2,2'-Dithiodipyridine

2,2'-Dithiodipyridine 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%;1,2-Di(pyridin-2-yl)disulfide;2-(2-Pyridinyldisulfanyl)pyridine;2,2'-Dipyridinyl disulfide
CAS:2127-03-9
MF:C10H8N2S2
MW:220.31
EINECS:218-343-1
Product Categories:Aromatics;Heterocycles;Peptide Synthesis;Synthetic Organic Chemistry;Miscellaneous Reagents;Sulfur & Selenium Compounds;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);2127-03-9
Mol File:2127-03-9.mol
2,2'-Dithiodipyridine Structure
2,2'-Dithiodipyridine Chemical Properties
Melting point 56-58 °C(lit.)
Boiling point 356.1±17.0 °C(Predicted)
density 1.3078 (rough estimate)
refractive index 1.5500 (estimate)
Fp 210 °C
storage temp. 2-8°C
solubility methanol: soluble50mg/mL, clear to very slightly hazy, colorless to faintly brownish-yellow
form powder
pka1.52±0.19(Predicted)
color Clear colorless to yellow to tan
Water Solubility 5 g/L (20 ºC)
BRN 154629
InChIKeyHAXFWIACAGNFHA-UHFFFAOYSA-N
LogP2.530 (est)
CAS DataBase Reference2127-03-9(CAS DataBase Reference)
NIST Chemistry ReferencePyridine, 2,2'-dithiobis-(2127-03-9)
EPA Substance Registry SystemPyridine, 2,2'-dithiobis- (2127-03-9)
Safety Information
Hazard Codes Xi,Xn
Risk Statements 36/37/38-37-20/22
Safety Statements 36/37/39-37/39-25-22-36-26
RIDADR UN 3335
WGK Germany 3
10-23
Autoignition Temperature340 °C
Hazard Note Irritant
TSCA Yes
HS Code 29333990
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
ALFA English
2,2'-Dithiodipyridine Usage And Synthesis
Chemical Propertieswhite to yellowish crystalline powder
Uses2,2'-Dipyridyldisulfide, sometimes known as DPS, is used for preparing thiols and activating or protecting carboxylic acid with triphenylphosphine.
Uses2,2'-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.
UsesAldrithiol?-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.
DefinitionChEBI: Aldrithiol is a member of the class of pyridines that is pyridine which is substituted by a pyridin-2-yldisulfanediyl group at position 2. It is a reagent used in molecular biology as an oxidizing agent. Also used in peptide synthesis and for detecting thiols. It has a role as an oxidising agent. It is an organic disulfide and a member of pyridines.
General DescriptionAldrithiol?-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 Actions2,2′-Dithiodipyridine mediates inter-unit disulfide cross-linking. It interacts with carbon nucleophiles to yield thiopyridyl derivatives.
Purification MethodsRecrystallise 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
Dibenzyl disulfide DI[5-(TRIFLUOROMETHYL)-2-PYRIDYL] DISULFIDE 4,4'-DITHIODIPYRIDINE,4,4Dipyridyldisulfide-(4,4dithiodipyridine) Diallyldisulfide THIODIGLYCOLIC ACID Diethyl 1,4-dihydro-2,6-dimethyl-3,5-pyridinedicarboxylate 2,2'-Bipyridine 2,2'-Dithiodipyridine 2,5-PYRIDINEDICARBOXYLIC ACID GGKPDLRPCHPPCHYIPRPKPR 2,6-Lutidine 2,2'-DITHIOBIS(5-NITROPYRIDINE) 4,4'-DIPYRIDYL DISULPHIDE, (4,4'-DITHIODIPYRIDINE) 6,6'-DITHIODINICOTINIC ACID 2,2'-DITHIO-BIS(3-NITROPYRIDINE) Dimethyl disulfide Allicin Pyridine

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