2-IMINOTHIOLANE Property

Melting point:

198-201 °C(lit.)

storage temp. 

2-8°C

solubility 

H₂O: 100 mg/mL

form 

powder

color 

White to Off-White

Water Solubility 

Freely soluble in water

BRN 

3620079

CAS DataBase Reference

4781-83-3(CAS DataBase Reference)

Safety

Safety Statements 

22-24/25

WGK Germany 

3

F 

1-3-10

HS Code 

29349990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H301Toxic if swalloed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P310IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.

P405Store locked up.

P501Dispose of contents/container to..…

2-IMINOTHIOLANE Chemical Properties,Usage,Production

Chemical Properties

White Crystalline Solid

Uses

Cross-linking reagent cleavable by thiols.

Uses

2-Iminothiolane hydrochloride is predominantly used as an amine reactive at pH 7-10 and is also an effective thiolation reagent for polysaccharides. It is also used as a RNA-protein crosslinking reagent as well as useful in cross-linking proteins..

Uses

2-Iminothiolane hydrochloride is a valuable tool in studies of cellular organelles and oligomeric enzymes, using the techniques of protein-protein cross-linking. It may also be used to introduce reactive sulfhydryl groups into proteins for subsequent reaction with alkylating agents or heavy metal compounds.

General Description

2-Iminothiolane hydrochloride (2-IT.HCl), a protein modification reagent, is commonly employed to attach thiol groups to proteins and peptides. Raman spectroscopic analysis of hair keratin fibers modified with 2-IT.HCl showed the formation of new disulfide groups.

Purification Methods

Recrystallise the hydrochloride from MeOH/Et2O (m 187-192o) or (MeOH/Me2CO), but after sublimation at ~180o/0.2mm the melting point rises to 202-203o. It has 1HNMR with 2.27 (2H, t), 3.25 (2H, t) and 3.52 (2H, t) in (CD3)2SO. [King et al. Biochemistry 17 1499 1978.] The free base is purifed by vacuum distillation (b 71-72o/6mm) with IR (film) with 1700 (C=N)cm-1 and 1HNMR (CDCl3) with at 3.58 (2H, t) and max 2.10-2.8 (4H, m). The free base is stable on storage but slowly hydrolyses in aqueous solutions with half-lives at 25o of 390hours at pH 9.1, 210hours at pH 10 and 18hours at pH 11. [Traut et al. Biochemistry 12 3266 1973, Biochemistry 17 399 1978, Alagon & King Biochemistry 19 4343 1980, Beilstein 17/9 V 12.]