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16133-26-9

Basic Information
CAS No.: 16133-26-9
Name: Pyridine-3-thiol
Article Data: 14
Molecular Structure:
Molecular Structure of 16133-26-9 (Pyridine-3-thiol)
Formula: C5H5NS
Molecular Weight: 111.167
Synonyms: 3-Mercaptopyridine;Pyridine-3-thiol;5-Mercaptopyridine;
Density: 1.166 g/cm3
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
PSA: 51.69000
LogP: 1.37030
Synthetic route
1120-90-7

3-iodopyridine

16133-26-9

pyridine-3-thiol

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogenchloride; tin(ll) chloride at 70℃;
636-73-7

3-pyridinesulfonic acid

16133-26-9

pyridine-3-thiol

Conditions
ConditionsYield
Yield given. Multistep reaction;
13511-89-2

3-(dimethylaminocarbonylthio)pyridine

16133-26-9

pyridine-3-thiol

Conditions
ConditionsYield
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
ConditionsYield
With potassium tert-butylate In tetrahydrofuran at -78℃; for 1h;80 mg
16133-26-9

pyridine-3-thiol

C39H44ClN9O8S2

C44H48N10O8S3

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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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.