16133-26-9

Basic information

• Product Name: Pyridine-3-thiol
• Synonyms: 3-Pyridinethiol;Pyridine-3-thiol
• CAS NO: 16133-26-9
• Molecular Formula: C₅H₅NS
• Molecular Weight: 111.16
• Product Categories: Chemical intermediate
• Mol File: 16133-26-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 78-80 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• Boiling Point: 194 °C at 760 mmHg
• Flash Point: 71.1 °C
• Appearance: /
• Density: 1.166 g/cm³
• Vapor Pressure: 0.631mmHg at 25°C
• Refractive Index: 1.598
• PKA: 2.73±0.10(Predicted)
• CAS DataBase Reference: Pyridine-3-thiol(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine-3-thiol(16133-26-9)
• EPA Substance Registry System: Pyridine-3-thiol(16133-26-9)

Safety Data

• Hazardous Substances Data: 16133-26-9(Hazardous Substances Data)

Usage

Description

Pyridine-3-thiol, also known as 3-mercaptopyridine, is a compound belonging to the class of organic substances known as pyridines and derivatives. It has a role as a poison and a solvent, characterized by its foul smell and molecular formula C5H5NS. Due to its hazardous properties, it requires careful handling and transportation, and is not approved for use as a food additive or flavoring agent.

Uses

Used in Analytical Chemistry:
Pyridine-3-thiol is used as a titrating agent in the field of analytical chemistry for its specific reactivity and properties that aid in the determination of certain substances.
Used in Solvent Applications:
As a solvent, Pyridine-3-thiol is utilized in various chemical processes where its unique solvency characteristics are required for dissolving specific compounds or facilitating reactions. However, its use is limited by its potential health risks and foul smell, necessitating strict safety measures during its application.

InChI:InChI=1/C5H5NS/c7-5-2-1-3-6-4-5/h1-4,7H

Synthetic route

3-iodopyridine (1120-90-7) → pyridine-3-thiol (16133-26-9)

Conditions	Yield
With copper(l) iodide; thiourea; L-proline; sodium t-butanolate In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	90%

2-ethylhexyl 3-(3-pyridylthio)propionate → pyridine-3-thiol (16133-26-9)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -78℃; for 1.5h;	30.4%

3-Bromopyridine (626-55-1) → pyridine-3-thiol (16133-26-9)

Conditions	Yield
With propylene glycol; copper; potassium hydrosulfide at 175℃;
With sodium thiomethoxide In N,N-dimethyl-formamide for 4h; Heating;
With copper(ll) sulfate pentahydrate; ethane-1,2-dithiol; potassium hydroxide In water; dimethyl sulfoxide at 110℃; for 20h; Inert atmosphere;
Multi-step reaction with 2 steps 1: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 2 h / 100 °C 2: potassium tert-butylate / tetrahydrofuran / 1 h / -78 °C View Scheme
Multi-step reaction with 2 steps 1: tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 2 h / 100 °C / Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 1.5 h / -78 °C View Scheme

pyridine-3-sulfonyl chloride hydrochloride (42899-76-3) → pyridine-3-thiol (16133-26-9)

Conditions	Yield
With hydrogenchloride; tin(ll) chloride at 70℃;

3-pyridinesulfonic acid (636-73-7) → pyridine-3-thiol (16133-26-9)

Conditions	Yield
Yield given. Multistep reaction;

3-(dimethylaminocarbonylthio)pyridine (13511-89-2) → pyridine-3-thiol (16133-26-9)

Conditions	Yield
Stage #1: 3-(dimethylaminocarbonylthio)pyridine With methanol; sodium for 2h; Reflux; Stage #2: In methanol at 20℃; pH=6; Acidic aqueous solution;
With methanol; sodium at 20℃; for 2h; Heating / reflux;

C15H23NO2S → pyridine-3-thiol (16133-26-9)

