4781-83-3 Usage
Description
2-Iminothiolane hydrochloride (2-IT.HCl) is a protein modification reagent commonly used to attach thiol groups to proteins and peptides. It is a white crystalline solid that has been shown to form new disulfide groups through Raman spectroscopic analysis of hair keratin fibers modified with 2-IT.HCl.
Uses
Used in Cellular Organelles and Oligomeric Enzymes Studies:
2-Iminothiolane is used as a cross-linking reagent for protein-protein cross-linking in studies of cellular organelles and oligomeric enzymes.
Used in Thiolation:
2-Iminothiolane hydrochloride is used as an amine reactive at pH 7-10 and is an effective thiolation reagent for polysaccharides.
Used in Cross-linking Reagent:
2-Iminothiolane hydrochloride is used as a cross-linking reagent that is cleavable by thiols.
Used in RNA-Protein Crosslinking:
2-Iminothiolane is used as an RNA-protein crosslinking reagent, as well as being useful in cross-linking proteins.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 4781-83-3 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,7,8 and 1 respectively; the second part has 2 digits, 8 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4781-83:
(6*4)+(5*7)+(4*8)+(3*1)+(2*8)+(1*3)=113
113 % 10 = 3
So 4781-83-3 is a valid CAS Registry Number.
InChI:InChI=1/C4H7NS/c5-4-2-1-3-6-4/h5H,1-3H2
4781-83-3Relevant articles and documents
Mild synthesis of mercaptonitriles from vinyl nitriles and their cyclization reactions
Caspari, Philip,Nüesch, Frank A.,Neels, Antonia,Opris, Dorina M.
, p. 98059 - 98065 (2016/11/02)
Thiol-ene addition of thioacetic acid A is widely used in the synthesis of thiols from vinyl precursors, but so far has not been conducted on non-conjugated vinyl nitriles. The challenge when vinyl nitriles are used is to selectively conduct the thiol-ene addition, while avoiding the nucleophilic addition of A to the nitrile group. We have found that vinyl nitriles give selective UV-induced thiol-ene addition in the presence of photoinitiators as long as a stoichiometric amount of A to the vinyl group and sterically unhindered vinyls are used. In contrast, when a sterically hindered vinyl is used, the nucleophilic addition of the nitrile is favoured. The prepared mercaptonitriles can easily undergo cyclization reactions in basic and acidic conditions as well as in the presence of silica gel. This illustrates the high reactivity of nitriles towards thiol addition. 1,2-Ethanedithiol B is presented as an alternative reagent to A as it allows conversion of vinyl nitriles directly into mercaptonitriles under mild and non-acidic reaction conditions.
