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4-Mercaptopyridine

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Name

4-Mercaptopyridine

EINECS 224-926-1
CAS No. 4556-23-4 Density 1.2 g/cm3
PSA 51.69000 LogP 1.37030
Solubility N/A Melting Point 182-189 °C
Formula C5H5NS Boiling Point 176.5 °C at 760 mmHg
Molecular Weight 111.167 Flash Point 60.5 °C
Transport Information N/A Appearance Yellow to light yellow crystalline powder
Safety 26-37/39-24/25 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 4556-23-4 (4-Mercaptopyridine) Hazard Symbols IrritantXi
Synonyms

4-Pyridinethiol;4-Sulfanylpyridine;4-Thiopyridine;NSC 76036;

Article Data 22

4-Mercaptopyridine Synthetic route

626-61-9

4-Chloropyridine

17356-08-0

thiourea

A

4556-23-4

pyridine-4-thiol

B

37968-97-1

4,4'-thiobispyridine

Conditions
ConditionsYield
With 4-(2-pyridyl)pyridine; potassium tert-butylate In ammonia at -40℃; electrolysis;A 75%
B 5%
With 4-(2-pyridyl)pyridine; potassium tert-butylate In ammonia at -40℃; Rate constant; electrochemical reaction;A 75%
B 5%
110-86-1

pyridine

22752-98-3

N-(4-pyridyl)pyridinium hydrochloride

4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With hydrogen sulfide at 140℃;
108-96-3

4-pyridone

4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With phosphorous (V) sulfide at 60 - 70℃;
With phosphorous (V) sulfide; xylene
626-61-9

4-Chloropyridine

4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With ethanol; water; potassium hydrosulfide at 140℃;
With sodium thioethylate In N,N-dimethyl-formamide for 16h; Heating;
With sodium hydrogen sulfide
19829-29-9

4-pyridinethione

4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
In cyclohexane Thermodynamic data; Free energy difference between protomers; other solvents;
7379-35-3

4-chlorpyridine hydrochloride

4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With sodium tetrahydroborate; sulfur 1.) 210 deg C, NaOH-KOH melt, 2 min.; 2.) water; Yield given. Multistep reaction;
5421-92-1

1-(4-pyridyl)pyridinium chloride hydrochloride

A

4556-23-4

pyridine-4-thiol

B

37968-97-1

4,4'-thiobispyridine

Conditions
ConditionsYield
With pyridine; thiourea at 150 - 180℃;
2645-22-9

bis(4-pyridyl) disulfide

Thiophosphoric acid S-octyl ester O-((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxy-cyclohexyl) ester

A

4556-23-4

pyridine-4-thiol

B

41158-67-2

myo-inositol-1,2-cyclic phosphate

Conditions
ConditionsYield
With phosphatidylinositol-specific phospholipase C from Bacillus cereus Product distribution; other reagents, relative velocities;
110-86-1

pyridine

7783-06-4

hydrogen sulfide

5421-92-1

1-(4-pyridyl)pyridinium chloride hydrochloride

4556-23-4

pyridine-4-thiol

2645-22-9

bis(4-pyridyl) disulfide

4556-23-4

pyridine-4-thiol

Conditions
ConditionsYield
With bovine serum albumin pH=4.5 - 10.5; Kinetics;
With trimethylphosphane In ethanol at 20℃; for 4h;

4-Mercaptopyridine Specification

The CAS registry number of 4-Mercaptopyridine is 4556-23-4. The IUPAC name is pyridine-4(1H)-thione. Its EINECS registry number is 224-926-1. In addition, the molecula formula is C5H5NS and the molecular weight is 111.16. It belongs to the class of Pyridine. And it is yellow to light yellow crystalline powder. It should be stored in a cool, ventilated and dry place.

Physical properties about this chemical are: (1)ACD/LogP: -0.49; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.47; (4)ACD/LogD (pH 7.4): -1.47; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 35.33 Å2; (13)Index of Refraction: 1.653; (14)Molar Refractivity: 33.73 cm3; (15)Molar Volume: 92 cm3; (16)Polarizability: 13.37 ×10-24cm3; (17)Surface Tension: 55 dyne/cm; (18)Density: 1.2 g/cm3; (19)Flash Point: 60.5 °C; (20)Enthalpy of Vaporization: 41.28 kJ/mol; (21)Boiling Point: 176.5 °C at 760 mmHg; (22)Vapour Pressure: 1.09 mmHg at 25°C.

Uses of 4-Mercaptopyridine: it can react with 3-chloromethyl-3H-benzooxazole-2-thione to get 3-(pyridin-4-ylsulfanylmethyl)-3H-benzooxazole-2-thione. This reaction will need reagent EtONa and solvent ethanol. The reaction time is 4 hours by heating. The yield is about 75%.

4-Mercaptopyridine can react with 3-chloromethyl-3H-benzooxazole-2-thione to get 3-(pyridin-4-ylsulfanylmethyl)-3H-benzooxazole-2-thione

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. What's more, you should avoid contact with skin and eyes. This material may have harm to the environment, especially to the water.

You can still convert the following datas into molecular structure:
(1)SMILES: S=C\1\C=C/N/C=C/1
(2)InChI: InChI=1/C5H5NS/c7-5-1-3-6-4-2-5/h1-4H,(H,6,7)
(3)InChIKey: FHTDDANQIMVWKZ-UHFFFAOYAP

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
bird - wild LD50 oral 750mg/kg (750mg/kg)   Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mouse LD50 intravenous 178mg/kg (178mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00422,

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