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h;	80 mg

pyridine-3-thiol (16133-26-9) + C39H44ClN9O8S2 → C44H48N10O8S3

Conditions	Yield
Stage #1: pyridine-3-thiol With sodium methylate In methanol at 20℃; for 0.5h; Cooling with ice; Stage #2: C39H44ClN9O8S2 In N,N-dimethyl-formamide at 20℃; for 0.5h;	100%

pyridine-3-thiol (16133-26-9) + 3-chloromethyl-7β-tert-butyloxycarbonylamino-3-cephem-4-carboxylic acid diphenylmethyl ester (112028-91-8) → diphenylmethyl 7β-tert-butoxycarbonylamino-3-(3-pyridyl)thiomethyl-3-cephem-4-carboxylate (288379-35-1)

Conditions	Yield
Stage #1: 3-chloromethyl-7β-tert-butyloxycarbonylamino-3-cephem-4-carboxylic acid diphenylmethyl ester With sodium iodide In N,N-dimethyl-formamide at 20℃; Substitution; Stage #2: pyridine-3-thiol In N,N-dimethyl-formamide Substitution;	99%

pyridine-3-thiol (16133-26-9) → 3-(2-(pyridine-3-yl)disulfanyl)pyridine (24367-50-8)

Conditions	Yield
With tetrachlorosilane; ammonium dichromate; silica gel at 80℃; for 0.0833333h;	95%
With sodium hydroxide; potassium hexacyanoferrate(III) In water at 20℃; for 0.25h;	82%
With oxygen at 60℃; for 12h;	38.4%
With oxygen at 60℃; for 12h;	38.4%

pyridine-3-thiol (16133-26-9) + ethyl halide → 3-(ethylthio)pyridine (26891-59-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 5h; Inert atmosphere;	94%

pyridine-3-thiol (16133-26-9) + (rac)-4-phenylbutane-2-thiol → (rac)-3-(4-phenylbutan-2-ylthio)pyridine (1493686-14-8)

Conditions	Yield
With 1,1'-bis-(diphenylphosphino)ferrocene; tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine In toluene for 3h; Inert atmosphere; Reflux;	93%

pyridine-3-thiol (16133-26-9) + (Bu4N)2{Fe4S4(1,3,5-tris((4,6-dimethyl-3-mercaptophenyl)thio)-2,4,6-tris(p-tolylthio)benzene)(SMe)} (137003-14-6) → (Bu4N)2{Fe4S4(1,3,5-tris((4,6-dimethyl-3-mercapto-phenyl)thio)-2,4,6-tris(p-tolylthio)benzene)(S-3-py)} (137050-96-5)

Conditions	Yield
In acetonitrile (N2); stirred under dynamic vacuum for 3 h; solvent removed; washed (toluene); dried;	92%

pyridine-3-thiol (16133-26-9) + 4-tolyl iodide (624-31-7) → 4-methylphenyl(3-pyridyl)sulfide (114827-44-0)

Conditions	Yield
With barium molybdate; potassium hydroxide In acetonitrile at 80℃; for 24h; Inert atmosphere;	89%
With CuMoO4; caesium carbonate In dimethyl sulfoxide at 30℃; for 12h; Inert atmosphere;	80%

pyridine-3-thiol (16133-26-9) + iodobenzene (591-50-4) → 3-phenylthiopyridine (28856-77-1)

Conditions	Yield
With barium molybdate; potassium hydroxide In acetonitrile at 80℃; for 24h; Inert atmosphere;	85%
With CuMoO4; caesium carbonate In dimethyl sulfoxide at 30℃; for 12h; Inert atmosphere;	82%

pyridine-3-thiol (16133-26-9) + diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(E)-2-(4-toluenesulfonyloxy)vinyl]-3-cephem-4-carboxylate → diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(E)-2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate (93068-78-1)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; Substitution;	83%

pyridine-3-thiol (16133-26-9) → Pyridine-3-sulfonyl chloride (16133-25-8)

Conditions	Yield
With chlorine In water; acetic acid at 15 - 17℃; for 0.5h;	81%

pyridine-3-thiol (16133-26-9) + Allyl chloroformate (2937-50-0) → C9H9NO2S

Conditions	Yield
With cetyltrimethylammonim bromide; sodium hydroxide at 10℃; for 5h;	81%

pyridine-3-thiol (16133-26-9) + 1-bromo-3,7-dimethyloctane (59965-20-7, 72746-96-4, 79434-89-2, 3383-83-3) → 3-((3,7-dimethyloctyl)thio)pyridine

