2,2'-Dithiodipyridine

Base Information

• Chemical Name: 2,2'-Dithiodipyridine
• CAS No.: 2127-03-9
• Deprecated CAS: 1623131-06-5,219143-69-8
• Molecular Formula: C10H8N2S2
• Molecular Weight: 220.319
• Hs Code.: 29333990
• European Community (EC) Number: 218-343-1
• NSC Number: 677438,94055
• UNII: L6X912UPBU
• DSSTox Substance ID: DTXSID70175517
• Nikkaji Number: J39.097F
• Wikipedia: 2,2%27-Dipyridyldisulfide,2'-Dipyridyldisulfide
• Wikidata: Q4596740
• Pharos Ligand ID: ACFCT3L3MTZV
• ChEMBL ID: CHEMBL118678
• Mol file: 2127-03-9.mol

Synonyms:2,2'-dipyridyl disulfide;2,2'-dithiodipyridine;2,2'-dithiopyridine;2,2-dithiobispyridine;2,2-PDS;Aldrithiol-2;orthopyridyl disulfide

Chemical Property of 2,2'-Dithiodipyridine

Chemical Property:

• Appearance/Colour: white to yellowish crystalline powder
• Melting Point: 56-58 °C(lit.)
• Refractive Index: 1.5500 (estimate)
• Boiling Point: 356.095 °C at 760 mmHg
• PKA: 1.52±0.19(Predicted)
• Flash Point: 169.16 °C
• PSA: 76.38000
• Density: 1.34 g/cm³
• LogP: 3.27600
• Storage Temp.: 2-8°C
• Solubility.: methanol: soluble50mg/mL, clear to very slightly hazy, colorless
• Water Solubility.: 5 g/L (20 ºC)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 220.01289061
• Heavy Atom Count: 14
• Complexity: 148

Purity/Quality:

98% ^*data from raw suppliers

2,2''-DipyridinylDisulfide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-37-20/22
• Safety Statements: 36/37/39-37/39-25-22-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Pyridines
• Canonical SMILES: C1=CC=NC(=C1)SSC2=CC=CC=N2
• Uses: 2,2'-Dipyridyldisulfide, sometimes known as DPS, is used for preparing thiols and activating or protecting carboxylic acid with triphenylphosphine. 2,2'-Dipyridyl disulfide is a useful reagent for determination of sulfhydryl groups, preparation of amino acid active esters and the thio esters of phosphoric acid. It acts as a peptide coupling reagent and as an oxidizing agent. It is also used for the activation of glycosides. Aldrithiol?-2 was used in the synthesis of adenosine-5′-phosphoimidazolide. It was employed with PPh3 as a condensing agent in the amidation of carboxylic acid enantiomers for HPLC separation.

Technology Process of 2,2'-Dithiodipyridine

There total 164 articles about 2,2'-Dithiodipyridine 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: 90.0%

(E)-3-Phenyl-acrylic acid 2-thioxo-2H-pyridin-1-yl ester (127878-52-8) → 2,2'-dipyridyldisulphide (2127-03-9) + cinnamic acid anhydride (538-56-7) + S-(pyridin-2-yl) pyridine-2-thiosulfonate (127878-50-6)

Guidance literature:

In dichloromethane; Product distribution; Irradiation;

DOI:10.1016/S0040-4039(00)94400-9

Reference yield: 58.0%

3-carboxy-2-mercaptopyridine (38521-46-9) → 2-Sulfanylpyridine (2637-34-5,73018-10-7) + 2,2'-dipyridyldisulphide (2127-03-9)

Guidance literature:

at 800 ℃; under 0.01 Torr;

DOI:10.1016/S0040-4039(02)01044-4

Reference yield: 56.0%

bromobenzene (108-86-1,52753-63-6) → 2,2'-dipyridyldisulphide (2127-03-9) + diphenyldisulfane (882-33-7)

Guidance literature:

With sodium sulfide; chloro-trimethyl-silane; In various solvent(s); at 190 ℃;

DOI:10.1021/jo00069a046

upstream raw materials:

2-choro-5-iodopyridine

Phenyl 2-pyridyl disulfide

pyridine-2-sulfonic acid hydrazide

ethanol

Downstream raw materials:

pyridine-2-thione

2-Sulfanylpyridine

[2S,3R,4S,6S]-6-(tert-butyldiphenylsilyloxymethyl)-3-hydroxy-4-phenylsulfonyl-2-(2-thiopyridyl)tetrahydro-2H-pyran

3-(2-pyridyldithio)propionic acid

Refernces

• 1、 Ziegler, Frederick E.,Harran, Patrick G.. "A Route to Chiral Epoxypyrroloindoles via Oxiranyl Radical Cyclization". . p. 4505 - 4508. Retrieved 1993.
• 2、 Varma, Rajender S.,Meshram, Harshadas M.,Dahiya, Rajender. "Solid state oxidation of thiols to disulfides using ammonium persulfate". . p. 1249 - 1255. Retrieved 2000.
• 3、 Edrissi et al.. "-". . p. 282. Retrieved 1974.
• 4、 Nikoorazm, Mohsen,Moradi, Parisa,Noori, Nourolah,Azadi, Gouhar. "l-Arginine complex of copper on modified core–shell magnetic nanoparticles as reusable and organic–inorganic hybrid nanocatalyst for the chemoselective oxidation of organosulfur compounds". . p. 467 - 478. Retrieved 2020/09/01.
• 5、 K?nig, Burkhard,Wang, Hua,Wang, Shun. "Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation". supporting information. p. 1653 - 1665. Retrieved 2021/06/17.