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2-Iminothiolane hydrochloride

≥98% (TLC), powder

2IT, 2-Thiolanimine hydrochloride, Dihydro-2(3H)-thiophenimine hydrochloride, Traut’s reagent
Empirical Formula (Hill Notation):
C4H7NS · HCl
CAS Number:
Molecular Weight:
MDL number:
PubChem Substance ID:

Quality Level


≥98% (TLC)




≤5% Free sulfhydryl groups


198-201 °C (lit.)


H2O: 100 mg/mL

storage temp.


SMILES string




InChI key


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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.


2-Iminothiolane hydrochloride has been used in the synthesis of thiolated PEG (poly(ethylene glycol). It may be used to synthesize PLA-SH (polyethylene glycol-thiol) and PLA-PEG-SH (polyethylene glycol–polylactic acid-thiol).
Thiolating reagent for primary amines. Reacts at pH 7-10 by amidine bond to present free sulfhydryl. Useful in preparation of disulfide and/or thioether linked conjugates.


1 g in glass bottle
100, 500 mg in glass bottle

Other Notes

Note that the amidine linkage preserves original primary amine positive charge. Incorporates a five atom linker.


Skull and crossbones

Signal Word


Hazard Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects



Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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Hafizah Mahmud et al.
International journal of molecular sciences, 19(3) (2018-03-03)
We recently have established a successful xenograft model of human glioblastoma cells by enriching hyaluronic acid-dependent spheroid-forming populations termed U251MG-P1 cells from U251MG cells. Since U251MG-P1 cells have been confirmed to express CD44 along with principal stemness marker genes, OCT3/4
Akio Kuzuhara
Biopolymers, 79(4), 173-184 (2005-09-08)
For the purpose of investigating in detail the influence of chemical modification using 2-iminothiolane hydrochloride (2-IT) on keratin fibers, the structure of cross-sections at various depths of white human hair, treated with 2-IT and then oxidized, was directly analyzed without
Alexander Ewe et al.
Nanomedicine : nanotechnology, biology, and medicine, 13(1), 209-218 (2016-08-25)
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Hohyeon Lee et al.
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Metastasis is the leading cause of cancer-related deaths. A number of chemotherapeutic and early diagnosis strategies, including nanomedicine, have been developed to target metastatic tumor cells. However, simultaneous inhibition and imaging of metastasis is yet to be fully achieved. Methods:
Doyeon Kim et al.
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One of the major obstacles to successful chemotherapy is multi-drug resistance (MDR). A multi-drug resistant cancerous cell abnormally overexpresses membrane transporters that pump anticancer drugs out of the cell, resulting in low anticancer drug delivery efficiency. To overcome the limitation


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