2127-03-9

Basic information

• Product Name: 2,2'-Dithiodipyridine
• Synonyms: NSC 94055;1,2-Di(pyridin-2-yl)disulfane;2,2'-Disulphanediyldipyridine, 2,2'-Dithiodipyridine;Di(pyridin-2-yl) disulphide;Aldrithiol(TM)-2 98%;2,2'-Dithiodipyridine, >=99%;Bis(pyridin-2-yl) disulfide;1,2-Di(pyridin-2-yl)disulfide
• CAS NO: 2127-03-9
• Molecular Formula: C₁₀H₈N₂S₂
• Molecular Weight: 220.31
• EINECS: 218-343-1
• Product Categories: Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry;Aromatics;Heterocycles;Miscellaneous Reagents;Sulfur & Selenium Compounds
• Mol File: 2127-03-9.mol
• Article Data: 168

Chemical Properties

• Melting Point: 56-58 °C(lit.)
• Boiling Point: 356.095 °C at 760 mmHg
• Flash Point: 210 °C
• Appearance: Clear colorless to yellow to tan/powder
• Density: 1.3078 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: 2-8°C
• Solubility: methanol: soluble50mg/mL, clear to very slightly hazy, colorless
• PKA: 1.52±0.19(Predicted)
• Water Solubility: 5 g/L (20 ºC)
• BRN: 154629
• CAS DataBase Reference: 2,2'-Dithiodipyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Dithiodipyridine(2127-03-9)
• EPA Substance Registry System: 2,2'-Dithiodipyridine(2127-03-9)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-37-20/22
• Safety Statements: 36/37/39-37/39-25-22-36-26
• RIDADR: UN 3335
• WGK Germany: 3
• F: 10-23
• TSCA: Yes
• Hazardous Substances Data: 2127-03-9(Hazardous Substances Data)

Usage

Chemical Properties

white to yellowish crystalline powder

Uses

Different sources of media describe the Uses of 2127-03-9 differently. You can refer to the following data:
1. 2,2'-Dipyridyldisulfide, sometimes known as DPS, is used for preparing thiols and activating or protecting carboxylic acid with triphenylphosphine.
2. 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.
3. 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.

General Description

Aldrithiol?-2 is a nucleocapsid zinc finger targeting compound and can abrogate the infectivity of human immunodeficiency virus type-1 virions. It is a thiol reagent.

Biochem/physiol Actions

2,2′-Dithiodipyridine mediates inter-unit disulfide cross-linking. It interacts with carbon nucleophiles to yield thiopyridyl derivatives.

Purification Methods

Recrystallise the disulfide H2O from *C6H6/pet ether (6:7), ligroin or *C6H6. The picrate has m 119o (from EtOH). [Walter et al. Justus Liebigs Ann Chem 695 7785 1966, Marckwald et al. Chem Ber 33 1556 1900, Brocklehurst & Little Biochem J 133 67,78 1973, Beilstein 21 III/IV 48.] It has been used as a 1mM solution in EtOH for the spectrophotometric estimation of thiols. Essentially the thiol displaces half the disulfide molecule liberating the 2-mercaptopyridine anion, thereby shifting the from 340nm (of the disulfide) to 268nm (of the anion) at pH 9, or 278nm in H2O. (Compare

Upstream product

• 69045-79-0 2-choro-5-iodopyridine 
• 24367-35-9 Phenyl 2-pyridyl disulfide 
• 100517-06-4 pyridine-2-sulfonic acid hydrazide 
• 64-17-5 ethanol 
• 2637-34-5 pyridine-2-thione 
• 67-56-1 methanol 
• 127-65-1 chloroamine-T 
• 30066-82-1 N-chloro-p-chlorobenzenesulfonamide sodium salt 
• 29917-03-1 N-chloro-p-methoxybenzenesulfonamide sodium salt 
• 127-52-6 chloramine-B 
• 2637-34-5 2-Sulfanylpyridine 
• 113548-13-3 N-(benzenesulfonyl)-3-phenyloxaziridine 
• 109-04-6 2-bromo-pyridine 
• 56-23-5 tetrachloromethane 

