4-Mercaptopyridine

4-Mercaptopyridine Basic information
Product Name:4-Mercaptopyridine
Synonyms:NOLA-009;4-PYRIDINETHIOL;4-PYRIDYL MERCAPTAN;4-MERCAPTOPYRIDINE;Pyridine-4-thiol;4-Mercaptopyridine, 96% 10GR;4-Mercaptopyridine, 96% 1GR;Pyridine-4-thiol, 4-Mercaptopyridine, 4-Sulphanylpyridine
CAS:4556-23-4
MF:C5H5NS
MW:111.16
EINECS:224-926-1
Product Categories:Building Blocks;C5;Pyridine;Chemical Synthesis;Heterocyclic Building Blocks;Pyridines;Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;bc0001
Mol File:4556-23-4.mol
4-Mercaptopyridine Structure
4-Mercaptopyridine Chemical Properties
Melting point 182-189 °C
Boiling point 194.0±13.0 °C(Predicted)
density 1.161 (estimate)
refractive index 1.5605 (estimate)
storage temp. 2-8°C
solubility DMSO, Methanol
form Crystalline Powder
pkapK1:1.43(+1);pK2:8.86(0) (20°C)
color Yellow to yellow-green or brown
InChIKeyFHTDDANQIMVWKZ-UHFFFAOYSA-N
CAS DataBase Reference4556-23-4(CAS DataBase Reference)
NIST Chemistry Reference4-Pyridinethiol(4556-23-4)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-37/39-24/25
WGK Germany 3
RTECS UT8578000
HS Code 29333990
MSDS Information
ProviderLanguage
4-Pyridinethiol English
SigmaAldrich English
ACROS English
4-Mercaptopyridine Usage And Synthesis
Chemical Properties4-Mercaptopyridine is Yellow to light yellow crystalline powder
Uses4-Mercaptopyridine is a pyridine derivative used as a redox reagents for the in vitro refolding of a recombinantly expressed single-chain Fv fragment (scFvOx). Used in studies along with thiosulfate to measure alliinase activity.
Usesmercaptopyridine is also known as sodium pyrithione. It is a preservative that is not commoly used.
Uses4-Mercaptopyridine was used as a probe molecule to study the performance of the gold nanorod (AuNR)/polycaprolactone (PCL) fibrous mesh.
Purification MethodsPurify the thiol by dissolving ~45g in boiling H2O (100mL) (charcoal), filter and precipitate it by adding 50% aqueous NaOH (~80mL) to pH ~6. Dissolve the precipitate in EtOH, evaporate it to dryness, then crystallise it from boiling EtOH (~100mL, charcoal) to give yellow flat hexagonal plates (m 186o). It sublimes readily in vacuo. [King & Ware J Chem Soc 873 1939.] The picrate forms yellow needles from H2O with m 222o(dec). The 4-methylmercaptopyridine derivative crystallises from pet ether (m 47o , also 44-45o was reported, with a pK2 0 of 5.97) and was prepared by treatment with MeI/NaOH. Its picrate has m 2 4 5o (from H2O, MeOH or EtOH). The N-methyl-4-pyridinethiol derivative has m 168.5-170o (from EtOH), a pK2 0 of 1.30 and is soluble in CHCl3. [Albert & Barlin J Chem Soc 2384 1959, Beilstein 21 II 35, 22 III/IV 373, 22/7 V 147.]
4-Mercaptopyridine Preparation Products And Raw materials
Raw materials4-chloropyridine-->Carbamimidothioic acid
Preparation ProductsS-METHYL-S-(4-PYRIDINYL) SULFOXIMINE-->4,4'-DIPYRIDYL SULFIDE
PYRITHIOXIN DIHYDROCHLORIDE Sodium thiomethoxide (4-Pyridylthio)acetic acid 4,4'-DIPYRIDYL SULFIDE 4-Mercaptopyridine 4,4'-DIPYRIDYL DISULFIDE 1,2-Ethanedithiol Methyl 2,3,5,6-tetrachloro-4-pyridyl sulfone PYRITHIOXIN SODIUM ETHANETHIOLATE RARECHEM AL FF 0040 METHYL MERCAPTAN 1-(4-METHYLPHENYL)-3-[(2,3,5,6-TETRACHLORO-4-PYRIDYL)THIO]PROP-2-EN-1-ONE Ethanethiol 2-[[2-(TRIFLUOROMETHYL)-4-QUINOLYL]THIO]ETHYLAMINE Pyridine 2-Ethylhexyl 10-ethyl-4-[[2-[(2-ethylhexyl)oxy]-2-oxoethyl]thio]-4-methyl-7-oxo-8-oxa-3,5-dithia-4-stannatetradecanoate 1-Dodecanethiol

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