2,2'-Dithiodipyridine

Synonym(s):2,2′-Dipyridyl disulfide;2,2′-Dithiodipyridine

CAS NO.：2127-03-9
Empirical Formula: C10H8N2S2
Molecular Weight: 220.31
MDL number: MFCD00006287
EINECS: 218-343-1
SAFETY DATA SHEET (SDS)
Update Date: 2024-08-05 10:34:28

What is 2,2'-Dithiodipyridine ?

Chemical properties

white to yellowish crystalline powder

The Uses of 2,2'-Dithiodipyridine

2,2'-Dipyridyldisulfide, sometimes known as DPS, is used for preparing thiols and activating or protecting carboxylic acid with triphenylphosphine.

The Uses of 2,2'-Dithiodipyridine

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.

The Uses of 2,2'-Dithiodipyridine

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.

Definition

ChEBI: 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 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

Properties of 2,2'-Dithiodipyridine

Melting point:	56-58 °C(lit.)
Boiling point:	356.1±17.0 °C(Predicted)
Density	1.3078 (rough estimate)
refractive index	1.5500 (estimate)
Flash point:	210 °C
storage temp.	2-8°C
solubility	methanol: soluble50mg/mL, clear to very slightly hazy, colorless to faintly brownish-yellow
form	powder
pka	1.52±0.19(Predicted)
color	Clear colorless to yellow to tan
Water Solubility	5 g/L (20 ºC)
BRN	154629
CAS DataBase Reference	2127-03-9(CAS DataBase Reference)
NIST Chemistry Reference	Pyridine, 2,2'-dithiobis-(2127-03-9)
EPA Substance Registry System	Pyridine, 2,2'-dithiobis- (2127-03-9)

Safety information for 2,2'-Dithiodipyridine

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07
GHS Hazard Statements	H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes	P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.