2-Mercaptopyridine

Base Information

• Chemical Name: 2-Mercaptopyridine
• CAS No.: 2637-34-5
• Deprecated CAS: 1120-96-3,123574-65-2,811801-36-2,1623130-98-2,123574-65-2,811801-36-2
• Molecular Formula: C5H5NS
• Molecular Weight: 111.167
• Hs Code.: 29339900
• European Community (EC) Number: 220-131-9,249-657-7,946-524-1
• NSC Number: 41337
• UNII: EE982KT952
• DSSTox Substance ID: DTXSID9062568
• Nikkaji Number: J51.344J
• Wikipedia: 2-Mercaptopyridine
• Wikidata: Q15274000,Q61739667
• Metabolomics Workbench ID: 56603
• ChEMBL ID: CHEMBL1235541
• Mol file: 2637-34-5.mol

Synonyms:2-mercaptopyridine;2-thiopyridine;2-thiopyridine lead salt (+2);2-thiopyridine sodium salt;2-thiopyridine titanium salt (+1);2-thiopyridine zinc salt;2-thiopyridone;pyridine-2-thione

Chemical Property of 2-Mercaptopyridine

Chemical Property:

• Appearance/Colour: yellow crystalline powder
• Vapor Pressure: 0.716mmHg at 25°C
• Melting Point: 127-130 °C(lit.)
• Refractive Index: 1.653
• Boiling Point: 184.9 °C at 760 mmHg
• PKA: pK1:－1.07(＋1);pK2:10.00(0) (20°C)
• Flash Point: 65.6 °C
• PSA: 51.69000
• Density: 1.2 g/cm³
• LogP: 1.37030
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Solubility.: Slightly soluble in chloroform, methanol and dimethyl sulfoxide.
• Water Solubility.: 50 g/L (20 ºC)
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 111.01427034
• Heavy Atom Count: 7
• Complexity: 135

Purity/Quality:

99% ^*data from raw suppliers

2-Thiopyridone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-36/38-22
• Safety Statements: 26-36-28A-22

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Sulfur Compounds
• Canonical SMILES: C1=CC(=S)NC=C1
• Uses: 2-Mercaptopyridine Can be used to coat porous media to purify plasmid DNA. Employed as a ligand in metal complexes.1,2 Employed as a ligand in metal complexes. It can be used to coat porous media to purify plasmid DNA.

Technology Process of 2-Mercaptopyridine

There total 88 articles about 2-Mercaptopyridine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) + O-(tert-butyl) S-(pyridin-2-yl)carbonothioate (105678-24-8) → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7)

Guidance literature:

With triethylamine; In water; N,N-dimethyl-formamide; for 12h; Ambient temperature;

DOI:10.1246/bcsj.58.3570

Reference yield: 92.0%

2,2'-dipyridyldisulphide (2127-03-9) + 2,4-dimethylbenzenesulfonic acid (88-61-9) + triphenylphosphine (603-35-0) → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + 2,4-dimethyl-thiophenol (13616-82-5) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

In benzene; for 2h; Product distribution; Mechanism; Heating; further reaction partners - various diaryl disulfides;

DOI:10.1246/bcsj.57.232

Reference yield: 90.0%

2,2'-dipyridyldisulphide (2127-03-9) → 2-Sulfanylpyridine (2637-34-5,73018-10-7)

Guidance literature:

With sodium tetrahydroborate; zirconium(IV) chloride; In tetrahydrofuran; at 35 ℃; for 0.166667h;

DOI:10.1080/00397910008086947

upstream raw materials:

2-chloropyridine

2-Sulfanylpyridine

2-methylsulfanyl-pyridine

2,2'-dipyridyldisulphide

Downstream raw materials:

2-(benzylthio)pyridine

2-((4-nitrophenyl)thio)pyridine

1-phenyl-2-(pyridin-2-ylthio)ethan-1-one

Phenyl 2-pyridyl disulfide

Refernces

• 1、 Tada, Hiroaki,Teranishi, Kazuaki,Inubushi, Yo-Ichi,Ito, Seishiro. "TiO2 photocatalytic reduction of bis(2-dipyridyl)disulfide to 2-mercaptopyridine by H2O: Incorporation effect of nanometer-sized Ag particles". . p. 2345 - 2346. Retrieved 1998.
• 2、 Van Der Vlies, André J.,Hasegawa, Urara,Hubbell, Jeffrey A.. "Reduction-sensitive tioguanine prodrug micelles". . p. 2812 - 2818. Retrieved 2012.
• 3、 Kupchan et al.. "-". . p. 1147,1150. Retrieved 1971.
• 4、 Cardoso, A. Sofia P.,Marques, M. Manuel B.,Srinivasan, Natarajan,Prabhakar, Sundaresan,Lobo, Ana M.. "A synthetic strategy using Witkop's pyrroloindole for (-)-debromoflustramine B, (+)-ent-debromoflustramine B and (+)-ent-debromoflustramide B". . p. 10211 - 10225. Retrieved 2007.
• 5、 Moran, Damian,Sukcharoenphon, Kengkaj,Puchta, Ralph,Schaefer III, Henry F.,Schleyer, Paul V.R.,Hoff, Carl D.. "2-Pyridinethiol/2-pyridinethione tautomeric equilibrium. A comparative experimental and computational study". . p. 9061 - 9069. Retrieved 2002.
• 6、 Chen, Yi,Huang, Feixiang,Jiang, Cailing,Jiang, Li. "Highly uniform self-assembled monolayers of silver nanospheres for the sensitive and quantitative detection of glutathione by SERS". . p. 10436 - 10445. Retrieved 2021.
• 7、 Chen, Wei,Xian, Ming. "Washington Red (WR) dyes and their imaging applications". . p. 149 - 163. Retrieved 2020/06/08.