3-Pyridinethiol supplier | CasNO.16133-26-9

Name
Pyridine-3-thiol
EINECS
CAS No. 16133-26-9
Article Data14
CAS DataBase
Density 1.166 g/cm³
Solubility
Melting Point 78-80 °C(Solv: benzene (71-43-2); hexane (110-54-3))
Formula C₅H₅NS
Boiling Point 194 °C at 760 mmHg
Molecular Weight 111.167
Flash Point 71.1 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 3-Mercaptopyridine;Pyridine-3-thiol;5-Mercaptopyridine;
PSA 51.69000
LogP 1.37030

Synthetic route

: 1120-90-7
3-iodopyridine

: 16133-26-9
pyridine-3-thiol

Conditions

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

: 16133-26-9
pyridine-3-thiol

Conditions

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

: 626-55-1
3-Bromopyridine

: 16133-26-9
pyridine-3-thiol

Conditions

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

: 42899-76-3
pyridine-3-sulfonyl chloride hydrochloride

: 16133-26-9
pyridine-3-thiol

Conditions

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

: 636-73-7
3-pyridinesulfonic acid

: 16133-26-9
pyridine-3-thiol

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 13511-89-2
3-(dimethylaminocarbonylthio)pyridine

: 16133-26-9
pyridine-3-thiol

Conditions

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

: 16133-26-9
pyridine-3-thiol

Conditions

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

: 16133-26-9
pyridine-3-thiol

: C39H44ClN9O8S2

: C44H48N10O8S3

Conditions

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%

: 16133-26-9
pyridine-3-thiol

: 112028-91-8
3-chloromethyl-7β-tert-butyloxycarbonylamino-3-cephem-4-carboxylic acid diphenylmethyl ester

: 288379-35-1
diphenylmethyl 7β-tert-butoxycarbonylamino-3-(3-pyridyl)thiomethyl-3-cephem-4-carboxylate

Conditions

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%

: 16133-26-9
pyridine-3-thiol

: 24367-50-8
3-(2-(pyridine-3-yl)disulfanyl)pyridine

Conditions

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%

: 16133-26-9
pyridine-3-thiol

ethyl halide: ethyl halide

: 26891-59-8
3-(ethylthio)pyridine

Conditions

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

: 16133-26-9
pyridine-3-thiol

: (rac)-4-phenylbutane-2-thiol

: 1493686-14-8
(rac)-3-(4-phenylbutan-2-ylthio)pyridine

Conditions

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%

: 16133-26-9
pyridine-3-thiol

: 137003-14-6
(Bu4N)2{Fe4S4(1,3,5-tris((4,6-dimethyl-3-mercaptophenyl)thio)-2,4,6-tris(p-tolylthio)benzene)(SMe)}

: 137050-96-5
(Bu4N)2{Fe4S4(1,3,5-tris((4,6-dimethyl-3-mercapto-phenyl)thio)-2,4,6-tris(p-tolylthio)benzene)(S-3-py)}

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 624-31-7
4-tolyl iodide

: 114827-44-0
4-methylphenyl(3-pyridyl)sulfide

Conditions

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%

: 16133-26-9
pyridine-3-thiol

: 591-50-4
iodobenzene

: 28856-77-1
3-phenylthiopyridine

Conditions

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%

: 16133-26-9
pyridine-3-thiol

: diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(E)-2-(4-toluenesulfonyloxy)vinyl]-3-cephem-4-carboxylate

: 93068-78-1
diphenylmethyl 7β-tert-butoxycarbonylamino-3-[(E)-2-(3-pyridyl)thiovinyl]-3-cephem-4-carboxylate

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 16133-25-8
Pyridine-3-sulfonyl chloride

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 2937-50-0
Allyl chloroformate

: C9H9NO2S

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 59965-20-7, 72746-96-4, 79434-89-2, 3383-83-3
1-bromo-3,7-dimethyloctane

