMBL
CHEMBL119888- ChEBI
CHEBI:59124- UNII
- CIP6LXN5XW
- EC Number
- 205-704-3
- Nikkaji
- J5.842D
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 38.3 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 1
- Heavy atoms
- 10
- Formal charge
- 0
- Complexity
- 136
Experimental & physicochemical properties
Chemical ClassesOther Classes -> Benzoic Acid Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsAntioxidant; Keratolytic; Reducing
SpringerMaterials PropertiesChemical shift
Color/Form
SULFUR-YELLOW FLAKES, PLATES, NEEDLES FROM GLACIAL ACETIC ACID OR ALCOHOL
LEAVES OR NEEDLES FROM WATER
CRYSTALS /SODIUM SALT/
Solubility
SOL IN WATER /SODIUM SALT/
SOL IN HOT WATER, ALCOHOL, ETHER, ACETIC ACID; SLIGHTLY SOLUBLE IN PETROLEUM ETHER
Melting Point168-169 °C
Physical DescriptionSulfur-yellow solid; Slightly soluble in hot water; [Merck Index] Yellow powder, soluble in water; [MSDSonline]
Stability/Shelf LifeEXPOSURE TO AIR YIELDS DITHIOSALICYLIC ACID
Other Experimental Properties
WHEN AN ALCOHOLIC SOLN OF THIOSALICYLIC ACID COMES IN CONTACT WITH FERRIC CHLORIDE, DITHIOSALICYLIC ACID IS PRODUCED
SOFTENS AT 158 °C; SUBLIMES
Physicochemical properties
- Melting point
- 162 · 162-165 °C (lit.)
- Boiling point
- 247.55 °C · 247.55°C (rough estimate)
- Density
- 1.49 · 1.49
- refractive index
- 1.51 · 1.5100 (estimate)
- Flash point
- 150 °C · 150 °C
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 1 · pK1:4.05(0) (20°C)
- form
- Fine Crystalline Powder
- color
- White to yellow
- Water Solubility
- soluble in hot water
- Sensitive
- Air & Light Sensitive
- Merck
- 14 · 14,9360
- BRN
- 508507 · 508507
- Cosmetics Ingredients Functions
- REDUCINGANTIOXIDANTKERATOLYTIC
- InChI
- 1S/C7H6O2S/c8-7(9)5-3-1-2-4-6(5)10/h1-4,10H,(H,8,9)
- InChIKey
- NBOMNTLFRHMDEZ-UHFFFAOYSA-N
- SMILES
- OC(=O)c1ccccc1S
- LogP
- 2.39 · 2.390
- CAS DataBase Reference
- 147 · 147-93-3(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 LXN5XW · CIP6LXN5XW
- NIST Chemistry Reference
- 2 · Benzoic acid, 2-mercapto-(147-93-3)
- EPA Substance Registry System
- 2 · Benzoic acid, 2-mercapto- (147-93-3)
- UNSPSC Code
- 12352106 · 12352106
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,Xn,N
- Risk Statements
- 36 · 36/37/38-20/21/22
- Safety Statements
- 26 · 26-36/37/39-36
- WGK Germany
- 3 · 3
- RTECS
- 3325000 · DH3325000
- F
- 9 · 9-23
- TSCA
- TSCA listed
- HS Code
- 29309070 · 29309070
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Hazardous Substances Data
- 147 · 147-93-3(Hazardous Substances Data)
- Toxicity
- 50 · mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689,
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 50 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzoic acid, 2-mercapto-
Thiosalicylic acid: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety & protection
Protective Action Criteria (PAC)
0.16 [mg/m3]
1.8 [mg/m3]
11 [mg/m3]
Toxicology
Non-Human Toxicity ExcerptsUNCOUPLING OF OXIDATIVE PHOSPHORYLATION IN RAT LIVER MITOCHONDRIA WAS INVESTIGATED WITH THIO ANALOGS OF SALICYLIC ACID. SIGNIFICANT ACTIVITY WAS OBSERVED.
Safety data
- F
- 9-23
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- DH3325000
- hs_code
- 29309070
- Toxicity
- mouse,LD50,intraperitoneal,50mg/kg (50mg/kg),National Technical Information Service. Vol. AD277-689,
- risk_code
- 36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,Xn,N
- safety_code
- 26-36/37/39-36
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
- Hazardous Substances Data
- 147-93-3(Hazardous Substances Data)
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationA subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS.
Uses & manufacturing
Uses
Used in the manufacture of thioindigo dyes and other chemicals and as a reagent for determination of iron; [HSDB]
MANUFACTURE OF THIOINDIGO DYES, REAGENT FOR DETERMINATION OF IRON
AS INTERMEDIATE
Methods of Manufacturing
PREPARED BY HEATING O-HALOGENATED BENZOIC ACIDS WITH ALKALINE HYDROSULFIDE IN PRESENCE OF COPPER; GERMAN PATENT 189,200 (1906); BY REDUCTION OF DITHIOSALICYLIC ACID: CLAASZ; BER 45, 2427 (1912); GERMAN PATENT 205,450; ALLEN, MACKAY, ORG SYN 12, 76 (1932).
Formulations/PreparationsGRADES: REAGENT; TECHNICAL, 80%; PHARMACEUTICAL.
Use ClassificationCosmetics -> Antioxidant; Keratolytic; Reducing
General Manufacturing InformationBenzoic acid, 2-mercapto-: ACTIVE
Applications
UsesThiosalicylic acid acts as a trapping agent, which is useful in the desulfenylation of 3-indolyl sulfides. It is used to prepare macrocyclic diamides by condensation with diamines. Further, it is used as a precursor to drug, which finds application for the treatment of atherosclerosis and melanoma. In addition to this, it is involved in the preparation of vaccine preservative thiomersal and thioindigo dyestuff.
Preparation methods
PreparationThiosalicylic acid can be prepared from anthranilic acid via diazotization followed by the addition of sodium sulfide and then reduction with zinc. It can also prepared by heating o-halogenated benzoic acids with alkaline hydrosulfide in presence of copper.
Upstream & downstream products
Upstream raw materials
Downstream products
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Additional notes
DefinitionChEBI: Thiosalicylic acid is a sulfanylbenzoic acid that is the 2-sulfanyl derivative of benzoic acid. It has a role as a non-narcotic analgesic and an antipyretic. It is a conjugate acid of a thiosalicylate(1-).
Related reactions
162 records
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