Downstream Products

• 102105-07-7 N-(diphenylmethylene)-2-pyridylsulfenamide 
• 110721-19-2 S-2-pyridyl (Z)-2-(2-aminothiazol-4-yl)-2-(cyclohexyloxyimino)thioacetate 
• 43091-17-4 2-(4-nitro-phenyl)-3-oxo-2,3-dihydro-thiazolo[3,2-a]pyridinylium 
• 17659-67-5 ethyl p-nitrophenyl phosphate 
• 15930-83-3 methyl (4-nitrophenyl)phosphate 
• 18123-85-8 Phosphorsaeure-n-propylester-<4-nitro-phenylester> 
• 2637-34-5 pyridine-2-thione 
• 18123-87-0 n-butyl p-nitrophenyl phosphate 
• 29314-28-1 bis-(p-nitrophenyl)pyrophosphate 
• 29690-44-6 (p-Nitrophenyl)-n-pentylhydrogenphosphat 
• 74352-41-3 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 144490-57-3 2-pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-αβ-D-glucopyranoside 
• 2637-34-5 2-Sulfanylpyridine 
• 91-60-1 2-Naphthalenethiol 

Relevant articles and documents

Thione-thiol tautomerism and stability of 2- and 4-mercaptopyridines and 2-mercaptopyrimidines

-

Visible-light-induced synthesis of benzothiophenes and benzoselenophenes via the annulation of thiophenols or 1,2-diphenyldiselane with alkynes

An effective metal-free photoredox-mediated tandem addition/cyclization reaction of thiophenols or 1,2-diphenyldiselane with alkynes leads to 2,3-disubstituted benzothiophenes and benzoselenophenes. Blue light irradiation of the organic dye, Mes-Acr-Mesu

Urea- Hydrogen Peroxide (UHP) oxidation of thiols to the corresponding disulfides promoted by maleic anhydride as mediator

Urea-hydrogen peroxide (UHP) was used in the presence of maleic anhydride as mediator in a simple and convenient method for the oxidation in high yield of some thiols to the corresponding disulfides. Peroxymaleic acid formed in situ from the reaction of U

Synthesis of pyridothietone by flash vacuum pyrolysis of 2-mercaptonicotinic acid

The temperature dependence of products formed from flash vacuum pyrolysis (FVP) of 2-mercaptonicotinic acid 4 has been studied. FVP of 4 at 550°C and ca. 1×10-2 torr gave pyridothietone 3b and a trimer 5 as the major products. At higher temperature (800°C), FVP of 4 gave 2-mercaptopyridine 6 as the major product and 2,2′-dipyridyl disulphide 7 as the minor one.

Copper based on diaminonaphthalene-coated magnetic nanoparticles as robust catalysts for catalytic oxidation reactions and C-S cross-coupling reactions

In this work, the immobilization of copper(ii) on the surface of 1,8-diaminonaphthalene (DAN)-coated magnetic nanoparticles provides a highly active catalyst for the oxidation reaction of sulfides to sulfoxides and the oxidative coupling of thiols to disulfides using hydrogen peroxide (H2O2). This catalyst was also applied for the one-pot synthesis of symmetrical sulfidesviathe reaction of aryl halides with thiourea as the sulfur source in the presence of NaOH instead of former strongly basic and harsh reaction conditions. Under optimum conditions, the synthesis yields of sulfoxides, symmetrical sulfides, and disulfides were about 99%, 95%, and 96% respectively with highest selectivity. The heterogeneous copper-based catalyst has advantages such as the easy recyclability of the catalyst, the easy separation of the product and the less wastage of products during the separation of the catalyst. This heterogeneous nanocatalyst was characterized by FESEM, FT-IR, VSM, XRD, EDX, ICP and TGA. Furthermore, the recycled catalyst can be reused for several runs and is economically effective.

Direct Synthesis of N-Difluoromethyl-2-pyridones from Pyridines

A novel method for the synthesis of N-difluoromethyl-2-pyridones was described. This protocol enables the synthesis of N-difluoromethyl-2-pyridones from readily available pyridines using mild reaction conditions that are compatible with a wide range of functional groups. The preliminary mechanistic study revealed that N-difluoromethylpyridinium salts were the key intermediates to complete this conversion.