Conditions	Yield
Stage #1: pyridine-3-thiol With sodium methylate In methanol at 20℃; for 0.25h; Stage #2: 1-bromo-3,7-dimethyloctane In N,N-dimethyl-formamide at 20℃; for 16h;	80%

pyridine-3-thiol (16133-26-9) + pleuromutilin tosylate (31716-01-5) → 14-O-(((pyridin-3-yl)sulfanyl)acetyl)mutilin (1577172-08-7)

Conditions	Yield
Stage #1: pyridine-3-thiol With sodium hydroxide In methanol; water at 20℃; for 0.333333h; Inert atmosphere; Stage #2: pleuromutilin tosylate In methanol; dichloromethane; water at 20℃; Inert atmosphere;	80%

pyridine-3-thiol (16133-26-9) + bromobenzene (108-86-1) → 3-phenylthiopyridine (28856-77-1)

Conditions	Yield
With CuMoO4; caesium carbonate In dimethyl sulfoxide at 30℃; for 20h; Inert atmosphere;	80%

pyridine-3-thiol (16133-26-9) + para-bromotoluene (106-38-7) → 4-methylphenyl(3-pyridyl)sulfide (114827-44-0)

Conditions	Yield
With CuMoO4; caesium carbonate In dimethyl sulfoxide at 30℃; for 22h; Inert atmosphere;	80%

pyridine-3-thiol (16133-26-9) + benzyl chloride (100-44-7) → benzyl (3-pyridyl) sulfide (343944-91-2)

Conditions	Yield
With sodium ethanolate In ethanol for 5h; Heating;	75%

pyridine-3-thiol (16133-26-9) + 2,6-dichloro-4-iodopyridine (98027-84-0) → 2,6-dichloro-4-(pyridine-3-sulfanyl)-pyridine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); N-ethyl-N,N-diisopropylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 110℃; for 3h; Inert atmosphere;	66%

pyridine-3-thiol (16133-26-9) + 1-(4-pyridyl)pyridinium chloride hydrochloride (5421-92-1) → 3,4'-thiobispyridine (72890-90-5)

Conditions	Yield
at 140 - 150℃; for 2h;	65%

pyridine-3-thiol (16133-26-9) + 3-Bromopyridine (626-55-1) → 3-(pyridine-3-ylsulfanyl)pyridine (57331-00-7)

Conditions	Yield
With copper(I) oxide; potassium carbonate at 180℃; for 6h; sealed tube;	63%

pyridine-3-thiol (16133-26-9) + benzyl chloride (100-44-7) → 3-(benzylsulfinyl)pyridine

Conditions	Yield
With iodine pentoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 90℃; for 8h;	50%

pyridine-3-thiol (16133-26-9) + acetylene (74-86-2) → 3-vinylthiopyridine (140472-72-6)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane; water at 180℃; under 11400 Torr; for 1h;	44%

pyridine-3-thiol (16133-26-9) + methyl iodide (74-88-4) → 3-methylsulfanylpyridine (18794-33-7)

Conditions	Yield
With sodium hydroxide for 2h; Ambient temperature;	40%
With sodium hydroxide; water

pyridine-3-thiol (16133-26-9) + diphenylmethyl 7β-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylate → diphenylmethyl 7β-formamido-3-(3-pyridyl)thio-3-cephem-4-carboxylate (103544-81-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Substitution;	29%

pyridine-3-thiol (16133-26-9) + 5-iodo-1-(2-fluorophenyl)-1H-pyrrole-3-carboxylic acid methyl ester → 1-(2-fluorophenyl)-5-(3-pyridylthio)-1H-pyrrole-3-carboxylic acid methyl ester

Conditions	Yield
With potassium phosphate; copper(l) iodide In 1,4-dioxane at 110℃; for 16h; Inert atmosphere;	15%

pyridine-3-thiol (16133-26-9) + 1-Chlorohexane (544-10-5) → 3-(hexylthio)pyridine (100056-23-3)

