2-(pyridin-2-yldisulfanyl)pyridine

• ChemBase ID: 81352
• Molecular Formular: C10H8N2S2
• Molecular Mass: 220.31392
• Monoisotopic Mass: 220.01289027
• SMILES: n1ccccc1SSc1ncccc1
• Canonical SMILES: c1ccc(nc1)SSc1ccccn1
• InChI: InChI=1S/C10H8N2S2/c1-3-7-11-9(5-1)13-14-10-6-2-4-8-12-10/h1-8H
• InChIKey: HAXFWIACAGNFHA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(pyridin-2-yldisulfanyl)pyridine
• IUPAC Traditional name: 2,2'-dipyridyldisulfide
• Synonyms: 2,2'-Dipyridyl disulfide; 2,2′-Dithiodipyridine; 2,2'-Dipyridyldisulphide; Aldrithiol-2; 2,2'-Dipyridyldisulfide; 2,2′-Dipyridyl disulfide; 2,2′-Dithiodipyridine; Aldrithiol™-2; Bis(pyridin-2-yl) disulphide; 2,2'-Dithiodipyridine; 2,2'-DIPYRIDYL DISULFIDE; 2,2'-二吡啶基 二硫醚; 2,2'-二吡啶基二硫醚; 2,2'-二硫二吡啶; 2,2'-二硫二吡啶

Database IDs

• CAS Number: 2127-03-9
• EC Number: 218-343-1
• MDL Number: MFCD00006287
• Beilstein Number: 154629
• PubChem SID: 162068471; 24848570; 24893969
• PubChem CID: 65093
• CHEMBL: 118678
• Chemspider ID: 58603
• Wikipedia Title: 2,2'-Dipyridyldisulfide

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.3267486
• LogD (pH = 7.4): 3.327308
• Log P: 3.327315
• Molar Refractivity: 58.7734 cm^3
• Polarizability: 24.270054 Å^3
• Polar Surface Area: 25.78 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: powder
• Melting Point: 56 - 58°C; 56-58 °C; 56-58 °C(lit.); 56-58°C; 56-59°C; 57-58 °C
• Flash Point: 210°C; 210°C(410°F)

Safety Information

• Storage Condition: 2-8°C
• Storage Warning: Irritant/Stench/Air Sensitive/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R36/37/38
• Safety Statements: 26-37; 36/37/39; S36/37/39
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• Main Hazard: Irritant (Xi)
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); ≥99.0% (GC); 98%
• Grade: purum
• Empirical Formula (Hill Notation): C10H8N2S2

DETAILS

MP Biomedicals - 02150987

Useful reagent for determination of sulfhydryl groups, preparation of amino acid active esters and thio esters of phosphoric acid.

Sigma Aldrich - 143049

Packaging
1, 5, 25, 500 g in glass bottle
Application
Thiol reagent.1,2 Employed with PPh3 as a condensing agent in the amidation of carboxylic acid enantiomers for HPLC separation.3,4
Legal Information
Aldrithiol is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 43792

Other Notes
Reagent used for the lactonization of hydroxy acids with PPh31; Reagent used for sulfenylations

Sigma Aldrich - 43791

Other Notes
For the determination of sulfhydryl groups in biological materials1

REFERENCES

• In combination with triphenylphosphine, acts as a peptide coupling reagent (see Appendix 6) in which water is removed by a mechanism whereby the phosphine is oxidized to the phosphine oxide and the disulfide reduced to the thiol: J. Am. Chem. Soc., 90, 4490 (1968); 91, 1554 (1969); Bull. Chem. Soc. Jpn., 43, 1271 (1970).
• The technique has also been widely applied for macrolactonization, via high-dilution cyclization of the 2-pyridine thioester: J. Am. Chem. Soc., 96, 5614 (1974); 97, 653, 654, 2287 (1975). The cyclization step can be catalyzed by silver ion: Helv. Chim. Acta, 57, 2661 (1974). See, e.g.: Org. Synth. Coll., 7, 470 (1990).
• In combination with tri-n-butylphosphine has been used for the activation of glycosides, e.g. in the formation of disaccarides: J. Am. Chem. Soc., 103, 4221 (1981); Tetrahedron, 47, 6435 (1991).