2,2'-Dithiodipyridine Property

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

InChIKey

HAXFWIACAGNFHA-UHFFFAOYSA-N

LogP

2.530 (est)

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

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

F 

10-23

Autoignition Temperature

340 °C

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29333990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

2,2'-Dithiodipyridine Chemical Properties,Usage,Production

Chemical Properties

white to yellowish crystalline powder

Uses

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.

Uses

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.

Uses

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

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