Conditions	Yield
With ethanol; sodium ethanolate

pyridine-3-thiol (16133-26-9) + 1-bromo-octane (111-83-1) → 3-octylmercapto-pyridine (91952-86-2)

Conditions	Yield
With ethanol; sodium ethanolate

pyridine-3-thiol (16133-26-9) + benzoyl chloride (98-88-4) → S-(3-pyridyl) benzothioate (93056-12-3)

Conditions	Yield
With sodium hydroxide; water

pyridine-3-thiol (16133-26-9) + 1-chlorododecane (112-52-7) → 3-dodecylsulfanylpyridine (102756-02-5)

Conditions	Yield
With ethanol; sodium ethanolate

Upstream product

• 13511-89-2 3-(dimethylaminocarbonylthio)pyridine 
• 1120-90-7 3-iodopyridine 
• 636-73-7 3-pyridinesulfonic acid 
• 42899-76-3 pyridine-3-sulfonyl chloride hydrochloride 
• 626-55-1 3-Bromopyridine 

Downstream Products

• 90356-81-3 N-(4-Cyano-3-trifluoromethyl-phenyl)-2-hydroxy-2-methyl-3-(pyridin-3-ylsulfanyl)-propionamide 
• 90356-71-1 2-Hydroxy-2-methyl-N-(4-nitro-3-trifluoromethyl-phenyl)-3-(pyridin-3-ylsulfanyl)-propionamide 
• 288379-35-1 diphenylmethyl 7β-tert-butoxycarbonylamino-3-(3-pyridyl)thiomethyl-3-cephem-4-carboxylate 
• 103544-81-6 diphenylmethyl 7β-formamido-3-(3-pyridyl)thio-3-cephem-4-carboxylate 
• 114827-44-0 4-methylphenyl(3-pyridyl)sulfide 
• 28856-77-1 3-phenylthiopyridine 
• 26891-59-8 3-(ethylthio)pyridine 
• 16133-25-8 Pyridine-3-sulfonyl chloride 
• 119016-32-9 3-dodecylmercapto-1-methyl-pyridinium; toluene-4-sulfonate 
• 115121-89-6 1-methyl-3-octylmercapto-pyridinium; toluene-4-sulfonate 
• 74203-47-7 1-benzyl-3-dimethylcarbamoylsulfanyl-pyridinium; bromide 
• 108757-90-0 3-benzoylmercapto-1-methyl-pyridinium; iodide 
• 79876-41-8 3-(benzylsulfonyl)pyridine 
• 4423-09-0 4-(3-pyridyl)toluene 

Relevant articles and documents

Heterocyclic derivatives as well as pharmaceutical compositions and application thereof

The invention discloses novel heterocyclic derivatives shown in a formula I, a formula II and a formula III, pharmaceutical compositions containing the heterocyclic derivatives and application of the heterocyclic derivatives in preparation of drugs for preventing and/or treating indications related to proton pump inhibition regulation. The heterocyclic derivatives disclosed by the invention are strong in drug effect and long in half-life period, are ideal efficient proton pump inhibitors, and can be used for treating or preventing diseases or diseases needing proton pump inhibition effect regulation, such as ulcer, esophagitis, gastritis, gastroesophageal reflux, helicobacter pylori infection, gastric cancer and the like.

Copper(II)-Catalyzed Single-Step Synthesis of Aryl Thiols from Aryl Halides and 1,2-Ethanedithiol

A highly efficient transition metal-catalyzed single-step synthesis of aryl thiols from aryl halides has been developed employing copper(II) catalyst and 1,2-ethanedithiol. The key features are use of readily available reagents, a simple operation, and relatively mild reaction conditions. This new protocol shows a broad substrate scope with excellent functional group compatibility. A variety of aryl thiols are directly prepared from aryl halides in high yields. Furthermore, the aryl thiols are used in situ for the synthesis of more advanced molecules such as diaryl sulfides and benzothiophenes.

CARBACEPHEM β-LACTAM ANTIBIOTICS

Carbacephem -lactam antibiotics having structure (I) are disclosed, including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar1, Ar2, R1 and R2 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.