: 3-((3,7-dimethyloctyl)thio)pyridine

Conditions

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%

: 16133-26-9
pyridine-3-thiol

: 31716-01-5
pleuromutilin tosylate

: 1577172-08-7
14-O-(((pyridin-3-yl)sulfanyl)acetyl)mutilin

Conditions

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%

: 16133-26-9
pyridine-3-thiol

: 108-86-1
bromobenzene

: 28856-77-1
3-phenylthiopyridine

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 106-38-7
para-bromotoluene

: 114827-44-0
4-methylphenyl(3-pyridyl)sulfide

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 100-44-7
benzyl chloride

: 343944-91-2
benzyl (3-pyridyl) sulfide

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 98027-84-0
2,6-dichloro-4-iodopyridine

: 2,6-dichloro-4-(pyridine-3-sulfanyl)-pyridine

Conditions

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%

: 16133-26-9
pyridine-3-thiol

: 5421-92-1
1-(4-pyridyl)pyridinium chloride hydrochloride

: 72890-90-5
3,4'-thiobispyridine

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 626-55-1
3-Bromopyridine

: 57331-00-7
3-(pyridine-3-ylsulfanyl)pyridine

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 100-44-7
benzyl chloride

: 3-(benzylsulfinyl)pyridine

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 74-86-2
acetylene

: 140472-72-6
3-vinylthiopyridine

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 74-88-4
methyl iodide

: 18794-33-7
3-methylsulfanylpyridine

Conditions

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

: 16133-26-9
pyridine-3-thiol

: diphenylmethyl 7β-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylate

: 103544-81-6
diphenylmethyl 7β-formamido-3-(3-pyridyl)thio-3-cephem-4-carboxylate

Conditions

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

: 16133-26-9
pyridine-3-thiol

: 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

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

: 16133-26-9
pyridine-3-thiol

: 544-10-5
1-Chlorohexane

: 100056-23-3
3-(hexylthio)pyridine

Conditions

Conditions	Yield
With ethanol; sodium ethanolate

: 16133-26-9
pyridine-3-thiol

: 111-83-1
1-bromo-octane

: 91952-86-2
3-octylmercapto-pyridine

Conditions

Conditions	Yield
With ethanol; sodium ethanolate

: 16133-26-9
pyridine-3-thiol

: 98-88-4
benzoyl chloride

: 93056-12-3
S-(3-pyridyl) benzothioate

Conditions

Conditions	Yield
With sodium hydroxide; water

: 16133-26-9
pyridine-3-thiol

: 112-52-7
1-chlorododecane

: 102756-02-5
3-dodecylsulfanylpyridine

Conditions

Conditions	Yield
With ethanol; sodium ethanolate

3-Pyridinethiol Specification

The 3-Pyridinethiol, with the CAS registry number 16133-26-9, is also known as 3-Mercaptopyridine. This chemical's molecular formula is C₅H₅NS and molecular weight is 111.16. What's more, its IUPAC name is pyridine-3-thiol.

Physical properties of 3-Pyridinethiol are: (1)ACD/LogP: 1.03; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.8; (4)ACD/LogD (pH 7.4): -1.06; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1.29; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 38.19 Å²; (13)Index of Refraction: 1.598; (14)Molar Refractivity: 32.51 cm³; (15)Molar Volume: 95.2 cm³; (16)Polarizability: 12.89×10^-24cm³; (17)Surface Tension: 47.3 dyne/cm; (18)Density: 1.166 g/cm³; (19)Flash Point: 71.1 °C; (20)Enthalpy of Vaporization: 41.26 kJ/mol; (21)Boiling Point: 194 °C at 760 mmHg; (22)Vapour Pressure: 0.631 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Sc1cccnc1
(2)Std. InChI: InChI=1S/C5H5NS/c7-5-2-1-3-6-4-5/h1-4,7H
(3)Std. InChIKey: FFWJHVGUAKWTKW-UHFFFAOYSA-N

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	250mg/kg (250mg/kg)		European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 18, Pg. 515, 1983.

Product Name

Pyridine-3-thiol

Synthetic route

3-Pyridinethiol Specification

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