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

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

Uses

Used in Chemical Synthesis:
2,2'-Dithiodipyridine is used as a reagent for the preparation of thiols and the activation or protection of carboxylic acids with triphenylphosphine. It facilitates the formation of desired products in chemical reactions and enhances the efficiency of the synthesis process.
Used in Analytical Chemistry:
2,2'-Dithiodipyridine is used as a reagent for the determination of sulfhydryl groups, preparation of amino acid active esters, and the thio esters of phosphoric acid. Its ability to react with specific functional groups makes it a valuable tool in the analysis and identification of various compounds.
Used in Peptide Synthesis:
As a peptide coupling reagent, 2,2'-Dithiodipyridine aids in the formation of peptide bonds between amino acid residues. It is particularly useful in the synthesis of complex peptides and proteins, contributing to the development of new pharmaceuticals and bioactive molecules.
Used in Oxidation Reactions:
2,2'-Dithiodipyridine acts as an oxidizing agent, enabling the conversion of specific functional groups to their oxidized forms. This property is useful in various chemical transformations and can be applied in the synthesis of a wide range of compounds.
Used in Glycoside Activation:
2,2'-Dithiodipyridine is used for the activation of glycosides, which are important intermediates in the synthesis of oligosaccharides and other carbohydrate-derived compounds. Its ability to activate glycosides facilitates the formation of glycosidic bonds, which are crucial for the biological activity of many molecules.
Used in Aldrithiol-2 Synthesis:
Aldrithiol-2, a derivative of 2,2'-Dithiodipyridine, is used in the synthesis of adenosine-5′-phosphoimidazolide. It is employed with PPh3 as a condensing agent in the amidation of carboxylic acid enantiomers for high-performance liquid chromatography (HPLC) separation. This application highlights the versatility of 2,2'-Dithiodipyridine and its derivatives in chemical synthesis and analysis.

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

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A solid state method for the oxidation of thiols is described that uses benign oxidant, ammonium persulfate.

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

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