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

General Description

Pyridine-3-thiol, also known as 3-mercaptopyridine, is a compound that belongs to the class of organic substances known as pyridines and derivatives. It has a role as a poison and a solvent. Its molecular formula is C5H5NS, and it is known for its foul smell. It is primarily used in the field of analytical chemistry, particularly as a titrating agent. Pyridine-3-thiol is associated with certain hazardous properties, leading to precautionary measures being taken during its handling and transportation. It is not typically approved for use as a food additive or flavoring agent due to its potential health risks.

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

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

Downstream Products

• 16133-25-8 Pyridine-3-sulfonyl chloride 
• 18794-33-7 3-methylsulfanylpyridine 
• 13511-89-2 3-(dimethylaminocarbonylthio)pyridine 
• 93056-12-3 S-(3-pyridyl) benzothioate 
• 100056-23-3 3-hexylthiopyridine 
• 114827-44-0 4-methylphenyl(3-pyridyl)sulfide 
• 28856-77-1 3-phenylthiopyridine 
• 26891-59-8 3-(ethylthio)pyridine 
• 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 

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